8 days in Hamptons Itinerary

8 days in Hamptons Itinerary

Created using Inspirock Hamptons trip maker

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Make it your trip
Fly to New York La Guardia, Train to Montauk
1
Montauk
— 3 nights
Drive
2
Shelter Island
— 2 nights
Drive
3
Westhampton Beach
— 2 nights
Drive to John F Kennedy International Airport, Fly to Dallas

S M T W T F S
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Montauk

— 3 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. Step off the beaten path and head to Gin Beach and Guild Hall. Get outdoors at Montauk Downs State Park Golf Course and Elizabeth A. Morton National Wildlife Refuge. Take a break from Montauk with a short trip to Foster Memorial Beach in Sag Harbor, about 38 minutes away. There's still lots to do: see the interesting displays at The Leiber Collection, pick up some local products at Round Swamp Farm, immerse yourself in nature at Montauk Downs State Park, and enjoy the sand and surf at Atlantic Avenue Beach.

To find maps, more things to do, where to stay, and other tourist information, refer to the Montauk tour website.

Dallas to Montauk is an approximately 8.5-hour combination of flight and train. You can also drive; or take a bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Traveling from Dallas in July, things will get little chillier in Montauk: highs are around 80°F and lows about 68°F. Cap off your sightseeing on the 20th (Tue) early enough to go by car to Shelter Island.

Things to do in Montauk

Parks · Outdoors · Beaches · Museums

Side Trips

Shelter Island

— 2 nights
Kick off your visit on the 21st (Wed): have fun and explore at Children's Museum of The East End, see the interesting displays at Sag Harbor Whaling and Historical Museum, then take an in-depth tour of Custom House Museum, and finally walk around Sag Harbor Marine Park. Keep things going the next day: examine the collection at South Fork Natural History Museum, then identify plant and animal life at Mashomack Preserve, then experience rural life at Sylvester Manor Educational Farm, and finally contemplate the long history of Shelter Island Historical Society.

To see other places to visit, more things to do, maps, and tourist information, you can read our Shelter Island online travel route planner.

You can drive from Montauk to Shelter Island in 1.5 hours. In July in Shelter Island, expect temperatures between 79°F during the day and 67°F at night. Finish up your sightseeing early on the 22nd (Thu) so you can go by car to Westhampton Beach.

Things to do in Shelter Island

Museums · Parks · Wildlife · Childrens Museums

Side Trips

Westhampton Beach

— 2 nights
The Incorporated Village of Westhampton Beach is an incorporated village on the southeast coast of Long Island. On the 23rd (Fri), stroll through Pike's Beach, join the crowd at Riverhead Raceway, and then stop by North Fork Chocolate Company.

For photos, where to stay, traveler tips, and tourist information, read Westhampton Beach tour planning website.

You can drive from Shelter Island to Westhampton Beach in 1.5 hours. In July, plan for daily highs up to 82°F, and evening lows to 64°F. On the 24th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Westhampton Beach

Parks · Beaches · Outdoors · Wildlife

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.