10 days in Massachusetts & Mid Coast Maine Itinerary

10 days in Massachusetts & Mid Coast Maine Itinerary

Created using Inspirock United States vacation planner

Make it your trip
Fly
1
Boston
— 2 nights
Drive
2
Hyannis
— 3 nights
Drive
3
Provincetown
— 2 nights
Drive
4
Boothbay Harbor
— 2 nights
Fly

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Boston

— 2 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.
Take a break from Boston with a short trip to Dolphin & Whale Watching in Gloucester, about 50 minutes away. There's still lots to do: stroll around Boston Public Garden, get to know the fascinating history of Freedom Trail, take an in-depth tour of John F. Kennedy Presidential Museum & Library, and admire the masterpieces at Museum of Fine Arts.

To see where to stay, other places to visit, photos, and tourist information, read our Boston trip itinerary maker website.

Chicago to Boston is an approximately 4.5-hour flight. You can also drive; or take a bus. You'll lose 1 hour traveling from Chicago to Boston due to the time zone difference. In August in Boston, expect temperatures between 81°F during the day and 65°F at night. Cap off your sightseeing on the 8th (Sun) early enough to go by car to Hyannis.

Things to do in Boston

Museums · Tours · Wildlife · Outdoors

Side Trip

Hyannis

— 3 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
You'll find plenty of places to visit near Hyannis: Nobska Point Lighthouse (in Woods Hole), Shining Sea Bikeway (in Falmouth) and Nickerson State Park (in Brewster). There's much more to do: get up close to creatures of the deep with Hyannis Whale Watcher Cruises, get curious at Sandwich Glass Museum, steep yourself in history at Captain Bangs Hallet House Museum, and enjoy the sand and surf at Corporation Beach.

To find photos and other tourist information, read our Hyannis day trip tool.

Getting from Boston to Hyannis by car takes about 1.5 hours. Other options: fly; or take a bus. In August in Hyannis, expect temperatures between 79°F during the day and 63°F at night. Cap off your sightseeing on the 11th (Wed) early enough to go by car to Provincetown.

Things to do in Hyannis

Outdoors · Parks · Beaches · Tours

Side Trips

Provincetown

— 2 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.
Kick off your visit on the 12th (Thu): pause for some photo ops at Pilgrim Monument & Provincetown Museum, get a sense of history and politics at Provincetown Town Hall, then take in the waterfront at MacMillan Wharf, then see majestic marine mammals with a dolphin and whale watching tour, and finally make a trip to Commercial Street. Keep things going the next day: enjoy the sand and surf at Race Point Beach, kick back and relax at Coast Guard Beach, and then get engrossed in the history at Salt Pond Visitor Center.

To find where to stay, more things to do, maps, and more tourist information, you can read our Provincetown trip planner.

Drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. August in Provincetown sees daily highs of 78°F and lows of 62°F at night. Finish your sightseeing early on the 13th (Fri) to allow enough time to drive to Boothbay Harbor.

Things to do in Provincetown

Outdoors · Beaches · Parks · Museums

Side Trip

Boothbay Harbor

— 2 nights
Boothbay Harbor is a town in Lincoln County, Maine, United States. Start off your visit on the 14th (Sat): see majestic marine mammals with Cap'n Fish's Cruises, head off the coast to Cabbage Island, and then pause for some serene contemplation at The Wilson Memorial Chapel. Get ready for a full day of sightseeing on the next day: look for gifts at Dirty Bird Pottery and then admire the natural beauty at Coastal Maine Botanical Gardens.

To see other places to visit, reviews, and tourist information, read our Boothbay Harbor trip itinerary planning tool.

Traveling by car from Provincetown to Boothbay Harbor takes 5.5 hours. Alternatively, you can do a combination of flight, bus, and taxi; or do a combination of ferry, bus, and taxi. Plan for little chillier nights when traveling from Provincetown in August since evenings lows in Boothbay Harbor dip to 57°F. Finish up your sightseeing early on the 15th (Sun) so you can travel back home.

Things to do in Boothbay Harbor

Parks · Tours · Wildlife · Outdoors

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.

Mid Coast Maine travel guide

4.6
Lighthouses · Gardens · Mountains