GUYS TRIP 2027 · 20–23 MAY

Six Dudes · Three nights · One ballgame

Guys Trip
2027

Sox are home all weekend, Friday night tickets are the plan, and everything else is walking distance or a short ride.

THU 20 MAY – SUN 23 MAY 2027 / BOSTON, MA / NO CAR

Dates

Thu–Sun

20–23 May 2027. Three nights.

Crew

One house, one table.

Ballgame

Fri 5/21

Red Sox vs. Rangers. Locked in.

Getting around

Foot + T

No rental car. Subway and a few Ubers.

Budget

$855–1,275

Each, not counting flights.

The Ballgame

Locked · Friday 7:10

MLB put out the 2027 schedule back in July, and the Sox are home all three days that weekend against the Texas Rangers. Friday is the pick.

Date	Game	Why
Fri 21 May	Rangers @ Red Sox	This one.Friday night games at Fenway are almost always 7:10, which leaves the whole day free for the Freedom Trail and keeps Saturday open for the harbor.
Sat 22 May	Rangers @ Red Sox	Backup onlySaturday start times swing anywhere from 1:35 to 7:15. If it lands in the afternoon it wipes out the sail.
Sun 23 May	Rangers @ Red Sox	Bonus, not the planA 1:35 day game still works for anyone on an evening flight home.

Heads up on the start time

MLB locks in dates long before start times; those come later with the TV schedule. 7:10 is the safe bet for a Friday, but it's worth checking the Red Sox schedule page before anyone buys a plane ticket.

Tickets: Red Sox single-game tickets, SeatGeek, or StubHub. Six seats in one row is the goal, and that gets harder the longer it waits. Budget is $120 a head, which lands in grandstand.

The Lay of the Land

Pins match the day colors

Boston is small. The whole weekend fits inside about four miles of city wrapped around a harbor and a river, and most of it connects on foot. The Map button in the top bar pulls this up from anywhere on the page, and the full subway map is worth a look before anyone tries to navigate the T.

Shoreline traced from real coastline data, so the wharves and channels are the actual shapes. Fenway to the North End is about three miles, and everything else sits inside a comfortable walk or a short T ride. Map data © OpenStreetMap contributors.

★Home base · North End Thu · arrive Fri · trail + Fenway Sat · harbor Sun · river Freedom Trail Harborwalk Sail loop Green Line Georges ferry

Flights

Chicago + Cincinnati

Both cities have nonstops into Logan, so nobody needs a connection. The trick is landing close enough together to share a ride and make dinner.

From	Nonstop airlines	Flight time	Search
Chicago (ORD)About 135 flights a week, so plenty of options	American, United, Delta, JetBlue	~2h 35m	Google Flights · Kayak Southwest also flies Midway (MDW) to Boston, which may be closer depending on the side of town.
Cincinnati (CVG)About 45 flights a week, so fewer options to work with	Delta, American	~2h 15m	Google Flights · Kayak First flight out is around 6:00am, last one lands about 11:45pm.

How to land together

Cincinnati picks first. CVG has a third as many flights as O'Hare, so the Cincinnati crew should find a Thursday flight that works and Chicago books around it. Going the other way round leaves somebody sitting at baggage claim for four hours.

Aim for a 4:00 to 7:00pm Thursday arrival. That puts everyone on the ground, into the city, and at a dinner table by 8:00 without burning a vacation day.

Same airline if possible. Delta and American both serve both cities. One airline means one terminal at Logan, which turns meeting up into a five-minute walk instead of a shuttle ride.

Sunday home: late afternoon or evening. Already agreed, and it leaves the 1:35 day game on the table for anyone flying out after 7:00pm.

Where We're Staying

No hotels · Registration rules

A house for the six of us, not hotel rooms. Boston is unusually strict about short-term rentals though, so the rule below is worth two minutes before anyone books.

The one rule that matters

Boston only allows short-term rentals in units where the owner actually lives. A registered "Home Share", meaning the owner's own place rented out while they're away, is legal and can sleep up to ten people. An investor who bought a condo purely to rent out is illegal, and the city takes those listings down. Sometimes days before check-in.

The check is simple: a legal listing shows a City of Boston registration number. If it isn't on the listing page, ask the host. No number, move on. Numbers can be verified against the city's registry, and the full rules are on Boston.gov.

Worth knowing: Cambridge and Somerville have the same owner-occupied rule, so hopping across the river doesn't get around it.

Three routes to a legal house for six. Availability shifts constantly, so these are live searches and real operators rather than fixed listings. The links show what's actually open on our dates.

Option 1, start here

Airbnb, filtered

Target $450–750 / night

Dates, six guests and 3+ bedrooms already plugged in. Sort by neighborhood: North End, Back Bay, Beacon Hill or the Seaport all put us in walking range. Every listing needs a registration number before it gets booked.

Search Airbnb →

Option 2

VRBO, filtered

Target $450–750 / night

Same dates and filters, different inventory. VRBO skews toward whole homes, which is what we want, and it sometimes surfaces places Airbnb doesn't. Same registration-number rule applies.

Search VRBO →

Option 3, the safe one

Licensed operators

Call for a quote

Companies that rent furnished townhouses and apartments by the night and handle the licensing themselves. Not hotels, actual houses. Worth a call since they hold inventory that never shows up on the big sites.

STARS of Boston → The Upton, South End →

Which neighborhood

North End or downtown near the waterfront is the pick. It's a walk to dinner, a walk to the Freedom Trail, and a walk to the boats on Saturday, with Fenway a straight shot on the Green Line or a 15-minute Uber (here is the whole subway map). Back Bay is the runner-up: closer to Fenway and the river, further from the harbor.

The Weekend

Four days

One main thing per day so nothing feels rushed. Every place below links out to a map and hours, and the Map button in the top bar shows how the whole thing fits together.

Day 1 · Thursday

20 May: Get in, eat well

Everyone lands at different times, so night one stays easy. Drop bags, walk around, get a big table.

Brick buildings and a hanging restaurant sign on Hanover Street in Boston's North End — Hanover Street, the main drag through the North End.

Afternoon

Land at Logan. It sits about 15 minutes from downtown, which is a nice change from most airports. Blue Line or an Uber, both easy. Whoever gets in first grabs the dinner table.

6:00p

Drop bags and walk Hanover Street end to end. It's the Italian neighborhood and it's about four blocks long.

