15 days in Hamptons Itinerary

15 days in Hamptons Itinerary

Created using Inspirock Hamptons planner

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Make it your trip
Fly to New York La Guardia, Train to Montauk
1
Montauk
— 7 nights
Drive
2
Shelter Island
— 2 nights
Drive
3
Riverhead
— 5 nights
Drive to John F Kennedy International Airport, Fly to Memphis

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Montauk

— 7 nights
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. Shop till you drop at Round Swamp Farm and Main Beach. Change things up with these side-trips from Montauk: Elizabeth A. Morton National Wildlife Refuge (in Noyack), East Hampton (Home Sweet Home Museum, LongHouse Reserve, &more) and Sag Harbor (First Presbyterian/Old Whaler's Church & Foster Memorial Beach). The adventure continues: make a trip to Montauk Point Lighthouse, see majestic marine mammals with Viking Fleet, take in the architecture and atmosphere at St. Therese of Lisieux Catholic Church, and walk around Navy Road Park.

To find reviews and other tourist information, read Montauk online trip itinerary builder.

Memphis to Montauk is an approximately 8.5-hour combination of flight and train. You can also drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Memphis to Montauk. While traveling from Memphis, expect slightly colder days and about the same nights in Montauk, ranging from highs of 65°F to lows of 53°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Shelter Island.

Things to do in Montauk

Parks · Outdoors · Beaches · Nature

Side Trips

Shelter Island

— 2 nights
Start off your visit on the 25th (Mon): explore the engaging exhibits at Children's Museum of The East End, contemplate the long history of Shelter Island Historical Society, then stroll through Mashomack Preserve, then experience rural life at Sylvester Manor Educational Farm, and finally indulge your thirst for a good beer at Shelter Island Craft Brewery. On the next day, walk around Sag Harbor Marine Park, get outside with Outdoor Activities, then get engrossed in the history at Custom House Museum, then examine the collection at Sag Harbor Whaling and Historical Museum, and finally enjoy the sand and surf at Havens Beach.

To find ratings, more things to do, photos, and tourist information, read our Shelter Island online road trip planner.

Getting from Montauk to Shelter Island by car takes about 1.5 hours. October in Shelter Island sees daily highs of 64°F and lows of 52°F at night. Finish your sightseeing early on the 26th (Tue) so you can drive to Riverhead.

Things to do in Shelter Island

Parks · Outdoors · Museums · Tours

Side Trips

Riverhead

— 5 nights
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Give yourself a bit of retail therapy at Tanger Outlets Riverhead and North Fork Chocolate Company. Next up on the itinerary: observe the fascinating underwater world at Long Island Aquarium, get engrossed in the history at Hallockville Museum Farm, stroll through Quogue Wildlife Refuge, and enjoy the sand and surf at Cupsogue Beach County Park.

Discover how to plan a Riverhead trip in just a few steps with Inspirock's itinerary builder.

Drive from Shelter Island to Riverhead in 1.5 hours. Expect a bit cooler evenings in Riverhead when traveling from Shelter Island in October, with lows around 45°F. Wrap up your sightseeing by early afternoon on the 31st (Sun) to allow time for travel back home.

Things to do in Riverhead

Parks · Outdoors · Beaches · Wineries

Side Trips

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.