52 days in Massachusetts Itinerary

52 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

Plan created by another user. Make it yours
1
Boston
— 19 nights
2
Provincetown
— 7 nights
3
Sandwich
— 6 nights
4
Oak Bluffs, Martha's Vineyard
— 6 nights
5
Nantucket
— 7 nights
6
Lenox
— 6 nights

19
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.
Venture out of the city with trips to Corporation Beach (in Dennis), Parkers River Beach (in West Yarmouth) and Salem (Salem Witch Trials Memorial, The House of the Seven Gables, &more). There's lots more to do: admire the masterpieces at Museum of Fine Arts, admire the natural beauty at Boston Public Garden, take an in-depth tour of Boston Tea Party Ships & Museum, and appreciate the extensive heritage of Freedom Trail.

To find maps, more things to do, photos, and other tourist information, use the Boston driving holiday planning site.

Hartford to Boston is an approximately 2-hour car ride. You can also take a bus; or take a train. In June, daily temperatures in Boston can reach 76°F, while at night they dip to 60°F. Finish your sightseeing early on the 29th (Mon) to allow enough time to ride a ferry to Provincetown.

Things to do in Boston

Museums · Historic Sites · Parks

Side Trips

Cambridge, Salem, Concord, Gloucester, Rockport
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

7
nights
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.
Change things up with these side-trips from Provincetown: Chatham (Monomoy National Wildlife Refuge & Chatham's Godfrey Windmill), Eastham (Captain Penniman House, Coast Guard Beach, &more) and Nauset Beach (in Orleans). And it doesn't end there: pause for some photo ops at Pilgrim Monument & Provincetown Museum, stroll through Herring Cove Beach, hike along Cape Cod Provincelands Trail, and enjoy the sand and surf at Race Point Beach.

To find where to stay, more things to do, traveler tips, and other tourist information, go to the Provincetown road trip website.

Traveling by ferry from Boston to Provincetown takes 2.5 hours. Alternatively, you can fly; or drive. In June, daily temperatures in Provincetown can reach 72°F, while at night they dip to 56°F. Finish your sightseeing early on the 6th (Mon) to allow enough time to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches

Side Trips

Eastham, Truro, Chatham, Wellfleet, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©
Pilgrim Monument & Provincetown Museum
Race Point Beach ©
Race Point Beach

6
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Change things up with these side-trips from Sandwich: New Bedford (Fort Taber Park, New Bedford Whaling Museum, &more), Nobska Point Lighthouse (in Woods Hole) and Falmouth (Highfield Hall & Gardens, Eight Cousins Bookshop, &more). There's still lots to do: see the interesting displays at Heritage Museums & Gardens, don't miss a visit to Old King's Hwy, take an in-depth tour of The Jenney, and appreciate the history behind Plymouth Rock.

For ratings, more things to do, reviews, and more tourist information, you can read our Sandwich itinerary planner.

Getting from Provincetown to Sandwich by car takes about 1.5 hours. Other options: take a bus. In July, plan for daily highs up to 80°F, and evening lows to 64°F. Finish your sightseeing early on the 12th (Sun) to allow enough time to travel to Oak Bluffs.

Things to do in Sandwich

Museums · Parks · Outdoors

Side Trips

Falmouth, Hyannis, Plymouth, New Bedford, Cape Cod Children's Museum
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum
Plimoth Plantation ©
Plimoth Plantation

6
nights
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. You'll find plenty of places to visit near Oak Bluffs: Chappaquiddick (in Edgartown), Menemsha Hills (in Chilmark) and Gay Head Lighthouse (in Aquinnah). There's lots more to do: make a trip to Flying Horses Carousel, tee off at Farm Neck Golf Club, visit Martha's Vineyard Camp meeting Association (MVCMA), and kick back and relax at Katama Beach/ South Beach.

For maps, more things to do, where to stay, and other tourist information, use the Oak Bluffs travel planner.

Traveling by combination of taxi and ferry from Sandwich to Oak Bluffs takes 1.5 hours. Expect a daytime high around 79°F in July, and nighttime lows around 63°F. Finish your sightseeing early on the 18th (Sat) so you can ride a ferry to Nantucket.

Things to do in Oak Bluffs

Parks · Outdoors · Beaches

Side Trips

Edgartown, Chilmark, West Tisbury, Aquinnah
Highlights from your plan
Mytoi ©
Mytoi
Flying Horses Carousel ©
Flying Horses Carousel
Trinity Park Tabernacle ©
Trinity Park Tabernacle

7
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your plan includes some of its best attractions: enjoy the sand and surf at Jetties Beach, take in nature's colorful creations at Oldest House (Jethro Coffin House) and Kitchen Garden, enjoy the sea views from Great Point Light, and tour the pleasant surroundings at Madaket Beach.

To find maps, more things to do, photos, and other tourist information, you can read our Nantucket trip itinerary builder tool.

You can ride a ferry from Oak Bluffs to Nantucket in 2 hours. In July, daytime highs in Nantucket are 76°F, while nighttime lows are 64°F. Finish your sightseeing early on the 25th (Sat) so you can travel to Lenox.

Things to do in Nantucket

Outdoors · Historic Sites · Parks
Highlights from your plan
Jetties Beach ©
Jetties Beach

6
nights
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Venture out of the city with trips to Westfield (Stanley park & Grandmother's Garden), Springfield (Springfield Museums & Watershops Pond) and Whiting Street Reservoir (in Holyoke). And it doesn't end there: explore the world behind art at Norman Rockwell Museum, get lost in a book at Chapin Library of Rare Books and Manuscripts, steep yourself in history at The Mount, Edith Wharton's Home, and take a memorable drive along Concepts of Art Lenox Judaica.

For traveler tips, maps, other places to visit, and tourist information, use the Lenox trip itinerary planning website.

Traveling by combination of ferry and car from Nantucket to Lenox takes 5.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of ferry and bus. Traveling from Nantucket in July, Lenox is a bit cooler at night with lows of 59°F. Wrap up your sightseeing by early afternoon on the 31st (Fri) to allow enough time to drive back home.

Things to do in Lenox

Parks · Museums · Outdoors

Side Trips

Westfield, Williamstown, Springfield, Stockbridge, Mohawk Trail
Highlights from your plan
Stanley park ©
Stanley park
Norman Rockwell Museum ©
Norman Rockwell Museum
The Clark Art Institute ©
The Clark Art Institute

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