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Boston, Massachusetts, USA

Historical Landmarks and Culinary Delights: 5-Day Trip to Boston and Surrounding Areas Itinerary

Published: 2023 Dec 13
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Boston's Iconic Landmarks and Harbor Views

Morning
Begin your Boston adventure with a hearty breakfast at The Black Rose, a historic pub in the heart of the city. Afterward, immerse yourself in the city's history with a Guided Walking Tour of the Freedom Trail. Visit iconic sites like the Paul Revere House, Granary Burying Ground, and the Old North Church.
Afternoon
For lunch, head to Bostonia Public House, known for its New England fare and craft cocktails. Spend your afternoon exploring the Boston Tea Party Ships and Museum Interactive Tour, where you'll learn about the historic event that took place in Boston Harbor. Afterward, enjoy a relaxing Historical Sightseeing Cruise to take in the city's skyline from the water.
Evening
Dine at Bleacher Bar, located right inside Fenway Park with a unique view of the field. After dinner, experience the lively atmosphere of Lansdowne Street, known for its bars and live music venues.
Bedtime
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Academic Marvels and Scenic River Cruises

Morning
Start your day with a delicious donut tour, visiting some of the best donut shops in the city with the Guided Delicious Donut Tour with Tastings. After satisfying your sweet tooth, take a Harbor Gourmet Brunch Cruise to enjoy a leisurely meal while cruising along the historic harbor.
Afternoon
Explore the prestigious campuses of Harvard and MIT with a Harvard University Student-Guided Walking Tour and a Massachusetts Institute of Technology Public Tour. For lunch, dine at Five Horses Tavern - South End, offering a wide selection of beers and a creative menu.
Evening
Enjoy a sophisticated dinner at Birch Bar, known for its elegant ambiance and innovative cocktails. Afterward, take a Boston Harbor Sunset Yacht Cruise to witness the city's skyline as the sun sets.
Bedtime
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Sports, Parks, and Evening Entertainment

Morning
Fuel up for the day with breakfast at Cheers, the famous bar from the TV show "Cheers." Afterward, take a guided tour of the historic Fenway Park, home of the Boston Red Sox, and then stroll through the beautiful Boston Common and Public Garden.
Afternoon
Enjoy a casual lunch at Porters Bar and Grill, offering a relaxed atmosphere and a menu with diverse options. Spend your afternoon at the New England Aquarium, where you can explore the marine life and even participate in a special animal encounter experience.
Evening
Dine at The Tip Tap Room, known for its unique selection of beers and a menu featuring various cuts of meat. After dinner, experience the vibrant atmosphere of Faneuil Hall Marketplace and catch a live performance or stand-up comedy at The Black Comedy Club.
Bedtime
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Academic Excellence and Riverside Serenity

Morning
Cross the Charles River and enjoy breakfast at The White Bull Tavern, known for its cozy atmosphere. Then, take a leisurely walk along the Charles River and explore the vibrant Kendall Square, a hub of innovation and technology.
Afternoon
For lunch, visit Emmets, a local favorite for its Irish-inspired dishes and a wide selection of beers. Spend your afternoon at the MIT Museum, where you can explore the intersection of science, technology, and art. Follow it with a visit to the serene Cambridge Common.
Evening
Dine at Solas Irish Pub, offering a warm and welcoming atmosphere with classic Irish dishes. Conclude your day with a delightful evening at Harvard Square, filled with bookstores, cafes, and a vibrant street performance scene.
Bedtime
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Witches, History, and Maritime Mystique

Morning
Begin your day with breakfast at Silvertone Bar & Grill, known for its classic American comfort food. Then, embark on a Salem Ghosts, Witches, & Warlocks Guided Walking Tour to explore the dark and mysterious history of Salem, including the infamous Salem Witch Trials.
Afternoon
Enjoy a lunch at jm Curley, a cozy spot with a menu featuring gourmet burgers and craft cocktails. Afterward, visit the Peabody Essex Museum, one of the oldest and fastest-growing museums in the country, to immerse yourself in art and culture.
Evening
Conclude your trip with a Salem Night Tour Haunt and History Guided Night Tour, where you'll hear chilling tales of the city's haunted past. For a memorable final dinner, head to 4th Wall Restaurant & Bar, known for its innovative cuisine and stylish ambiance.
Bedtime
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