7:30p

Dinner in the North End. Bricco is the nicer one, Antico Forno does wood-fired everything and runs a little more casual. Both take reservations and both can seat six. Neptune Oyster is the one everyone recommends. It's excellent, but it's tiny and doesn't take reservations, so it's an hour-plus wait standing up. Not worth it with a group this size.

9:30p

Cannoli. Mike's and Modern sit across the street from each other and people have strong opinions. Get both and settle it.

10:15p

One more at Bell in Hand, open since 1795 and a five-minute walk. Touristy, but a fun first stop. For a proper cocktail instead, Ward 8 is right there too.

Day 2 · Friday

21 May: Freedom Trail, then Fenway

History in the morning, baseball at night. The whole day stays open because the game isn't until 7:10.

Game day

The Green Monster left field wall at Fenway Park with its hand-operated scoreboard — The Green Monster. That scoreboard is still turned by hand, by guys standing behind the wall.

9:30a

The Freedom Trail, a red brick line set into the sidewalk that runs the whole route. Two and a half miles from Boston Common past Faneuil Hall and the Paul Revere House to the Old North Church. Flat, free, and easy to cut short at any point.

1:00p

Walk over the bridge to Charlestown for the USS Constitution and Bunker Hill, then a beer at the Warren Tavern (1780). If legs are shot by then, the ferry runs back across the harbor.

3:30p

Regroup at Trillium Fort Point. Best brewery taproom in the city, with plenty of room to stand around.

5:15p

Head to Fenway. Green Line to Kenmore. Pre-game at Bleacher Bar, built into the wall under the center field bleachers, with a garage door that looks straight out onto the field. It packs out about an hour before first pitch, so 5:30 at the latest. Otherwise Cask 'n Flagon across the street.

7:10p

Red Sox vs. Rangers at Fenway Park. Oldest park in baseball, and small enough that there isn't really a bad seat.

10:30p

Everyone spills onto Lansdowne Street after the game. Loretta's Last Call has live country and cheap beer, or Time Out Market is a food hall with a dozen vendors when nobody can agree on food.

Day 3 · Saturday

22 May: Out on the water

Slow morning, a couple of hours on a sailboat in the afternoon, then the big night out in the Seaport.

Harbor day

The schooner Liberty Star under full sail in Boston Harbor with the city skyline behind — The *Liberty Star* out in the harbor. One of the two boats below.

10:00a

Late breakfast, nothing scheduled.

11:30a

Walk the Harborwalk from Long Wharf through Fort Point into the Seaport. Flat, right on the water, about two and a half miles.

2:30p

Sail Boston Harbor. Two operators, both running public trips. Details below, and the group picks which one.

6:30p

Dinner in the Seaport. Row 34 for oysters and a serious beer list, or Committee for Greek small plates in a louder room. Book either one ahead.

9:00p

Harpoon Brewery beer hall. Long communal tables, warm pretzels the size of a dinner plate, an easy place to park six guys for a couple of hours.

11:00p

The Seaport stays busy later than downtown does, so last call is wherever the night ends up.

The sail, for anyone who hasn't done one

Simpler than it sounds. Buy a ticket like a movie, show up at the dock 15 minutes early, and step onto a real tall ship with the sails up. A crew of three does the sailing. Passengers can help haul lines or just sit on deck with a beer and watch the skyline go by.

Two options, both good. Group vote before anyone books.

Boat	Cost	Length	Leaves from
Liberty Star67ft wooden schooner. The one in the photo. Cheaper and a little more hands-on.	$35–70	1.5 hrs	Fan Pier MarinaBeer and Boston-made spirits sold onboard. (617) 742-0333
Schooner Adirondack80ft pilot schooner, bigger and a bit more polished. Runs daily.	up to $74	1.5–2 hrs	60 Rowes WharfBeer $6, wine $7, cocktails $9. No outside drinks or coolers. (617) 951-2460

There's also a sunset sail at around $100 a head that goes out as the sun drops behind the skyline. Better photos, but it pushes dinner to 8:30 or later. Same group vote.

Day 4 · Sunday

23 May: One last walk, then home

A walk along the river, brunch, then out. Flights are late afternoon or evening.

Back Bay brownstones reflected in the still water of the Charles River at golden hour — The Esplanade, looking across at the Back Bay brownstones.

9:30a

The Charles River Esplanade, a park path running right along the water with the brownstones on the far bank. Flat the whole way, and it can be two miles or five depending on how everyone's feeling.

11:30a

Brunch in Back Bay or the South End, both a short walk from the river.

1:35p

Optional: the Sunday day game against the same Rangers. Works for anyone on an evening flight who wants a second crack at Fenway.

Late afternoon

Blue Line back to Logan. About 20 minutes door to terminal.

Book In This Order

Two urgent, three relaxed

Tickets and the house are the two that actually run out. Everything else can wait until closer to the trip.

When	What	Timing	Each
Now-ish	Red Sox tickets, Fri 21 MaySix seats in one row at around $120 each. Single-game sales for 2027 usually open in December, and seats are already showing up on resale.	Dec 2026	$120
Now-ish	The house, 3 nightsLegal inventory is thin because of the owner-occupied rule, so good places go early. Registration number required.	Nov 2026–Jan 2027	$225–375
Then	FlightsCincinnati picks the time, Chicago matches it. Same airline if possible. Sunday departures late afternoon or evening.	4–5 months out	Varies
Then	Saturday sailSmall boats and a popular slot on a May Saturday. Group picks the boat first.	1 month out	$35–75
Easy	Dinner reservationsSaturday in the Seaport matters most. Thursday in the North End is forgiving.	2–4 weeks out	n/a

The Money

Per person, no flights

Line	Basis	Each
The house3 nights, split six ways	$450–750 / night	$225–375
Red Sox ticketGrandstand, agreed at $120	Friday night	$120
Harbor sailPublic trip, roughly 2 hours	Saturday	$35–75
Food and drinksThree and a half days, two big nights	~$110 / day	$350–500
Ballpark extrasPre-game beers, food, team store damage	Friday	$75–125
Getting aroundT fares and a handful of Ubers	No car	$50–80
Total	Rough estimate	$855–1,275

Comfortably inside the range the group set. Skipping the sail would take another $35 to $75 off each.

