8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner

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Route & dates

8 days in Massachusetts Itinerary

Start: Richmond
Fly:  4​h 45​min
1
Boston
— 2 nights
train:  30​min
2
Salem
— 1 day
Drive:  3​h
3
Provincetown
— 1 night
Drive:  2​h 15​min
4
Nantucket
— 1 night
Drive:  3​h
5
Edgartown, Martha's Vineyard
— 2 nights
+2
Fly + subway + train:  6​h
End: Richmond


Learn more about your trip

2
nights
Boston

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.
Start off your visit on the 6th (Thu): hunt for treasures at Quincy Market.

To see photos, reviews, more things to do, and tourist information, read Boston vacation planner .

Richmond to Boston is an approximately 5-hour combination of flight and bus. You can also do a combination of train, taxi, flight, and bus; or drive. Traveling from Richmond in September, expect nights in Boston to be about the same, around 59°F, while days are slightly colder, around 75°F. Finish your sightseeing early on the 8th (Sat) so you can drive to Salem.

Things to do in Boston

Parks Wildlife Nature

Side Trips

Blue Hills Reservation, Adams National Historical Park
Highlights from your plan
Adams National Historical Park ©
Adams National Historical Park
Blue Hills Reservation ©
Blue Hills Reservation
New England Holocaust Memorial ©
New England Holocaust Memorial

1
day
Salem

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
On the 8th (Sat), identify plant and animal life at Winter Island Park, then look for gifts at Ye Olde Pepper Companie, and then stop by Bewitched in Salem.

Before you visit Salem, use our trip planner to discover what you can do and see there.

Salem is just a short distance from Boston. Traveling from Boston in September, you can expect nighttime temperatures to be little chillier in Salem, with lows of 53°F. Finish your sightseeing early on the 8th (Sat) so you can drive to Provincetown.

Things to do in Salem

Parks Wildlife Shopping
Highlights from your plan
Winter Island Park ©
Winter Island Park
Ye Olde Pepper Companie ©
Ye Olde Pepper Companie
Bewitched in Salem ©
Bewitched in Salem

1
night
Provincetown

Provincetown ©
A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Kick off your visit on the 9th (Sun): see majestic marine mammals with a dolphin and whale watching tour and then stroll through Race Point Beach.

To see reviews, other places to visit, where to stay, and other tourist information, read our Provincetown trip planner .

Traveling by car from Salem to Provincetown takes 3 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus and ferry. In September in Provincetown, expect temperatures between 71°F during the day and 56°F at night. Finish your sightseeing early on the 9th (Sun) to allow enough time to travel to Nantucket.

Things to do in Provincetown

Outdoors Tours Wildlife
Highlights from your plan
Race Point Beach ©
Race Point Beach
Dolphin & Whale Watching

1
night
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 10th (Mon): admire the natural beauty at Oldest House (Jethro Coffin House), steep yourself in history at Greater Light, and then enjoy the sand and surf at Jetties Beach.

To find other places to visit, photos, where to stay, and more tourist information, you can read our Nantucket trip builder tool .

Getting from Provincetown to Nantucket by combination of taxi and ferry takes about 2.5 hours. Other options: do a combination of bus and ferry. In September, daytime highs in Nantucket are 70°F, while nighttime lows are 57°F. Finish up your sightseeing early on the 10th (Mon) so you can travel to Edgartown.

Things to do in Nantucket

Parks Historic Sites Outdoors
Highlights from your plan
Greater Light ©
Greater Light

2
nights
Edgartown, Martha's Vineyard

Edgartown ©
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 11th (Tue), enjoy the sand and surf at Bend in the Road Beach, enjoy the sand and surf at Joseph Sylvia State Beach, and then visit a coastal fixture at Edgartown Lighthouse. Keep things going the next day: kick back and relax at Lucy Vincent Beach and then enjoy the sand and surf at Menemsha Hills.

To see more things to do, where to stay, other places to visit, and more tourist information, go to the Edgartown day trip site .

Getting from Nantucket to Edgartown by combination of flight and bus takes about 3 hours. Other options: do a combination of ferry and bus. In September, plan for daily highs up to 73°F, and evening lows to 53°F. Wrap up your sightseeing on the 12th (Wed) to allow time to travel back home.

Things to do in Edgartown

Parks Outdoors Beaches

Side Trips

Chilmark, Joseph Sylvia State Beach
Highlights from your plan
Menemsha Hills ©
Menemsha Hills
Edgartown Lighthouse ©
Edgartown Lighthouse
Lucy Vincent Beach ©
Lucy Vincent Beach

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