8 days in Kissimmee & Virginia Itinerary

8 days in Kissimmee & Virginia Itinerary

Created using Inspirock United States tour itinerary maker

Plan created by another user. Make it yours

Route & dates

1
Kissimmee
— 2 nights
2
Virginia Beach
— 1 night
3
Williamsburg
— 2 nights
4
Luray
— 1 night
5
Arlington
— 1 night

2
nights
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.
When in Kissimmee, make a side trip to see Legoland Florida Resort in Winter Haven, approximately Winter Haven away. Pack the 4th (Tue) with family-friendly diversions at Old Town. There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, walk around Kissimmee Lakefront Park, and whizz through the canopy at Orlando Tree Trek Adventure Park.

For traveler tips, other places to visit, ratings, and more tourist information, you can read our Kissimmee online vacation builder.

New York City to Kissimmee is an approximately 6.5-hour flight. You can also drive; or take a bus. When traveling from New York City in August, plan for a bit warmer days in Kissimmee, with highs around 91°F, while nights are about the same with lows around 76°F. Cap off your sightseeing on the 6th (Thu) early enough to travel to Virginia Beach.

Things to do in Kissimmee

Theme Parks · Outdoors · Tours

Side Trips

Legoland Florida Resort, Boat Tours & Water Sports
Highlights from your plan
Boat Tours & Water Sports
Legoland Florida Resort ©
Legoland Florida Resort
Orlando Tree Trek Adventure Park ©
Orlando Tree Trek Adventure Park

1
night
Virginia Beach

Virginia Beach ©
Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
Kick off your visit on the 7th (Fri): observe the fascinating underwater world at Virginia Aquarium & Marine Science Center, kick back and relax at Virginia Beach, and then take in the waterfront at Virginia Beach Boardwalk.

To find where to stay, photos, more things to do, and more tourist information, read Virginia Beach online holiday planner.

Getting from Kissimmee to Virginia Beach by flight takes about 5.5 hours. Other options: drive; or do a combination of train and tram. Traveling from Kissimmee in August, you will find days in Virginia Beach are slightly colder (86°F), and nights are about the same (72°F). Wrap up your sightseeing on the 7th (Fri) to allow time to drive to Williamsburg.

Things to do in Virginia Beach

Parks · Zoos & Aquariums · Childrens Museums
Highlights from your plan
Virginia Aquarium & Marine Science Center ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Virginia Beach ©
Virginia Beach

2
nights
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
On the 8th (Sat), cool off at Busch Gardens Williamsburg. Get ready for a full day of sightseeing on the 9th (Sun): steep yourself in history at Jamestown Settlement and then steep yourself in history at Colonial Williamsburg.

For traveler tips, where to stay, maps, and other tourist information, use the Williamsburg trip planner.

Traveling by car from Virginia Beach to Williamsburg takes 1.5 hours. Alternatively, you can take a bus; or take a bus. In August, plan for daily highs up to 89°F, and evening lows to 70°F. Finish up your sightseeing early on the 9th (Sun) so you can go by car to Luray.

Things to do in Williamsburg

Theme Parks · Historic Sites · Museums
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Colonial Williamsburg ©
Colonial Williamsburg
Jamestown Settlement ©
Jamestown Settlement

1
night
Luray

Luray ©
Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
On the 10th (Mon), trek along Stony Man Mountain Overlook, then trot along with Jordan Hollow Stables, then examine the collection at Cooter's in Luray, and finally take in breathtaking views at Luray Caverns.

To see ratings, other places to visit, reviews, and tourist information, you can read our Luray day trip planning website.

Drive from Williamsburg to Luray in 3.5 hours. Alternatively, you can do a combination of bus and car; or do a combination of train and car. Expect slightly colder temperatures when traveling from Williamsburg in August; daily highs in Luray reach 83°F and lows reach 63°F. Finish your sightseeing early on the 10th (Mon) to allow enough time to drive to Arlington.

Things to do in Luray

Parks · Outdoors · Nature

Side Trip

Jordan Hollow Stables
Highlights from your plan
Jordan Hollow Stables ©
Jordan Hollow Stables
Luray Caverns ©
Luray Caverns
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook

1
night
Arlington

Arlington ©
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Start off your visit on the 11th (Tue): appreciate the history behind Pentagon Memorial, get to know the fascinating history of The Tomb of the Unknown Soldier, then stroll the grounds of Arlington National Cemetery, and finally make a trip to John F. Kennedy Grave Site.

To find photos, reviews, maps, and tourist information, you can read our Arlington route planner.

You can drive from Luray to Arlington in 2 hours. Other options are to do a combination of taxi and bus; or do a combination of taxi, bus, and subway. Traveling from Luray in August, expect a bit warmer with lows of 71°F in Arlington. Finish up your sightseeing early on the 11th (Tue) so you can travel back home.

Things to do in Arlington

Historic Sites
Highlights from your plan
Arlington National Cemetery ©
Arlington National Cemetery
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Pentagon Memorial ©
Pentagon Memorial

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