Friday

6 p.m. | Twirl around the Ice

If you want to feel like you're bringing a Currier & Ives print to life, head to the seasonal ice rink at Frog Pond on Boston Common, rent some ice skates, and twirl around the ice skating rink.  A "life is good!" feeling will sweep over you. To try out Boston's newest skating venue, visit the huge ice skating path at City Hall Plaza.  The whole area transforms into a winter paradise, complete with places to eat and drink, and even a European-style Holiday Market where vendors and artisans offer specialty products.

10 a.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. 

Saturday

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.

Sunday

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. On display through June 2017, you can see more than 50 works by Robert McCloskey, the beloved author and children’s book illustrator who penned the Boston-based Make Way for Ducklings.