If Something Goes Sideways

Backups

Sunlight falling through a window into a bare stone and brick casemate inside Fort Warren — Inside Fort Warren on Georges Island, the best rainy-day swap on the list.

If it's too windy to sail

Take the ferry to Georges Island from Long Wharf instead and walk around Fort Warren, a Civil War granite fort with dark tunnels that can be explored on foot with a flashlight. Ferries run Thursday through Sunday starting mid-May, so our dates work, but the 2027 season needs confirming once it's posted.

If it rains all Saturday

Drop the water day. Sam Adams brewery tour, the ICA out on the water, and a long lunch at Time Out Market.

If someone wants an actual hike

Blue Hills has real elevation and a view back at the skyline, but it needs a car, which is the one thing this plan avoids. Costs a half day plus a rental. Group decision.

If Friday's first pitch moves

Friday just slides with it. If it somehow ends up an afternoon game, swap Friday and Saturday completely: sail Friday, ballgame Saturday. Nothing else changes.

GUYS TRIP 2027 · 20–23 MAY

Six Dudes · Three nights · No passports

Guys Trip
2027

Same weekend as the Boston plan, except it's 88 degrees, everything still takes US dollars, and the big night is a plaza where the bars spill into the street.

THU 20 MAY – SUN 23 MAY 2027 / SAN JUAN, PR / ONE VAN, ONE DAY

Dates

Thu–Sun

20–23 May 2027. Three nights.

Crew

One house, one table.

Big night

Fri 5/21

La Placita de Santurce.

Getting around

Foot + Uber

One rented van, Saturday only.

Budget

$825–1,170

Each, not counting flights.

The Big Night

Free · Friday, late

There's no ballgame to build the weekend around, so the anchor is La Placita de Santurce — a produce market by day that turns into about twenty bars around one plaza after dark, with the drinking happening in the street between them. No tickets, no covers, no reservations. Friday is the night.

Night	What it's like	Why
Fri 21 May	Full tilt	This one.Friday and Saturday are the two big nights and Friday leaves Saturday free for the water. Live salsa in several of the chinchorros, and the plaza doesn't really fill until 10.
Sat 22 May	Just as busy	Backup onlyEqually good, but we'll have been on a boat since one o'clock. Saturday night wants to be dinner and a shorter leash.
Thu 20 May	Warm-up	Wrong neighborhoodThursday runs, but night one belongs in Old San Juan while everyone's still landing at different times.

How La Placita actually works

It's a working market building in the middle of a plaza in Santurce. During the day people buy plantains there. From about 6pm Wednesday through Sunday the surrounding bars open, and by 10 the streets around the plaza are closed to cars and packed.

Nobody sits down. You buy a drink at a window, stand in the street, and move when you feel like it. That's the whole format, and it's the best possible setup for six people who can't agree on anything.

It's a 10-minute Uber from Condado and about 15 from Old San Juan. Going home late is the one time the whole group should split two cars rather than wait for a six-seater.

The Lay of the Land

Pins match the day colors

San Juan is a thin strip of city between the Atlantic and a set of lagoons, which is why everything lines up east to west. Old San Juan sits on its own islet at the far end; we'd stay in the middle, in Condado. The Map button in the top bar pulls this up from anywhere on the page.

Shoreline traced from real OpenStreetMap coastline data, so the islet, the bay and all four lagoons are the actual shapes. Old San Juan to Condado is about two and a half miles. El Yunque and Fajardo are off the right-hand edge, 30 to 40 miles east. Map data © OpenStreetMap contributors.

★Home base · Condado Thu · arrive Fri · forts + La Placita Sat · east coast Sun · beach The walls Paseo del Morro Cataño ferry Airport run Van east

Flights

Chicago direct · Cincinnati connects

This is the one place San Juan is harder than Boston. Chicago has plenty of nonstops. Cincinnati has none at all, so the Cincinnati crew is connecting no matter what.

From	Airlines	Flight time	Search
Chicago (ORD)About 11 nonstops a week — fewer than to Boston, so pick dates early	American, United, Frontier, Spirit — nonstop	~4h 45m	Google Flights · Kayak Frontier and Spirit are cheap and will be the ones that hurt if anything slips. On a three-night trip, pay up for American or United.
Cincinnati (CVG)No nonstop service to San Juan at all	One stop — Charlotte, Atlanta, Miami or O'Hare	~6–8h	Google Flights · Kayak The neat option is connecting through O'Hare and joining the Chicago guys on the same nonstop down.

How to land together

Try to put everyone on the same ORD–SJU nonstop. If the Cincinnati crew connects through Chicago, the whole group walks off one plane in San Juan. That's worth an early alarm and a tight-ish layover.

Aim for a 3:00 to 6:00pm Thursday arrival. SJU is about 20 minutes from Condado, so a 5pm landing still makes an 8pm table in Old San Juan comfortably.

Nothing to do on arrival. It's a domestic flight into a US territory: no passports, no customs, no currency, and phones work normally. Bags come out and you're in an Uber.

Sunday home: late afternoon or evening. Same as the Boston plan, and it leaves Sunday morning free for a swim.

Where We're Staying

No hotels · Registration rules

A house for the six of us, same as Boston. Puerto Rico has its own licensing regime for short-term rentals, and San Juan added a layer on top, so the rule below is worth two minutes before anyone books.

The one rule that matters

Every legal short-term rental in Puerto Rico is registered with the Puerto Rico Tourism Company as an innkeeper (hostelero), and the PRTC number is supposed to appear on the listing. On top of that, San Juan's Ordinance 39 requires an annual municipal licence for every unit inside city limits.

The check is the same as it was in Boston: look for the registration number on the listing page. If it isn't there, ask the host. A host who can't produce one is either unlicensed or evasive, and both are reasons to move on.

There's also a 7% room occupancy tax remitted to the PRTC. A legitimate listing will show it in the price breakdown rather than asking for cash on arrival.

Worth knowing: unlike Boston, Puerto Rico does not require the owner to live there, so legal inventory is far deeper than it was in the North End. This is a paperwork check, not a scavenger hunt.

Three neighborhoods that work for six guys with no car. Availability shifts constantly, so these are live searches rather than fixed listings.

Option 1, start here

Condado

Target $400–650 / night

The strip between the ocean and the lagoon. Walkable beach, a real restaurant row on Ashford Avenue, ten minutes to La Placita and fifteen to Old San Juan. The most convenient base and the reason it's the home base on the map.

