Fenway. Harvard. Clam Chowdah. Saying ”Wicked” and “It’s 20 minutes away”. Boston.
The Location: I'm going to introduce you to my personal favorite neighborhood in Boston, The North End. The great thing about this area is you can have an amazing, authentic Italian meal, and be just a block from the fun. When you’re done at the bars, head back towards the restaurants and get some late night Italian pastries. Most people will tell you to go to Mike’s Pastry on Hanover but as someone who used to live right above Bova’s - that’s the better option. Less tourists, shorter line, a bouncer to keep you in check, open all night and gasp, better cannolis. The only thing to worry about in this neighborhood is getting too drunk and thinking it’s a good idea to go down the cop slide.
You're also close to the harbor (pronounced, habah) and TD Garden, which brings us to the hook…
The Hook: There aren't many sports towns better than Boston. Yeah, they're probably the most spoiled fanbases in America, but all of ‘em are historic. The Redsox play at Fenway Park. the oldest Baseball stadium still in use by a professional team. TD Garden is home to the Celtics, and Bruins. Both venues host concerts and shows all year round.
Before or after your chosen event you’ll likely be strolling up and down Lansdowne, or Kenmore Square, where there’s no shortage of bars.
Massachusetts is where Basketball was invented so if your groom is a hooper, The BasketBall Hall of Fame is definitely in play. It is located in Springfield Mass and at the risk of offending some Springfield residents, there really isn’t much else to do there. Your best option is to stay in the city.
Time Wasters: If you’re into sports bars and Irish pubs (and let’s be real, who isn’t?), they’re everywhere, but if you want games with your beer, hit Cheeky Monkey for some competitive drinking. If the crew is feeling the club scene, Seaport’s got spots like Sissy K’s and The Grand to keep the party going. Want to flex on your friends for knowing Boston history? Bell in Hand is the city’s oldest pub, right next to the T stop for easy access. Need to kill a few hours? Chinatown is a goldmine for cheap, incredible food, and Quincy Market at Faneuil Hall is perfect for grabbing bites and checking out Newbury Comics (even if you think you’re too cool for it, trust me, you’re not). Feeling cultured? The New England Aquarium slaps—especially on a weekday when there’s no line. Want to be that guy and do the touristy thing? Duck Tours are actually a good time, and even locals admit it. If gambling’s your game, Empire Casino has your fix, and if you just want to drink with a killer waterfront view, Tall Ships is the move.
Tips for the Perfect Trip: There isn't worse public transit around than MBTA or ‘The T’ but honestly it'll get the job done for a weekend, so skip renting a car. It’s not only possible to be in bumper to bumper at a random hour on a Tuesday, it’s likely. You’ll also pay through the nose for parking if you can find any - skip it. You don't need a T pass (Charlie Card), and honestly it might be hard to get your hands on one so skip that too. There are metro machines in every station, load up a temporary card for the weekend, or load it every other stop if you’re afraid of losing it! Boston is incredibly safe so although you don’t have to worry about being on the train late at night, know that they stop running around 1am. Don’t get stranded and budget for ride shares if you plan on going late. Explore different neighborhoods, don’t be that guy that spends every night in Seaport!
The Golf:
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Granite Links Golf Club (~$140+) – Top 50 course according to Top100 - one of the only publics
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Newton Commonwealth Golf Course (~$45) – 4.2 from GolfPass
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There's a Topgolf, but it's halfway to Providence! Tons of sims around The North End and downtown. I can vouch for FiveIron, but the food and drinks are pricey
Not sold on Boston? Click HERE to view the entire catalog of BachTix Bachelor Party Guides!