How to spend 36 hours in Boston with Copley Square Hotel as your base camp.
6 p.m. | Free Flicks on the Hatch Shell
While the movies don’t start until sundown (summers only), come early to secure your spot on the lawn of this bowl-style outdoor stage, made famous by the Boston Pops Orchestra, on the south bank of the Charles River. Expect featured films to have been previous huge box office successes, both recent and modern classics.
10 p.m. | Dinner at Beacon Hill Cheers
Originally founded as the Bull & Finch pub in 1969, this late-night restaurant has now adopted the name for the show it inspired back in the 1980s: Cheers. While the show itself wasn’t filmed here, the producers modeled its Hollywood version off it and showcased the iconic facade in the opening credits. Naturally, the menu pays tribute to the characters with names like Carla’s Meatballs & Linguini and the Norm Burger.
10 a.m. | Walk the Freedom Trail
Starting at Boston Common, the two-and-a-half-mile self-guided Freedom Trail wends its way through 16 Revolutionary Era sites, from the Boston Massacre in front of the Old State House to the Paul Revere House in the North End. The walk can take all day if you plan to stop and tour every site, so we suggest first perusing the full map and keeping your stroll focused to just your favorites.
1 p.m. | Lunch at the Butcher Shop
Inspired by the chef’s travels throughout France and Italy, this tribute to European boucheries in the South End is both a neighborhood wine bar and full-service butcher shop. Enjoy a glass of wine along with handmade charcuterie, antipasti, and bistro-inspired dishes.
3 p.m. | Isabella Stewart Gardner Museum
If you’re wearing Red Sox memorabilia, you receive discounted admission to this Fenway-Kenmore museum that houses philanthropist Isabella Gardner’s eccentric art collection. As you peruse the collection, note the handful of empty frames. It’s not a mistake but a sad reminder of the US’s biggest art heist that whisked away 13 masterpieces more than 25 years ago, including a Rembrandt, a Vermeer, and a Manet.
8 p.m. | Dinner at Lucky’s Lounge
Descending the stairs into this Frank Sinatra–themed bar is like stepping through a portal into a swinging hipster lounge straight out of the ’50s. Every Saturday night, from 7 to 10 p.m., a tribute jazz band covers the best of Old Blue Eyes.
10 a.m. | Brunch at Boston Chops
You might not think of a steak house when you think of brunch, but this South End restaurant will make you think twice. Expect steak house staples with a twist, like shank and grilled tongue hash, beef tournedo and eggs, and huevos rancheros with machaca beef cheeks.
12 p.m. | Visit the Museum of Fine Arts (MFA)
This venerable Boston institution is the fourth largest museum in the United States, containing more than 450,000 works of art, from ancient Egyptian to contemporary.