Search Airbnb → Search VRBO →

Option 2

Ocean Park

Target $350–600 / night

Quieter and more residential, one neighborhood east, with the better beach of the two and a lot of standalone guesthouses. Cheaper for the same square footage. You'll Uber more.

Search Airbnb → Search VRBO →

Option 3, the fun one

Old San Juan

Target $450–750 / night

A 400-year-old townhouse inside the city walls, which is a genuinely great place to wake up. The trade-offs are real: no beach, narrow stairs, street noise on San Sebastián, and no parking for the van on Saturday.

Search Airbnb →

Which neighborhood

Condado is the pick. It's the only one of the three that's a walk to a swimmable beach, a walk to dinner, and a short ride to both Old San Juan and La Placita. Old San Juan is the more romantic choice and the worse base.

Wherever it lands, get the van's parking sorted before Saturday. Condado and Ocean Park houses often come with a spot or a driveway. Inside the old city, they don't.

The Weekend

Four days

One main thing per day, same as Boston. Friday is the long walk and the big night, Saturday is the water, and the van only exists for one of the four days. Every place below links out to a map and hours.

Day 1 · Thursday

20 May: Get in, eat well

Everyone lands at different times, so night one stays easy. Drop bags, walk the old city at golden hour, get a big table.

Umbrellas strung above a narrow street in Old San Juan — Calle Fortaleza under the umbrellas. Photo: Mariordo, CC BY-SA 4.0.

Afternoon

Land at SJU. It's about 20 minutes from Condado and there's no customs line, because it isn't international. Uber works normally here and is cheap. Whoever gets in first grabs the dinner table.

6:00p

Into Old San Juan and walk the Paseo de la Princesa out to the fountain, then up Calle Fortaleza. Flat, about a mile all in, and the light on the blue cobblestones at that hour is the whole reason to do it first.

7:30p

Dinner in the old city. Marmalade is the nicer one and takes reservations; Café El Punto and Deaverdura are the honest criollo options at half the price. Order mofongo once as a group so everyone can say they did, then order what you actually want.

9:30p

La Factoría on Calle San Sebastián. No sign on the door, six connected bars inside, each with its own menu and its own music, and you drift between them through unmarked doorways. It was named the best bar in the Caribbean in 2026. Go early-ish, because the line after 11 is real.

11:30p

The rest of Calle San Sebastián is four solid blocks of bars, so the night ends whenever it ends and the Uber home is fifteen minutes.

Day 2 · Friday

21 May: The forts, then La Placita

Five hundred years of Spanish military engineering in the morning, a rum distillery after lunch, and the loudest plaza in the Caribbean at night.

Big night

The entrance to the Santurce market hall, stacked with plantains and produce — La Placita in its day job. By 10pm the streets outside are closed to cars. Photo: Šarūnas Burdulis, CC BY-SA 2.0.

9:00a

Castillo San Felipe del Morro the moment it opens, before the cruise crowd and the heat. Six levels of gun batteries on a headland, with the lighthouse from the top of this page. $10 covers both forts for 24 hours, so keep the receipt. Under-16s are free.

10:30a

Walk the Paseo del Morro, the paved path along the base of the city wall at the water's edge, then back up through the Santa María Magdalena cemetery and Cuartel de Ballajá. This is the Freedom Trail equivalent: about two and a half miles, flat, and you can bail into a bar at any point.

12:30p

Castillo San Cristóbal at the other end of the old city — bigger than El Morro, far emptier, and the tunnels are the best part. Same ticket.

2:30p

Walk down to Pier 2 and take the AcuaExpreso ferry across the bay to Cataño for Casa Bacardí. The ferry is about $1.50 round trip and takes 12 minutes. The distillery tour is $40–45; the mixology class is $89 and better if the group's into it.

6:30p

Back across, clean up, and eat something real before the plaza. Santaella is a hundred yards from La Placita and exactly the right call, so book it.

9:30p

La Placita de Santurce. Don't arrive early. The plaza fills around 10 and the streets close to traffic after that. Live salsa in several of the bars. Jungle Bird is two blocks away if anyone wants a proper cocktail and a seat.

Late

It runs until 3 or later, and nobody has to drive. Split into two Ubers going home instead of waiting twenty minutes for one six-seater.

Day 3 · Saturday

22 May: The van day east

Rainforest before it gets hot, a catamaran to a deserted island in the afternoon, and roadside fritters on the drive home.

Water day

The forested peaks of El Yunque seen from the Yokahu observation tower — El Yunque from the Yokahú tower, about ten minutes' walk from the road. Photo: Jami430, CC BY-SA 4.0.

7:15a

Van out of Condado. This is the one early start of the trip and the only day we need a vehicle. An eight-seater from SJU or a Condado agency runs about $120–150 for the day. Split six ways it's cheaper than paying for six tour pickups.

8:00a

El Yunque, the only tropical rainforest in the US Forest Service system. Free, no reservation needed, gates open at 8. Do the Yokahú tower first for the view, then the Angelito trail down to the swimming hole on the Río Mameyes. La Mina Falls, Big Tree and Baño de Oro are all closed, so ignore every blog that sends you there.

11:30a

Back in the van, 30 minutes east to Villa Marina in Fajardo. Check-in is at noon.

1:00p

Catamaran to Cayo Icacos, an uninhabited island off Fajardo. Four hours, back at the dock at 5. Lunch, snorkel gear, kayaks and tropical drinks are all included. Details in the box below.

5:45p

Stop at the Luquillo kiosks on the way back — about sixty family-run stalls in a row along PR-3, right by the beach. Alcapurrias, bacalaítos, whole fried snapper, and a beer for three dollars. This is the best food of the weekend and it costs nothing.

8:00p

Back in San Juan. Late, low-key dinner on Calle Loíza, which is a ten-minute walk from Condado and where people actually live.

The catamaran, for anyone who hasn't done one

Same idea as the Boston sail, warmer water. You buy a ticket like a movie, show up at the marina fifteen minutes early, and step onto a 50-foot catamaran with a crew of three. It motors 45 minutes out to a reef, everyone snorkels, then it anchors off a sand beach with nothing on it and stays a couple of hours.

