24 days in Greater Boston Itinerary

24 days in Greater Boston Itinerary

Created using Inspirock Greater Boston route planner

Plan created by another user.Make it yours

Route & dates

Start: Portland
Fly:  8 h 15 min
— 23 nights
Fly:  8 h 15 min
End: Portland


Boston ©
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.
Popular historic sites such as Freedom Trail and Trinity Church are in your itinerary. Museum of Fine Arts and USS Constitution Museum will appeal to museum buffs. Explore Boston's surroundings by going to Ashland State Park (in Ashland), Framingham (Cushing Memorial Park & Cochituate Rail Trail) and Wellesley (Brook Path, Wellesley College Greenhouses, &more). And it doesn't end there: take an in-depth tour of John F. Kennedy Presidential Museum & Library, explore the galleries of The Paul Revere House, walk around Boston Common, and admire the masterpieces at Isabella Stewart Gardner Museum.

For maps, where to stay, more things to do, and tourist information, refer to the Boston driving holiday planner.

Portland to Boston is an approximately 8.5-hour flight. You can also drive; or take a train. You'll lose 3 hours traveling from Portland to Boston due to the time zone difference. In October, daytime highs in Boston are 64°F, while nighttime lows are 50°F. Finish your sightseeing early on the 30th (Fri) so you can travel back home.

Things to do in Boston

Parks Historic Sites Outdoors

Side Trips

Cambridge, Quincy, Wellesley, Framingham, Milton
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail
John F. Kennedy Presidential Museum & Library ©