Curator’s statement
Boston, a historic gem nestled along the Atlantic, is a city that effortlessly blends the charm of then with the vibrancy of now. Cobblestone streets and iconic landmarks invite leisurely strolls, while its culinary scene offers everything from coastal bites to global cuisine. The historic Freedom Trail takes you on a tour of Boston's rich history and stunning architecture. As the birthplace of the American revolution, the first public park, the first underground metro train station, the city boasts numerous historical sites. Whether you're exploring the city's vibrant neighborhoods, indulging in seafood delicacies or immersing yourself in its cultural offerings.
The Fora Difference
Book with Lauren 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 Lauren to book your trip.
Day 1: Tour and local fare
Start your weekend early and take the morning flight to Boston. The airport is conveniently located, within 10 minutes of the downtown city center. I recommend Yotel, located in the Seaport neighborhood. Drop off your luggage with the hotel staff. Indulge in a delightful breakfast or brunch at Tatte, a popular local eatery.
Next, take a short walk to Boston Common where you'll meet up for the Freedom Trail tour at the Visitors Center. This 2-hour immersive walking tour experience will take you through the city's rich history. Stop at some of Boston's historic sites, including Boston Common, Granary Burying Ground, the Boston Massacre site and Paul Revere's House. You'll learn about the American Revolution and the city's role in shaping the nation.
Upon completing the tour, head back to the hotel to freshen up. Enjoy stunning sunset city views and refreshing drinks at Deck 12, on Yotel’s rooftop. The day concludes with a delectable dinner at Committee, a renowned local Greek-fusion restaurant a couple blocks from the hotel. If you happen to be traveling over the winter holidays, you might be in town for Snowport, a pop-up holiday village for dessert.
Recap
Morning:
Arrive at hotel
Breakfast/Brunch at Tatte near Boston Common
Afternoon:
Freedom Trail Tour at Boston Common Visitors Center
Evening:
Drinks at Deck 12
Dinner at Committee
Day 2: Museum and seafood
Start your day with breakfast at Lakon Patisserie and Coffee. They offer beautiful pastries that look almost too good to eat, and are well-known for their tiramisu latte. Explore the Seaport neighborhood and stroll along the waterfront.
Next, immerse yourself in the history of the Boston Tea Party Ships & Museum. This interactive museum offers a captivating journey back in time, allowing you to experience the events of December 16, 1773. The tour typically lasts around 90 minutes and takes you through a series of exhibits and reenactments. You'll learn about the political tensions, the role of the Sons of Liberty and the dramatic events that led to the Boston Tea Party. You'll even get to "dump tea" overboard, and become one of the Sons of Liberty (albeit 250 years too late.)
After you’ve worked up an appetite for committing “treason”, savor a classic New England clam chowder at Union Oyster House. No need to wait for a table. Order it to go and enjoy it ‘ al fresco’ on the benches nearby. Afterward, explore the vibrant Faneuil Hall Marketplace. If you're still hungry, indulge in a mouthwatering lobster roll at a food counter, like Neptune Oyster or Pauli's, both famous seafood restaurants in the North End.
Spend the rest of your afternoon wandering around and exploring all that the neighborhoods have to offer. A few recommendations:
The Gardner museum
Harvard in Cambridge
The original “Cheers” bar
Beacon Hill, a historic neighborhood known for its charming cobblestone streets, federal-style architecture and gaslit lamps. While primarily residential, Charles Street offers a variety of shops, restaurants and cafes. Acorn Street, one of America's most photographed streets, is a must-visit for its picturesque beauty.
For dinner, check out one of the many Italian restaurants in the North End neighborhood — you can’t walk down Hanover Street without seeing all your options. We ended up choosing Villa Francesca. It was delicious! Finally, cap off the evening with a sweet treat from Bova's, Mike's Pastry or Modern Pastry. All are very popular, so expect a line.
Recap
Morning:
Breakfast at Lakon Patisserie and Coffee
Tea Party Museum
Afternoon:
Union Oyster House
Explore Faneuil Hall Marketplace
Evening:
Dinner & desserts in the North End neighborhood.
Need to know
Boston is the perfect starting point for a memorable weekend getaway. With its rich history, vibrant culture and delicious food scene, the city offers something for everyone… but the fun doesn't stop there! Boston's strategic location makes it an ideal base for exploring other stunning destinations. Take a ferry to the picturesque islands of Nantucket or Martha's Vineyard. Or delve into the dark history of Salem. There are all easily achievable day trips, should you want to extend your trip.
Let's talk about customizing this itinerary for you. Or, about other destinations.
Travel Advisor
Lauren Baroevich
Get in touch with Lauren
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 Lauren 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.