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Ultimate 5-Day Boston and Cambridge Adventure

Ultimate 5-Day Boston and Cambridge Adventure Itinerary

Last updated: 2024 Jun 14

Historical Boston and Harbor Cruise

Morning
Start your day with a delicious breakfast at Mike's Pastry, known for its mouthwatering pastries and Italian desserts. After breakfast, head to the Boston Tea Party Ships and Museum Interactive Tour to immerse yourself in the history of the Boston Tea Party. Then, take a leisurely stroll through the Boston Common, the oldest public park in the United States, and visit the nearby Paul Revere House and the Granary Burying Ground.
Afternoon
For lunch, enjoy the fresh seafood at Legal Sea Foods. Afterward, take a Boston Historical Sightseeing Cruise to explore the historic sites along the Boston Harbor. In the afternoon, visit the USS Constitution, the world's oldest commissioned warship afloat, and the adjacent Charlestown Navy Yard.
Evening
In the evening, experience the stunning sunset views on a Boston Harbor Sunset Yacht Cruise. After the cruise, enjoy a delightful dinner at Top of the Hub, where you can savor gourmet cuisine while overlooking the city from the 52nd floor of the Prudential Tower.
Bedtime
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Boston Common

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Freedom Trail and North End Food Tour

Morning
Enjoy a hearty breakfast at Neptune Oyster, a renowned seafood spot in the North End. Then, embark on a Boston Guided Walking Tour of the Freedom Trail to explore the iconic landmarks of Boston's revolutionary history, including the Faneuil Hall Marketplace, the Old State House, and the Old North Church.
Afternoon
For lunch, indulge in a variety of Italian specialties on a Boston's North End Secret Food Tour. Afterward, visit the New England Aquarium to discover the wonders of the ocean and its fascinating marine life.
Evening
In the evening, take a leisurely walk along the Charles River and enjoy the scenic views. For dinner, experience the vibrant atmosphere and authentic Italian cuisine at Mamma Maria, a charming restaurant in the heart of the North End.
Bedtime
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Faneuil Hall Marketplace

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Harvard and MIT Exploration

Morning
Start your day with a delightful breakfast at Craigie on Main, known for its innovative and locally sourced dishes. Then, embark on a Cambridge Harvard University Student-Guided Walking Tour to explore the historic campus and learn about the prestigious university's rich history and traditions.
Afternoon
For lunch, savor the flavors of the Mediterranean at Oleana, a critically acclaimed restaurant in Cambridge. Afterward, visit the MIT Museum to discover the fascinating world of science and technology at the renowned Massachusetts Institute of Technology.
Evening
In the evening, take a relaxing stroll through the Kendall Square and enjoy the vibrant atmosphere of this innovative and entrepreneurial hub. For dinner, experience the culinary excellence at O Ya, a Japanese restaurant known for its exquisite sushi and innovative dishes.
Bedtime
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Witch Trials and Haunted History

Morning
Enjoy a delicious breakfast at Abe & Louie's, a classic American steakhouse in Boston. Then, take a scenic drive to Salem and begin your day with a visit to the Salem Witch Museum Admission Ticket to learn about the infamous witch trials and the history of witchcraft in Salem.
Afternoon
For lunch, enjoy the casual and welcoming atmosphere of Giacomo's Ristorante, known for its generous portions of classic Italian dishes. Afterward, explore the spooky side of Salem on a Salem Night Tour Haunt and History Guided Night Tour to uncover the city's haunted history and mysterious legends.
Evening
In the evening, join the Salem Boos and Brews Haunted Pub Crawl to visit some of Salem's most haunted pubs and hear chilling tales of the city's ghostly inhabitants. After the tour, enjoy a well-deserved dinner at No. 9 Park, a sophisticated restaurant known for its refined cuisine and elegant ambiance.
Bedtime
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Fenway Park and Farewell Dinner

Morning
Start your day with a visit to the iconic Fenway Park, home of the Boston Red Sox. Take a Fenway Park Guided Ballpark Tour with Options to explore the historic stadium and learn about its legendary moments.
Afternoon
For lunch, enjoy the casual and convivial atmosphere of Row 34, a seafood-focused restaurant in Boston's Fort Point neighborhood. Afterward, visit the Isabella Stewart Gardner Museum to admire its remarkable collection of art and explore the beautiful courtyard garden.
Evening
In the evening, savor a memorable farewell dinner at L'Espalier, a renowned French-inspired restaurant known for its exquisite cuisine and impeccable service. After dinner, take a leisurely walk along the Rose Kennedy Greenway and enjoy the vibrant public art installations and green spaces.
Bedtime
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