60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour planner
Make it your trip
Drive
1
Stockbridge
— 7 nights
Drive to Hyannis, MA, Ferry to Nantucket
2
Nantucket
— 10 nights
Ferry
3
Oak Bluffs, Martha's Vineyard
— 8 nights
Ferry to 227 Clinton St., Falmouth, MA, Taxi to Sandwich
4
Sandwich
— 10 nights
Drive
5
Provincetown
— 10 nights
Fly
6
Boston
— 14 nights

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Stockbridge — 7 nights

Stockbridge is a town in Berkshire County in western Massachusetts, United States. Get out of town with these interesting Stockbridge side-trips: Maple Corner Farm Cross Country Ski Area (in Granville), North Adams (Appalachian Trail & MASS MoCA) and Williamstown (Chapin Library of Rare Books and Manuscripts & The Clark Art Institute). The adventure continues: hit the slopes at Ski Butternut, pause for some photo ops at Dr. Seuss National Memorial Sculpture Garden, explore the world behind art at Norman Rockwell Museum, and do a tasting at Balderdash Cellars.

You can plan Stockbridge trip in no time by asking Inspirock to help create your itinerary.

Boston to Stockbridge is an approximately 2.5-hour car ride. You can also take a train; or take a bus. Plan for little chillier temperatures traveling from Boston in February, with highs in Stockbridge at 34°F and lows at 15°F. Finish your sightseeing early on the 8th (Sat) so you can travel to Nantucket.
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Parks · Outdoors · Museums · Winter Sports
Side Trips

Nantucket — 10 nights

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 trip includes some of its best attractions: tee off at Miacomet Golf Club, contemplate the long history of Oldest House (Jethro Coffin House) and Kitchen Garden, enjoy the sea views from Great Point Light, and get to know the fascinating history of Milestone Bog.

Plan my Nantucket trip by asking Inspirock to come up with tips and suggestions.

Traveling by combination of car and ferry from Stockbridge to Nantucket takes 6.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and ferry. Traveling from Stockbridge in February, things will get somewhat warmer in Nantucket: highs are around 40°F and lows about 28°F. Wrap up your sightseeing on the 18th (Tue) early enough to ride a ferry to Oak Bluffs.
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Historic Sites · Parks · Museums · Outdoors

Oak Bluffs, Martha's Vineyard — 8 nights

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: Aquinnah (Aquinnah Lighthouse & Gay Head Lighthouse). There's much more to do: play a few rounds at Farm Neck Golf Club, get lost in a book at Vineyard Haven Public Library, visit West Chop, and stop by Chilmark Chocolates.

For traveler tips, more things to do, photos, and more tourist information, you can read our Oak Bluffs travel app.

Traveling by ferry from Nantucket to Oak Bluffs takes 2 hours. In February, daily temperatures in Oak Bluffs can reach 40°F, while at night they dip to 25°F. Finish your sightseeing early on the 26th (Wed) to allow enough time to travel to Sandwich.
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Parks · Wildlife · Historic Sites · Outdoors
Side Trips

Sandwich — 10 nights

Sandwich is a town in Barnstable County, Massachusetts, United States. You'll find plenty of places to visit near Sandwich: 1699 Historic Winslow House & Cultural Center (in Marshfield), Blake Planetarium (in Plymouth) and Lizzie Borden House (in Fall River). The adventure continues: explore the landscape on two wheels at Shining Sea Bikeway, examine the collection at Heritage Museums & Gardens, explore the engaging exhibits at Cape Cod Children's Museum, and immerse yourself in nature at Nickerson State Park.

For traveler tips, ratings, photos, and more tourist information, use the Sandwich trip planner.

Traveling by combination of ferry and taxi from Oak Bluffs to Sandwich takes 1.5 hours. Alternatively, you can do a combination of ferry and bus. In February, plan for daily highs up to 40°F, and evening lows to 22°F. Wrap up your sightseeing on the 7th (Sat) early enough to drive to Provincetown.
more
Museums · Parks · Historic Sites · Outdoors
Side Trips

Provincetown — 10 nights

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.
Get out of town with these interesting Provincetown side-trips: Orleans (Addison Art Gallery, Jonathan Young Windmill, &more), Eastham (Captain Penniman House, Eastham Historical Society, &more) and Chatham (Pilgrim's Landing, Chatham Railroad Museum, &more). The adventure continues: enjoy the sand and surf at Race Point Beach, see the interesting displays at Provincetown Art Association and Museum, explore the wealth of natural beauty at Cape Cod National Seashore, and tour the pleasant surroundings at Herring Cove Beach.

To find photos, where to stay, and more tourist information, go to the Provincetown trip itinerary app.

Drive from Sandwich to Provincetown in 1.5 hours. Alternatively, you can take a bus. In March in Provincetown, expect temperatures between 41°F during the day and 30°F at night. Finish your sightseeing early on the 17th (Tue) to allow enough time to fly to Boston.
more
Outdoors · Parks · Beaches · Museums
Side Trips

Boston — 14 nights

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 Salem (Salem Maritime National Historic Site, Salem Witch Museum, &more), Louisa May Alcott's Orchard House (in Concord) and Gropius House (in Lincoln). There's still lots to do: stroll around Boston Public Garden, take a stroll around TD Garden, engage your brain at Museum of Science, and get to know the fascinating history of Freedom Trail.

To find more things to do, other places to visit, maps, and tourist information, use the Boston travel route planner.

You can fly from Provincetown to Boston in 2 hours. Alternatively, you can ride a ferry; or drive. In March, daily temperatures in Boston can reach 43°F, while at night they dip to 29°F. Wrap up your sightseeing by early afternoon on the 31st (Tue) to allow enough time to travel back home.
more
Museums · Historic Sites · Parks · Shopping
Side Trips

Massachusetts travel guide

4.3
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.
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