History, harbor views, and wicked good times
Fenway game with the cheap deli sandwich beforehand, oysters at Neptune in the North End, beers at Sunset Tap on Brighton Ave, and a closer at Bukowski. The college-bachelor format played as adults — walkable, sports-coded, with steamers and chowder anchoring every meal.
sports event • 1 hour
Behind-the-scenes tour of America's oldest ballpark
boat cruise • 2 hours
Sunset harbor cruise with skyline views and drinks
brewery tour • 1.5 hours
Tour and tastings at Harpoon's Seaport taproom
axe throwing • 1.5 hours
BYOB axe throwing in Somerville with tournament-style games
club • unhinged • $$$
Multi-level Theater District mega-club with rotating DJs
cocktail bar • chill • $$$
No-menu craft cocktail bar in Fort Point — tell the bartender your mood
dueling piano • unhinged • $$
Dueling pianos and sing-alongs on the waterfront
rooftop • balanced • $$$
Seaport rooftop with harbor and skyline panoramas
club • unhinged • $$$
Two-floor Seaport nightclub with VIP bottle service
Dress code: Upscale casual; no athletic wear
comedy club • balanced • $$
Hilarious improv shows in the North End
dive bar • chill • $
Classic no-frills dive in the Theater District with cheap drinks
sports bar • balanced • $$
Bar built into Fenway Park's center field wall with a view of the field
lounge • balanced • $$$
Upscale supper club and lounge in Downtown Crossing
Dress code: Smart casual
Seafood • $$$ • Best for: dinner
Tiny North End spot with the best lobster roll in Boston
Steakhouse • $$$$ • Best for: group-dinner
Back Bay power steakhouse with exceptional cuts
Bakery/Dessert • $ • Best for: late-night
Legendary North End cannoli shop — the Boston must-do
Seafood • $$$ • Best for: group-dinner
Industrial-chic Fort Point seafood and craft beer spot
Mediterranean/Cafe • $$ • Best for: brunch
Instagram-worthy brunch with shakshuka and pastries
Pizza • $$ • Best for: dinner
North End brick-oven pizza since 1926
Seafood • $$ • Best for: dinner
Casual waterfront seafood shack on the Fort Point Channel
Mexican • $$ • Best for: group-dinner
Funky Back Bay Mexican with killer margaritas
boutique-hotel • Max 2 guests
Converted Charles Street jail with upscale bar scene and Beacon Hill location
hotel • Max 2 guests
Modern Seaport hotel with rooftop terrace and compact smart rooms
airbnb • Max 10 guests
Full houses in Southie near waterfront bars and restaurants
boutique-hotel • Max 2 guests
Rock-and-roll themed hotel steps from Fenway Park
airbnb • Max 10 guests
Brownstone condos in Boston's most walkable neighborhood
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