New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Historical and Culinary Delights of Boston in 5 Days Itinerary
Last updated: 2024 Jun 14Freedom Trail and North End Exploration
Morning
Begin your Boston adventure with a guided walking tour of the Freedom Trail, visiting iconic landmarks like the Massachusetts State House, Granary Burying Ground, and the Old North Church. After the tour, enjoy a classic Italian breakfast at Mike's Pastry, known for its delectable cannoli and other pastries.
Afternoon
Immerse yourself in the vibrant atmosphere of the North End, Boston's "Little Italy." Enjoy a guided North End Pizza Tour with 3 slices of authentic Neapolitan pizza and a visit to the historic Paul Revere House. Afterward, take a leisurely walk to the scenic Christopher Columbus Waterfront Park and enjoy the views of the harbor.
Evening
Dine at Giacomo's Ristorante, a local favorite for its traditional Italian dishes. After dinner, take a stroll through the lively Faneuil Hall Marketplace and enjoy street performances and shopping. End the evening with a refreshing drink at The Salty Pig, known for its extensive charcuterie selection.
Bedtime
Find amazing hotels in Boston.
4.61Freedom Trail
Book Now
4.61Freedom Trail
Book Now
4.51North End
Book Now
4.51North End
Book Now
Harbor History and Haunted Evening
Morning
Start your day with a historical sightseeing cruise on the Boston Harbor. Learn about the city's maritime past and enjoy the refreshing sea breeze. After the cruise, have a hearty breakfast at Row 34, known for its fresh seafood and oyster bar.
Afternoon
Explore the eerie side of Boston with a visit to the Salem Witch Trials Sites. Take a self-guided walk through the town's historic streets and visit the Witch House and Salem Witch Trials Memorial. For lunch, indulge in the seafood delights of Legal Sea Foods.
Evening
As the sun sets, join the Salem Night Tour Haunt and History Guided Night Tour for a spine-tingling experience. Learn about the witch trials and the city's haunted past. After the tour, return to Boston and enjoy a late dinner at The Capital Grille - Boston, known for its elegant ambiance and fine steaks.
Bedtime
Find amazing hotels in Boston.
4.56Boston Harbor
Book Now
4.56Boston Harbor
Book Now
4.26Salem Witch Trials Sites
Book Now
4.26Salem Witch Trials Sites
Book Now
Academic and Cultural Excursion
Morning
Spend the morning exploring the prestigious Harvard University in nearby Cambridge. Take a self-guided walk around the campus, visiting highlights such as the John Harvard Statue and Harvard Square. For breakfast, enjoy the cozy atmosphere and baked goods at Flour Bakery + Cafe - Fort Point.
Afternoon
After Harvard, visit the innovative Massachusetts Institute of Technology (MIT) and explore the MIT Museum. For lunch, head to Coppa Enoteca for a taste of their renowned Italian small plates and wine selection. Afterward, take a leisurely walk along the picturesque Charles River and enjoy the views of the Boston skyline.
Evening
Dine at Bar Mezzana, where you can savor modern coastal Italian cuisine in a stylish setting. After dinner, experience the city from a different perspective with the Boston After Dark at View Boston Observatory (Adults Only). Enjoy panoramic views of the city lights and skyline, accompanied by a drink from the observatory's bar.
Bedtime
Find amazing hotels in Boston.
4.25Harvard University
Book Now
4.25Harvard University
Book Now
3.69John Harvard Statue
Book Now
3.69John Harvard Statue
Book Now
Revolutionary History and Culinary Delights
Morning
Start with a guided visit to the Boston Tea Party Ships and Museum Interactive Tour, where you'll immerse yourself in the events that sparked the American Revolution. Afterward, enjoy a historical breakfast at Yvonne's, housed in a former speakeasy with a unique ambiance.
Afternoon
Continue your historical journey with a visit to the Longfellow House (Washington's Headquarters), the former home of poet Henry Wadsworth Longfellow. For lunch, indulge in the creative dishes at Shojo Boston, known for its Asian-inspired cuisine and craft cocktails.
Evening
As the day winds down, take a guided walking tour of the Freedom Trail to revisit some of the trail's highlights at a more relaxed pace. Conclude the evening with a delightful dinner at The Butcher Shop, offering a menu focused on the finest meats and seasonal produce.
Bedtime
Find amazing hotels in Boston.
4.75Boston Tea Party Ships and Museum Interactive Tour
Book Now
4.75Boston Tea Party Ships and Museum Interactive Tour
Book Now
4.33Longfellow House (Washington's Headquarters)
Book Now
4.33Longfellow House (Washington's Headquarters)
Book Now
City Highlights and Observatory Experience
Morning
Enjoy a comprehensive overview of the city with a Boston Hop-on Hop-off Old Town Trolley Tour. Use this flexible transportation to visit attractions you may have missed, and disembark for a morning coffee at Pammy's Cambridge, known for its Italian-inspired cuisine and warm hospitality.
Afternoon
Visit the Boston View Boston Observatory Entry Ticket during the day to take in the panoramic views of the city and beyond. For lunch, head to The Butcher Shop for a selection of charcuterie and sandwiches. Afterward, take a relaxing walk through the Public Garden and Boston Common, the oldest public park in the United States.
Evening
4.50Boston Hop-on Hop-off Old Town Trolley Tour
Book Now
4.50Boston Hop-on Hop-off Old Town Trolley Tour
Book Now
4.65Boston View Boston Observatory Entry Ticket
Book Now
4.65Boston View Boston Observatory Entry Ticket
Book Now
Top Boston Travel Videos
Find the right stay during your trip.