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: Boston
Drive:  4​h
— 4 nights
Drive:  1​h 30​min
— 5 nights
ferry + train:  4​h 30​min
End: Boston


Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. The Thomas Halsey Homestead and Southampton History Museum will appeal to museum buffs. Do some cultural sightseeing at Paumanok Vineyards and Palmer Vineyards. When in Riverhead, make a side trip to see Duck Walk Vineyard in Water Mill, approximately 34 minutes away. There's lots more to do: revel in the low prices at Tanger Outlets, enjoy the sand and surf at Cupsogue Beach County Park, tour the pleasant surroundings at Cooper's Beach, and admire the masterpieces at Parrish Art Museum.

Plan my trip to Riverhead with suggested itineraries provided by Inspirock.

Boston to Riverhead is an approximately 4-hour car ride. Expect a daytime high around 9°C in December, and nighttime lows around -1°C. Wrap up your sightseeing on the 27th (Fri) to allow time to drive to Montauk.

Things to do in Riverhead

Wineries Parks Outdoors

Side Trips

Southampton, Water Mill, Hampton Bays, Cupsogue Beach County Park
Find places to stay Dec 23 — 27:
Highlights from your plan
Paumanok Vineyards ©
Paumanok Vineyards
Parrish Art Museum ©
Parrish Art Museum
The Thomas Halsey Homestead ©
The Thomas Halsey Homestead


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 a sense of the local culture at Montauk Point Lighthouse and Channing Daughters Winery. You'll explore and learn at Guild Hall and The Leiber Collection. Venture out of the city with trips to Wolffer Estate Vineyard (in Sagaponack), Bridgehampton (Children's Museum of The East End & South Fork Natural History Museum) and Sag Harbor (Sag Harbor Whaling and Historical Museum, Custom House Museum, & more). There's lots more to do: indulge your thirst for a good beer at Montauk Brewing Company, stroll through Main Beach, see the interesting displays at Osborn-Jackson House, and steep yourself in history at Pollock-Krasner House and Study Center.

To find photos, more things to do, ratings, and more tourist information, you can read our Montauk sightseeing planner.

Drive from Riverhead to Montauk in 1.5 hours. Traveling from Riverhead in December, Montauk is a bit warmer at night with lows of 3°C. Finish your sightseeing early on the 1st (Wed) to allow enough time to travel back home.

Things to do in Montauk

Museums Historic Sites Parks

Side Trips

East Hampton, Sag Harbor, Bridgehampton, Wolffer Estate Vineyard
Find places to stay Dec 27 — Jan 1:
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Main Beach ©
Main Beach
Guild Hall ©
Guild Hall