How many days do you need in Boston?

This itinerary covers 5 days in Boston, which is a great amount of time to explore the main highlights. Depending on your pace and interests, you could extend or shorten the trip.

What is the best itinerary for Boston?

Plan your perfect 5 days trip to Boston. This detailed travel itinerary includes daily activities, local recommendations, and insider tips to make your journey unforgettable.

Boston: 5-Day City Experience Itinerary

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Boston: 5-Day City Experience Itinerary

Day 1: Freedom Trail

Start at Boston Common, 10:00 AM

1.8 miles, 2 hours

Walk the famous Freedom Trail and visit historic sites from the American Revolution. Highlights include Boston Common, Massachusetts State House, Paul Revere House, and Bunker Hill Monument.
Day 2: Seaport District

Start at Institute of Contemporary Art, 10:00 AM

2.3 miles, 3 hours

Explore Boston's trendy Seaport District, also known as the Innovation District. Visit the Institute of Contemporary Art, walk along the HarborWalk, and enjoy a seafood lunch at Row 34.
Day 3: Fenway/Kenmore

Start at Fenway Park, 11:00 AM

2.5 miles, 3 hours

Experience Boston's sports culture with a behind-the-scenes tour of Fenway Park, the oldest Major League ballpark in America. Afterwards, head to the nearby Kenmore Square for a beer at the iconic Cheers bar.
Day 4: Back Bay

Start at Boston Public Library, 11:00 AM

1.8 miles, 2 hours

Stroll through picturesque Back Bay and admire its Victorian brownstones and high-end shopping district. Visit the Boston Public Library and Trinity Church before indulging in a sweet treat at Flour Bakery.
Day 5: North End

Start at Paul Revere House, 10:00 AM

1.6 miles, 2 hours

Experience Boston's Italian heritage with a visit to the historic North End neighborhood. Highlights include Paul Revere House, Old North Church, and the best cannolis in town from Mike's Pastry.

Time and Cost Estimates

Boston Common (2 hours, free)
Massachusetts State House (30 minutes, free)
Paul Revere House (30 minutes, $5)
Bunker Hill Monument (1 hour, free)
Institute of Contemporary Art (1.5 hours, $15)
HarborWalk (1 hour, free)
Row 34 (1 hour, $30)
Fenway Park (1 hour, $25)
Cheers bar (1 hour, $20)
Boston Public Library (1 hour, free)
Trinity Church (30 minutes, free)
Flour Bakery (30 minutes, $10)
Paul Revere House (30 minutes, $5)
Old North Church (30 minutes, $8)
Mike's Pastry (30 minutes, $10)
Total Estimated Costs: $138

Useful Tips

If you have more time, consider taking a day trip to Salem or Cambridge to visit Harvard University. If you have less time, skip the Fenway/Kenmore and Back Bay neighborhoods and spend more time on the Freedom Trail and in the North End.

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