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Ultimate 5-Day Adventure in Boston and Beyond

Ultimate 5-Day Adventure in Boston and Beyond Itinerary

Last updated: 2024 Jun 14

Boston's Historical & Haunted Beginnings

Morning
Begin your day with a delightful breakfast at Mike's Pastry in the North End, famous for its cannolis. Afterward, embark on a guided walking tour of the Freedom Trail, exploring significant historical sites like the Boston Tea Party Ships & Museum.
Afternoon
For lunch, savor the seafood at Legal Sea Foods near the waterfront. In the afternoon, take a Boston Harbor Sunset Yacht Cruise to enjoy the city's skyline from the water. End your afternoon with a visit to the New England Aquarium.
Evening
As the sun sets, join the Salem Night Tour Haunt and History Guided Night Tour to experience the eerie tales of Salem's past. Afterward, enjoy a late dinner at Giacomo's Ristorante, known for its Italian cuisine.
Bedtime
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Boston Freedom Trail Walking Tour

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Boston Tea Party Ships & Museum

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Boston Harbor Sunset Yacht Cruise

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Barcelona 24 or 48-Hour Hop-On Hop-Off Bus Tour

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Salem Night Tour Haunt and History Guided Night Tour

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Boston's Academic & Culinary Delights

Morning
Start your day with a hearty breakfast at Row 34, known for its seafood. Then, take a student-guided walking tour of Harvard University in Cambridge.
Afternoon
For lunch, head to Eastern Standard Kitchen & Drinks in Kenmore Square. Spend the afternoon exploring the Massachusetts Institute of Technology (MIT) and its museum. Later, enjoy a leisurely walk along the Charles River.
Evening
Indulge in a fine dining experience at O Ya, a Japanese restaurant in the Back Bay area, known for its exquisite sushi and sashimi.
Bedtime
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Harvard University

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Massachusetts Institute of Technology (MIT)

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Charles River

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Boston's Iconic Landmarks & Haunted Pubs

Morning
Enjoy a leisurely breakfast at Myers + Chang, offering Asian-inspired dishes. Then, visit the Fenway Park for a guided tour of this iconic baseball stadium.
Afternoon
For lunch, head to Union Oyster House, the oldest continuously operating restaurant in the U.S. Spend the afternoon exploring the Boston Public Library and the Boston Public Garden.
Evening
Join the Boston Haunted Pub Crawl of Historic Pubs and Taverns for a spooky yet entertaining evening. Conclude the night with a late dinner at Neptune Oyster, known for its fresh seafood.
Bedtime
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Fenway Park

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Boston Public Library

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Boston Public Garden

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Boston Haunted Pub Crawl of Historic Pubs and Taverns

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Salem's Witchcraft & History

Morning
Travel to Salem and start your day with breakfast at Abe & Louie's, a classic steakhouse. Then, immerse yourself in the history of the Salem Witch Museum Admission Ticket.
Afternoon
For lunch, try the famous pizza at Santarpio's Pizza. Spend the afternoon exploring the Salem, MA History & Hauntings Guided Walking Tour and the Salem Ghosts, Witches, & Warlocks Guided Walking Tour.
Evening
Enjoy a unique dining experience at Top of the Hub, located on the 52nd floor of the Prudential Tower in Boston, offering stunning views of the city.
Bedtime
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Salem Witch Museum Admission Ticket

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Salem, MA History and Hauntings Guided Walking Tour

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Salem Ghosts, Witches, & Warlocks Guided Walking Tour

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Boston's Culinary & Academic Treasures

Morning
Start your day with a delicious breakfast at Menton, a fine dining French restaurant. Then, explore the Boston View Boston Observatory Entry Ticket for panoramic views of the city.
Afternoon
For lunch, savor the Spanish tapas at Toro. Spend the afternoon at the Boston Fenway Park Guided Ballpark Tour with Options and the Boston Historical Sightseeing Cruise.
Evening
Conclude your adventure with a memorable dinner at L'Espalier, known for its elegant French cuisine and exceptional service.
Bedtime
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Boston View Boston Observatory Entry Ticket

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Boston Fenway Park Guided Ballpark Tour with Options

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Boston Historical Sightseeing Cruise

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Adjacent Cities

PortlandGorhamWoodstockKentNewportCape Cod

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