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5-Day Boston and Cambridge Exploration with Iconic Landmarks and Culinary Delights

5-Day Boston and Cambridge Exploration with Iconic Landmarks and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Historical Landmarks and Scenic Views

Morning
Begin your Boston adventure with a panoramic view of the city from the Boston View Boston Observatory. After taking in the sights, head to the historic Boston Tea Party Ships and Museum for an interactive tour that brings the American Revolution to life.
Afternoon
For lunch, savor the flavors of Boston's North End on the Boston's North End Secret Food Tour. Afterward, immerse yourself in history with a guided walking tour of the Freedom Trail, visiting iconic sites like the Paul Revere House and the Granary Burying Ground.
Evening
As the sun sets, experience the city after dark with the Boston After Dark at View Boston Observatory (Adults Only). Then, enjoy a delightful dinner at Lincoln Tavern & Restaurant, known for its innovative American cuisine and vibrant atmosphere.
Bedtime
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Visit Boston View Boston Observatory Entry Ticket in Boston
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Academic and Athletic Icons

Morning
Start your day with a guided tour of the world-renowned Harvard University in nearby Cambridge. Explore the historic campus and learn about its prestigious history.
Afternoon
After the tour, enjoy a leisurely lunch at Five Horses Tavern - South End, offering a diverse menu and a cozy ambiance. Post-lunch, visit the legendary Fenway Park for a guided ballpark tour, immersing yourself in the rich traditions of America's oldest Major League Baseball stadium.
Evening
Dine at Bleacher Bar, where you can enjoy a unique dining experience with a view directly into Fenway Park. Afterward, take a stroll through the vibrant atmosphere of Kenmore Square and enjoy the evening in this lively neighborhood.
Bedtime
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Maritime History and Culinary Delights

Morning
Embark on a historical sightseeing cruise to learn about Boston's maritime past and enjoy the city's skyline from the water on the Boston Historical Sightseeing Cruise. After the cruise, grab a delicious breakfast at Clarke's at Faneuil Hall, located in the heart of the city.
Afternoon
Spend your afternoon exploring the lively Faneuil Hall Marketplace and Quincy Market, where you can indulge in a variety of cuisines from local vendors. Afterward, take a self-guided tour of the USS Constitution, the world's oldest commissioned warship afloat.
Evening
Enjoy a memorable dinner at OAK Long Bar + Kitchen, known for its extensive drink selection and upscale American fare. End your evening with a stroll along the charming streets of the North End, also known as Boston's "Little Italy."
Bedtime
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Cambridge Cultural Immersion and Haunted History

Morning
Begin your day with a visit to the Massachusetts Institute of Technology (MIT), where you can explore the campus and its innovative spirit. Afterward, enjoy a delightful breakfast at The Tip Tap Room, known for its unique beer selection and diverse menu.
Afternoon
Take a guided walking tour of the Cambridge Harvard University Student-Guided Walking Tour to gain insights into the student experience and the history of this prestigious institution. For lunch, head to Yard House for a wide range of dishes and an extensive beer list.
Evening
As the night falls, immerse yourself in the Salem Night Tour Haunt and History Guided Night Tour in the nearby historic town of Salem. Explore the spooky side of the city and learn about its haunted past. After the tour, enjoy a late-night drink at The Bell In Hand Tavern, one of the oldest taverns in the United States.
Bedtime
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Literary Legacies and Scenic Strolls

Morning
Begin with a visit to the Longfellow House (Washington's Headquarters) in Cambridge, the former home of renowned poet Henry Wadsworth Longfellow. Then, enjoy a guided tour of the Harvard Museum of Natural History, where you can explore a vast collection of specimens and exhibits.
Afternoon
For lunch, head to Emmets for an authentic Irish dining experience. Afterward, take a leisurely walk along the picturesque Charles River and enjoy the serene views of the water and the city skyline.
Evening
Conclude your Boston journey with a delicious dinner at The White Bull Tavern, offering a warm and inviting atmosphere. Reflect on your trip as you enjoy a meal in this historic city.
Bedtime
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