Curator’s statement
Boston holds a special place in my heart, as I went to Boston College and lived in Boston for two years after graduating. Now, I enjoy visiting for a long weekend, and was there recently with my family. Boston is the perfect place to visit if you’re looking for a balance of historic charm, a lively sports city, art/culture/museums and a continually growing restaurant and bar scene. Here are my recommendations for a fantastic family-friendly weekend in Boston. Reach out for help planning your trip, or to VIP your stay at some of the amazing hotels in Boston.
The Fora Difference
Book with Megan to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Megan to book your trip.
Day 1: Historic Boston
Start your visit to Boston by taking in the historic charm on Beacon Hill. Walk along picturesque Charles Street and pop in and out of shops. Stop for a bite to eat at one of the several restaurants, or enjoy a Boston-staple, JP Licks ice cream. Venture to the Esplanade. See the Charles River, the Hatch Shell (famously known as the spot where the Boston Pops perform each July 4th) or take a break at the playground along the water. If you’re craving some TV nostalgia, stop by Cheers Boston.
Your walk will take you right towards the Boston Public Garden, which was the first botanical garden in America. Here you can take a swan boat ride, check out the Make Way for Ducklings sculptures or just rest and enjoy the green space.
The base of the Public Garden leads into Newbury Street, where you can stroll through shops and take in the classic architecture of the Back Bay neighborhood. If you’re hungry, stop at one of the many fantastic restaurants like Tatte Bakery & Cafe or Stephanie’s on Newbury. If you have a moment for a kid-free dinner, try Saltie Girl.
Day 2: Food, shopping and museums
Head to the Faneuil Hall Marketplace and Quincy Market. Here you can explore many shops, dining options and a bit of history mixed in.
Next, explore the New England Aquarium or the Boston Children’s Museum, perfect for kids to enjoy. If you have time, check out the neighboring Seaport district. It is home to the site of the Boston Tea Party, as well as a blossoming area full of dining, art and events.
Then take a short walk to the North End for Boston’s Little Italy. Stop by the historic Paul Revere House and the Old North Church. Enjoy a slice at the original Regina Pizza, and finish with dessert at competing pastry shops both known for their excellent cannoli: Mike’s Pastry and Modern Pastry.
Day 3: Classic sights
Even if you’re not a sports fan, it’s worth exploring Fenway Park. It is the oldest ballpark in the MLB. Check the schedule in advance to either watch a game or check out a tour of the stadium.
Then head towards the Prudential Center, one of Boston’s skyscrapers that serves as a large mall with several dining options, such as the popular Eataly. Ride to the top of the Pru through the View Boston experience, which has panoramic views of the city. Perfect way to close your weekend seeing a bird’s eye view of Boston.
Need to know
Reach out for help planning your trip to Boston!
Travel Advisor
Megan Freedman
Get in touch with Megan
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Megan within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
For more inspiration and insider recommendations, visit our Boston page.