19 days in Long Island & Kissimmee Itinerary

19 days in Long Island & Kissimmee Itinerary

Created using Inspirock United States trip itinerary maker

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Route & dates

19 days in Long Island & Kissimmee Itinerary

Start: Orlando
Fly + Drive:  5​h 15​min
1
Massapequa
— 2 nights
Drive:  1​h 15​min
2
Riverhead
— 3 nights
Drive:  1​h 15​min
3
Montauk
— 4 nights
Drive:  1​h 15​min
4
Shelter Island
— 1 night
Drive:  3​h 30​min
5
Ocean Beach, Fire Island
— 2 nights
+2
Drive + Fly + Drive:  5​h 45​min
6
Kissimmee
— 5 nights
train:  30​min
End: Orlando

2
nights
Massapequa

Massapequa ©
Massapequa is a hamlet and census-designated place (CDP) in the southern part of the Town of Oyster Bay in southeastern Nassau County, New York, on Long Island, east of New York City. Start off your visit on the 30th (Sun): walk around Norman J. Levy Park & Preserve. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Point Lookout Beach, then stroll through Gilgo Beach, and then stroll around Marjorie R. Post Community Park.

Inspirock's itinerary builder makes planning a Massapequa trip simple and quick.

Orlando to Massapequa is an approximately 5.5-hour flight. You can also drive. Plan for slightly colder temperatures traveling from Orlando in June, with highs in Massapequa at 77°F and lows at 62°F. Finish up your sightseeing early on the 2nd (Tue) so you can travel to Riverhead.

Things to do in Massapequa

Parks Wildlife Beaches

Side Trips

Babylon, Our Lady of Grace Roman Catholic Church, Norman J. Levy Park & Preserve, Bayard Cutting Arboretum, Point Lookout Beach
Highlights from your plan
Point Lookout Beach ©
Point Lookout Beach
Marjorie R. Post Community Park ©
Marjorie R. Post Community Park
Captree State Park ©
Captree State Park

3
nights
Riverhead

Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Change things up with a short trip to Joel L. Lefkowitz Park at West Meadow Beach in Stony Brook (about 46 minutes away). And it doesn't end there: get up close and personal with brilliant marine life at Long Island Aquarium, awaken your taste buds at some of the top wineries in the area, enjoy the sand and surf at Ponquogue Beach, and test your problem-solving skills at popular escape rooms.

To find photos, reviews, and tourist information, go to the Riverhead road trip site .

You can drive from Massapequa to Riverhead in an hour. Traveling from Massapequa in July, Riverhead is slightly colder at night with lows of 64°F. Cap off your sightseeing on the 5th (Fri) early enough to go by car to Montauk.

Things to do in Riverhead

Parks Beaches Outdoors

Side Trips

Ponquogue Beach, Cupsogue Beach County Park, The East End Mushroom Company, Wine Tours & Tastings, Baiting Hollow Hummingbird Sanctuary
Highlights from your plan
Cupsogue Beach County Park ©
Cupsogue Beach County Park
Long Island Aquarium ©
Long Island Aquarium
Wine Tours & Tastings

4
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. Venture out of the city with trips to Sag Harbor (Sag Harbor Marine Park & Custom House Museum), Orient (Oysterponds Historical Society & Orient Beach State Park) and Guild Hall (in East Hampton). There's much more to do: visit a coastal fixture at Montauk Point Lighthouse, immerse yourself in nature at Montauk Point State Park, make a trip to St. Therese of Lisieux Catholic Church, and get a new perspective on things with Boat Tours & Water Sports.

For where to stay, traveler tips, photos, and more tourist information, refer to the Montauk trip planner .

Getting from Riverhead to Montauk by car takes about 1.5 hours. In July in Montauk, expect temperatures between 80°F during the day and 68°F at night. Finish your sightseeing early on the 9th (Tue) so you can drive to Shelter Island.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

Sag Harbor, Orient, East Hampton
Highlights from your plan
Montauk Point State Park ©
Montauk Point State Park
Fishing Charters & Tours
Montauk Point Lighthouse ©
Montauk Point Lighthouse

1
night
Shelter Island

Shelter Island ©
Shelter Island is a hamlet and census-designated place (CDP) within the Town of Shelter Island in Suffolk County, New York, United States. Kick off your visit on the 10th (Wed): identify plant and animal life at Mashomack Preserve, then contemplate the long history of Shelter Island Historical Society, and then take a peaceful walk through Sylvester Manor Educational Farm.

To find ratings, other places to visit, maps, and other tourist information, refer to the Shelter Island road trip planner .

You can drive from Montauk to Shelter Island in 1.5 hours. In July, plan for daily highs up to 79°F, and evening lows to 67°F. Finish your sightseeing early on the 10th (Wed) to allow enough time to travel to Ocean Beach.

Things to do in Shelter Island

Parks Wildlife Historic Sites
Highlights from your plan
Mashomack Preserve ©
Mashomack Preserve
Shelter Island Historical Society ©
Shelter Island Historical Society
Sylvester Manor Educational Farm ©
Sylvester Manor Educational Farm

2
nights
Ocean Beach, Fire Island

Ocean Beach ©
Ocean Beach is a village in the southern part of the Town of Islip, on Fire Island, within Suffolk County, New York, United States.The Incorporated Village of Ocean Beach is a popular tourist destination, due to its beachfront location accompanied by a commercial district featuring nightlife, hotels, bayfront restaurants and a variety of stores. Start off your visit on the 11th (Thu): immerse yourself in nature at Robert Moses State Park and then enjoy the sand and surf at Kismet Beach. On your second day here, visit a coastal fixture at Fire Island Lighthouse, go for a stroll along the water at Sailors Haven Visitor Center, and then take a peaceful walk through The Sunken Forest.

Planning Ocean Beach trip won't be overwheling when you use's Insprock itinerary maker.

Getting from Shelter Island to Ocean Beach by car takes about 2.5 hours. In July, plan for daily highs up to 84°F, and evening lows to 69°F. Wrap up your sightseeing on the 12th (Fri) to allow time to travel to Kissimmee.

Things to do in Ocean Beach

Parks Nature Beaches

Side Trips

Fire Island, Kismet Beach
Highlights from your plan
Robert Moses State Park ©
Robert Moses State Park
Sailors Haven Visitor Center ©
Sailors Haven Visitor Center
Fire Island Lighthouse ©
Fire Island Lighthouse

5
nights
Kissimmee

Kissimmee ©
A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.
Explore Kissimmee's surroundings by going to Tampa (Busch Gardens, Room Escape Games, & more), Munn Park (in Lakeland) and Legoland Florida Resort (in Winter Haven). Next up on the itinerary: take a stroll through Old Town, find something for the whole family at Fun Spot America Kissimmee, take a leisurely stroll along Cocoa Beach Pier, and examine the collection at Osceola County Welcome Center and History Museum.

To see traveler tips, where to stay, and other tourist information, read Kissimmee trip itinerary maker tool .

The Route module can help you plan travel from Ocean Beach to Kissimmee. Traveling from Ocean Beach in July, things will get a bit warmer in Kissimmee: highs are around 90°F and lows about 75°F. Cap off your sightseeing on the 18th (Thu) early enough to catch the train back home.

Things to do in Kissimmee

Theme Parks Parks Neighborhoods

Side Trips

Tampa, Cocoa Beach, Legoland Florida Resort, Munn Park
Highlights from your plan
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
Old Town ©
Old Town
Legoland Florida Resort ©
Legoland Florida Resort

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