8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour itinerary planner
Make it your trip
— 1 day
— 1 night
Taxi to Harwich Port, Harwich, MA, Ferry to Nantucket
— 3 nights
Oak Bluffs, Martha's Vineyard
— 3 nights


Boston — 1 day

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.
Start off your visit on the 19th (Tue): ponder the world of politics at Old State House, then take in nature's colorful creations at Boston Public Garden, and then buy something for everyone on your list at Faneuil Hall Marketplace.

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

Los Angeles to Boston is an approximately 7-hour flight. You can also drive; or take a bus. The time zone changes from Pacific Standard Time to Eastern Standard Time, which is usually a 3 hour difference. July in Boston sees daily highs of 83°F and lows of 67°F at night. Wrap up your sightseeing on the 19th (Tue) to allow time to drive to Chatham.
Parks · Shopping · Historic Sites · Museums

Chatham — 1 night

Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. On the 20th (Wed), get engrossed in the history at Atwood Museum, enjoy the sand and surf at Chatham Lighthouse Beach, then examine the collection at Chatham Railroad Museum, and finally look for gifts at Chatham Pier and Fish Market.

For photos, reviews, and other tourist information, you can read our Chatham trip itinerary builder.

Traveling by car from Boston to Chatham takes 2 hours. Alternatively, you can take a bus. In July in Chatham, expect temperatures between 79°F during the day and 65°F at night. Cap off your sightseeing on the 20th (Wed) early enough to travel to Nantucket.
Beaches · Parks · Shopping · Outdoors

Nantucket — 3 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Do some cultural sightseeing at Sankaty Head Lighthouse and Nantucket Shipwreck & Lifesaving Museum. Explore hidden gems such as Jetties Beach and Surfside Beach. There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, stroll through Siasconset Beach, and examine the collection at Nantucket Lightship Basket Museum.

To see more things to do and other tourist information, use the Nantucket route planner.

Traveling by combination of taxi and ferry from Chatham to Nantucket takes 2.5 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. Wrap up your sightseeing on the 23rd (Sat) to allow time to ride a ferry to Oak Bluffs.
Outdoors · Beaches · Parks · Museums

Oak Bluffs, Martha's Vineyard — 3 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 Shining Sea Bikeway and Boat Tours & Water Sports. Your cultural itinerary includes sights like Martha's Vineyard Camp meeting Association (MVCMA) and Aquinnah Cliffs. Change things up with these side-trips from Oak Bluffs: Nobska Point Lighthouse (in Woods Hole) and Menemsha Public Beach (in Menemsha). There's still lots to do: kick back and relax at Katama Beach/ South Beach, admire the natural beauty at Mytoi, visit a coastal fixture at Edgartown Lighthouse, and make a trip to Flying Horses Carousel.

For ratings, maps, photos, and more tourist information, use the Oak Bluffs trip planning site.

You can ride a ferry from Nantucket to Oak Bluffs in 2 hours. In July in Oak Bluffs, expect temperatures between 79°F during the day and 63°F at night. Wrap up your sightseeing on the 26th (Tue) to allow time to fly back home.
Parks · Outdoors · Beaches · Historic Sites
Side Trips

Massachusetts travel guide

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.