5 days in Massachusetts Itinerary

5 days in Massachusetts Itinerary

Created using Inspirock Massachusetts vacation maker

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Boston
— 4 nights
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Boston

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Deepen your sense of the past at sights like Freedom Trail and Minuteman National Park - Old North Bridge. Satisfy your inner culture vulture at Museum of Fine Arts and North End. Get out of town with these interesting Boston side-trips: Salem (Peabody Essex Museum, The House of the Seven Gables, &more), Louisa May Alcott's Orchard House (in Concord) and Dolphin & Whale Watching (in Gloucester). There's much more to do: get engrossed in the history at John F. Kennedy Presidential Museum & Library, get a sense of history and politics at Old State House, walk around Boston Public Garden, and admire the masterpieces at Isabella Stewart Gardner Museum.

To see traveler tips, more things to do, reviews, and more tourist information, use the Boston visit planning website.

Indianapolis to Boston is an approximately 5.5-hour flight. You can also drive; or take a bus. Expect a daytime high around 64°F in October, and nighttime lows around 50°F. Wrap up your sightseeing on the 21st (Wed) early enough to travel back home.

Things to do in Boston

Museums · Historic Sites · Parks · Outdoors

Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.