10 days in Hamptons Itinerary

10 days in Hamptons Itinerary

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Route & dates

10 days in Hamptons Itinerary

Start: Boston
Drive:  4 h
— 4 nights
Drive:  1 h 15 min
— 5 nights
Ferry + Train:  4 h 15 min
End: Boston


Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Head to Tanger Outlets and North Fork Chocolate Companyfor plenty of shopping. The Thomas Halsey Homestead and Southampton History Museum will appeal to museum buffs. Go for a jaunt from Riverhead to Water Mill to see Duck Walk Vineyard about 34 minutes away. There's still lots to do: do a tasting at Paumanok Vineyards, observe the fascinating underwater world at Long Island Aquarium, pause for some serene contemplation at Church of St. Rosalie, and examine the collection at Southampton Arts Center.

To see ratings, photos, traveler tips, and more tourist information, go to the Riverhead trip itinerary builder app .

Boston to Riverhead is an approximately 4-hour car ride. In December, plan for daily highs up to 47°F, and evening lows to 29°F. Wrap up your sightseeing on the 26th (Thu) early enough to drive to Montauk.

Things to do in Riverhead

Wineries Parks Outdoors

Side Trips

Southampton, Cupsogue Beach County Park
Find places to stay Dec 22 — 26:
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. Popular historic sites such as Montauk Point Lighthouse and First Presbyterian/Old Whaler's Church are in your itinerary. Guild Hall and Channing Daughters Winery are good opportunities to explore the local culture. You'll find plenty of places to visit near Montauk: Wolffer Estate Vineyard (in Sagaponack), Sag Harbor (Sag Harbor Whaling and Historical Museum & Custom House Museum) and Bridgehampton (Children's Museum of The East End & South Fork Natural History Museum). There's still lots to do: sample the tasty concoctions at Montauk Brewing Company, see the interesting displays at Home Sweet Home Museum, contemplate the long history of Pollock-Krasner House and Study Center, and pause for some serene contemplation at St. Therese of Lisieux Catholic Church.

For reviews, other places to visit, where to stay, and more tourist information, refer to the Montauk itinerary app .

Traveling by car from Riverhead to Montauk takes 1.5 hours. Traveling from Riverhead in December, plan for a bit warmer nights in Montauk, with lows around 37°F. Finish your sightseeing early on the 31st (Tue) to allow enough time to travel back home.

Things to do in Montauk

Museums Historic Sites Parks

Side Trips

East Hampton, Bridgehampton, Sag Harbor, Wolffer Estate Vineyard
Find places to stay Dec 26 — 31:
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Main Beach ©
Main Beach
The Leiber Collection ©
The Leiber Collection