Boston is the ultimate playground for a weekend with the guys. From stadiums and breweries to steak dinners, racing simulators, and late-night laughs, the city delivers nonstop energy and experiences worth toasting. Grab your crew, plan your stops, and let Boston take care of the rest.
Catch a Game
Sports are practically a religion in Boston, and no guys’ weekend is complete without taking in a game. Head to Fenway Park to watch the Red Sox play at America’s ballpark, or book a behind-the-scenes tour if it’s the off-season. More of a basketball or hockey fan? TD Garden is home to the Celtics and Bruins and is always buzzing on game night, with plenty of pre- and post-game bar options nearby. Football and soccer fans can even make the short trip down to Gillette Stadium in Foxborough to catch the Patriots or the Revolution in action.
Brewery Hopping
Boston’s craft beer scene has exploded, making brewery-hopping an essential activity. Grab a pint at Harpoon Brewery & Beer Hall, where you can snack on fresh pretzels and sip seasonal brews at communal tables. Trillium Brewing in Fort Point or Fenway offers some of the city’s most buzzed-about IPAs in sleek, modern spaces. Night Shift Brewing at Lovejoy Wharf is perfect before a Garden game, while Dorchester Brewing delivers rooftop views, an on-site BBQ counter, and a relaxed vibe for lingering with friends. Want a taste of Nantucket in the city? Head to Cisco Brewers Fenway, where live music, food trucks, and summery brews create an instant beach-party atmosphere all year long. Or check out Castle Island Brewing in South Boston, a massive beer hall with great food and plenty of space for the whole crew.
Eat Like Kings
Fueling up is half the fun of a guys’ weekend, and Boston doesn’t disappoint. Head to the North End for Italian staples: heaping bowls of pasta, wood-fired pizza, and late-night cannoli runs. For seafood, grab lobster rolls at Neptune Oyster or oysters at Row 34, two of Boston’s most iconic seafood spots. And when it’s time for a classic steakhouse night, you can’t go wrong with Grill 23 or Abe & Louie’s, where martinis and perfectly cooked ribeye set the tone for a memorable evening.
Hit the Bars
Boston’s nightlife is tailor-made for guys on the town. Start on Lansdowne Street near Fenway, home to staples like Loretta’s Last Call, Lansdowne Pub, Game On, Bleacher Bar (with a window that looks directly into Fenway Park), and House of Blues.
If you’re after a waterfront vibe, the Seaport District is buzzing with sleek cocktail lounges and beer halls. Sip inventive drinks at Lookout Rooftop with skyline and harbor views, settle into the tropical vibes at Para Maria, or try The Smoke Shop BBQ’s bar for whiskey-heavy cocktails paired with ribs and brisket. For a polished cocktail experience, check out Drink Seaport or Vela Seaport and enjoy creative pours.
For something more old-school, the Financial District and Downtown are packed with Irish pubs like The Black Rose, The Dubliner, JJ Foley’s, and Mr. Dooley’s—perfect for a late-night Guinness with live music and plenty of banter.
Daytime Adventures
Balance out the late nights with some daytime fun. For the sports-minded crew, golf is always a great call – whether you tee off at one of the nearby courses or keep it casual at Five Iron Golf in the Seaport, where state-of-the-art simulators, craft drinks, and snacks make it easy to play a quick round without leaving the city. If darts are more your speed, Flight Club offers an elevated twist on the pub classic, pairing digital scoring with cocktails in a lively lounge atmosphere. And for those who never turn down a little friendly competition, Puttshack in the Seaport reinvents mini golf with high-tech scoring, creative holes, and a party vibe that’s perfect for groups.
If you want to push the adrenaline a little further, F1 Arcade in the Seaport brings Formula 1 thrills to Boston. With head-to-head racing simulators, full bar service, and a high-energy environment, it’s the kind of place where you can easily spend an entire afternoon racing your buddies, trash-talking, and celebrating over cocktails. For something equally fun but more low-key, check out PKL x Pig Beach BBQ, where rounds of pickleball meet smoky barbecue – the kind of combo you never knew you needed.
Of course, not every daytime activity has to be a competition. A Boston Harbor whale-watching cruise with City Cruises offers a chance to get out on the water, while the Freedom Trail is a must for history buffs. You can keep it educational with a guided tour from Boston By Foot or make it livelier with a historic pub crawl along the trail with Boston Crawling. And if you’re feeling lucky, Encore Boston Harbor serves up casino gaming, restaurants, and a Vegas-style nightlife experience without ever leaving the city.
Late-Night Fun
Keep the party going after dinner with Boston’s lively entertainment scene. Catch a concert at MGM Music Hall, Big Night Live, or Paradise Rock Club, or laugh it up at Improv Asylum in the North End and Laugh Boston in the Seaport. For something more low-key, wind down with scotch and cigars at Stanza dei Sigari, a classic cigar lounge tucked away on Hanover Street. And if your crew can’t get enough competition, swing back to F1 Arcade, Flight Club, or Puttshack, where games, drinks, and nightlife vibes run late into the evening.