The 1:00pm departure is the one that makes Saturday work, because it leaves the whole morning for the rainforest. Most operators only push the 8:00am trip, so book the afternoon deliberately.

Operator	Cost	Runs	Leaves from
Al Este — afternoon IcacosThe one this plan is built around. Deli lunch, open bar, kayaks and a sea ladder.	$100	1:00–5:00p	Villa Marina, FajardoCheck in at noon. There's a minimum headcount, so confirm it — six of us is most of the way there. (787) 863-2821
East Island ExcursionsThe big operator, bigger boats, full-day only. Worth a call to ask about an afternoon charter for six.	$130–195	Full day	Puerto del Rey, FajardoIf we take a full day here, El Yunque moves to Sunday morning. (787) 860-3434

Either way, the boat is the thing to book first after the house. A May Saturday in Fajardo is a popular slot and these are small boats.

Heads up: the bio bay won't work this weekend

Fajardo's bioluminescent lagoon — Laguna Grande, where the water lights up when you move it — is the obvious thing to add to a day already spent in Fajardo. It's also the one thing the calendar takes away from us.

20 May 2027 is a full moon. The glow is caused by microscopic plankton, and it only reads against a genuinely dark sky. Thursday is the full moon, and Friday and Saturday are barely better, with a bright waning moon up most of the night. Every operator will still happily sell you a ticket.

If someone wants to go anyway, it's an $85–125 paddle through a mangrove channel that's worth doing on its own terms — just don't expect the photos. The new moon was 6 May. If the group would rather have the bio bay than the Grand Prix weekend in Montréal, moving the whole trip two weeks earlier is the move, and it's worth saying out loud now rather than in April.

Day 4 · Sunday

23 May: One last swim, then home

The only morning with nothing scheduled. Walk to the water, eat a long breakfast, go to the airport.

The beach at Condado, San Juan, with the hotel strip behind it — Condado beach, a three-minute walk from the house. Photo: MJCdetroit, CC BY-SA 3.0.

9:00a

Balneario El Escambrón, a protected cove tucked under the old city walls with a reef close enough to swim to. It's the best snorkeling inside city limits and it's free. Fifteen minutes on foot from Condado along the water, or a four-dollar Uber. Lifeguards, showers, and a kiosk for coffee.

11:00a

Breakfast on Calle Loíza or in Ocean Park. Both are a walk rather than a ride, and Sunday is when the neighborhood is out.

1:00p

Optional: if the flights are late enough, Piñones is 15 minutes east — a road through the mangroves lined with open-air kiosks, with a bike path along the dunes.

Mid afternoon

Uber to SJU. About 20 minutes from Condado, and the terminal is small enough that 90 minutes is plenty.

Book In This Order

Two urgent, three relaxed

Nothing here sells out the way Red Sox tickets do. The house and the boat are the only two with real scarcity.

When	What	Timing	Each
Now-ish	The house, 3 nightsMay is shoulder season so prices are soft, but three-bedroom places that sleep six in Condado are a thin slice of the market. PRTC registration number required.	Dec 2026–Feb 2027	$200–325
Now-ish	FlightsOnly 11 ORD–SJU nonstops a week, and the Cincinnati crew needs a connection that lines up. This is the constraint, not the hotel.	4–6 months out	Varies
Then	Saturday catamaranSmall boats, popular slot, and we specifically need the 1:00pm departure rather than the 8:00am one. Confirm the minimum headcount.	1–2 months out	$100
Then	The van, Saturday onlyAn eight-seater for one day. Reserve it, but they're rarely tight in May.	2–4 weeks out	$30–40
Easy	Dinner reservationsSantaella on Friday and Marmalade on Thursday are the two worth booking. Everything else takes walk-ins.	2–3 weeks out	n/a
Easy	Forts and Casa BacardíThe forts are walk-up. Casa Bacardí tours can be booked online a few days ahead.	That week	$55

The Money

Per person, no flights

Line	Basis	Each
The house3 nights, split six ways	$400–650 / night	$200–325
Catamaran to IcacosFour hours, lunch and drinks included	Saturday	$100
Forts + Casa Bacardí$10 for both forts, $45 distillery tour, $1.50 ferry	Friday	$57
Food and drinksThree and a half days, one of them at the kiosks	~$95 / day	$330–460
La Placita nightNo cover anywhere, but it's a long night	Friday	$60–100
The vanEight-seater, one day, plus gas and tolls	Saturday	$30–40
Getting aroundUbers all weekend and the airport both ways	No car otherwise	$50–80
Total	Rough estimate	$827–1,162

A little under the Boston number, mostly because the anchor event is free and one day's food happens at a roadside kiosk. The flights are where San Juan gets its money back — it's twice the distance and Cincinnati has to connect.

If Something Goes Sideways

Backups

Looking out across the water from the ramparts of the San Juan city walls — The ramparts at San Juan National Historic Site — the best wet-weather swap on the list. Photo: AlbertHerring, CC BY-SA 3.0.

If the trade winds kill the boat

May can blow hard enough that Icacos trips get cancelled the morning of. Drive 20 minutes further to Balneario Seven Seas instead — a sheltered bay with calm water, shade and a walk out to hidden coves. Costs $6 to park and nothing else.

If it rains all Saturday

Go anyway. El Yunque is a rainforest and it rains there most days; that's the point, and the swimming hole doesn't care. If it's genuinely torrential, the fallback is the Museo de Arte de Puerto Rico, the Casa Bacardí mixology class, and the forts, which are half indoors.

If someone wants a real hike

Mount Britton tower and up Forest Road 10 toward El Yunque Peak is a proper climb with real elevation, and it's the one trail system in the park still fully open. Add 90 minutes to Saturday morning and start at 7:00 instead of 7:15.

If the group wants the bio bay

Then the dates have to move. The new moon is 6 May 2027, so a Thu 6 – Sun 9 May version of this exact trip gets a dark sky, dodges the Grand Prix problem in Montréal entirely, and changes nothing else on this page. Worth a vote before anyone books flights.

If sargassum shows up early

The seaweed season usually starts late May and mostly spares the north-facing city beaches. If Condado looks rough, Escambrón is protected by its reef and stays clean when the open beaches don't.

GUYS TRIP 2027 · 20–23 MAY

Six Dudes · Three nights · Race week

Guys Trip
2027

Our exact weekend turns out to be the one weekend a year Montréal loses its mind. We're skipping the race and taking the free half, which is the better half anyway.

