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Historical Landmarks and Culinary Delights in Boston and Beyond Itinerary
Last updated: 2024 Jun 14Boston's Iconic Sights and Harbor Cruises
Morning
Start your Boston adventure with a visit to the historic Boston Tea Party Ships and Museum. Immerse yourself in the interactive exhibits and learn about the famous event that sparked the American Revolution. Afterward, enjoy a hearty breakfast at Mr. Dooley's Boston.
Afternoon
After breakfast, take a guided tour of the legendary Fenway Park, home of the Boston Red Sox. For lunch, head to Fin Point Oyster Bar + Grille for a taste of New England's finest seafood. Spend your afternoon exploring the exhibits at the New England Aquarium, where you can witness a stunning variety of marine life.
Evening
As the sun sets, embark on a relaxing Boston Harbor Sunset Yacht Cruise. Enjoy the city's skyline from the water and indulge in a delightful dinner onboard. After the cruise, take a leisurely stroll through the vibrant Faneuil Hall Marketplace and enjoy the street performances. End your evening with a nightcap at The Bell In Hand Tavern, one of the oldest bars in the United States.
Bedtime
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Freedom Trail and North End Gastronomy
Morning
Begin your day with a guided walking tour of the Freedom Trail. Explore the rich history of Boston as you visit significant landmarks including the USS Constitution and the Granary Burying Ground. For breakfast, savor the flavors of the city on a Boston's North End Secret Food Tour, where you'll taste authentic Italian cuisine and learn about the neighborhood's history.
Afternoon
After the food tour, take a break at the picturesque Boston Common. Then, continue your historical journey with a visit to the Paul Revere House and the Old North Church. For lunch, enjoy the ambiance and cuisine at North 26 Bar & Restaurant.
Evening
Spend your evening in the lively atmosphere of the North End. Explore the quaint streets and perhaps indulge in a delightful dessert at one of the local pastry shops. For dinner, experience the flavors of the neighborhood at CLINK. and The Liberty Bar. Afterward, enjoy a post-dinner drink at a nearby lounge.
Bedtime
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Harbor Cruises and Harvard History
Morning
Start your morning with a gourmet brunch cruise on the Boston Harbor Gourmet Brunch Cruise. Enjoy a delicious meal while taking in the scenic views of the harbor and the city. After the cruise, take a walk along the Charles River and enjoy the serene atmosphere.
Afternoon
In the afternoon, cross the river to Cambridge and explore the prestigious Harvard University. Take a self-guided tour of the campus and visit iconic spots such as the John Harvard Statue. For lunch, dine at Bar Cicchetti Boston, known for its delectable small plates and Italian-inspired cocktails.
Evening
As the evening sets in, continue your exploration of Cambridge with a visit to the Massachusetts Institute of Technology (MIT). Take a public tour of the campus and learn about its cutting-edge research and innovation. For dinner, indulge in the vibrant atmosphere and cuisine at Silvertone Bar & Grill.
Bedtime
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Trolley Tours and Holiday Cruises
Morning
Hop on the Hop-on Hop-off Old Town Trolley Tour to get an overview of the city's major attractions. Disembark at the Boston View Boston Observatory and enjoy panoramic views of the city. Grab a quick breakfast at the observatory's cafe.
Afternoon
For lunch, experience the festive season with the Boston Cocoa and Carols Holiday Cruise. Sip on hot cocoa and enjoy the holiday tunes as you cruise along the harbor. Afterward, visit the Longfellow House (Washington's Headquarters) in Cambridge to learn about the life of the famous poet.
Evening
Dine at Elephant & Castle, a cozy restaurant with a British pub ambiance. After dinner, join the Boston Holiday Sights and Festive Nights Trolley Tour to see the city adorned with holiday lights and decorations. End the night with a visit to the Boston Harbor After Dark at View Boston Observatory (Adults Only) for a unique evening experience.
Bedtime
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Haunted Salem and Evening Pub Crawl
Morning
Take a day trip to the historic town of Salem. Begin with a guided walking tour of Salem Ghosts, Witches, & Warlocks to learn about the infamous witch trials and the town's spooky history. For breakfast, enjoy the morning at 4th Wall Restaurant & Bar.
Afternoon
Explore the attractions of Salem including the Peabody Essex Museum and the House of the Seven Gables. For lunch, visit Solas Irish Pub for a warm and welcoming meal. Afterward, join the Salem Boos and Brews Haunted Pub Crawl to experience the town's haunted past while enjoying some local brews.
Evening
Return to Boston and relax with dinner at Better Sorts Social Club, known for its sophisticated cocktails and refined cuisine. Afterward, if you're up for more haunting tales, join the Salem Night Tour Haunt and History Guided Night Tour for a spine-tingling evening.
Bedtime
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Culinary Delights and Museum Visits
Morning
Enjoy a leisurely morning with breakfast at Blake's Kitchen + Bar. Then, visit the MIT Museum in Cambridge to explore the world of science, technology, and innovation. Take your time to appreciate the fascinating exhibits.
Afternoon
For lunch, head to Causeway Boston for a classic American meal. Afterward, visit the Harvard Museum of Natural History to marvel at its extensive collections, including the famous Glass Flowers and dinosaur skeletons.
Evening
Conclude your trip with a delightful dinner at The Street Bar, where you can enjoy a variety of culinary offerings in a vibrant setting. Reflect on your journey as you enjoy your meal, and perhaps take a post-dinner walk to revisit your favorite spots in the city.
Bedtime
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