10 days in Hamptons Itinerary

10 days in Hamptons Itinerary

Created using Inspirock Hamptons vacation planner

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Route & dates

10 days in Hamptons Itinerary

Start: Newark
Drive:  2​h
1
Riverhead
— 3 nights
Drive:  1​h 15​min
2
Shelter Island
— 2 nights
Drive:  1​h 15​min
3
Montauk
— 4 nights
Drive:  3​h
End: Newark

3
nights
Riverhead

Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Riverhead is known for zoos & aquariums, wineries, shopping, fun & games, and breweries & distilleries. Your plan includes some of its best attractions: get up close and personal with brilliant marine life at Long Island Aquarium, learn about winemaking at Martha Clara Vineyards, revel in the low prices at Tanger Outlets Riverhead, and kick back and relax at Ponquogue Beach.

To see ratings, other places to visit, where to stay, and other tourist information, refer to the Riverhead travel itinerary planner.

Newark to Riverhead is an approximately 2-hour car ride. Prepare for little chillier weather when traveling from Newark in May: high temperatures in Riverhead hover around 66°F and lows are around 46°F. Wrap up your sightseeing on the 31st (Sun) early enough to drive to Shelter Island.

Things to do in Riverhead

Parks Outdoors Beaches

Side Trips

Southampton, Cupsogue Beach County Park, Ponquogue Beach, Parrish Art Museum
Find places to stay May 28 — 31:
Highlights from your plan
Long Island Aquarium ©
Long Island Aquarium
Tanger Outlets Riverhead ©
Tanger Outlets Riverhead
Cooper's Beach ©
Cooper's Beach

2
nights
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. Kick off your visit on the 1st (Mon): take an in-depth tour of Custom House Museum, then have fun and explore at Children's Museum of The East End, then steep yourself in history at Shelter Island Historical Society, and finally look for all kinds of wild species at Mashomack Preserve. Here are some ideas for day two: examine the collection at South Fork Natural History Museum, see the interesting displays at Sag Harbor Whaling and Historical Museum, and then stroll around Sag Harbor Marine Park.

To see more things to do, reviews, ratings, and more tourist information, you can read our Shelter Island planner .

You can drive from Riverhead to Shelter Island in 1.5 hours. Expect somewhat warmer evenings in Shelter Island when traveling from Riverhead in May, with lows around 52°F. Finish your sightseeing early on the 2nd (Tue) so you can drive to Montauk.

Things to do in Shelter Island

Museums Parks Childrens Museums

Side Trips

Sag Harbor, Bridgehampton
Find places to stay May 31 — Jun 2:
Highlights from your plan
Children's Museum of The East End ©
Children's Museum of The East End
Mashomack Preserve ©
Mashomack Preserve
Shelter Island Historical Society ©

4
nights
Montauk

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 Montauk's surroundings by going to East Hampton (LongHouse Reserve & Guild Hall) and Wolffer Estate Vineyard (in Sagaponack). And it doesn't end there: visit a coastal fixture at Montauk Point Lighthouse, steep yourself in history at Pollock-Krasner House and Study Center, immerse yourself in nature at Montauk Point State Park, and stroll through Main Beach.

For reviews, traveler tips, and tourist information, refer to the Montauk trip planner .

You can drive from Shelter Island to Montauk in 1.5 hours. In June in Montauk, expect temperatures between 74°F during the day and 60°F at night. Wrap up your sightseeing on the 6th (Sat) to allow time to travel back home.

Things to do in Montauk

Parks Outdoors Nature

Side Trips

East Hampton, Wolffer Estate Vineyard
Find places to stay Jun 2 — 6:
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Gosman's Restaurant ©
Gosman's Restaurant