THU 20 MAY – SUN 23 MAY 2027 / MONTRÉAL, QC / NO CAR · PASSPORTS

Dates

Thu–Sun

20–23 May 2027. Three nights.

Crew

Three rooms, or one big suite.

Big night

Fri 5/21

Crescent Street. Free.

Getting around

Métro

C$21.75 covers three days.

Budget

$810–1,285

Each, not counting flights.

Race Week, No Ticket

Free · Thu–Sun, 11a–11p

Formula 1 published its 2027 calendar and the Canadian Grand Prix lands on 21–23 May at Circuit Gilles-Villeneuve — the same three days we'd already picked. That's either the best coincidence of the trip or an expensive accident, depending on whether you buy a ticket. The plan is not to.

Option	Cost each	What you get
Crescent Street	$0	This one.The Festival Grand Prix sur Crescent closes four downtown blocks for four days — live music, real F1 cars on the pavement, every terrasse open, and roughly 600,000 people through it over the weekend. Free, 11am to 11pm. It's a five-minute walk from anywhere downtown.
Friday-only GA	~C$150–250	The cheap way inIf someone has to hear the cars, a single Friday practice-day general admission is a fraction of a weekend pass, and it doesn't cost the group anything else — Friday's plan is already downtown.
3-day GA	from C$300	Not this tripGeneral admission is standing at a fence. Grandstands run well past that, and either one eats the whole per-person budget on its own.

Heads up: this is the expensive weekend

Skipping the race doesn't get us out of race-week pricing. Grand Prix weekend is the single biggest tourist event in Canada. Hotels run about 95% full and mid-range rooms have gone for $600–900 a night. That, not the racing, is the real cost of these dates, and it's why the lodging section below looks nothing like Boston's.

The 2027 festival dates aren't posted yet. Crescent Street has run Thursday through Sunday of race week for 25 years, and with a Sunday 23 May race that should mean 20–23 May — exactly our weekend. Worth confirming on crescentgrandprix.com before anyone buys a plane ticket, the same way we'd check a first pitch.

If the group would rather not do race week at all, everything else on this page works untouched on a quieter May weekend, and the lodging gets roughly $100 a head cheaper. That's a real vote to take.

The Lay of the Land

Pins match the day colors

Montréal is an island in the middle of the St Lawrence with a small mountain in the middle of it. Downtown sits between the mountain and the river, the old city is on the waterfront, and the circuit is on a man-made island just offshore. Almost all of it is walkable, and the rest is two métro stops.

River, islands and shoreline traced from real OpenStreetMap data, so Île Sainte-Hélène, Île Notre-Dame and the Lachine Canal are the actual shapes — and the red loop on the island offshore is the actual Circuit Gilles-Villeneuve. Downtown to the Old Port is about a mile and a half. Map data © OpenStreetMap contributors.

★Home base · downtown Thu · arrive Fri · mountain + Crescent Sat · river Sun · market The climb Jet boat run Lachine Canal 747 airport bus To the circuit

Flights

Both cities nonstop

This is the best flight picture of the three destinations. Both home cities have nonstops, both are short, and for once Cincinnati isn't the problem.

From	Nonstop airlines	Flight time	Search
Chicago (ORD)About 44 flights a week, so there's a flight whenever you want one	Air Canada, United, American	~2h 20m	Google Flights · Kayak Shorter than the Boston flight. Air Canada and United each run about 21 a week.
Cincinnati (CVG)Seven Air Canada nonstops a week — roughly one a day	Air Canada	~1h 45m	Google Flights · Air Canada One flight a day means one option, so Cincinnati still picks first — but they get a nonstop, which San Juan can't offer at all.

The one thing this trip needs that the others don't

Six valid passports. This is an international trip and there's no way around it. A passport card is not enough for air travel — it has to be the book. Renewals have run 6 to 10 weeks, so anyone whose passport expires before November 2027 should check the date this week, not in April.

Book race weekend early or not at all. Grand Prix flights into YUL fill and climb. If the group commits to these dates, flights want booking about the same time as the rooms, not after.

Nothing else is different. Canada takes cards everywhere, US phone plans mostly roam fine, and the border at YUL for six Americans on a weekend trip is a two-minute conversation. Bring the passport, not a story.

Sunday home: evening. The race finishes mid-afternoon and the city empties into YUL right after, so either fly out before the traffic or well after it.

Where We're Staying

The house plan doesn't work here

This is the one section where Montréal breaks the format. The "one house, one table" plan that worked in Boston and works in San Juan is essentially illegal here in May, and it's worth understanding why before anyone sends around an Airbnb link.

The one rule that matters

Montréal only allows short-term rentals in residential areas between 10 June and 10 September. Our dates are in May. That means almost every "whole home for six" listing you'll find for this weekend is either outside the legal window, on one of a handful of specifically zoned commercial streets, or simply not legal.

Québec also requires every short-term rental to carry a CITQ registration number displayed on the listing, and the city adds its own municipal permit on top. As of September 2026 hosts must also renew written consent from the building owner or condo board every year or the registration lapses.

The practical upshot: an unlicensed listing can be pulled days before check-in, and on the busiest weekend of the Canadian year there is no backup inventory to move into. That's a much worse failure mode than Boston's.

So the plan here is rooms, not a house — but there's a way to do that without it feeling like a business trip. The three options below are all legal year-round.

Three routes to six beds downtown on race weekend. All three are walking distance to Crescent Street.

Option 1, the budget play

University residences

C$65–180 / room / night

McGill's summer residences open around 15 May. La Citadelle on Sherbrooke has private rooms with private bathrooms and A/C, four blocks from Crescent Street. Concordia's Grey Nuns is a converted convent and starts near C$65. Legal, central, and immune to race-week pricing.

McGill summer stays → Concordia Grey Nuns →

Option 2, closest to a house

Aparthotel suites

C$400–900 / night

Licensed apartment hotels with full kitchens and multi-bedroom units — the nearest thing to the Boston plan that's legal in May. Eurostars Old Montreal Suites, Maison Rasco and ApartHotelMontreal all have units that sleep six to eight. Expect race-week rates, and book these first.

