20 days in New England Itinerary

20 days in New England Itinerary

Created using Inspirock New England tour builder

Make it your trip
Fly to Boston, Ferry to Provincetown
1
Provincetown
— 3 nights
Drive
2
Sandwich
— 3 nights
Drive
3
Newport
— 3 nights
Drive
4
Ogunquit
— 1 night
Drive
5
Boothbay Harbor
— 2 nights
Drive
6
Bar Harbor, Mount Desert Island
— 2 nights
Fly
7
Boston
— 4 nights
Fly

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Provincetown

— 3 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.
Explore Provincetown's surroundings by going to Eastham (Salt Pond Visitor Center, Captain Penniman House, &more) and Atwood Museum (in Chatham). Next up on the itinerary: pause for some photo ops at Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Cape Cod National Seashore, snap pictures at Uncle Tim's Bridge, and admire the masterpieces at Provincetown Art Association and Museum.

To see more things to do, other places to visit, maps, and other tourist information, refer to the Provincetown road trip planner.

Jeddah, Saudi Arabia to Provincetown is an approximately 21-hour combination of flight and ferry. The time zone difference when traveling from Jeddah to Provincetown is minus 8 hours. Traveling from Jeddah in October, things will get cooler in Provincetown: highs are around 20°C and lows about 11°C. Wrap up your sightseeing on the 4th (Mon) early enough to drive to Sandwich.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Sandwich

— 3 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Go for a jaunt from Sandwich to Falmouth to see Highfield Hall & Gardens about 34 minutes away. There's much more to do: examine the collection at Heritage Museums & Gardens, steep yourself in history at Hoxie House, get curious at Sandwich Glass Museum, and make a trip to Old King's Hwy.

To find ratings, more things to do, photos, and tourist information, you can read our Sandwich attractions planner.

You can drive from Provincetown to Sandwich in 1.5 hours. Another option is to take a bus. In October, daytime highs in Sandwich are 20°C, while nighttime lows are 9°C. Finish up your sightseeing early on the 7th (Thu) so you can go by car to Newport.

Things to do in Sandwich

Museums · Outdoors · Wildlife · Parks

Side Trips

Newport

— 3 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Take a break from Newport with a short trip to Mystic Aquarium in Mystic, about 1 hour away. There's lots more to do: examine the collection at The Breakers, take a memorable drive along Ocean Drive Historic District, pause for some serene contemplation at St. Mary's Catholic Church, and take in the local highlights with Rhode Island Red Food Tours.

To find maps, more things to do, reviews, and more tourist information, read Newport holiday planning website.

You can drive from Sandwich to Newport in 1.5 hours. Other options are to take a bus; or do a combination of bus and train. In October, daily temperatures in Newport can reach 20°C, while at night they dip to 11°C. Wrap up your sightseeing on the 10th (Sun) to allow time to drive to Ogunquit.

Things to do in Newport

Tours · Historic Sites · Outdoors · Parks

Side Trips

Ogunquit

— 1 night
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.
Kick off your visit on the 11th (Mon): head outdoors with Fisherman's Walk, then visit a coastal fixture at Nubble Lighthouse, then explore the striking landscape at Perkins Cove, and finally appreciate the extensive heritage of Marginal Way Walkway.

For maps, reviews, where to stay, and tourist information, you can read our Ogunquit trip itinerary planner.

Traveling by car from Newport to Ogunquit takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Newport in October, plan for a bit cooler nights in Ogunquit, with lows around 3°C. Cap off your sightseeing on the 11th (Mon) early enough to go by car to Boothbay Harbor.

Things to do in Ogunquit

Historic Sites · Nature · Parks · Outdoors

Side Trip

Boothbay Harbor

— 2 nights
Boothbay Harbor is a town in Lincoln County, Maine, United States. On the 12th (Tue), look for all kinds of wild species at Boothbay Region Land Trust, then take in nature's colorful creations at Coastal Maine Botanical Gardens, and then make a trip to Doubling Point Lighthouse. Get ready for a full day of sightseeing on the next day: get up close to creatures of the deep with Cap'n Fish's Cruises, visit a coastal fixture at Pemaquid Point Lighthouse, and then take in the architecture and atmosphere at The Wilson Memorial Chapel.

To find ratings, traveler tips, more things to do, and tourist information, read our Boothbay Harbor road trip planning tool.

You can drive from Ogunquit to Boothbay Harbor in 2 hours. Other options are to do a combination of taxi and train; or do a combination of bus and taxi. October in Boothbay Harbor sees daily highs of 19°C and lows of 5°C at night. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Bar Harbor.

Things to do in Boothbay Harbor

Wildlife · Parks · Outdoors · Tours

Side Trips

Bar Harbor, Mount Desert Island

— 2 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 14th (Thu): take in the dramatic natural features at Schoodic Point, then contemplate the waterfront views at Frenchman Bay, and then take a tour by water with Boat Tours & Water Sports. Get ready for a full day of sightseeing on the next day: identify plant and animal life at Shore Path, see the interesting displays at The Seal Cove Auto Museum, and then take in the awesome beauty at Cadillac Mountain.

Plan trip to Bar Harbor with our itinerary maker to find out where to go and what to do.

You can drive from Boothbay Harbor to Bar Harbor in 3 hours. Another option is to do a combination of taxi and bus. In October, plan for daily highs up to 17°C, and evening lows to 6°C. Wrap up your sightseeing on the 15th (Fri) to allow time to travel to Boston.

Things to do in Bar Harbor

Parks · Nature · Wildlife · Outdoors

Side Trips

Boston

— 4 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. Next up on the itinerary: take in nature's colorful creations at Boston Public Garden, admire the masterpieces at Museum of Fine Arts, take an in-depth tour of John F. Kennedy Presidential Museum & Library, and take a stroll through North End.

To find more things to do, reviews, where to stay, and more tourist information, use the Boston tour itinerary planning website.

Getting from Bar Harbor to Boston by flight takes about 4.5 hours. Other options: drive; or take a bus. Expect a bit warmer evenings in Boston when traveling from Bar Harbor in October, with lows around 11°C. Finish up your sightseeing early on the 19th (Tue) so you can travel back home.

Things to do in Boston

Museums · Parks · Historic Sites · Wildlife

Side Trips