9 days in United States Itinerary

9 days in United States Itinerary

Created using Inspirock United States travel route planner

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Route & dates

9 days in United States Itinerary

Start: New York City
Drive:  2​h 45​min
1
Colchester
— Few hours
Drive:  1​h 30​min
2
Newport
— 1 night
Drive:  1​h 30​min
3
Hyannis Port
— 1 night
Drive:  3​h
4
Oak Bluffs
— 1 night
Drive:  2​h 30​min
5
Boston
— 2 nights
Drive:  1​h 45​min
6
Kennebunkport
— 1 night
Drive:  1​h 30​min
7
Gilford
— 1 night
Drive:  1​h 45​min
8
Woodstock
— 1 night
Drive:  5​h
End: New York City

few
hours
Colchester

Colchester
Colchester is a town in New London County, Connecticut, United States. To see more things to do, photos, traveler tips, and more tourist information, use the Colchester tour itinerary planning app .

New York City to Colchester is an approximately 2.5-hour car ride. Traveling from New York City in May, you can expect nighttime temperatures to be a bit cooler in Colchester, with lows of 49°F. You'll set off for Newport on the 20th (Mon).

Things to do in Colchester

Theme Parks Nature Parks

1
night
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 21st (Tue): view the masterpieces at Thames Glass, cruise along Ocean Drive Historic District, then examine the collection at The Breakers, and finally appreciate the extensive heritage of Cliff Walk.

For reviews, photos, where to stay, and more tourist information, you can read our Newport trip website .

You can drive from Colchester to Newport in 1.5 hours. While traveling from Colchester, expect slightly colder days and about the same nights in Newport, ranging from highs of 65°F to lows of 49°F. Finish your sightseeing early on the 21st (Tue) so you can travel to Hyannis Port.

Things to do in Newport

Outdoors Historic Sites Museums
Highlights from your plan
Ocean Drive Historic District ©
Ocean Drive Historic District
The Breakers ©
The Breakers

1
night
Hyannis Port

Hyannis Port ©
On the 22nd (Wed), learn about all things military at Cape Cod Maritime Museum.

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

Traveling by car from Newport to Hyannis Port takes 2 hours. May in Hyannis Port sees daily highs of 65°F and lows of 49°F at night. On the 22nd (Wed), you'll have the morning to explore before heading off to Oak Bluffs.

Things to do in Hyannis Port

Museums
Highlights from your plan
Cape Cod Maritime Museum ©
Cape Cod Maritime Museum

1
night
Oak Bluffs

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 23rd (Thu): tee off at Farm Neck Golf Club, visit a coastal fixture at Edgartown Lighthouse, then admire the natural beauty at Mytoi, and finally admire the landmark architecture of Trinity Park Tabernacle.

To see where to stay, maps, photos, and more tourist information, refer to the Oak Bluffs online journey maker .

You can drive from Hyannis Port to Oak Bluffs in 2 hours. May in Oak Bluffs sees daily highs of 65°F and lows of 47°F at night. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel to Boston.

Things to do in Oak Bluffs

Golf Outdoors Historic Sites

Side Trip

Edgartown
Highlights from your plan
Farm Neck Golf Club ©
Farm Neck Golf Club
Trinity Park Tabernacle ©
Trinity Park Tabernacle
Edgartown Lighthouse ©
Edgartown Lighthouse

2
nights
Boston

Boston ©
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 24th (Fri), pause for some photo ops at New England Holocaust Memorial, admire the masterpieces at Museum of Fine Arts, and then explore and take pictures at Fenway Park. On your second day here, take in nature's colorful creations at Boston Public Garden, browse the different shops at Faneuil Hall Marketplace, then wander the streets of North End, and finally get to know the fascinating history of Freedom Trail.

For where to stay, reviews, ratings, and tourist information, you can read our Boston road trip planning site .

You can do a combination of ferry and car from Oak Bluffs to Boston in 2.5 hours. Other options are to fly; or do a combination of ferry and bus. In May, plan for daily highs up to 67°F, and evening lows to 50°F. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Kennebunkport.

Things to do in Boston

Museums Historic Sites Neighborhoods
Highlights from your plan
Freedom Trail ©
Freedom Trail
North End ©
North End
Fenway Park ©
Fenway Park

1
night
Kennebunkport

Kennebunkport ©
Kennebunkport is a town in York County, Maine, United States. Start off your visit on the 26th (Sun): stop by Scalawags Pet Boutique, then stroll through Ogunquit Beach, then stroll through Footbridge Beach, and finally get to know the fascinating history of Marginal Way Walkway.

To find where to stay, maps, traveler tips, and more tourist information, refer to the Kennebunkport road trip planning site .

Traveling by car from Boston to Kennebunkport takes 2 hours. Alternatively, you can take a bus; or take a train. Expect a bit cooler evenings in Kennebunkport when traveling from Boston in May, with lows around 43°F. Wrap up your sightseeing on the 26th (Sun) early enough to travel to Gilford.

Things to do in Kennebunkport

Beaches Parks Outdoors

Side Trip

Ogunquit
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Ogunquit Beach ©
Ogunquit Beach
Scalawags Pet Boutique ©
Scalawags Pet Boutique

1
night
Gilford

Gilford ©
Gilford is a town in Belknap County, New Hampshire, United States. On the 27th (Mon), take an in-depth tour of Wright Museum of WWII, then see the interesting displays at Clark House Museum, and then explore and take pictures at Rusty Wallace Racing Experience.

To find where to stay, more things to do, traveler tips, and more tourist information, read our Gilford trip builder app .

Drive from Kennebunkport to Gilford in 2 hours. In May, daytime highs in Gilford are 67°F, while nighttime lows are 46°F. Finish your sightseeing early on the 27th (Mon) to allow enough time to travel to Woodstock.

Things to do in Gilford

Museums

Side Trips

Wolfeboro, Rusty Wallace Racing Experience
Highlights from your plan
Wright Museum of WWII ©
Wright Museum of WWII

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. On the 28th (Tue), explore the striking landscape of Marsh - Billings - Rockefeller National Historical Park and then take in the views from Quechee Bridge.

To find traveler tips, where to stay, ratings, and other tourist information, you can read our Woodstock tour planner .

Traveling by car from Gilford to Woodstock takes 2 hours. In May, daytime highs in Woodstock are 70°F, while nighttime lows are 45°F. Finish your sightseeing early on the 28th (Tue) to allow enough time to drive back home.

Things to do in Woodstock

Nature Parks Historic Sites

Side Trip

Quechee Bridge
Highlights from your plan
Quechee Bridge ©
Quechee Bridge

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