Eurostars Old Montreal → Maison Rasco →

Option 3, the pressure valve

Off-core hotel rooms

C$250–450 / room / night

Three doubles in the Plateau, Griffintown, Verdun, or across the river in Longueuil — one stop on the Yellow Line and materially cheaper than downtown on this weekend. You give up the five-minute stumble home from Crescent Street; the métro runs until 1am and Ubers exist.

Search Booking.com →

Which one

Price the aparthotel first, then decide. If a six-sleeper suite comes in near C$600 a night, it's the best version of this trip and it keeps the one-table feeling. If race week pushes it past C$900, the McGill residences are genuinely good, genuinely central, and save something like $150 a head — which is the difference between this trip landing inside the Boston budget and blowing past it.

Whatever we pick, book it before the flights. Rooms are the scarce thing on this weekend, not seats.

The Weekend

Four days

One main thing per day. Friday is the long walk and the big night, Saturday is the water, and nothing on this page needs a car — a three-day transit pass is C$21.75 and covers the airport bus both ways.

Day 1 · Thursday

20 May: Get in, eat well

Everyone lands at different times, so night one stays easy. Drop bags, walk the old city, get a big table.

The waterfront promenade and basins of the Old Port of Montreal — The Old Port. The jet boat leaves from the quay at the far end. Photo: Jeangagnon, CC BY-SA 4.0.

Afternoon

Land at YUL. The 747 bus runs 24 hours to downtown in about 45 minutes and is included in the three-day pass. Buy the C$21.75 three-day pass at the airport kiosk on arrival. It covers métro, bus and this shuttle, and it's the last transport decision anyone has to make.

6:00p

Drop bags and walk down into Vieux-Montréal — Place Jacques-Cartier, along Rue Saint-Paul, out to the Old Port waterfront. Cobblestones, 18th-century stone warehouses, and terrasses on every corner. It's about 20 minutes downhill from downtown.

7:30p

Dinner in the old city. Garde Manger is the one to try for — a small seafood-forward room with a chalkboard menu that changes daily. Modavie on Saint-Paul is the reliable fallback and has live jazz most nights.

9:30p

AURA at Notre-Dame Basilica — a 30-minute projection-mapped light and orchestral show inside the basilica, which is one of the most ornate interiors in North America to begin with. About $40. Skeptics get won over by this one. If the group would rather drink, the terrasses on Saint-Paul are fifty yards away.

11:00p

Back uphill for one on Crescent Street, which will already be set up for the festival. A look at what Friday's going to be.

Day 2 · Friday

21 May: The mountain, then Crescent Street

Up the mountain in the morning, a bagel-and-smoked-meat crawl down the other side, and a closed-off street full of F1 cars at night.

Big night

People queuing on the sidewalk outside Schwartz's smoked meat deli in Montreal — The line outside Schwartz's, which is permanent and moves faster than it looks. Photo: Ccyyrree, CC0.

9:30a

Walk up Rue Peel to the Kondiaronk Belvedere on Mount Royal — the view at the top of this page. It's a real climb of about 700 steps or a gentler switchback path, your choice, and it takes 40 minutes. Free, and the park is genuinely huge. Anyone who'd rather not climb can take the 11 bus to the same spot.

11:30a

Down the north side into the Plateau — outdoor staircases, painted triplexes, and murals. Keep going to Mile End for a bagel at St-Viateur or Fairmount, wood-fired and open 24 hours. Pick one and argue about it. The whole walk from the summit is about three flat miles.

1:00p

Lunch at Schwartz's on Saint-Laurent. Smoked meat on rye, medium fat, with a pickle and a cherry cola. Cash-friendly, no reservations, communal tables. The line looks bad and isn't — it turns over fast. Next door does takeout if the group would rather eat in the park.

3:00p

Wander Boulevard Saint-Laurent back toward downtown, with a stop at Dieu du Ciel if anyone wants the best brewery in the city.

6:00p

Crescent Street. Four blocks closed to traffic, F1 cars and team displays on the pavement, live bands, and every bar on the street running an outdoor bar. Free and open 11am to 11pm. It gets genuinely crowded after 8, which is the point.

9:00p

Eat without leaving. The Crescent and de la Montagne restaurants all have terrasses open onto the festival, so dinner is wherever there's a table. If the group wants a plan instead: Bar George is two blocks off the noise in a Victorian mansion, and takes reservations.

Late

Crescent runs till 11, then the night moves to Saint-Denis or Saint-Laurent, where last call is 3am. Poutine at La Banquise is open 24 hours and is the correct end to this day.

Day 3 · Saturday

22 May: Out on the water

Slow morning, an hour getting soaked in class-three rapids, a floating spa to recover, and the best dinner of the trip.

Water day

A yellow jet boat full of passengers in the standing waves of the Lachine Rapids — Saute-Moutons in the Lachine Rapids. Everyone on board is wearing a poncho for a reason. Photo: André Héroux, CC BY 3.0.

10:00a

Late breakfast, nothing scheduled. Qualifying is on TV around 2pm if anyone cares.

11:30a

Walk the Lachine Canal path from Atwater Market down to the Old Port. Flat, right on the water, about three miles, and lined with the industrial buildings that made the city. Bixi bikes are all along it if three miles sounds like a lot.

2:00p

Saute-Moutons jet boat from the Clock Tower Quay. One hour: 15 minutes out, 30 minutes in the Lachine Rapids, 15 minutes back. About $64. The season opens 15 May, so our weekend is live. Details below.

3:30p

Bota Bota, a spa built into a converted ferry moored in the Old Port, two minutes' walk from the dock. Hot baths, cold plunges, saunas, and a silent deck looking at the river. $70–95 for three hours. Going straight from the rapids into this is the single best sequence on any of the three itineraries.

7:30p

The big dinner. Joe Beef in Little Burgundy is the famous one — six is the maximum they'll take online, so it's exactly our size. Au Pied de Cochon in the Plateau is the other answer and the more excessive one. Book this two months out. Both are Michelin-listed and both are small.

10:30p

Back to Crescent for the last night of the festival, or Saint-Laurent if everyone's had enough of racing.

The jet boat, for anyone who hasn't done one

Simpler than it sounds and not remotely dangerous. You buy a ticket like a movie, show up at the Clock Tower Quay half an hour early, and they hand you a poncho and a life jacket. The boat runs upriver to the Lachine Rapids — standing waves in the St Lawrence big enough that they stopped shipping here for 300 years until they dug the canal — and then spends half an hour driving into them on purpose.

