⚓ Boston Guys’ Getaway – 6 Days of Baseball, Booze & Colonial Swagger

Morning & Afternoon:
Arrive in Boston and transfer to your luxe digs at a stylish waterfront or downtown hotel. Ease into the adventure with beers and burgers at Trillium Brewing in Fort Point. Stroll the Seaport District, where modern vibes meet historic charm.

Evening:
Indulge in fresh lobster rolls and stunning waterfront views at Legal Harborside, then head over to Lookout Rooftop at the Envoy Hotel for skyline cocktails. Wrap up the evening with an optional whiskey and cigar nightcap at Stanza Dei Sigari for a perfect start to your Boston escape.

Accommodation: The Liberty Hotel

Morning & Afternoon:
Start your day with a hearty breakfast or shakshuka at Tatte Bakery. Take a leisurely stroll toward Fenway Park for a photo op in front of this legendary stadium. Pregame with beers and pub bites at spots like Bleacher Bar or Cask ’n Flagon.

Evening:
Cheer on the Red Sox at an afternoon or evening game at Fenway Park, one of baseball’s most historic venues. Grab post-game BBQ at Sweet Cheeks Q and, if the energy’s still high, head to The Bell in Hand Tavern for more good times with your crew.

Accommodation: The Liberty Hotel 

Morning & Afternoon:
Head out on a scenic Boston Harbor Cruise, taking in views of the skyline, surrounding islands, and historic landmarks. Refuel with a seafood lunch at Yankee Lobster Co. or the sought-after Neptune Oyster.

Spend the afternoon exploring the vibrant Quincy Market and Faneuil Hall, then join a Freedom Trail pub tour, which combines whiskey flights with Boston’s rich colonial history.

Evening:
End the day dining at one of the North End’s Italian gems like Carmelina’s or Giacomo’s, followed by a must-try cannoli from Mike’s Pastry or Modern Pastry.

Accommodation: The Liberty Hotel

Option A:

Morning & Afternoon:
Immerse yourself in Boston’s craft beer culture on a curated brewery crawl. Highlights include classics like Samuel Adams, waterfront brews at Harpoon Brewery, and the modern vibes at Night Shift Brewing. Stop for a pizza lunch at iconic Regina Pizzeria in the North End, then continue beer tasting as you relax on the Greenway or Boston Common.

Evening:
Wrap up the day with laughs at a comedy show at Laugh Boston or Improv Asylum in the North End.

Option B:

Take a day trip exploring nearby New England attractions. Visit Salem, with its storied witch trials history and coastal charm, or head to Cape Cod for a relaxing beach day capped with a lobster roll and chilled drinks.

Accommodation: The Liberty Hotel

Morning & Afternoon:
Savor brunch with jazz and cocktails at The Beehive in Boston’s South End. Choose between renting kayaks on the Charles River for relaxing views or biking along the Esplanade. Culture buffs may opt for a visit to the Isabella Stewart Gardner Museum or the interactive Boston Tea Party Museum.

Evening:
Wind down the trip with dinner at the elegant OAK Long Bar + Kitchen. Night owls can dance off indulgences at The Grand or keep it casual with a nightcap at JM Curley.

Accommodation: The Liberty Hotel 

Morning:
Treat yourself to a farewell brunch at the historic Union Oyster House, famous for its creamy clam chowder and classic New England vibe. Stroll along Newbury Street for window shopping or grab souvenirs to commemorate the trip.

Afternoon:
Transfer to the airport for your flight home, heads full of laughter, food, and iconic Boston moments.