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10 Days Exploring Historical Massachusetts Itinerary
Last updated: 2024 Jun 14Boston's Freedom Trail Adventure
Morning
Start your journey with the Boston Guided Walking Tour of the Freedom Trail. This tour will take you through 16 historical sites, including Boston Common and the State House. It's a great way to get an overview of Boston's rich history.
Afternoon
After the tour, head to Faneuil Hall Marketplace for lunch. This historic marketplace offers a variety of food options and is a perfect spot to relax and enjoy some local cuisine.
Evening
In the evening, embark on the Boston History Pub Crawl Tour Along the Freedom Trail. This tour combines history with visits to some of Boston's oldest pubs. It's a fun way to end your first day in Boston.
Bedtime
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Harbor Views and Historic Sites
Morning
Begin your day with a visit to the Boston Tea Party Ships and Museum Interactive Tour. This interactive museum offers a unique look at one of the most pivotal events in American history.
Afternoon
For lunch, enjoy some seafood at one of Boston's highly-rated restaurants near Rowes Wharf. Afterward, take the Boston Harbor Champagne Sunset Sail from Rowes Wharf for stunning views of the city from the water.
Evening
Conclude your day with a stroll through Back Bay, known for its beautiful architecture and vibrant nightlife. Have dinner at one of Back Bay's renowned restaurants.
Bedtime
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Boston's Revolutionary Roots
Morning
Boston Massacre Site is where tensions between colonists and British soldiers erupted into violence in 1770. Start your day by visiting this historic site.
Afternoon
Custom House offers panoramic views of Boston from its observation deck. Afterward, have lunch at a nearby restaurant before exploring more of Boston’s historical landmarks.
Evening
Boston North End Food Experience with Pizza, Meats & Cheese is a delightful way to spend your evening. Enjoy delicious food while learning about Boston’s Italian heritage.
Bedtime
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Boston's Cultural Finale
Morning
Begin your final day in Massachusetts with the Boston 2.5-Hour City View Bike Tour. This tour provides an excellent overview of Boston’s neighborhoods and landmarks from a unique perspective.
Afternoon
After the bike tour, have lunch at one of Boston’s highly-rated cafes. Spend your afternoon visiting the Boston Charles River Sightseeing Cruise, which offers scenic views of Boston from the water.
Evening
End your trip with a memorable dinner at one of Boston’s top-rated restaurants before taking an evening stroll through Back Bay once more to soak in the city’s vibrant atmosphere.
Bedtime
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Cambridge Exploration Day
Morning
Head over to Cambridge and start your day at Kendall Square. Known as 'the most innovative square mile on Earth,' it's home to tech companies and startups.
Afternoon
Have lunch at one of Kendall Square’s trendy cafes before visiting the MIT Museum. The museum showcases fascinating exhibits on science and technology.
Evening
Spend your evening exploring Cambridge Common, a historic park where George Washington once gathered troops during the Revolutionary War. Enjoy dinner at one of Cambridge’s historic eateries.
Bedtime
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Historic Highlights in Cambridge
Morning
Begin your day by visiting Longfellow House (Washington's Headquarters). This historic site served as George Washington’s headquarters during the Siege of Boston.
Afternoon
Afterward, have lunch at one of Cambridge’s charming cafes before heading over to explore Harvard Square. Known for its vibrant atmosphere and historic significance, it’s a must-visit spot in Cambridge.
Evening
End your day with dinner at one of Harvard Square’s renowned restaurants before taking an evening stroll through this iconic area.
Bedtime
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Salem's Witchy Wonders
Morning
Travel to Salem and start your morning with a visit to the famous Salem Witch Museum. Learn about the infamous witch trials that took place here in 1692.
Afternoon
For lunch, dine at one of Salem’s charming cafes before heading over to explore Pickering Wharf, a bustling waterfront area filled with shops and maritime history.
Evening
End your day by visiting the poignant Salem Witch Trials Memorial. Reflect on this somber part of history before having dinner at one of Salem’s historic restaurants.
Bedtime
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Salem's Maritime and Mystical History
Morning
Start your day with a visit to the Salem Pirate Museum with Authentic Treasures Entry Ticket. This museum offers a fascinating look at Salem's maritime history and pirate lore, featuring authentic treasures and artifacts.
Afternoon
For lunch, head to one of Salem’s waterfront restaurants. Afterward, explore Bewitched Statue, a tribute to the famous TV show filmed in Salem. This quirky statue is a fun photo opportunity and a nod to pop culture history.
Evening
Conclude your day with a visit to Salem Ferry. Enjoy an evening ferry ride along the coast, offering beautiful views of the harbor and city skyline. Have dinner at one of Salem’s historic restaurants.
Bedtime
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Exploring Plymouth's Pilgrim Past
Morning
Start your day with a visit to the Mayflower II. This full-scale reproduction of the ship that brought the Pilgrims to America in 1620 offers a fascinating glimpse into early colonial life.
Afternoon
After exploring the Mayflower II, head to a nearby restaurant for lunch. In the afternoon, visit Burial Hill, one of the oldest cemeteries in America and the final resting place of many Mayflower passengers.
Evening
Conclude your day with a stroll along Plymouth's waterfront and enjoy dinner at one of its historic seafood restaurants.
Bedtime
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Newport's Historic Mansions
Morning
Bellevue Avenue is home to some of America's most opulent mansions. Start your day with a tour of The Breakers, an iconic Gilded Age mansion.
Afternoon
Ocean Drive offers stunning coastal views and is perfect for an afternoon drive or bike ride. Stop for lunch at one of Newport's seaside cafes.
Evening
Touro Synagogue National Historic Site is the oldest synagogue in America. Visit this historic site in the evening before dining at one of Newport's renowned restaurants.
Bedtime
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