22 days in Long Island Itinerary

22 days in Long Island Itinerary

Created using Inspirock Long Island travel planner

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Route & dates

22 days in Long Island Itinerary

Start: Washington DC
Fly + Drive:  5​h
1
Riverhead
— 9 nights
Drive:  1​h 15​min
2
Montauk
— 7 nights
Drive:  2​h 15​min
3
Freeport
— 5 nights
Drive + Fly:  3​h 45​min
End: Washington DC

9
nights
Riverhead

Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Head to Alex Ferrone Gallery and St. James General Storefor some retail therapy. Sannino Bella Vita Vineyard and Bedell Cellars are good opportunities to explore the local culture. Change things up with these side-trips from Riverhead: Long Island Maritime Museum (in West Sayville), Lavender By The Bay (in East Marion) and Kontokosta Winery (in Greenport). There's still lots to do: tour the pleasant surroundings at Cooper's Beach, stroll around Shinnecock East County Park, revel in the low prices at Tanger Outlets, and do a tasting at Waters Crest Winery.

To see traveler tips, where to stay, reviews, and tourist information, read our Riverhead itinerary maker .

Washington DC to Riverhead is an approximately 5-hour flight. You can also drive. Traveling from Washington DC in July, expect Riverhead to be little chillier, temps between 82°F and 64°F. Cap off your sightseeing on the 28th (Sun) early enough to go by car to Montauk.

Things to do in Riverhead

Parks Outdoors Beaches

Side Trips

Cutchogue, Southampton, Hampton Bays, Peconic, Lavender By The Bay
Highlights from your plan
Cooper's Beach ©
Cooper's Beach
Ponquogue Beach ©
Ponquogue Beach
Cupsogue Beach County Park ©
Cupsogue Beach County Park

7
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. Give yourself a bit of retail therapy at Main Beach and Round Swamp Farm. Get some cultural insight at Montauk Point Lighthouse and St. Therese of Lisieux Catholic Church. Get out of town with these interesting Montauk side-trips: Orient (Orient Beach State Park & Oysterponds Historical Society), Guild Hall (in East Hampton) and South Fork Natural History Museum (in Bridgehampton). There's much more to do: enjoy the sand and surf at Amsterdam Beach Preserve, tour the pleasant surroundings at Kirk Park Beach, get interesting insight from Tours, and admire the majestic nature at Hither Hills State Park.

To find traveler tips, ratings, reviews, and other tourist information, go to the Montauk online travel route builder .

Traveling by car from Riverhead to Montauk takes 1.5 hours. In July, plan for daily highs up to 80°F, and evening lows to 68°F. Wrap up your sightseeing on the 4th (Sun) early enough to travel to Freeport.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

East Hampton, Orient, Sag Harbor, Wolffer Estate Vineyard, South Fork Natural History Museum
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Main Beach ©
Main Beach
Orient Beach State Park ©
Orient Beach State Park

5
nights
Freeport

Freeport ©
Freeport is a village in the town of Hempstead, Nassau County, New York, USA, on the South Shore of Long Island. Satisfy your inner culture vulture at Sagamore Hill National Historic Site and Freeport's Nautical Mile. Popular historic sites such as Sands Point Preserve and Queens County Farm Museum are in your itinerary. You'll find plenty of places to visit near Freeport: Vanderbilt Museum and Planetarium (in Centerport), Tanger Outlets (in Deer Park) and Our Lady of Grace Roman Catholic Church (in West Babylon). There's lots more to do: tour the pleasant surroundings at Lido Beach, explore the world behind art at Nassau County Museum of Art, kick back and relax at Jones Beach State Park, and stop by Jericho Cider Mill.

To find traveler tips, reviews, photos, and other tourist information, read Freeport trip builder app .

Drive from Montauk to Freeport in 2 hours. In August, daytime highs in Freeport are 82°F, while nighttime lows are 67°F. Cap off your sightseeing on the 9th (Fri) early enough to travel back home.

Things to do in Freeport

Museums Parks Historic Sites

Side Trips

Garden City, Our Lady of Grace Roman Catholic Church, Jericho Cider Mill, Old Bethpage Village Restoration, Long Beach
Highlights from your plan
Sagamore Hill National Historic Site ©
Cradle of Aviation Museum ©
Cradle of Aviation Museum
Jones Beach State Park ©
Jones Beach State Park

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