Gavin DeGraw shows you around Boston
Gavin DeGraw explores

Boston in 48 hours

Day 1


OK, this one is personal for me. Coming from a long line of Irishmen and even living here for a while has given me a lot of local know-how and even more Boston pride.

One great way to start the morning—or maybe end the night?—is by taking the Morning Mash In Tour at the Samuel Adams brewery. They give you a behind-the-scenes look that’s unlike “normal” tours, including a specialty tasting—usually of a new beer they’re testing out only in Boston.

I personally like to grab a late breakfast/early lunch at the Flour Bakery in the South End. You can’t go wrong with a blueberry muffin cake, banana bread with walnuts, old-fashioned sour cream coffee cake or all of the above.

Cambridge Center Roof Garden (Source: Michael Harlan)


Just across the Charles River in Cambridge is one of my favorite places in and around Boston. The Cambridge Center Roof Garden is an amazing, almost-secret hideaway with unbelievable views. Lots of greenery, benches, pathways—all on top of a parking garage, surprisingly enough. It’s the perfect escape for an hour or an entire afternoon.

I stay at The Ames Boston, a Curio Collection by Hilton hotel because it’s a perfect location for exploring all that the city has to offer – The Freedom Trail path even begins right outside the front door. And I’ll definitely be back soon, with the opening of the hotel’s new sustainable restaurant, Cultivar, planned for November.


I like places the locals like, and everybody likes The Whiskey Priest. Most nights, there’s a live band or a DJ with dancing on the rooftop deck. True to its name, whiskey tastings are a frequent occurrence from their stock of over 100 whiskeys from around the world. Nothing like a “new” Old Fashioned.


Day 2

Institute of Contemporary Art (Source:Vanderwarker)


After a good night sleep at Ames Boston to cap off a day of eating and drinking, I’m ready for breakfast. No beer for breakfast this time, but the American Continental buffet served at Library will really fill you up. You’ll find it on the lobby level of Ames Boston.

Switch up your mode of transportation and borrow one of The Ames Boston’s complimentary bikes and pedal just 8 minutes over to the Institute of Contemporary Art. Right on the waterfront, the ICA has amazing views—outside, of the Boston Harbor; and inside, of contemporary artwork presented in all media imaginable. As a musician, I’m always inspired by the amazing work of other artists—and the ICA has plenty to offer.

Post 390 (Source: Michael Piazza)


If you’ve worked up a hunger by now, you’ve gotta go for Boston-area specialties. New England clam chowder or fresh oysters from Martha’s Vineyard at Post 390 in Back Bay are perfect sitting next to a four-sided fireplace on a chilly day.

Newbury Street and its 30 or more art galleries, antique shops and cool stores is the perfect place for a leisurely stroll. Many of the shops are in restored Victorian mansions, which are as beautiful as the goods inside.

Even if I’m not hungry I always make a trip to DeLuca’s Market, one of the oldest grocery stores in Boston, serving the Back Bay area for over a century.


OK, more food.

A great place to eat on the North End is Nebo, for true Italian cuisine. A local favorite is the zucchini lasagna, a zesty “Throwdown with Bobby Flay”–winning entrée.

Then, what could be more “Boston” than partying at Ned Devine’s, smack dab in the heart of historic Faneuil Hall and Quincy Market?

Thanks, Boston—and Ames Boston. I’ll be back.