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Boston's Best: 5-Day Historical, Cultural, and Culinary Journey Itinerary
Last updated: 2024 Jun 14Boston's Beginnings and Harbor Highlights
Morning
Start your Boston adventure with a hearty breakfast at The Pour House, known for its classic American fare. Afterward, immerse yourself in history with a visit to the Boston Tea Party Ships and Museum Interactive Tour. Experience the events that sparked the American Revolution.
Afternoon
For lunch, head to Porters Bar and Grill and enjoy their pub-style cuisine. Spend your afternoon exploring the Boston Harbor Gourmet Brunch or Dinner Cruise and witness the city's skyline from the water.
Evening
Dine at Bostonia Public House, where you can savor a blend of contemporary and classic dishes. After dinner, take a leisurely stroll along the Boston Harbor Sunset Yacht Cruise and enjoy the city lights reflecting on the harbor.
Bedtime
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Freedom Trail and Culinary Delights
Morning
Begin with a delicious breakfast at The Black Rose, an iconic Irish pub. Then, join a Guided Walking Tour of the Freedom Trail to visit 16 historical sites, including the Massachusetts State House and the Paul Revere House.
Afternoon
Refuel at Five Horses Tavern - South End, known for its craft beer selection and diverse menu. Afterward, explore the marine wonders at the New England Aquarium Skip-the-Line Entry Ticket and witness the vibrant underwater life.
Evening
Experience the vibrant Italian district with Boston's North End Secret Food Tour. Sample the best of the neighborhood's cuisine, from fresh pasta to cannoli. Conclude the evening with a drink at Bleacher Bar, offering a unique view of Fenway Park.
Bedtime
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Harvard, MIT, and Cambridge Charm
Morning
Enjoy a delightful breakfast at Emmets, an Irish pub with a warm atmosphere. Then, take a morning stroll through the prestigious Harvard University campus with a Harvard University Student-Guided Walking Tour.
Afternoon
For lunch, head to The Tip Tap Room and indulge in their diverse menu. Spend your afternoon exploring the innovative exhibits at the Massachusetts Institute of Technology Public Tour and the MIT Museum.
Evening
Dine at Yvonne's, a sophisticated supper club with a touch of mystery. Afterward, take a leisurely walk around the charming streets of Harvard Square and enjoy the vibrant atmosphere.
Bedtime
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Salem's Spooky Stories and Haunted History
Morning
Start your day with breakfast at Solas Irish Pub, offering a cozy ambiance. Then, take a day trip to Salem and join the Ghosts, Witches, & Warlocks Guided Walking Tour to explore the city's eerie past.
Afternoon
Enjoy a lunch at Rock & Rye American Bar, known for its innovative cocktails and American cuisine. Afterward, visit the Salem Witch Museum to gain insight into the infamous Salem witch trials.
Evening
Conclude your Salem visit with the Salem Night Tour Haunt and History Guided Night Tour, where you'll hear chilling tales as you walk through the city's mysterious streets. Return to Boston for a late dinner at Birch Bar, offering a cozy and intimate setting.
Bedtime
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Iconic Landmarks and Culinary Capstone
Morning
Enjoy a delightful breakfast at The White Bull Tavern, known for its warm hospitality. Then, take a guided tour of the iconic Fenway Park, home of the Boston Red Sox, and immerse yourself in the history of this legendary ballpark.
Afternoon
For lunch, head to Back Bay Social and savor their contemporary American cuisine. Afterward, explore the vibrant atmosphere of Faneuil Hall Marketplace and indulge in some shopping and people-watching.
Evening
Conclude your Boston journey with a grand dinner at 21st Amendment, offering a diverse menu in a historic setting. After dinner, take a stroll through the serene Longfellow House (Washington's Headquarters) and reflect on your memorable trip.
Bedtime
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