Boston Itinerary 5 Days

Best Itineraries for 5 Day Trip to Boston

Recent Itineraries: Boston Trips for 5 Days

Make your travel planning easier by using these perfect 5 days in Boston itineraries from our users and travel experts. Look out for wisely chosen places you would like to explore during 5 days in Boston.

Boston Itinerary 5 Days

Presenting visitors with an eclectic mix of history, heritage, and gastronomy, Boston is a fascinating city in Massachusetts. A city that has witnessed the American Revolution, Boston today stands tall as a popular tourist destination in the United States. Romance history, relax amidst natural beauty and shop to your heart’s content in this tourist hub. Go through this Boston itinerary 5 days to plan a memorable holiday in this vibrant city.

Day 1 and 2 in Boston

Boston Freedom trail, perhaps the most popular tourist attraction in Boston, is a 2.5-mile-long red-lined route that takes you around 16 historically significant sites in the city. Presenting you with the perfect opportunity to acquaint yourselves with the rich history of American Revolution, this trail which begins from Boston Common and ends at the Bunker Hill Monument in Charlestown guides you through museums, meetinghouses, churches, and burying grounds.

Dating from 1634, Boston Common is the oldest city park in the United States. It is the central public park which is also the starting point of the Boston Freedom Trail. Boston Common has been a stage for free speech and public assembly throughout history. Housing softball fields, the Frog Pond, trees, fountains and statuary, this park is now a recreational spot for locals and tourists alike.

Trinity Church located in Copley Square is a parish of the Episcopal Diocese of Massachusetts. Historically considered a Broad-Church parish, the church is an architecturally stunning piece of work. Resting over 4,000 wooden piles that were put to strengthen the foundation of the church, the monument was designed by Henry Hobson Richardson in a Richardsonian Romanesque style.

Day 3, 4 and 5 in Boston

John F Kennedy Presidential Library and Museum is not just the official repository for original papers and correspondence of the Kennedy Administration but also the place which exhibits a collection of various artifacts, videos and rare photos of the 35th President of the United States. A visit to this place will give you a glimpse into the various aspects of the personal life and political career of Kennedy.

If you are interested to know more about alcoholic beverages and especially beer, then you can always plan to visit the Samuel Adams brewery. For the past 30 years, the brewery has been delivering best quality beers. Using modern technology and maintaining the pioneering quality, this brewery produces its popular beers.

A historical tour in amphibious animal shaped vehicles… this is a kid’s Neverland. Within a couple of hours filled with information and bad jokes told by the "conDUCKtors", the tour will take you around the best landmarks of Boston.

Harpoon Brewery & Beer Hall is where the beer happens. If you don’t mind that beer belly or beer is your favorite drink, then you’re sure to have a ball at this brewery.

Best Hotels in Boston for 5 Day Trip

These are some of the hotels added in the past by our travelers to their Boston itinerary 5 days. Check out the hotels that suit you and add them to your trip plan.

Looking for a Shorter or Longer Itineraries for Boston

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