32 days in Hamptons Itinerary

32 days in Hamptons Itinerary

Created using Inspirock Hamptons journey planner

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Plan created by another user. Make it yours
Fly to John F Kennedy International Airport, Drive to Westhampton Beach
1
Westhampton Beach
— 12 nights
Drive
2
Shelter Island
— 9 nights
Drive
3
Montauk
— 10 nights
Drive to John F Kennedy International Airport, Fly to Leonardo da Vinci–Fiumicino Airport

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12
nights
Westhampton Beach

The Incorporated Village of Westhampton Beach is an incorporated village on the southeast coast of Long Island. Explore the numerous day-trip ideas around Westhampton Beach: Southampton (Hildreth's, The Thomas Halsey Homestead, &more), Elizabeth A. Morton National Wildlife Refuge (in Noyack) and Fairview Farm (in Bridgehampton). There's lots more to do: kick back and relax at Cupsogue Beach County Park, get some fabulous bargains at Tanger Outlets Riverhead, bet on your favorite at Riverhead Raceway, and look for all kinds of wild species at Quogue Wildlife Refuge.

To see reviews, ratings, maps, and tourist information, read Westhampton Beach trip planning app.

Rome, Italy to Westhampton Beach is an approximately 15-hour combination of flight and car. The time zone changes from Central European Standard Time (CET) to Eastern Standard Time (EST), which is usually a -6 hour difference. Expect a bit cooler temperatures when traveling from Rome in October; daily highs in Westhampton Beach reach 22°C and lows reach 8°C. Finish your sightseeing early on the 22nd (Tue) to allow enough time to drive to Shelter Island.

Things to do in Westhampton Beach

Parks · Outdoors · Museums · Wineries

Side Trips

Find places to stay Oct 10 — 22:

9
nights
Shelter Island

Explore Shelter Island's surroundings by going to Sag Harbor (Sag Harbor Marine Park, Custom House Museum, &more), Hank's Pumpkintown (in Water Mill) and Bridgehampton (Bridge Gardens, South Fork Natural History Museum, &more).

For traveler tips, maps, other places to visit, and more tourist information, read Shelter Island holiday maker app.

You can drive from Westhampton Beach to Shelter Island in 1.5 hours. Traveling from Westhampton Beach in October, Shelter Island is somewhat warmer at night with lows of 13°C. On the 31st (Thu), you're off to Montauk.

Things to do in Shelter Island

Parks · Museums · Beaches · Breweries & Distilleries

Side Trips

Find places to stay Oct 22 — 31:

10
nights
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. Explore the numerous day-trip ideas around Montauk: First Presbyterian/Old Whaler's Church (in Sag Harbor), Sagaponack (Wolffer Estate Vineyard & Madoo Conservancy) and Channing Daughters Winery (in Bridgehampton). The adventure continues: enjoy the sea views from Montauk Point Lighthouse, immerse yourself in nature at Shadmoor State Park, cast your line with a fishing tour, and indulge your thirst for a good beer at Montauk Brewing Company.

For maps, photos, traveler tips, and tourist information, go to the Montauk travel itinerary planner.

Traveling by car from Shelter Island to Montauk takes 1.5 hours. In October, daytime highs in Montauk are 21°C, while nighttime lows are 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 · Historic Sites

Side Trips

Find places to stay Oct 31 — Nov 10:

Hamptons travel guide

4.1
Lighthouses · Beaches · Dolphin & Whale Watching
A historical summer retreat, the Hamptons is one of the United States' most expensive residential areas. The series of hamlets and villages in Southampton is known for its isolated charm and luxury. The small villages swell in population during the summer, as New York City's most recognizable residents escape here to frequent restaurants, retail outlets, and the colorful art community. Secluded mansions are interspersed with golf courses and tennis clubs, where socialites gather during daylight hours.