8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

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Route & dates

8 days in Massachusetts Itinerary

Start: San Jose
Drive:  12​h
1
Provincetown
— 3 nights
ferry:  1​h 30​min
2
Boston
— 3 nights
Fly:  10​h
End: San Jose

3
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.
Your cultural itinerary includes sights like Edward Gorey House and Captain Bangs Hallet House Museum. Appreciate the collections at Pilgrim Monument & Provincetown Museum and Provincetown Art Association and Museum. Venture out of the city with trips to Church of the Transfiguration (in Orleans) and Chatham (Monomoy National Wildlife Refuge & Ducks in the Window). Next up on the itinerary: enjoy the sand and surf at Cape Cod National Seashore, stroll through Race Point Beach, and identify plant and animal life at Wildlife Areas.

To see other places to visit, reviews, ratings, and tourist information, go to the Provincetown trip planner .

San Jose, Costa Rica to Provincetown is an approximately 12-hour combination of flight, bus, and ferry. You can also do a combination of bus, flight, and ferry; or drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Expect colder temperatures when traveling from San Jose in December; daily highs in Provincetown reach 7°C and lows reach 1°C. Finish your sightseeing early on the 7th (Fri) to allow enough time to ride a ferry to Boston.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Chatham, Yarmouth Port, Church of the Transfiguration, Cape Cod National Seashore
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Edward Gorey House ©
Edward Gorey House
Race Point Beach ©
Race Point Beach

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.
Your inner history buff will appreciate Freedom Trail and Trinity Church. Head to Faneuil Hall Marketplace and Brookline Booksmithfor some retail therapy. There's lots more to do: explore the world behind art at Museum of Fine Arts, stop by Harvard Book Store, take a stroll through North End, and shop like a local with Newbury Street.

To find photos, where to stay, reviews, and more tourist information, go to the Boston driving holiday planning site .

Ride a ferry from Provincetown to Boston in 1.5 hours. Alternatively, you can do a combination of flight and bus; or drive. In December, daytime highs in Boston are 7°C, while nighttime lows are 0°C. On the 10th (Mon), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Boston

Historic Sites Shopping Neighborhoods

Side Trips

Brookline Booksmith, Harvard Book Store
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail
Fenway Park ©
Fenway Park

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