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5-Day Boston and Salem History, Haunts, and Culinary Delights Itinerary
Last updated: 2024 Jun 14Freedom Trail, Historical Cruise, and North End Gastronomy
Morning
Begin your Boston adventure with a hearty breakfast at Flour Bakery + Cafe - Fort Point, known for its delectable pastries and coffee. Afterward, embark on a Guided Walking Tour of the Freedom Trail to explore the city's rich history, passing by iconic sites such as the Massachusetts State House, Granary Burying Ground, and Paul Revere House.
Afternoon
For lunch, indulge in the famous seafood at B&G Oysters in the South End. Post-lunch, enjoy a leisurely Historical Sightseeing Cruise on the harbor, taking in the skyline and learning about Boston's maritime past. After the cruise, take a walk around the charming streets of the Boston's North End, also known as Little Italy, and enjoy the neighborhood's ambiance.
Evening
As the sun sets, savor an authentic Italian dinner at Giacomo's Ristorante, a North End staple. Afterward, join the Boston North End Pizza Tour with 3 Slices and Cannoli to taste some of the best slices in the city. End the evening with a sweet treat from Mike's Pastry, famous for its cannolis and other pastries.
Bedtime
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4.85Guided Walking Tour of the Freedom Trail
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4.85Guided Walking Tour of the Freedom Trail
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4.56Historical Sightseeing Cruise
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4.56Historical Sightseeing Cruise
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Harvard, MIT, and Cambridge Exploration
Morning
Start your day with a visit to the prestigious Harvard University in Cambridge. Afterward, enjoy a guided Harvard University Student-Guided Walking Tour to learn about the history and culture of the campus. For breakfast, head to Pammy's Cambridge for a delightful meal in a cozy atmosphere.
Afternoon
Explore the innovative and artistic side of Cambridge by visiting the Massachusetts Institute of Technology (MIT) and the MIT Museum. For lunch, dine at Coppa Enoteca, known for its Italian small plates and extensive wine selection. Afterward, take a stroll through the vibrant Kendall Square area.
Evening
Enjoy a sophisticated dinner at Bar Mezzana, offering a modern take on coastal Italian cuisine. After dinner, if you're up for some entertainment, catch a performance at the Central Square Theater, known for its thought-provoking shows.
Bedtime
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4.25Harvard University
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4.25Harvard University
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4.57Harvard University Student-Guided Walking Tour
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4.57Harvard University Student-Guided Walking Tour
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Fenway Park, Observatory Views, and Upscale Dining
Morning
Fuel up for the day with breakfast at The Butcher Shop, a European-style bistro with a focus on prime cuts and charcuterie. Afterward, take a guided Boston Fenway Park Guided Ballpark Tour with Options to immerse yourself in the history of one of the most iconic baseball stadiums in the country.
Afternoon
Enjoy a panoramic view of the city from the Boston View Boston Observatory Entry Ticket, where you can also grab a light lunch. Later, explore the trendy neighborhood of the South End and have a sumptuous meal at Toro, known for its outstanding Spanish cuisine and lively atmosphere.
Evening
For a memorable fine dining experience, make a reservation at Menton, a Relais & Châteaux restaurant offering exquisite French-inspired dishes. After dinner, take a leisurely walk along the South End, known for its beautiful Victorian brownstones and diverse art galleries.
Bedtime
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4.79Boston Fenway Park Guided Ballpark Tour with Options
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4.79Boston Fenway Park Guided Ballpark Tour with Options
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4.65Boston View Boston Observatory Entry Ticket
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4.65Boston View Boston Observatory Entry Ticket
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Witches, History, and Haunted Tours
Morning
Begin your day with a breakfast at The Salty Pig in Boston. Then, take a day trip to the nearby city of Salem. Explore the Salem Witch Museum and immerse yourself in the history of the infamous Salem witch trials. Afterward, join the Salem Secrets of Salem Hidden History Walking Tour to discover the lesser-known stories of the city's past.
Afternoon
Enjoy a lunch at Santarpio's Pizza, a local favorite known for its classic pies. Spend the rest of the afternoon visiting other Salem attractions such as the Peabody Essex Museum or simply strolling through the historic streets and browsing the unique shops.
Evening
As the sun sets, experience the eerie side of Salem with the Salem Haunted Footsteps Ghost Tour. Learn about the city's paranormal history and visit some of its most haunted locations. After the tour, head back to Boston and have a late dinner at Row 34, a stylish seafood spot with an extensive raw bar selection.
Bedtime
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4.56Salem Secrets of Salem Hidden History Walking Tour
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4.56Salem Secrets of Salem Hidden History Walking Tour
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4.52Peabody Essex Museum
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4.52Peabody Essex Museum
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Culinary Delights and Evening Entertainment
Morning
Start your morning with a guided Delicious Donut Tour with Tastings to sample some of the best donuts in the city. The tour will take you to hidden gems and local favorites, providing a sweet start to your day. After the tour, take a walk along the picturesque Charles River and enjoy the morning breeze.
Afternoon
For lunch, head to Shojo Boston for a unique blend of Asian flavors in a stylish setting. Post-lunch, explore the historic Longfellow House (Washington's Headquarters) in Cambridge, a National Historic Landmark that offers a glimpse into the life of the famous poet Henry Wadsworth Longfellow.
Evening
Conclude your trip with a memorable dinner at Yvonne's, a sophisticated supper club with a speakeasy vibe. Afterward, if you're in the mood for some post-dinner entertainment, catch a show at the Harvard Square, known for its vibrant live music and performing arts scene.
Bedtime
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4.79Delicious Donut Tour with Tastings
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4.79Delicious Donut Tour with Tastings
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4.54Charles River
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4.54Charles River
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