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Ultimate Boys Weekend in Boston Itinerary
Last updated: 2024 Jun 14Historic Trails and Haunted Tales
Morning
Kick off your boys weekend with a hearty breakfast at Mike's Pastry in the North End, famous for its cannolis and pastries. After fueling up, take a self-guided tour of the Freedom Trail, visiting iconic landmarks such as the Massachusetts State House, Paul Revere House, and the USS Constitution.
Afternoon
For lunch, head to Neptune Oyster for some of the best seafood in the city. Afterward, enjoy a guided tour of the Boston Tea Party Ships and Museum, where you'll learn about the historic event that sparked the American Revolution. Take the opportunity to participate in the interactive exhibits.
Evening
As the sun sets, embark on the Boston Harbor Sunset Yacht Cruise for stunning views of the city skyline. For dinner, experience the vibrant Italian cuisine of the North End at Mamma Maria. End the evening with a Ghosts and Gravestones Tour to uncover Boston's haunted history.
Bedtime
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4.85Freedom Trail
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4.85Freedom Trail
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4.75Boston Tea Party Ships and Museum
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4.75Boston Tea Party Ships and Museum
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Sports, Beers, and Cheers
Morning
Start your day with a visit to the iconic Fenway Park for a guided ballpark tour. Immerse yourself in the history of the Boston Red Sox and the legendary stadium. After the tour, grab a classic Fenway Frank for a true Boston sports experience.
Afternoon
Enjoy a casual lunch at Row 34, known for its fresh oysters and craft beers. Post-lunch, hop on the Old Town Trolley Tour for a convenient way to explore the city's top attractions. Feel free to hop off at spots that catch your eye, such as the New England Aquarium or Faneuil Hall Marketplace.
Evening
For a sophisticated dinner, make a reservation at Top of the Hub, where you'll enjoy panoramic views of the city while savoring fine dining cuisine. Afterward, head to Eastern Standard Kitchen & Drinks for post-dinner cocktails in a lively, speakeasy-style setting.
Bedtime
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4.19Fenway Park
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4.19Fenway Park
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4.50Old Town Trolley Tour
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4.50Old Town Trolley Tour
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Harvard Hops and Cambridge Crawls
Morning
Take a trip across the river to Cambridge and start your day with breakfast at Giacomo's Ristorante, a local favorite known for its Italian dishes. Afterward, join a Harvard University Student-Guided Walking Tour to explore the historic campus and learn about its prestigious history.
Afternoon
For lunch, indulge in the famous pizzas at Santarpio's Pizza, a Boston institution. Post-lunch, visit the Massachusetts Institute of Technology (MIT) for a public tour to witness cutting-edge innovation and technology.
Evening
Return to Boston for a memorable dinner at Craigie on Main, known for its inventive, French-inspired cuisine. Cap off the evening with a History Pub Crawl Tour Along the Freedom Trail, exploring the city's historic pubs and taverns while enjoying a few drinks.
Bedtime
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4.57Harvard University Student-Guided Walking Tour
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4.57Harvard University Student-Guided Walking Tour
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4.33Massachusetts Institute of Technology (MIT)
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4.33Massachusetts Institute of Technology (MIT)
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