14 days in Massachusetts Itinerary

14 days in Massachusetts Itinerary

Created using Inspirock Massachusetts visit planner
Make it your trip
Fly
1
Boston
— 4 nights
Drive
2
Truro
— 2 nights
Drive
3
Falmouth
— 4 nights
Drive
4
Williamsburg
— 1 night
Drive
5
Boston
— 2 nights
Fly

S M T W T F S
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Boston — 4 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year.
Let the collections at Museum of Fine Arts and Buckman Tavern capture your imagination. Visiting Dolphin & Whale Watching and Long Sands Beach will get you outdoors. You'll find plenty of places to visit near Boston: Ogunquit (Ogunquit Beach & Marginal Way Walkway), Hampton Beach State Park (in Hampton) and Louisa May Alcott's Orchard House (in Concord). It doesn't end there: appreciate the extensive heritage of Freedom Trail.

To see traveler tips, maps, more things to do, and tourist information, you can read our Boston day trip planning website.

San Francisco to Boston is an approximately 7-hour flight. You can also drive; or do a combination of subway, train, and bus. Traveling from San Francisco to Boston, you'll lose 3 hours due to the time zone difference. Plan for a bit warmer temperatures traveling from San Francisco in July, with highs in Boston at 83°F and lows at 67°F. Finish your sightseeing early on the 5th (Fri) so you can drive to Truro.
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Outdoors · Beaches · Parks · Historic Sites
Side Trips
Find places to stay Jul 1 — 5:

Truro — 2 nights

Truro is a town in Barnstable County, Massachusetts, United States, comprising two villages: Truro and North Truro. Kick off your visit on the 6th (Sat): cast your line with a fishing tour, then trek along Pilgrim Spring Trail, and then enjoy the sea views from Highland Light. On the 7th (Sun), you'll have a packed day of sightseeing: enjoy the sand and surf at Head of the Meadow Beach, stroll through Corn Hill Beach, and then take an in-depth tour of Truro Historical Museum.

To find reviews, more things to do, where to stay, and tourist information, you can read our Truro vacation planner.

Drive from Boston to Truro in 2 hours. In July in Truro, expect temperatures between 79°F during the day and 64°F at night. Finish your sightseeing early on the 7th (Sun) to allow enough time to drive to Falmouth.
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Outdoors · Parks · Beaches · Tours
Find places to stay Jul 5 — 7:

Falmouth — 4 nights

Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Museum-lovers will get to explore Heritage Museums & Gardens and Highfield Hall & Gardens. Your cultural itinerary includes sights like Plimoth Patuxet Museums and Plymouth Rock. Change things up with these side-trips from Falmouth: Dolphin & Whale Watching (in Plymouth) and Craigville Beach (in Centerville). And it doesn't end there: grab your bike and head to Shining Sea Bikeway, engage your brain at Sandwich Glass Museum, and kick back and relax at Old Silver Beach.

To find other places to visit, maps, where to stay, and other tourist information, read our Falmouth vacation planner.

You can drive from Truro to Falmouth in 1.5 hours. July in Falmouth sees daily highs of 80°F and lows of 64°F at night. Finish your sightseeing early on the 11th (Thu) so you can drive to Williamsburg.
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Outdoors · Parks · Museums · Beaches
Side Trips
Find places to stay Jul 7 — 11:

Williamsburg — 1 night

Williamsburg is a town in Hampshire County, Massachusetts, United States. On the 11th (Thu), steep yourself in history at Historic Deerfield and then identify plant and animal life at Magic Wings Butterfly Conservatory and Gardens.

To plan Williamsburg vacation without wasting time, ask Inspirock to design an itinerary.

You can drive from Falmouth to Williamsburg in 3 hours. Expect a daytime high around 85°F in July, and nighttime lows around 63°F. Finish your sightseeing early on the 12th (Fri) so you can drive to Boston.
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Parks · Wildlife · Nature · Historic Sites
Side Trips
Find places to stay Jul 11 — 12:

Boston — 2 nights

Beantown

Kick off your visit on the 13th (Sat): explore the world behind art at Peabody Essex Museum, contemplate the long history of The House of the Seven Gables, and then take an in-depth tour of USS Constitution Museum. Keep things going the next day: take an in-depth tour of Boston Tea Party Ships & Museum, then take an in-depth tour of John F. Kennedy Presidential Museum & Library, then pause for some serene contemplation at Old North Church & Historic Site, and finally take a stroll through North End.

For photos, traveler tips, reviews, and more tourist information, read our Boston trip planner.

Getting from Williamsburg to Boston by car takes about 2 hours. Wrap up your sightseeing on the 14th (Sun) early enough to fly back home.
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Side Trip
Find places to stay Jul 12 — 14:

Massachusetts travel guide

4.3
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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