8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

Created using Inspirock Massachusetts vacation maker

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Route & dates

8 days in Massachusetts Itinerary

Start: Charlotte
Fly:  6​h
1
Nantucket
— 1 night
Drive:  2​h 30​min
2
Oak Bluffs, Martha's Vineyard
— 1 night
Drive:  2​h 45​min
3
Provincetown
— 1 night
Drive:  1​h 30​min
4
Plymouth
— 1 day
Train:  1​h
5
Boston
— 3 nights
Train:  45​min
6
Salem
— Few hours
Fly:  5​h 30​min
End: Charlotte

1
night
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. On the 24th (Thu), enjoy the sea views from Sankaty Head Lighthouse.

To see where to stay, photos, ratings, and tourist information, you can read our Nantucket online itinerary maker .

Charlotte to Nantucket is an approximately 6-hour flight. You can also do a combination of flight and ferry; or do a combination of train, bus, and ferry. Traveling from Charlotte in September, expect nights in Nantucket to be about the same, around 59°F, while days are slightly colder, around 71°F. Wrap up your sightseeing on the 25th (Fri) early enough to drive to Oak Bluffs.

Things to do in Nantucket

Historic Sites Museums
Highlights from your plan
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse
Whaling Museum ©
Whaling Museum
Greater Light ©
Greater Light

1
night
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 26th (Sat): enjoy the sand and surf at Inkwell Beach, enjoy the sand and surf at Oak Bluffs Town Beach, visit a coastal fixture at Edgartown Lighthouse, then kick back and relax at Bend in the Road Beach, and finally take a stroll through Martha's Vineyard Camp meeting Association (MVCMA).

To see reviews, maps, more things to do, and other tourist information, you can read our Oak Bluffs trip itinerary planning site .

Getting from Nantucket to Oak Bluffs by car takes about 2.5 hours. Expect a bit cooler evenings in Oak Bluffs when traveling from Nantucket in September, with lows around 54°F. Finish your sightseeing early on the 26th (Sat) so you can drive to Provincetown.

Things to do in Oak Bluffs

Parks Outdoors Beaches

Side Trip

Edgartown
Highlights from your plan
Oak Bluffs Town Beach ©
Oak Bluffs Town Beach
Edgartown Lighthouse ©
Edgartown Lighthouse
Bend in the Road Beach ©
Bend in the Road Beach

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 27th (Sun): grab your bike and head to Province Lands Bike Trail, hike along Cape Cod Provincelands Trail, appreciate the extensive heritage of Wellfleet Bay Wildlife Sanctuary, then visit a coastal fixture at Highland Light, and finally explore the galleries of Pilgrim Monument & Provincetown Museum.

To see more things to do, traveler tips, and tourist information, you can read our Provincetown tour itinerary builder tool .

Traveling by car from Oak Bluffs to Provincetown takes 3 hours. In September, daily temperatures in Provincetown can reach 71°F, while at night they dip to 57°F. Cap off your sightseeing on the 28th (Mon) early enough to go by car to Plymouth.

Things to do in Provincetown

Parks Trails Outdoors

Side Trips

Wellfleet Bay Wildlife Sanctuary, Highland Light
Highlights from your plan
Cape Cod Provincelands Trail ©
Cape Cod Provincelands Trail
Wellfleet Bay Wildlife Sanctuary ©
Wellfleet Bay Wildlife Sanctuary
Highland Light ©
Highland Light

1
day
Plymouth

Plymouth ©
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.
Start off your visit on the 28th (Mon): explore the different monuments and memorials at Burial Hill, steep yourself in history at Mayflower II, then steep yourself in history at Plymouth Rock, then steep yourself in history at Jabez Howland House, and finally get engrossed in the history at Pilgrim Hall Museum.

Plan trip to Plymouth with our itinerary maker to find out where to go and what to do.

Getting from Provincetown to Plymouth by car takes about 1.5 hours. Other options: take a bus; or do a combination of ferry and bus. In September, daily temperatures in Plymouth can reach 75°F, while at night they dip to 55°F. Wrap up your sightseeing on the 28th (Mon) early enough to take a train to Boston.

Things to do in Plymouth

Historic Sites Museums
Highlights from your plan
Burial Hill ©
Burial Hill
Pilgrim Hall Museum ©
Pilgrim Hall Museum
Mayflower II ©
Mayflower II

3
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.
Minute Man National Historical Park and Hancock-Clarke House will appeal to history buffs. Your cultural itinerary includes sights like Adams National Historical Park and Lexington Green. Step out of Boston to go to Sutton and see Purgatory Chasm State Reservation, which is approximately 1h 10 min away. And it doesn't end there: explore the different monuments and memorials at Sleepy Hollow Cemetery, steep yourself in history at Saugus Iron Works, ponder the world of politics at Old State House, and take in the architecture and atmosphere at King's Chapel.

To find more things to do, traveler tips, other places to visit, and other tourist information, read Boston trip planner .

Getting from Plymouth to Boston by train takes about an hour. Other options: drive; or take a bus. In September, plan for daily highs up to 75°F, and evening lows to 59°F. Wrap up your sightseeing by early afternoon on the 1st (Thu) to allow enough time to take a train to Salem.

Things to do in Boston

Historic Sites Parks Nature

Side Trips

Concord, Lexington, Saugus Iron Works, Purgatory Chasm State Reservation, Adams National Historical Park
Highlights from your plan
Minute Man National Historical Park ©
Adams National Historical Park ©
Adams National Historical Park
Sleepy Hollow Cemetery ©
Sleepy Hollow Cemetery

few
hours
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.
Start off your visit on the 1st (Thu): admire the landmark architecture of Ropes Mansion and then contemplate the long history of The Custom House.

For where to stay, more things to do, ratings, and tourist information, refer to the Salem travel route planner .

Traveling by train from Boston to Salem takes an hour. Alternatively, you can drive; or take a bus. Plan for little chillier nights when traveling from Boston in October since evenings lows in Salem dip to 45°F. Wrap up your sightseeing on the 1st (Thu) early enough to travel back home.

Things to do in Salem

Historic Sites
Highlights from your plan
The Custom House ©
The Custom House
Ropes Mansion ©
Ropes Mansion

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