7 days in Hamptons Itinerary

7 days in Hamptons Itinerary

Created using Inspirock Hamptons sightseeing planner
Make it your trip
— 1 night
— 3 nights
Shelter Island
— 2 nights


Riverhead — 1 night

Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. On the 22nd (Sun), admire nature's wide array of creatures at Long Island Aquarium, then get some fabulous bargains at Tanger Outlets Riverhead, and then indulge your thirst for a good beer at Crooked Ladder Brewery. Get ready for a full day of sightseeing on the next day: do a tasting at Martha Clara Vineyards and then sample some tasty brews at Urban Pedal Tours Long Island.

To find maps, where to stay, more things to do, and tourist information, read Riverhead trip planner.

New York City to Riverhead is an approximately 1.5-hour car ride. Traveling from New York City in May, expect a bit cooler with lows of 46°F in Riverhead. Wrap up your sightseeing on the 23rd (Mon) early enough to drive to Montauk.
Breweries & Distilleries · Parks · Shopping · Tours

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: make a trip to Montauk Point Lighthouse, immerse yourself in nature at Camp Hero State Park, cast your line with a fishing tour, and tour the pleasant surroundings at Ditch Plains.

To find traveler tips, ratings, maps, and tourist information, you can read our Montauk day trip planning website.

You can drive from Riverhead to Montauk in 1.5 hours. In May, daily temperatures in Montauk can reach 65°F, while at night they dip to 50°F. Wrap up your sightseeing on the 26th (Thu) early enough to drive to Shelter Island.
Parks · Nature · Outdoors · Historic Sites

Shelter Island — 2 nights

Kick off your visit on the 27th (Fri): steep yourself in history at Shelter Island Historical Society, see the interesting displays at Sag Harbor Whaling and Historical Museum, then get a new perspective on things with Boat Tours & Water Sports, and finally walk around Sag Harbor Marine Park. Get ready for a full day of sightseeing on the 28th (Sat): examine the collection at South Fork Natural History Museum and then tour the pleasant surroundings at Mashomack Preserve.

To see reviews, photos, maps, and other tourist information, refer to the Shelter Island online day trip planner.

You can drive from Montauk to Shelter Island in 1.5 hours. In May, daytime highs in Shelter Island are 64°F, while nighttime lows are 52°F. Cap off your sightseeing on the 28th (Sat) early enough to travel back home.
Parks · Museums · Wildlife · Tours
Side Trips

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.