8 days in Hamptons Itinerary

8 days in Hamptons Itinerary

Created using Inspirock Hamptons route planner
Make it your trip
Fly to New York La Guardia, Train to Montauk
— 3 nights
Shelter Island
— 2 nights
— 2 nights
Drive to John F Kennedy International Airport, Fly to Chicago


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. Montauk is known for wildlife, historic sites, and nature. Your trip includes some of its best attractions: cast your line with a fishing tour, visit a coastal fixture at Montauk Point Lighthouse, wander the streets of Main Beach, and kick back and relax at Ditch Plains.

You can plan Montauk trip in no time by asking Inspirock to help create your itinerary.

Chicago to Montauk is an approximately 8-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. In July in Montauk, expect temperatures between 80°F during the day and 68°F at night. Finish your sightseeing early on the 12th (Tue) so you can drive to Shelter Island.
Parks · Outdoors · Nature · Historic Sites
Side Trip

Shelter Island — 2 nights

Kick off your visit on the 13th (Wed): walk around Sag Harbor Marine Park, then head outdoors with Outdoor Activities, and then examine the collection at Sag Harbor Whaling and Historical Museum. On the 14th (Thu), you'll have a packed day of sightseeing: steep yourself in history at Shelter Island Historical Society, then tour the pleasant surroundings at Mashomack Preserve, and then experience rural life at Sylvester Manor Educational Farm.

To see photos, ratings, traveler tips, and tourist information, go to the Shelter Island online travel planner.

You can drive from Montauk to Shelter Island in 1.5 hours. Expect a daytime high around 79°F in July, and nighttime lows around 67°F. Wrap up your sightseeing on the 14th (Thu) to allow time to drive to Riverhead.
Parks · Wildlife · Museums · Historic Sites
Side Trip

Riverhead — 2 nights

Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. On the 15th (Fri), meet the residents at Long Island Aquarium, then get some fabulous bargains at Tanger Outlets Riverhead, and then sample the tasty concoctions at Crooked Ladder Brewery. On your second day here, stroll through Cupsogue Beach County Park.

For traveler tips, other places to visit, ratings, and other tourist information, use the Riverhead travel planning app.

You can drive from Shelter Island to Riverhead in 1.5 hours. July in Riverhead sees daily highs of 82°F and lows of 64°F at night. Wrap up your sightseeing by early afternoon on the 16th (Sat) to allow enough time to travel back home.
Parks · Shopping · Breweries & Distilleries · Zoos & Aquariums
Side Trip

Hamptons travel guide

Lighthouses · Dolphin & Whale Watching · Beaches
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.