5 days in Long Island Itinerary

5 days in Long Island Itinerary

Created using Inspirock Long Island trip itinerary maker

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Route & dates

5 days in Long Island Itinerary

Start: Boston
Drive:  3​h 30​min
1
Cutchogue
— 2 nights
Drive:  1​h 30​min
2
Montauk
— 2 nights
ferry + train:  4​h 15​min
End: Boston

2
nights
Cutchogue

Cutchogue ©
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Change things up with these side-trips from Cutchogue: Amazing Olive (in Port Jefferson) and Room Escape Games (in Ronkonkoma). The adventure continues: experience rural life at The East End Mushroom Company, get up close and personal with brilliant marine life at Long Island Aquarium, kick back and relax at Cooper's Beach, and do a tasting at Sannino Bella Vita Vineyard.

To find reviews, more things to do, ratings, and more tourist information, use the Cutchogue trip planner .

Boston to Cutchogue is an approximately 3.5-hour car ride. October in Cutchogue sees daily highs of 64°F and lows of 52°F at night. Finish your sightseeing early on the 19th (Sat) to allow enough time to drive to Montauk.

Things to do in Cutchogue

Wineries Parks Tours

Side Trips

Greenport, Room Escape Games, Cooper's Beach, Sparkling Pointe Vineyards & Winery, Amazing Olive
Highlights from your plan
Sannino Bella Vita Vineyard ©
Sannino Bella Vita Vineyard
Room Escape Games
Long Island Aquarium ©
Long Island Aquarium

2
nights
Montauk

Montauk ©
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 20th (Sun): see what you can catch with a fishing tour, then visit a coastal fixture at Montauk Point Lighthouse, and then don't miss a visit to Gosman's Restaurant. Keep things going the next day: immerse yourself in nature at Montauk Point State Park, admire the majestic nature at Hither Hills State Park, and then learn about winemaking at Wolffer Estate Vineyard.

For ratings, traveler tips, maps, and tourist information, you can read our Montauk online trip itinerary planner .

Drive from Cutchogue to Montauk in 1.5 hours. In October, daily temperatures in Montauk can reach 65°F, while at night they dip to 53°F. Finish your sightseeing early on the 21st (Mon) to allow enough time to travel back home.

Things to do in Montauk

Nature Parks Tours

Side Trip

Wolffer Estate Vineyard
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Montauk Point State Park ©
Montauk Point State Park

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