10 days in Massachusetts Itinerary

10 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour planner
Make it your trip
— 1 day
— 3 nights
Drive to Woods Hole, Ferry to Martha's Vineyard, Drive to Edgartown
— 2 nights
— 4 nights


Boston — 1 day

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.
On the 20th (Mon), admire the masterpieces at Museum of Fine Arts, then stroll around Boston Public Garden, and then appreciate the extensive heritage of Freedom Trail.

For reviews and more tourist information, refer to the Boston day trip planner.

The Route module shows you all the different ways you can get to Boston. June in Boston sees daily highs of 76°F and lows of 60°F at night. Finish up your sightseeing early on the 20th (Mon) so you can go by car to Plymouth.
Museums · Parks · Historic Sites

Plymouth — 3 nights

Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Kick off your visit on the 21st (Tue): see the interesting displays at Heritage Museums & Gardens, see majestic marine mammals with Hyannis Whale Watcher Cruises, and then contemplate the long history of Hoxie House. Get ready for a full day of sightseeing on the 22nd (Wed): get engrossed in the history at The Jenney, take an in-depth tour of Plimoth Patuxet Museums, then contemplate the long history of Mayflower II, and finally appreciate the history behind Plymouth Rock.

To see ratings, photos, traveler tips, and more tourist information, read Plymouth trip planner.

Drive from Boston to Plymouth in an hour. Alternatively, you can take a train; or take a bus. Expect a daytime high around 76°F in June, and nighttime lows around 56°F. Finish up your sightseeing early on the 23rd (Thu) so you can travel to Edgartown.
Museums · Outdoors · Tours · Wildlife
Side Trips

Edgartown — 2 nights

Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 23rd (Thu): kick back and relax at Menemsha Public Beach, take in the dramatic natural features at Aquinnah Cliffs, and then kick back and relax at Katama Beach/ South Beach. On the 24th (Fri), you'll have a packed day of sightseeing: stop by Martha's Vineyard Camp meeting Association (MVCMA), then admire the landmark architecture of Trinity Park Tabernacle, then admire the natural beauty at Mytoi, and finally head off the coast to Chappaquiddick.

For more things to do, traveler tips, photos, and more tourist information, go to the Edgartown trip planner.

You can do a combination of car and ferry from Plymouth to Edgartown in 2.5 hours. Another option is to do a combination of bus and ferry. In June, daily temperatures in Edgartown can reach 73°F, while at night they dip to 54°F. Finish up your sightseeing early on the 25th (Sat) so you can catch the flight to Worcester.
Parks · Outdoors · Historic Sites · Beaches
Side Trips

Worcester — 4 nights

Worcester is a city and the county seat of Worcester County, Massachusetts, United States. Step out of the city life by going to Elizabeth Park and Zipline. Change things up with these side-trips from Worcester: Gillette Castle State Park (in East Haddam), Six Flags New England (in Agawam) and Bridge of Flowers (in Shelburne Falls). And it doesn't end there: browse the exhibits of The Mark Twain House & Museum, test your team's savvy at popular escape rooms, identify plant and animal life at Broad Brook Meadow Conservation Area, and appreciate the history behind Massachusetts Vietnam Veterans Memorial.

To find where to stay, maps, traveler tips, and other tourist information, use the Worcester trip maker app.

Fly from Edgartown to Worcester in 2.5 hours. Alternatively, you can do a combination of car and ferry; or drive. June in Worcester sees daily highs of 75°F and lows of 56°F at night. Wrap up your sightseeing on the 29th (Wed) early enough to drive to Boston.
Parks · Museums · Outdoors · Historic Sites
Side Trips


To see other places to visit, ratings, reviews, and tourist information, read Boston planning site.

You can drive from Worcester to Boston in an hour. Other options are to take a bus; or take a train. You will leave for home on the 29th (Wed).
Parks · Outdoors · Tours · Museums

Massachusetts travel guide

History Museums · Art Museums · Nightlife
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.