Summer of Go: Boston

Summer of Go: Boston


In true Tommy Bahama fashion, we're celebrating the season of sun in style from coast to coast. Over the years, we've made friends in all the right places: Boston, Baltimore, Tampa, Chicago, New Orleans, Seattle, San Francisco and Kona, to name a few. During this “Summer of Go,” we'll share our favorite things to see, do and experience in each of those locales.


Let’s talk about Titletown. The Hub. The City on the Hill. That’s right, Boston, we’re looking at you. And what a great site you are. A true metropolis that celebrates sports, beer, the arts and seafaring right alongside the founding of this great land? Sign us up.

A historical epicenter for colonial America, Boston is home to many famous people and events. In fact, five U.S. presidents hailed from this great city: John Adams (#2), John Quincy Adams (#6), Calvin Coolidge (#30), John F. Kennedy (#35) and George H.W. Bush (#41). And this is just the beginning of the list. We can't forget patriots like Benjamin Franklin, Samuel Adams, Elbridge Gerry, Robert Treat Paine and John Hancock, all of whom signed a little document we like to call the Declaration of Independence. How do you like them apples?

Today, Boston is a thriving metropolis that starts at the sea and sprawls for miles in every direction. From cobblestone streets to 8-lane interstates, there's a route for every adventure. Sports, history, arts... and the FOOD! There really is something here for everyone. Here are a few of our favorites:


Freedom Trail
Follow in the footsteps of American history (literally!) by walking the Freedom Trail, a historic 2.5-mile tour featuring 16 sites related to the Revolutionary War. Costumed tours depart hourly – or, better yet, download a route map and go at your own pace. Highlights include Paul Revere's home, the Old North Church (of “one if by land, two if by sea” fame) and the Old State House Museum.

Get an Art History Lesson
The Boston Art Commission’s Public Art Walk will wind you through Back Bay, Beacon Hill, the Financial District and the North End, giving you access to some of the most important contemporary and historic art on display. Murals of every culture and era seem to wrap the city; be sure to get a look at the stunning Sargents in the MFA, the latest installation at Dewey Square and the work done by the Mayor’s Mural Crew. And the harbor view from the glass cantilevered rear of the Institute of Contemporary Art just can’t be beat.

Go Down to The Cape
Get some sand between your toes, New England-style, and take a side trip to Cape Cod. After tapping into your “calm reserves” for the Bridge traffic, head to seemingly endless Nauset Beach for relaxation and seal spotting. Make your way south to Chatham; few spots on the whole of the East Coast can surpass the view from the lighthouse. Fans of Jaws (and picturesque beauty) won’t want to miss Martha’s Vineyard: rent a bike for sightseeing in charming Oak Bluffs, crossing over Lagoon Pond for a stop at the famous Black Dog Bakery. Cap off your full day by enjoying Edgartown’s fantastic pubs and pristine harbor views.

Fenway Park
In the heart of Boston lies Fenway Park, a.k.a. the native Red Sox fan's natural habitat. Home to the iconic “Green Monster,” this baseball mecca is America's oldest MLB™ stadium. In the Bleacher Bar (“the world's most unique sports bar," per CNN), enjoy a clear view of the game from beneath the center-field stands. And here’s one of Boston's best-kept secrets: the Scalp Free Zone on Lansdowne Street sells game-day tickets at face value 90 minutes before game time – but cash only, please.

JFK Library
Located on a 10-acre park on Boston's waterfront, the John F. Kennedy Presidential Library and Museum offers a first-hand experience of John F. Kennedy's life, legacy and leadership. From interactive displays of his actual White House appointment diary to historic exhibits related to the Space Race, the Cuban Missile Crisis and his innovative use of television (he was the first president to "perfect" the art of televised press conferences), this library offers a comprehensive look at one of America's most famous leaders.

"A man may die, nations may rise and fall, but an idea lives on."

- John F. Kennedy

Enjoy Recreation for Miles
Stretching for three miles along the Charles River is The Esplanade, a beautiful, public green space with countless opportunities for fun and fitness. Bike paths, running trails, ball fields, basic workout equipment and outdoor entertainment — and that's just what you'll find on terra firma. Head to the Community Boating facility (the oldest public sailing organization in the United States, operating since 1946) and you have your choice of sailing, kayaking, windsurfing and more. They offer lessons for sailors of every skill level and kids 10–18 can sail for as little as $1/day! Get out there and have some fun.

