2 Days in Boston - An Itinerary for a Weekend in Boston

A Boston Trolley ride is the perfect way to start your Boston vacation. You’ll see all the best sights of the city and feel better oriented when you start to go off on your own to explore. Best of all, you can board and disembark at your leisure, so you don’t need to ride the full loop if something interests you. Your pass is good for two days, so you can hop on and off at any time to explore during your entire weekend trip.

Remember to get your trolley ticket in advance at one of the designated pickup locations. There are 17 stops in total, so the full loop could take up to an hour and 45 minutes. While it can be tempting to use the trolley to get around the city, traffic could make this a slower option than the T (the city's affordable and easy-to-use subway system).

If it's a nice day, hop off the Trolley Tour at the Boston Common and explore this beautiful urban park in the heart of Boston. Here, you'll find people and animals enjoying the green space, gardens, and water features throughout the park. Come here to people-watch or to take photos of the beautiful flowers in the Public Gardens.

A visit to these charming green spaces is a great way to see a different side of Boston. If the Swan Boats are operating, get in line for a quick, relaxing cruise along the lagoon powered by pedaling. (You can just sit on one of the benches!). It's one of the most quintessential Boston experiences.

After lunch, hop back on the trolley towards the Museum of Fine Arts. This prestigious art museum has something to appeal to every taste, from its extensive collection of early colonial art and furnishings to the beautiful modern art selection and beyond. Don’t forget to stop in the gift shop! The MFA shop is one of the best places for unique souvenirs in all of Boston.

Be sure to check their site to see what temporary exhibits they're featuring during your visit. We recommend reserving at least 2 hours for the MFA, although you may want more time if you’ve got some big art lovers in the family.

We can’t think of a better way to end your first day in Boston than with a trip to the top of this must-see attraction. Located 750ft above the city, atop the Prudential Center, the View Boston Observation Deck provides unparalleled, 360-degree views of the city below and the iconic Boston skyline. During certain times of the year, you can catch stunning sunsets.

Don’t forget to check out Boston 365 – this remarkable 3D model of the city brings Boston to life by revealing highlights of its seasons, spirit, and celebrations. The Cloud Terrace on the 51st floor has a 360-degree open-air roof terrace and a cocktail bar.

The whole family will love a visit to the renowned New England Aquarium. From Caribbean coral reefs to bustling penguin colonies, the aquarium contains marine life from around the globe. You’ll encounter those lovable penguins, seals, sharks, jellies, sea turtles, tropical fish, and many more species on your visit.

Don’t forget to stop by the Shark & Ray Touch Tank exhibit for a chance at “hands-on” fun. We recommend saving between 1-2 hours for the Aquarium, perhaps more if you have kids.

Visit one of the most important historical sites in downtown Boston – the Old State House. Here, you’ll learn all about the history of colonial Boston and Revolutionary America through artifacts (including recovered tea from the Tea Party!), exhibits, and tours. Roam through accurately decorated period rooms – many with real historic furniture and artifacts – and see important spaces in the building, like the recently restored King’s Council Chamber.

It’s a stop along the Freedom Trail, but you can certainly come here on your own any time to soak up the atmosphere and peruse the exhibits. Keep an eye out for John Hancock’s bright red velvet coat!

Continue your waterfront adventures with a cruise of Boston's Inner Harbor to visit the USS Constitution, aka "Old Ironsides." The cruise highlights the waterfront's other historical and contemporary landmarks, including Old North Church, and Charlestown’s Bunker Hill Monument. Operating hours change seasonally so be sure to check the official website for the exact schedule.