You will get soaked to the skin. That's the product. Leave phones and wallets in the lockers they provide, wear something that dries, and book Bota Bota for straight afterwards.

Option	Cost	Length	Leaves from
Saute-Moutons jet boatThe one in the photo. Big open boat, about 40 people, several departures a day.	~$64	1 hr	Clock Tower QuayPonchos, life jackets, lockers and changing rooms all included. Season runs 15 May to late September.
Rafting the same rapidsSame water, smaller boat, more work. Runs from Lachine rather than the Old Port, so add a métro ride each way.	~$55–70	2 hrs	Rafting Montréal, LachineBetter if the group wants to paddle rather than be driven. Kills the Bota Bota pairing though.

Group vote before anyone books, same as the Boston sail. The jet boat is the one this plan assumes, because it's a ten-minute walk from the spa and from dinner.

Day 4 · Sunday

23 May: Race day, from a terrasse

A market, a long brunch, and the Grand Prix on a patio TV with the actual cars audible across the river. Flights are evening.

Produce stalls under the awnings of Jean-Talon Market in Montreal — Jean-Talon Market in Little Italy, the biggest open-air market in North America. Photo: Jeangagnon, CC BY-SA 3.0.

9:30a

Jean-Talon Market in Little Italy, four métro stops up the Orange Line. Open-air, enormous, and on a Sunday morning it's the whole neighborhood doing its shopping. Eat your way through it rather than sitting down — cheese, charcuterie, oysters, and a cortado at the far end.

11:30a

Brunch in Mile End on the walk back down, or on Saint-Denis. Montréal takes brunch more seriously than it should and the lines prove it.

2:00p

The race, from a patio. First-class engine noise carries clear across the river from Île Notre-Dame, and every terrasse in the city has it on. Find one on Saint-Denis with a TV and sit outside. Roughly two hours. It's a better way to watch a Grand Prix than standing at a fence, and it costs the price of a beer.

Late afternoon

The 747 back to YUL, about 45 minutes and already paid for. The city empties toward the airport right after the race, so leave a buffer or wait it out over one more drink.

One thing not to plan for Sunday

Parc Jean-Drapeau is the racetrack. The island park with the beach, the Biosphère and the Piknic Électronik party is inside the circuit fence on race weekend — no ticket, no entry. Piknic doesn't run, and the Yellow Line métro to Jean-Drapeau will be shoulder-to-shoulder with 100,000 ticket holders.

Every guide to Montréal will recommend that island. On these three days it's off the board, which is exactly why Sunday points north to the market instead.

Book In This Order

Rooms are the bottleneck

On any other weekend Montréal would be the relaxed one. On this weekend, beds are the scarce commodity and everything else follows.

When	What	Timing	Each
Right now	PassportsCosts nothing to check and it's the one thing that can't be fixed late. Anyone expiring before November 2027 renews now.	This week	$0–165
Now-ish	Rooms, 3 nightsRace weekend runs ~95% full. Price an aparthotel suite against three McGill residence rooms and pick, but do it early — this is the whole budget swing.	Nov 2026–Jan 2027	$180–450
Then	FlightsCincinnati has one nonstop a day, so they pick and Chicago matches. Both are short.	4–5 months out	Varies
Then	Saturday dinnerJoe Beef takes a maximum of six online and books out months ahead. Au Pied de Cochon the same. This is the only reservation that really matters.	2 months out	$90–140
Easy	Jet boat and Bota BotaBook the 2pm boat and the 3:30 spa slot together a couple of weeks out. Bota Bota does sell out on nice Saturdays.	2–3 weeks out	$135–160
Easy	AURA and the transit passAURA online a few days ahead for a Thursday slot. The pass is bought at the airport on arrival.	That week	$56

The Money

Per person, no flights

Line	Basis	Each
Rooms3 nights. Low end is the university residences, high end an aparthotel suite on race weekend	Wide range	$180–450
Crescent Street festivalThe anchor event, and it's free	Thu–Sun	$0
Jet boatOne hour in the Lachine Rapids	Saturday	$64
Bota BotaThree hours, straight off the boat	Saturday	$70–95
AURA at Notre-DameOptional, but everyone who goes is glad they did	Thursday	$40
Food and drinksThree and a half days, one serious dinner, two big nights	~$130 / day	$420–570
Transit passThree days, all modes, including the airport bus both ways	C$21.75	$16
IncidentalsA couple of late Ubers and the odd cover charge	No car	$40–70
Total	Rough estimate	$830–1,305

That top number only holds because the anchor event is free. The lodging choice is the whole ballgame here: the residence route lands this comfortably inside the Boston budget, and the aparthotel route pushes past it. Buying race tickets on top would add $300–700 each and take the trip somewhere else entirely.

If Something Goes Sideways

Backups

The vaulted blue and gold interior of Notre-Dame Basilica in Montreal — Inside Notre-Dame Basilica — the best rainy-day swap on the list, and it rains here 12 days in an average May. Photo: Diliff, CC BY-SA 3.0.

If the rooms price out of reach

Move the weekend. Everything on this page except the Crescent Street festival works identically on any May weekend, and off race week the same beds are roughly $100 a head cheaper. The anchor event would become the mountain and the rapids, which is a perfectly good trip.

If it rains all Saturday

The jet boat runs in the rain — you're getting soaked regardless — but it does cancel for weather. If it does, Bota Bota is indoors and better in bad weather, the Museum of Fine Arts is free-ish and enormous, and the Underground City means you can cross downtown without going outside.

If someone has to hear the cars

Buy one Friday general admission ticket rather than a weekend pass. Friday practice is a fraction of the price, the circuit is 15 minutes from downtown on the Yellow Line, and it doesn't wreck anyone else's day — Friday's plan is downtown anyway and they can rejoin at Crescent Street.

If someone wants real elevation

Mount Royal's full summit loop from Parc Jeanne-Mance adds a couple of miles and about 700 feet, and there's a second lookout on the east side over the Olympic Stadium that almost nobody walks to. No car, no ticket, still inside the city.

If a passport doesn't come through

This is the failure mode with no workaround, which is why it's first on the booking list. If one guy can't make it international, San Juan is the same weekend, the same budget, and needs nothing but a driver's licence.