Boston in 1 Day Itinerary
We would use half of it to Complete the Freedom Trail (See Half day itinerary) and then proceed to the Waterfront. Another option is to start the morning with the Old Town Trolley Tour, you can board and re-board at any designated stop.
Definitely stop and see the New England Aquarium, featuring a Giant Ocean Tank, and IMAX theatre. Also in the area the Boston Children’s Museum for those with kids. Be sure to take a walk along the Boston Harbor Walk. Enjoy the sunset from outside the Boston Harbor Hotel at Rowes Wharf.
If you prefer a Dinner Cruise, Odyssey I departs from 60 Rowes Wharf – you will need to book this ahead of time. Not a seafood person – head back at Quincy Market and Durgin Park for a real slice of New England cooking. Stop for a Drink at the Black Rose Pub, or a catch a show at the Comedy Connection.
Spending a 2nd Day in Boston? Here's What You Can Do
Explore the Back Bay Area starting with the Museum of Fine Arts it’s accessible by the Green Line T. You can spend the morning there and the afternoon at the Stewart Gardner Museum. If that’s too much culture for one day head back up to Newbury Street and grab lunch at Stephanies sidewalk café instead, it’s a Boston Institution.
After Lunch head down Newbury Street for a little shopping, or just people watching. You can grab a Ducks tour right outside the Prudential Shops Entrance. Later Head to the Skywalk for a 360 degree view of Boston. The Top of the Hub is also the perfect place for that romantic dinner or drink, located on the 52nd Floor of the Prudential.
If you are traveling alone you might try a Margarita at the Cactus Club for more of a singles scene. If a neighborhood bar is more your speed Clery’s bar on Dartmouth Street is a good choice.
Third Day? There is still plenty to do!
Use the morning to explore Beacon Hill starting with the Black Heritage trail, a self-guided walking tour – map and guide available. The 1.6 mile (2.5 km) Black Heritage Trail connects 14 sites. Be sure to visit the Massachusetts State House overlooking Boston Common as well as Louisburg Square, Boston’s most prestigious address. Fans of the TV show may want to stop for lunch at Cheers Bar, or perhaps Fig’s for Gourmet Pizza. We recommend seeing the Nichols House Museum for a look at the domestic life of a typical family of Beacon Hill at the turn of the last century.
Walk across Beacon Street to the Boston Commons – America’s oldest public park. Head up to the West End and Science Park to the Boston Museum of Science. At the end of the day enjoy a romantic dinner at No. 9 Park, or grab a drink with some of the local politicians at the Black Goose. If that’s not enough night life cross over to the Theater district which has many clubs and bars to choose from.
The Sweetwater Cafe and the Big Easy Bar are located in the Alley cluster of bars and cater to more of a college type crowd. If that’s not for you try the more upscale Aria located beneath the Wilbur theater. FELT restaurant features four levels of entertainment, including billiards, dancing and a lounge. After all that you can head down to Chau Chow City in Chinatown for a very late night Dim Sum at – Opened till 4am.