Shop ‘til You See the Whites of their Eyes
The best shopping is in the Back Bay neighborhood. There’s a line of tony shops and high-end boutiques on Newbury Street (where, coincidentally, you’ll find the local Tommy Bahama); a few blocks south there’s the Prudential Center and Copley Place malls. If you like a little history with your hunting, go to Faneuil Hall Marketplace. This charming collection of shops, restaurants and outdoor entertainment has also been the backdrop to many famous speeches through the years. 


Neptune Oyster Bar
63 Salem St / 617.742.3474 /
Why we love it: It may be tiny (35-ish seats and barstools in all), but their 12 varieties of oysters, inventive menu, prompt service and cool vibe will put a huge smile on any seafood lover’s face.

Santarpio’s Pizza
111 Chelsea St / 617.567.9871 /
Why we love it: Because we love great pizza. Isn’t that reason enough? Santarpio’s is famously the best in Boston. You’ll see it on the way to and from Logan International.

47 Massachusetts Ave / 617.585.9575 /
Why we love it: Local ingredients fuel the meticulously designed three-, five- and eight-course New American tasting menus. How comfortable or adventurous you get is up to you (and your wallet). An unfussy atmosphere and gracious service balance the high-concept food.   

Hungry Mother
233 Cardinal Medeiros Ave / 617.499.0090 /
Why we love it: It’s the best Southern food (shrimp, grits, catfish) you’ll find this far north of the Mason-Dixon line, but it’s the infusion of French culinary arts that really sets it apart.

255 Washington St, Somerville / 617.776.9900 /
Why we love it: Handcrafted wursts, pretzels and mustards bring a taste of contemporary Germany to artistic Union Square – a rarity for these parts and a refreshing break from the ubiquitous Irish pub. Try the Brondog, potato pancakes and the blood sausage (trust us).

Mike's Pastry
300 Hanover St, Boston / 617.742.3050 /
Why we love it: It should be no surprise that you can find amazing flavors in a neighborhood known as Little Italy. But no matter where you choose to dine, be sure to save some room for one of Mike's cannolis. A North End tradition for generations, this light, flaky, creamy treat is one you won't want to share. There aren't enough adjectives in the thesaurus to accurately describe the incredible deliciousness.

69 Church St / 617.426.6969 /
Why we love it: Chef Charles Draghi’s award-winning restaurant gives old-school Italian cuisine a contemporary edge. A robust wine list and local, seasonal ingredients make it a welcome find.


Lord Hobo
92 Hampshire St, Cambridge / 617.250.8454 /
Why we love it: An extensive menu of rare and daily-changing drafts and bottles makes this a beer-lovers’ haven. And the healthy dose of irreverence that comes alongside the great service is enjoyed by both out-of-towners and locals alike.

348 Congress St / 617.695.1806 /
Why we love it: Hidden beneath an Italian restaurant, this Fort Point enclave’s expert bartenders make customized drinks based on what you’re in the mood for. Get way off-kilter and sidle up to the serpentine bar on Tiki Sunday.

Eastern Standard
528 Commonwealth Ave / 617.532.9100 /
Why we love it: With incredible menus for breakfast, brunch, lunch, dinner and late-night, we could return again and again. From champagne brunches to after-work cocktails, the sophisticated atmosphere is perfect for any gathering, whether you're there with a date or a business partner.

Trina’s Starlite Lounge
3 Beacon St, Somerville / 617.576.0006 /
Why we love it: Of all the retro-inspired, divey-yet-classy joints where one can order gourmet cocktails and hot dogs in the same breath at 11pm, this is our favorite.

The Hawthorne
500 A Commonwealth Ave / 617.532.9150 /
Why we love it: With its comfortable, residential feel, clean flavors and meticulous mixology with a wink (a “Phil Collins,” anyone?) are the focus here. Swanky, date-night ambiance is fused with friendly, generous service.

Brick & Mortar
567 Massachusetts Ave, Cambridge / 617.491.0016 /
Why we love it: A cool vibe, inventive drink-slingers and eclectic downtown guests keep this watering hole busy seven days a week. Grab a seat at the hammered-copper bar and peruse the creative cocktails and mouth-watering bar menu (hello, Oyster Po' Boy).

The Druid
1357 Cambridge St, Cambridge / 617.497.0965 /
Why we love it: From the authentic Irish decor to the pipe- and fiddle-playing musicians and the ever-flowing Guinness, this pub, tucked away in Inman Square, will charm your socks off.