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🇺🇸United States of America

Three days in Boston
3 day travel itinerary

by TripMapper

Historically significant, abundantly cultured and passionately about sport!

3 Days
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As one of the oldest cities in the United States, Boston offers a rich tapestry of experiences that range from exploring revolutionary landmarks to enjoying its thriving arts scene and renowned educational institutions.

The city played a pivotal role in the American Revolution, and visitors can walk the Freedom Trail, a red-brick path that leads to key historical sites like the Massachusetts State House, Paul Revere's House, and the Old North Church.

The city's prestigious universities and colleges contribute to its intellectual and cultural dynamism. Home to Harvard University and MIT, among others, Boston has a youthful energy that fuels its arts, innovation, and research scenes.

Beneath its historical façade, Boston buzzes with modern life and cultural diversity. Neighbourhoods like Beacon Hill exude classic charm, while districts like the Seaport and the Innovation District showcase the city's progressive spirit.

Boston's culinary landscape is another highlight. From clam chowder and lobster rolls to farm-to-table dining experiences, the city offers a delectable journey through New England flavours. Historic Faneuil Hall Marketplace and the North End, Boston's Little Italy, are both culinary havens where you can savour local delicacies.

Whether attending a Red Sox game at Fenway Park, exploring bustling markets, or soaking in the views along the Charles River Esplanade, Boston offers a perfect blend of historical significance and contemporary charm.

Use TripMapper as your trip organizer. If you are in need of a little inspiration to get you started click 'Customise' to use our interactive Boston itinerary (below) for the best things to see and do in Boston - then customise to make your own!

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* Please check all relevant government guidance prior to, and during, your travels. Please also check any opening & closing times for all establishments contained within our itinerary. Find our Terms of Service here.

Itinerary Highlights

  • Immerse yourself in American history by walking the Freedom Trail, a red-brick path that connects 16 historically significant sites.
  • Explore the iconic Faneuil Hall Marketplace, a historic meeting hall turned vibrant shopping and dining hub. Adjacent to Faneuil Hall, Quincy Market offers many food vendors and local specialities.
  • Wander through the charming North End, Boston's Little Italy. Discover narrow streets lined with Italian restaurants, bakeries, and historic sites.
  • Enjoy a scenic ride along the Charles River Esplanade. Rent a bike and soak in picturesque views of the water, Boston's skyline, and the lush parks that line the riverbank.
  • Visit Boston Common, the oldest public park in the country, and enjoy its green spaces.
  • Indulge in lunch and shopping along Newbury Street, a stylish boulevard lined with boutiques, cafes, and restaurants. Explore a mix of high-end fashion and unique local finds.
  • Attend a Red Sox game at the iconic Fenway Park.
  • Venture to nearby Cambridge and explore Harvard University, one of the world's most prestigious institutions.
  • Discover the modern Seaport District, a revitalized waterfront area featuring contemporary architecture, art installations, shops, restaurants, and waterfront parks.