32 days in Hamptons Itinerary

32 days in Hamptons Itinerary

Created using Inspirock Hamptons journey planner

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Route & dates

32 days in Hamptons Itinerary

Start: Rome
Fly + Drive:  15 h
Westhampton Beach
— 12 nights
Drive:  1 h 15 min
Shelter Island
— 9 nights
Drive:  1 h 15 min
— 10 nights
Drive + Fly:  15 h 45 min
End: Rome

Westhampton Beach

Westhampton Beach ©
The Incorporated Village of Westhampton Beach is an incorporated village on the southeast coast of Long Island. Get out of town with these interesting Westhampton Beach side-trips: Water Mill (Duck Walk Vineyard & Parrish Art Museum), Fairview Farm (in Bridgehampton) and Elizabeth A. Morton National Wildlife Refuge (in Noyack). There's lots more to do: get up close and personal with brilliant marine life at Long Island Aquarium, bet on your favorite at Riverhead Raceway, take an in-depth tour of The Thomas Halsey Homestead, and enjoy the sand and surf at Ponquogue Beach.

To find maps, photos, more things to do, and more tourist information, go to the Westhampton Beach tour itinerary planning tool .

Rome, Italy to Westhampton Beach is an approximately 15-hour combination of flight and car. The time zone difference moving from Central European Time to Eastern Standard Time is minus 6 hours. Expect slightly colder temperatures when traveling from Rome in October; daily highs in Westhampton Beach reach 22°C and lows reach 8°C. Finish up your sightseeing early on the 22nd (Tue) so you can go by car to Shelter Island.

Things to do in Westhampton Beach

Parks Outdoors Museums

Side Trips

Southampton, Riverhead, Quogue Wildlife Refuge, Fairview Farm, Elizabeth A. Morton National Wildlife Refuge
Find places to stay Oct 10 — 22:
Highlights from your plan
Long Island Aquarium ©
Long Island Aquarium
Cupsogue Beach County Park ©
Cupsogue Beach County Park
Cooper's Beach ©
Cooper's Beach

Shelter Island

Shelter Island ©
Shelter Island is a hamlet and census-designated place (CDP) within the Town of Shelter Island in Suffolk County, New York, United States. Explore Shelter Island's surroundings by going to Hank's Pumpkintown (in Water Mill), Bridgehampton (Bridge Gardens, South Fork Natural History Museum, & more) and Sag Harbor (Sag Harbor Marine Park, Custom House Museum, & more). And it doesn't end there: look for all kinds of wild species at Mashomack Preserve, indulge your thirst for a good beer at Shelter Island Craft Brewery, enjoy the sand and surf at Havens Beach, and steep yourself in history at Shelter Island Historical Society.

For maps, other places to visit, where to stay, and tourist information, you can read our Shelter Island trip planner .

You can drive from Westhampton Beach to Shelter Island in 1.5 hours. Plan for a bit warmer nights when traveling from Westhampton Beach in October since evenings lows in Shelter Island dip to 13°C. You will leave for Montauk on the 31st (Thu).

Things to do in Shelter Island

Parks Museums Beaches

Side Trips

Sag Harbor, Bridgehampton, Hank's Pumpkintown
Find places to stay Oct 22 — 31:
Highlights from your plan
Mashomack Preserve ©
Mashomack Preserve
Shelter Island Historical Society ©
Shelter Island Historical Society
Sylvester Manor Educational Farm ©
Sylvester Manor Educational Farm


Montauk ©
Montauk is a census-designated place (CDP) that includes the hamlet with the same name located in the town of East Hampton in Suffolk County, New York, on the eastern end of the South Shore of Long Island. Get out of town with these interesting Montauk side-trips: Sagaponack (Wolffer Estate Vineyard & Madoo Conservancy), Channing Daughters Winery (in Bridgehampton) and First Presbyterian/Old Whaler's Church (in Sag Harbor). There's lots more to do: enjoy the sea views from Montauk Point Lighthouse, immerse yourself in nature at Camp Hero State Park, make a trip to Gosman's Restaurant, and see what you can catch with a fishing tour.

To see traveler tips, where to stay, more things to do, and tourist information, read our Montauk trip planner .

Traveling by car from Shelter Island to Montauk takes 1.5 hours. In October, daily temperatures in Montauk can reach 21°C, while at night they dip to 13°C. Finish your sightseeing early on the 10th (Sun) to allow enough time to travel back home.

Things to do in Montauk

Parks Nature Outdoors

Side Trips

East Hampton, Sagaponack, First Presbyterian/Old Whaler's Church, Channing Daughters Winery
Find places to stay Oct 31 — Nov 10:
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Montauk Point State Park ©
Montauk Point State Park