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Boston, Massachusetts, USA

Historical and Haunted Boston: 5-Day Itinerary with Festive Nights Itinerary

Published: 2023 Dec 15
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Historic Boston Beginnings

Morning
Start your Boston journey with a hearty breakfast at OAK Long Bar + Kitchen, known for its elegant ambiance and delicious morning fare. After breakfast, immerse yourself in the city's history with a guided walking tour of the Freedom Trail, visiting iconic sites like the Boston Common and the Paul Revere House.
Afternoon
For lunch, head to Bostonia Public House, where you can enjoy a mix of traditional and contemporary American cuisine. Post-lunch, take a leisurely stroll through the North End, Boston's oldest residential community, and indulge in some of the best Italian pastries at the local bakeries.
Evening
Dine at Yvonne's, a unique spot with a speakeasy vibe and a menu that's as intriguing as the decor. After dinner, experience the city's festive nights with the Boston Harbor Sunset Yacht Cruise, offering stunning views of the Boston skyline as the sun sets over the harbor.
Bedtime
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Revolutionary Boston and Culinary Delights

Morning
Enjoy a classic Boston breakfast at The Black Rose, an Irish pub with a warm atmosphere. Post-breakfast, explore the interactive exhibits at the Boston Tea Party Ships and Museum, where you'll learn about the historic event that played a crucial role in the American Revolution.
Afternoon
Savor a seafood lunch at The Tip Tap Room, known for its fresh and innovative dishes. Afterward, take a leisurely stroll through the New England Aquarium, home to thousands of aquatic animals including the majestic sea lions.
Evening
Dine at Birch Bar, a cozy spot with a focus on craft cocktails and a menu that highlights local and seasonal ingredients. Cap off the evening with the Boston Harbor Gourmet Dinner Cruise, enjoying a three-course meal and live entertainment as you cruise along the harbor.
Bedtime
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Cambridge and MIT Exploration

Morning
Start your day with breakfast at Cheers, the iconic bar from the TV show "Cheers." Afterward, cross the Charles River to Cambridge and take a self-guided tour of the prestigious Harvard University and the nearby Harvard Square.
Afternoon
Enjoy a casual lunch at Bukowski Tavern, a neighborhood bar with a relaxed vibe and a wide selection of beers. Spend your afternoon exploring the innovative exhibits at the MIT Museum and taking a leisurely walk through the Kendall Square area.
Evening
For dinner, head to Porters Bar and Grill, a local favorite known for its laid-back atmosphere and diverse menu. Afterward, enjoy a live performance at a nearby venue or take a leisurely evening walk along the Charles River Esplanade.
Bedtime
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Fenway Park and Evening Entertainment

Morning
Start your day with a breakfast at Emmets, an Irish pub with a warm and welcoming atmosphere. After breakfast, take a guided tour of the iconic Fenway Park, home of the Boston Red Sox, and immerse yourself in the history of America's favorite pastime.
Afternoon
Enjoy a classic American lunch at 21st Amendment, a lively spot with a menu that pays homage to the Prohibition era. Post-lunch, visit the Longfellow House (Washington's Headquarters) in nearby Cambridge, and explore the historic home and its beautiful gardens.
Evening
Dine at Silvertone Bar & Grill, a retro-style bar and restaurant known for its comfort food and extensive drink menu. After dinner, experience the city's vibrant nightlife with a visit to a local comedy club or live music venue.
Bedtime
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Haunted Salem and Witch City Wonders

Morning
Enjoy a delicious breakfast at The Bell In Hand Tavern, the oldest tavern in America. After breakfast, take a day trip to nearby Salem and immerse yourself in the city's spooky history with guided tours such as the Salem Ghosts, Witches, & Warlocks Guided Walking Tour or the Salem Secrets of Salem Hidden History Walking Tour.
Afternoon
For lunch, try the innovative dishes at 4th Wall Restaurant & Bar, a hidden gem in the theater district. Afterward, visit the Peabody Essex Museum to explore its extensive collection of art and cultural artifacts.
Evening
Conclude your trip with a memorable dinner at Solas Irish Pub, known for its lively atmosphere and authentic Irish fare. After dinner, take the Salem Night Tour Haunt and History Guided Night Tour to experience the city's eerie ambiance after dark.
Bedtime
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