10 Things Every (Cool) Group Should Do On a Boston Vacation

We finally figured it out for you. An itinerary for your next Boston group hang-out that will please everyone. (Okay, fine, we all have that one friend who will still complain that the gluten-free options aren’t up to snuff or that it’s too long a walk to the Boston Symphony Orchestra.) In all seriousness though, planning a group trip to Boston that pleases all palates is no easy feat. That’s why we took meticulous notes on our recent travels, consulted with Boston travel pros, and texted local pals for their must-sees and dos in Beantown.

Ahead, our rundown of how to make the most out of your crew’s Boston getaway.

Why? Because we want to let our insider Boston secrets out and tell you these two hot spots are well worth planning an evening around when you’re in town. First up is Café Sauvage where the champignon de Paris and glazed eggplant will keep you dreaming of returning to this fine French-inspired haunt. Then, Hecate, a mere 10-minute stroll away, has what a local described as “a whole underground vibe as a speakeasy.” Translation: Named after the Greek Goddess of magic and witchcraft, you can swill craft cocktails under dim lighting, if you can find the right door hidden in an alley, that is.

Yes, in Boston. Venture upon the famous Charles River or nearby lakes by canoe or kayak for an adventure you won’t soon forget. You can rent equipment or join guided group tours where you’ll enjoy narrated insight on the history of the region and its ecology. For something more low-key, traverse Boston Common and plop down for a group picnic in Public Garden. If you didn’t do a pre-trip grocery haul (make sure to split up your sandwich spending via Zelle®), grab a quick bite from Boston burrito fave Boloco Boston Common or Sal’s Pizza’s Tremont Street outpost. These adjacent green spaces also make for great people-watching. (And if you happen to find yourself back in Boston in the spring or summer, the Public Garden has swan boat rides.)

Last but not least, Boston Harbor Islands National and State Park is oft overlooked for Beantown’s indoorsy delights but it’s certain to be a hit for your posse. To get there, you can take a ferry from Long Wharf to Boston Harbor Islands. Hike, picnic, or just observe the pristine harbor and skyline views. If whale-watching is your cup of tea, another fun option is one of Boston’s whale-watching tours, which operate seasonally. P.S. Love leaf peeping? Check out the most stunning ways to see fall foliage in New England from a gondola to a cliff walk here.

Yes, these are great but Harvard Museum of Natural History is stellar, too. As is Isabella Stewart Gardner Museum, which showcases a wide range of European, Asian, and American art and is home to a lovely courtyard and the site of a notorious robbery in 1990. The Institute of Contemporary Art is another museum not to be overlooked. If the weather is good, head on over to the Arnold Arboretum.

As any traveler knows, one of the best ways to acquaint yourself with a new locale is to lace up your sneaks and get to ambling. The quintessential option in Boston is the city’s famed Freedom Trail, which weaves tourists through American Revolution sites for a hearty dose of mid-18th century history. Expect to see the greatest hits like Boston Common, Massachusetts State House, King’s Chapel and King’s Chapel Burying Ground, the Old State House, Boston Massacre Meeting Site, and Faneuil Hall on the Walk Into History tour. Or, enlist in a tour of the North End to see Paul Revere’s House, Old North Church, and more storied locales in Boston’s oldest neighborhood. For those who want a more intimate experience, you can book a private and/or customized tour directly through The Freedom Trail’s website here and create your dream agenda.

Many Boston guides leave out attractions in this part of the city. Their loss. In East Boston, you can get some of the best sunset views in the city at Piers Park or at the outdoor venue, Tall Ship, a literal tall ship turned oyster bar. You won’t want to miss the district’s fantastic Latin food (La Hacienda is a top pick for authentic Mexican and Salvadorian fare). Or, if you find yourself around for brunch, earn the crew’s eternal praise by sidling up to a table at Angela’s. There’s even a decent beach called Constitution Beach Park where you see a lot of airplanes coming into and out of Logan Airport just across the water.

Or shall we say, go chowder crazy. The Boston Secret Food Tours is the best of the bunch. On this epicurean adventure, you’ll start in the Blackstone Block Historic District where you can enjoy the real-deal New England clam chowder in one of the oldest restaurants in America. Then, it’s onto the Boston Public Market food hall and marketplace to taste one of the juiciest lobster rolls your lips have ever met (pronounced “lobstah” in these parts). Save room for North End, an alcove of all things Italian, where you’ll dine on pizza or prosciutto and aged provolone cheese, followed by a cannoli and schooling on the Boston Cannoli Wars. All Secret Food Tours also feature a “secret dish” so there’s that to look forward to, as well.

If cooking is more your speed, we recommend groups try a CozyMeal cooking class
which run the gamut from Nepalese cuisine to gnocchi intensives. We also recommend
Self Up’s Asian Dumplings Team Building class, where you’ll whip up Dim Sum style dumplings, pot stickers, and Jiaozi dumplings (a traditional and allegedly auspicious dish served for Chinese New Year) from scratch.

Because your group wants to sweat for its supper, right? If your excursion to Boston is in mid-November through mid-March, whirl around the ice at the Frog Pond Skating Rink. Or, swap ice skates for climbing shoes and scale the walls at Rock Spot Climbing in South Boston. You can arrange a group visit here.

Yankees fans, feel free to proceed to the next section. Everyone else (or New Yorkers who can stomach being on enemy grounds), an outing to Fenway Park, the oldest ballpark in Major League Baseball, whether for a ball game or a tour or both, is well worth slotting into your itinerary. See the tour schedule here and wear your finest MLB cap. Within walking distance from Fenway there’s a strip of bars, and virtually any is guaranteed to be a good time. For the best time, go to Bill’s Bar, known for its lively ambience and hosting local bands.
 

Two heels may be better than four wheels in America’s Walking City but taking on Boston by bike is also an epic way to experience the town. Urban AdvenTours is our go-to outfitter for bike tours or rentals with the Emerald Necklace Tour featuring Boston’s green spaces and Tour de Cambridge to see Harvard Square (keep your eyes peeled as this spot can be a bit seedy these days) and the Charles River being two of our favorites. For something unique, book the bikes@night tour, on which you can view the sun dip into the harbor from Black Falcon Pier and make your way to the happening North End, where you can swap sweating for suds.

Say bottoms up with City Brew Tours Boston, and you’ll be recommending this stellar outing to every beer snob you know. On the experience you’ll be driven around Boston for samples of up to 12 different craft beers and noshing on food pairings, too. You’ll also get to visit the iconic Cheers bar of TV show fame. To combine your buzz with Boston history, sign up for Boston Crawling’s Independence Pub Crawl of the Freedom Trail which seeks to “uncover the stories they left out of 8th-grade social studies” chased by epic brewskis. Whatever you do, soak up all that beer with a bowl of the swoon-worthy clam chowder at Union Oyster House, which has been doling out chowdah, ahem, chowder and other seafood classics since the 1820s. And if you’re seeking more booze after all that sustenance, The Bell In Hand Tavern is a minute away and tipped over its first pour in 1795.