39 days in New England Itinerary

39 days in New England Itinerary

Created using Inspirock New England trip planner
Make it your trip
Fly
1
Nantucket
— 4 nights
Ferry
2
Hyannis
— 6 nights
Drive
3
Provincetown
— 5 nights
Fly
4
Newport
— 6 nights
Drive
5
Boston
— 6 nights
Drive
6
Ogunquit
— 5 nights
Drive
7
Bar Harbor, Mount Desert Island
— 6 nights
Fly

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Nantucket — 4 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your trip includes some of its best attractions: see the interesting displays at Whaling Museum, get a new perspective on things with Boat Tours & Water Sports, kick back and relax at Jetties Beach, and stroll through Madaket Beach.

Quickly create a custom-made itinerary for Nantucket using our trip planner.

Newark to Nantucket is an approximately 3.5-hour flight. You can also do a combination of car and ferry; or do a combination of train, bus, and ferry. Expect a bit cooler temperatures when traveling from Newark in June; daily highs in Nantucket reach 69°F and lows reach 57°F. Finish your sightseeing early on the 14th (Tue) to allow enough time to ride a ferry to Hyannis.
Outdoors · Historic Sites · Parks · Beaches

Hyannis — 6 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Explore Hyannis' surroundings by going to Shining Sea Bikeway (in Falmouth), Chatham (Chatham Railroad Museum, Atwood Museum, &more) and Cape Cod Canal (in Buzzards Bay). Next up on the itinerary: examine the collection at Heritage Museums & Gardens, enjoy the sand and surf at Nauset Beach, immerse yourself in nature at Nickerson State Park, and get engrossed in the history at Plimoth Patuxet.

To see other places to visit, traveler tips, and more tourist information, read our Hyannis sightseeing planning site.

You can ride a ferry from Nantucket to Hyannis in 2 hours. Alternatively, you can fly. In June, plan for daily highs up to 73°F, and evening lows to 58°F. Finish your sightseeing early on the 20th (Mon) so you can drive to Provincetown.
Parks · Outdoors · Museums · Trails
Side Trips

Provincetown — 5 nights

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.
You'll find plenty of places to visit near Provincetown: Eastham (Coast Guard Beach, Salt Pond Visitor Center, &more). And it doesn't end there: browse the exhibits of Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Long Point, tour the pleasant surroundings at Race Point Beach, and explore the wealth of natural beauty at Cape Cod National Seashore.

To see other places to visit, ratings, maps, and more tourist information, go to the Provincetown route planning website.

You can drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. In June, daytime highs in Provincetown are 72°F, while nighttime lows are 56°F. Wrap up your sightseeing on the 25th (Sat) to allow time to fly to Newport.
Outdoors · Parks · Beaches · Nature
Side Trips

Newport — 6 nights

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Get out of town with these interesting Newport side-trips: Lizzie Borden House (in Fall River), New Bedford Whaling Museum (in New Bedford) and Colt State Park (in Bristol). Next up on the itinerary: admire all the interesting features of Cliff Walk, admire the striking features of Marble House, contemplate the long history of The Elms, and get to know the fascinating history of Ocean Drive Historic District.

For reviews, traveler tips, and other tourist information, read Newport tour itinerary maker site.

You can fly from Provincetown to Newport in 2 hours. Other options are to drive; or do a combination of ferry and bus. In June in Newport, expect temperatures between 73°F during the day and 58°F at night. Wrap up your sightseeing on the 1st (Fri) to allow time to drive to Boston.
Historic Sites · Museums · Tours · Outdoors
Side Trips

Boston — 6 nights

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.
Venture out of the city with trips to Dolphin & Whale Watching (in Gloucester) and Salem Maritime National Historic Site (in Salem). There's still lots to do: explore the world behind art at Museum of Fine Arts, get engrossed in the history at Boston Tea Party Ships & Museum, engage your brain at Museum of Science, and wander the streets of North End.

To find traveler tips, maps, photos, and more tourist information, use the Boston online trip builder.

Traveling by car from Newport to Boston takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In July, plan for daily highs up to 83°F, and evening lows to 67°F. Finish your sightseeing early on the 7th (Thu) to allow enough time to drive to Ogunquit.
Museums · Historic Sites · Parks · Neighborhoods
Side Trips

Ogunquit — 5 nights

Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Explore Ogunquit's surroundings by going to Cabbage Island (in Boothbay Harbor), Portland (Maine Craft Distilling & Beer Tastings & Tours) and Rusty Wallace Racing Experience (in Loudon). The adventure continues: get to know the fascinating history of Marginal Way Walkway, stroll around Grist Mill Park, take in the pleasant sights at Coastal Maine Botanical Gardens, and enjoy the sea views from Nubble Lighthouse.

For photos, where to stay, ratings, and other tourist information, read our Ogunquit itinerary maker tool.

Traveling by car from Boston to Ogunquit takes 1.5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Expect a bit cooler evenings in Ogunquit when traveling from Boston in July, with lows around 58°F. Wrap up your sightseeing on the 12th (Tue) to allow time to drive to Bar Harbor.
Parks · Historic Sites · Nature · Tours
Side Trips

Bar Harbor, Mount Desert Island — 6 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Get out of town with these interesting Bar Harbor side-trips: Mount Battie (in Camden) and Schoodic Point (in Winter Harbor). There's much more to do: get a new perspective on things with Boat Tours & Water Sports, trek along Gorham Mountain Trail, stroll through Great Head Trail, and admire all the interesting features of Park Loop Road.

For reviews, traveler tips, and more tourist information, read Bar Harbor road trip app.

Getting from Ogunquit to Bar Harbor by car takes about 4 hours. Other options: do a combination of bus and flight; or do a combination of taxi, train, and bus. Traveling from Ogunquit in July, expect nights in Bar Harbor to be about the same, around 58°F, while days are little chillier, around 75°F. Finish your sightseeing early on the 18th (Mon) so you can fly back home.
Parks · Outdoors · Trails · Nature
Side Trips