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5-day Boston and Surroundings Adventure Itinerary
Last updated: 2024 Jun 14Historical Boston Beginnings
Morning
Start your day with a classic breakfast at Mike's Pastry, known for its delectable pastries and Italian treats. After fueling up, take a stroll through the charming North End, also known as Little Italy, and explore the historic neighborhood's narrow streets and old architecture. Don't miss the chance to visit the Paul Revere House and the nearby Granary Burying Ground.
Afternoon
For lunch, head to Union Oyster House, the oldest restaurant in the United States, and enjoy their famous oyster bar. Post-lunch, immerse yourself in the history of the American Revolution with a visit to the Boston Tea Party Ships & Museum. Participate in the interactive tour and experience the "single most important event leading up to the American Revolution."
Evening
As the sun sets, indulge in a sophisticated dining experience at No. 9 Park, offering a perfect blend of European and American influences. After dinner, take a leisurely walk through the Boston Common, the oldest public park in the United States, and enjoy the serene atmosphere.
Bedtime
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4.51North End
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4.51
North End
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4.49Paul Revere House
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4.49
Paul Revere House
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4.54Granary Burying Ground
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4.54
Granary Burying Ground
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4.22Boston Tea Party Ships & Museum
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4.22
Boston Tea Party Ships & Museum
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4.49Boston Common
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4.49
Boston Common
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Freedom Trail and Scenic Views
Morning
Kick off your morning with a hearty breakfast at Legal Sea Foods, a Boston classic known for its fresh seafood. After breakfast, embark on a guided walking tour of the Freedom Trail, a 2.5-mile-long path that passes by 16 significant historical sites. Take in the rich history of Boston as you visit landmarks such as the USS Constitution and the Massachusetts State House.
Afternoon
For lunch, enjoy a casual yet upscale experience at Row 34, specializing in fresh oysters and other seafood. Post-lunch, take a hop-on hop-off ride on the Old Town Trolley Tour to explore the city at your own pace. Make sure to stop at the Boston View Boston Observatory to get a panoramic view of the city.
Evening
Dine at Top of the Hub, where you can savor delicious cuisine while enjoying breathtaking views of the Boston skyline. After dinner, consider taking an After Dark at View Boston Observatory (Adults Only) experience to see the city lights in a whole new way.
Bedtime
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4.61Freedom Trail
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4.61
Freedom Trail
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4.74USS Constitution
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4.74
USS Constitution
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4.31Massachusetts State House
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4.31
Massachusetts State House
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4.50Old Town Trolley Tour
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4.50
Old Town Trolley Tour
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4.65Boston View Boston Observatory
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4.65
Boston View Boston Observatory
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4.11After Dark at View Boston Observatory (Adults Only)
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4.11
After Dark at View Boston Observatory (Adults Only)
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Harvard and MIT Exploration
Morning
Start your day with a visit to the prestigious Harvard University. Take a self-guided walk around the campus, and don't miss the iconic John Harvard Statue. For breakfast, head to Craigie on Main for a memorable dining experience featuring local and seasonal ingredients.
Afternoon
After exploring Harvard, visit the Massachusetts Institute of Technology (MIT) and take a public tour to learn about its cutting-edge research and innovation. For lunch, enjoy the Mediterranean-inspired cuisine at Oleana, known for its vibrant flavors and cozy atmosphere.
Evening
For dinner, indulge in the Spanish tapas at Toro, a lively spot perfect for sharing small plates. Afterward, take a walk around the vibrant Kendall Square area and enjoy the innovative technology and biotech companies that call it home.
Bedtime
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4.25Harvard University
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4.25
Harvard University
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3.69John Harvard Statue
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3.69
John Harvard Statue
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4.33Massachusetts Institute of Technology (MIT)
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4.33
Massachusetts Institute of Technology (MIT)
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4.82Kendall Square
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4.82
Kendall Square
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Witch Trials and Haunted Tales
Morning
Begin your day with a visit to the Salem 1692 Witchcraft Trials Walk, where you'll learn about the infamous witch trials that took place in the late 17th century. For breakfast, enjoy a classic slice at Santarpio's Pizza, a local favorite known for its thin-crust pies.
Afternoon
Explore the Salem Witch Museum and gain insight into the witchcraft hysteria that gripped the town. For lunch, head to Giacomo's Ristorante for some hearty Italian dishes in a cozy, family-owned setting. Afterward, take a stroll through the Salem Secrets of Salem Hidden History Walking Tour to uncover the lesser-known stories of the city.
Evening
For a unique experience, join the Salem Night Tour Haunt and History Guided Night Tour to explore the spooky side of Salem. End your day with a delightful dessert at Mike's Pastry, where you can choose from a wide selection of cannolis and other treats.
Bedtime
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4.26Salem 1692 Witchcraft Trials Walk
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4.26
Salem 1692 Witchcraft Trials Walk
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4.19Salem Witch Museum
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4.19
Salem Witch Museum
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4.56Salem Secrets of Salem Hidden History Walking Tour
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4.56
Salem Secrets of Salem Hidden History Walking Tour
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4.59Salem Night Tour Haunt and History Guided Night Tour
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4.59
Salem Night Tour Haunt and History Guided Night Tour
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Culinary Delights and Evening Strolls
Morning
Begin with a guided walking tour of the North End, Boston's oldest residential community, on the Boston's North End Secret Food Tour. Sample a variety of Italian specialties and learn about the neighborhood's history and culture. Savor the flavors of the Longfellow House (Washington's Headquarters) as you pass by.
Afternoon
Enjoy a leisurely lunch at Myers + Chang, offering a fusion of Chinese, Taiwanese, Thai, and Vietnamese cuisines in a trendy, casual setting. After lunch, take a relaxing Boston Historical Sightseeing Cruise to admire the city's skyline and iconic landmarks from the water.
Evening
For your final dinner in Boston, dine at Menton, a fine dining restaurant that offers an exceptional culinary experience with French-inspired dishes. Afterward, take a walk through the Faneuil Hall Marketplace and enjoy the lively street performances and shops, soaking in the vibrant atmosphere of the city.
Bedtime
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4.51North End
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4.51
North End
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4.72Boston's North End Secret Food Tour
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4.72
Boston's North End Secret Food Tour
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4.33Longfellow House (Washington's Headquarters)
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4.33
Longfellow House (Washington's Headquarters)
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4.56Boston Historical Sightseeing Cruise
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4.56
Boston Historical Sightseeing Cruise
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4.59Faneuil Hall Marketplace
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4.59
Faneuil Hall Marketplace
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