8 days in Kissimmee & Virginia Itinerary

8 days in Kissimmee & Virginia Itinerary

Created using Inspirock United States tour itinerary maker

Make it your trip
Fly
1
Kissimmee
— 2 nights
Fly
2
Virginia Beach
— 1 night
Drive
3
Williamsburg
— 2 nights
Drive
4
Luray
— 1 night
Drive
5
Arlington
— 1 night
Fly

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Kissimmee

— 2 nights

Gateway to Fun

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. There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, find something for the whole family at Old Town, stroll around Kissimmee Lakefront Park, and whizz through the canopy at Orlando Tree Trek Adventure Park.

To find ratings, more things to do, other places to visit, and tourist information, read our Kissimmee attractions planner.

New York City to Kissimmee is an approximately 4.5-hour flight. You can also drive; or take a bus. When traveling from New York City in August, plan for somewhat warmer days in Kissimmee, with highs around 91°F, while nights are about the same with lows around 76°F. Finish your sightseeing early on the 6th (Thu) to allow enough time to fly to Virginia Beach.

Things to do in Kissimmee

Theme Parks · Tours · Outdoors · Adventure

Side Trips

Virginia Beach

— 1 night

The Resort City

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 3.5 hours. Other options: drive; or take a train. 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 · Museums · Zoos & Aquariums · Childrens Museums

Williamsburg

— 2 nights

Colonial Capital

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 get engrossed in the 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 do a combination of bus and train. 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

Luray

— 1 night

Cabin Capital of Virginia

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 explore the fascinating underground world of 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 train and car; or do a combination of bus 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 · Trails

Side Trip

Arlington

— 1 night

National History, Local Flavor

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 fly; or do a combination of taxi and bus. 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 catch the flight back home.

Things to do in Arlington

Historic Sites

Virginia travel guide

4.6
History Museums · Wineries & Vineyards · Historic Sites
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.