14 days in New England Itinerary

14 days in New England Itinerary

Created using Inspirock New England sightseeing planner
Make it your trip
Fly
1
Nantucket
— 1 night
Unknown
2
Aquinnah, Martha's Vineyard
— 1 night
Drive
3
Eastham
— 2 nights
Drive
4
Boston
— 2 nights
Fly
5
Rockland
— 3 nights
Fly
6
Newport
— 3 nights
Ferry
7
New Shoreham, Block Island
— 1 night
Ferry to Great Island At Ferry Terminal, Fly to Newark

S M T W T F S
28
29
30
31
1
2
3
4
5
6
7
8
9
10

Nantucket — 1 night

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. On the 28th (Sun), examine the collection at Nantucket Lightship Basket Museum, visit a coastal fixture at Sankaty Head Lighthouse, and then visit a coastal fixture at Great Point Light. On the 29th (Mon), you'll have a packed day of sightseeing: see the interesting displays at Whaling Museum, visit a coastal fixture at Brant Point Lighthouse, and then stroll through Surfside Beach.

To see maps, photos, other places to visit, and tourist information, read our Nantucket tour itinerary maker site.

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. Traveling from Newark in August, things will get a bit cooler in Nantucket: highs are around 76°F and lows about 63°F. Cap off your sightseeing on the 29th (Mon) early enough to travel to Aquinnah.
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Historic Sites · Parks · Museums · Beaches

Aquinnah, Martha's Vineyard — 1 night

Aquinnah is a town located on the island of Martha's Vineyard in Massachusetts. On the 30th (Tue), enjoy the sea views from Gay Head Lighthouse and then explore the striking landscape at Aquinnah Cliffs.

For other places to visit, maps, photos, and other tourist information, read Aquinnah trip planner.

Traveling by journey from Nantucket to Aquinnah takes 3 hours. In August, daytime highs in Aquinnah are 79°F, while nighttime lows are 59°F. Wrap up your sightseeing on the 30th (Tue) to allow time to travel to Eastham.
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Historic Sites · Parks · Nature
Highlights from your trip

Eastham — 2 nights

Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Kick off your visit on the 31st (Wed): get to know the fascinating history of Fort Hill Rural Historic District, then visit a coastal fixture at Chatham Lighthouse, and then see the interesting displays at Chatham Railroad Museum. On your second day here, admire the masterpieces at Atwood Museum, steep yourself in history at Captain Penniman House, then admire all the interesting features of Wellfleet Bay Wildlife Sanctuary, and finally enjoy the sea views from Nauset Lighthouse.

For maps, reviews, more things to do, and tourist information, read our Eastham trip itinerary builder site.

Traveling by car from Aquinnah to Eastham takes 3 hours. Alternatively, you can drive. In August in Eastham, expect temperatures between 78°F during the day and 63°F at night. Finish your sightseeing early on the 1st (Thu) so you can drive to Boston.
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Historic Sites · Parks · Wildlife · Museums
Side Trips

Boston — 2 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.
On the 2nd (Fri), explore the historical opulence of Hammond Castle Museum and then identify plant and animal life at Wildlife Areas. Here are some ideas for day two: stroll the grounds of Granary Burying Ground, then admire the natural beauty at Boston Public Garden, then buy something for everyone on your list at Faneuil Hall Marketplace, and finally get to know the fascinating history of Freedom Trail.

For traveler tips, more things to do, other places to visit, and tourist information, read Boston trip itinerary builder website.

Drive from Eastham to Boston in 2 hours. Alternatively, you can fly; or take a bus. In September, plan for daily highs up to 75°F, and evening lows to 59°F. Finish up your sightseeing early on the 3rd (Sat) so you can catch the flight to Rockland.
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Historic Sites · Tours · Wildlife · Outdoors
Side Trip

Rockland — 3 nights

Rockland is a city in Knox County, Maine, in the United States. Visit Pemaquid Point Lighthouse and Owls Head Lighthouse for their historical value. You'll discover tucked-away gems like Farnsworth Art Museum and Maine Lighthouse Museum. Take a break from Rockland with a short trip to Marshall Point Lighthouse Museum in Port Clyde, about 34 minutes away. It doesn't end there: get outside with Outdoor Activities.

For other places to visit, reviews, where to stay, and more tourist information, use the Rockland tour planner.

Getting from Boston to Rockland by flight takes about 3 hours. Other options: drive; or take a bus. Plan for little chillier temperatures traveling from Boston in September, with highs in Rockland at 69°F and lows at 51°F. Wrap up your sightseeing on the 6th (Tue) early enough to fly to Newport.
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Historic Sites · Museums · Shopping · Tours
Side Trips

Newport — 3 nights

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Discover out-of-the-way places like Lizzie Borden House and Fort Adams State Park. Popular historic sites such as Rough Point Museum and Cliff Walk are in your itinerary. The adventure continues: visit a coastal fixture at Beavertail Lighthouse and Park, see what you can catch with Fish'n Tales Adventures, contemplate the long history of Wickford Village, and examine the collection at The Breakers.

For ratings, where to stay, more things to do, and tourist information, use the Newport trip planner.

Fly from Rockland to Newport in 3 hours. Alternatively, you can drive; or take a bus. Traveling from Rockland in September, Newport is somewhat warmer at night with lows of 58°F. Finish your sightseeing early on the 9th (Fri) to allow enough time to ride a ferry to New Shoreham.
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Historic Sites · Museums · Parks · Outdoors
Side Trips

New Shoreham, Block Island — 1 night

New Shoreham is a town in Washington County, Rhode Island, United States. Start off your visit on the 10th (Sat): visit a coastal fixture at North Lighthouse, then explore the striking landscape at Mohegan Bluffs, and then enjoy the sea views from South East Lighthouse.

To find reviews, photos, where to stay, and other tourist information, read our New Shoreham trip itinerary site.

You can ride a ferry from Newport to New Shoreham in 2 hours. Another option is to do a combination of taxi and ferry. In September in New Shoreham, expect temperatures between 71°F during the day and 61°F at night. Finish your sightseeing early on the 10th (Sat) so you can travel back home.
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Historic Sites · Parks · Trails · Nature