5 days in Hamptons Itinerary

5 days in Hamptons Itinerary

Created using Inspirock Hamptons trip planner

Make it your trip
Fly to New York JFK, Train to Montauk
— 2 nights
— 2 nights
Drive to John F Kennedy International Airport, Fly to Miami



— 2 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. Start off your visit on the 16th (Sun): see what you can catch with a fishing tour. On the 17th (Mon), you'll have a packed day of sightseeing: immerse yourself in nature at Hither Hills State Park, then steep yourself in history at Pollock-Krasner House and Study Center, then don't miss a visit to Gosman's Restaurant, and finally admire the majestic nature at Montauk Point State Park.

For other places to visit, where to stay, maps, and tourist information, go to the Montauk online day trip planner.

Miami to Montauk is an approximately 9-hour combination of flight and train. You can also drive; or take a bus. Plan for colder temperatures traveling from Miami in May, with highs in Montauk at 65°F and lows at 50°F. Finish your sightseeing early on the 18th (Tue) so you can drive to Southampton.

Things to do in Montauk

Outdoors · Parks · Wildlife · Nature

Side Trip


— 2 nights
Southampton is known for beaches, museums, and wineries. Your plan includes some of its best attractions: kick back and relax at Cooper's Beach, take a tour by water with Boat Tours & Water Sports, tour the pleasant surroundings at Meschutt Beach, and relax and rejuvenate at House of Wellness.

To see where to stay, maps, photos, and other tourist information, use the Southampton road trip planning tool.

You can drive from Montauk to Southampton in an hour. In May in Southampton, expect temperatures between 64°F during the day and 52°F at night. Finish up your sightseeing early on the 20th (Thu) so you can travel back home.

Things to do in Southampton

Outdoors · Parks · Beaches · Wineries

Side Trips

Hamptons travel guide

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.