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Boston Suggested Travel Itinerary

Suggested attractions, museums, hotels, tours, restaurants in Boston.

Half day in Boston

Start at the Boston Commons and go through the beginning of the Freedom Trail. You can grab a quick Starbucks right after you pass the Old City Hall. Along the way you will see the State House, Park Street Church, Granary Cemetery, Kings Chapel and Burying Ground. There is a marker where the first Public School was built.

Continue on to see the Old Corner Bookstore, Old South Meeting House, and the Old State House. Outside the Old State House is a circle of cobblestones commemorating the Boston Massacre. It is in a small island area in the middle of the busy road. If you are not looking for it you won’t see it. Continue on to Faneuil Hall. You can stop in the Quincy Market area for a bite to eat, or continue on through the North End and continue the tour.

Depending on your time you might opt to cut the walk short and stop after the Copp's Burial Grounds. Bring yourself back to the North End and stop in one of the many Italian Restaurants, or grab a cannoli at famous Mikes Pastry Shop. If you have more time you can continue on to Charlestown to see the USS Constitution and Bunker Hill. Stop in the Pavilion to see the video “The Whites of their Eyes”


Full Day in Boston

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. Stop for dinner at either Jimmy's Harborside (award winning seafood), or for something less formal try the Barking Crab.

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.


Second Day in Boston

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 Pru.

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 in Boston

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.