31 days in Massachusetts Itinerary

31 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip builder

Make it your trip
Fly
1
Boston
— 9 nights
Fly
2
Provincetown
— 6 nights
Drive
3
Sandwich
— 6 nights
Taxi to Hyannis, MA, Ferry to Nantucket
4
Nantucket
— 5 nights
Ferry
5
Oak Bluffs, Martha's Vineyard
— 4 nights
Fly

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Boston

— 9 nights

Beantown

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.
Do your shopping at Faneuil Hall Marketplace and When Pigs Fly Company Store. Freedom Trail and Marginal Way Walkway will appeal to history buffs. You'll find plenty of places to visit near Boston: World's End (in Hingham), Concord (Louisa May Alcott's Orchard House, Minuteman National Park - Old North Bridge, &more) and Salem Food Tours (in Salem). There's still lots to do: get to know the fascinating history of HarborWalk, explore the different monuments and memorials at Mount Auburn Cemetery, steep yourself in history at Copp's Hill Burying Ground, and get engrossed in the history at Hancock-Clarke House.

To find maps, traveler tips, more things to do, and other tourist information, read our Boston route maker site.

Los Angeles to Boston is an approximately 7-hour flight. You can also drive; or take a bus. You'll lose 3 hours traveling from Los Angeles to Boston due to the time zone difference. June in Boston sees daily highs of 76°F and lows of 60°F at night. Cap off your sightseeing on the 23rd (Wed) early enough to catch the flight to Provincetown.

Things to do in Boston

Historic Sites · Museums · Parks · Outdoors

Side Trips

Provincetown

— 6 nights

Birthplace of American Liberty

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.
Give yourself a bit of retail therapy at Marine Specialties and Cortile Gallery. Take a break from the city and head to Herring Cove Beach and First Encounter Beach. Explore Provincetown's surroundings by going to Orleans (Church of the Transfiguration & Rock Harbor Marsh), Marconi Wireless Station (in Wellfleet) and Eastham (Nauset Light Beach, Nauset Lighthouse, &more). The adventure continues: kick back and relax at Head of the Meadow Beach, delve into the lush surroundings at Beech Forest, Provincetown, appreciate the history behind Pilgrim Monument & Provincetown Museum, and tour the pleasant surroundings at Cape Cod National Seashore.

Plan a Provincetown trip in moments using our itinerary builder.

Getting from Boston to Provincetown by flight takes about 2 hours. Other options: ride a ferry; or drive. In June in Provincetown, expect temperatures between 72°F during the day and 56°F at night. Finish your sightseeing early on the 29th (Tue) to allow enough time to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Sandwich

— 6 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. You'll explore the less-touristy side of things at Hyannis Whale Watcher Cruises and Colt State Park. Get some cultural insight at Heritage Museums & Gardens and Burial Hill. Venture out of the city with trips to Kalmus Beach (in Hyannis), Bristol (Linden Place Mansion & Herreshoff Marine Museum) and Oak Grove Cemetery (in Fall River). And it doesn't end there: admire the masterpieces at Sandwich Glass Museum, stroll through Shining Sea Bikeway, contemplate the long history of National Monument to the Forefathers, and contemplate in the serene atmosphere at Seamen's Bethel.

For photos, ratings, other places to visit, and more tourist information, read our Sandwich trip planner.

Getting from Provincetown to Sandwich by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 73°F in June, and nighttime lows around 55°F. Wrap up your sightseeing on the 5th (Mon) early enough to travel to Nantucket.

Things to do in Sandwich

Historic Sites · Parks · Outdoors · Museums

Side Trips

Nantucket

— 5 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Get some historical perspective at Sankaty Head Lighthouse and Greater Light. Get outdoors at Madaket Beach and Surfside Beach. The adventure continues: tour the pleasant surroundings at Jetties Beach, steep yourself in history at Quaker Meeting House, get engrossed in the history at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum, and get to know the fascinating history of Altar Rock.

To find traveler tips, reviews, more things to do, and tourist information, you can read our Nantucket trip itinerary builder tool.

Do a combination of taxi and ferry from Sandwich to Nantucket in 2 hours. Alternatively, you can do a combination of bus and ferry. In July in Nantucket, expect temperatures between 76°F during the day and 64°F at night. Finish your sightseeing early on the 10th (Sat) so you can ride a ferry to Oak Bluffs.

Things to do in Nantucket

Historic Sites · Outdoors · Museums · Parks

Oak Bluffs, Martha's Vineyard

— 4 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. You'll explore the less-touristy side of things at Martha's Vineyard Camp meeting Association (MVCMA) and Aquinnah Cliffs. Escape the urban bustle at Katama Beach/ South Beach and Joseph Sylvia State Beach. When in Oak Bluffs, make a side trip to see Menemsha Hills in Chilmark, approximately Chilmark away. Next up on the itinerary: visit a coastal fixture at Edgartown Lighthouse, contemplate the long history of Vincent House Museum, stroll through Oak Bluffs Town Beach, and enjoy the sand and surf at Norton Point Beach.

To find ratings, reviews, maps, and other tourist information, read our Oak Bluffs road trip website.

Traveling by ferry from Nantucket to Oak Bluffs takes 2 hours. In July, daily temperatures in Oak Bluffs can reach 79°F, while at night they dip to 63°F. Finish your sightseeing early on the 14th (Wed) so you can fly back home.

Things to do in Oak Bluffs

Parks · Outdoors · Beaches · Wildlife

Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
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.