37 days in Virginia & Smoky Mountains & Cherokee Itinerary
Created using Klarna Trips United States itinerary planner
Start: Jeddah
Fly
1
Arlington
— 5 nights
Drive
2
Chincoteague Island
— 4 nights
Drive
3
Virginia Beach
— 6 nights
Drive
4
Williamsburg
— 5 nights
Drive
5
Shenandoah National Park
— 4 nights
Drive
6
Luray
— 5 nights
Fly
7
Cherokee
— 6 nights
Drive to Asheville Regional Airport, Fly to Jeddah
End: Jeddah
Fri, Jun 9 - Sat, Jul 15
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Arlington — 5 nights

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.Take a break from the city and head to Great Falls Park and Wolf Trap National Park for the Performing Arts. Eschew the tourist crowds and head to Air Force Memorial and Torpedo Factory Art Center. Venture out of the city with trips to Steven F. Udvar-Hazy Center (in Chantilly), National Museum of the Marine Corps (in Triangle) and Westmoreland State Park (in Colonial Beach). There's much more to do: buy something for everyone on your list at Tysons Corner Center, test your team's savvy at popular escape rooms, steep yourself in history at Arlington National Cemetery, and appreciate the extensive heritage of The Tomb of the Unknown Soldier.
For where to stay, ratings, and tourist information, use the Arlington attractions planner.
Jeddah, Saudi Arabia to Arlington is an approximately 17-hour flight. Traveling from Jeddah to Arlington, you'll gain 8 hours due to the time zone difference. Prepare for slightly colder weather when traveling from Jeddah in June: high temperatures in Arlington hover around 35°C and lows are around 24°C. Finish your sightseeing early on the 14th (Wed) to allow enough time to drive to Chincoteague Island.
Side Trips
Find places to stay Jun 9 — 14:
Highlights from your trip
Chincoteague Island — 4 nights
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.Give yourself a bit of retail therapy at MamerSass and Tryfan Gallery. Eschew the tourist crowds and head to Dolphin & Whale Watching and Chincoteague Veteran's Memorial Park. Step out of Chincoteague Island to go to Onancock and see Hopkins & Bros. Store, which is approximately 44 minutes away. Spend the 17th (Sat) exploring nature at Chincoteague National Wildlife Refuge. There's much more to do: get engrossed in the history at Museum of Chincoteague, pause for some photo ops at Robert N. Reed Downtown Waterfront Park, make a trip to Chincoteague Island Waterman's Memorial, and grab your bike and head to Bike Depot.
To find photos, more things to do, where to stay, and other tourist information, you can read our Chincoteague Island trip planner.
Getting from Arlington to Chincoteague Island by car takes about 4 hours. Other options: do a combination of flight and bus; or do a combination of subway, train, bus, and taxi. June in Chincoteague Island sees daily highs of 32°C and lows of 22°C at night. Finish your sightseeing early on the 18th (Sun) to allow enough time to drive to Virginia Beach.
Side Trips
Find places to stay Jun 14 — 18:
Highlights from your trip
Virginia Beach — 6 nights

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.Eschew the tourist crowds and head to Military Aviation Museum and First Landing State Park. Attractions like Cape Henry Lighthouse and Zipline make great kid-friendly stops. Change things up with these side-trips from Virginia Beach: Hampton Roads Bridge-Tunnel (in Hampton), Richmond (Carytown & American Civil War Museum- Historic Tredegar) and Cape Charles (Cape Charles Beach, Kiptopeke State Park, &more). There's much more to do: kick back and relax at Sandbridge Beach, don't miss a visit to Flame of Hope Memorial, take a leisurely stroll along Virginia Beach Boardwalk, and test your team's savvy at popular escape rooms.
Start your trip to Virginia Beach by creating a personalized itinerary on Klarna Trips.
Getting from Chincoteague Island to Virginia Beach by car takes about 2.5 hours. Other options: take a bus; or take a bus. In June, daytime highs in Virginia Beach are 34°C, while nighttime lows are 24°C. Wrap up your sightseeing on the 24th (Sat) early enough to drive to Williamsburg.
Side Trips
Find places to stay Jun 18 — 24:
Highlights from your trip
Williamsburg — 5 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.Shop till you drop at Yankee Candle Village and Williamsburg Premium Outlets. Discover out-of-the-way places like College of William & Mary and York River State Park. And it doesn't end there: find something for the whole family at Busch Gardens Williamsburg, explore the landscape on two wheels at Newport News Park, take in the architecture and atmosphere at Bruton Parish Episcopal Church, and get outside with Outdoor Activities.
To find photos, more things to do, ratings, and tourist information, go to the Williamsburg trip itinerary tool.
You can drive from Virginia Beach to Williamsburg in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In June, daytime highs in Williamsburg are 36°C, while nighttime lows are 23°C. Cap off your sightseeing on the 29th (Thu) early enough to go by car to Shenandoah National Park.
Side Trips
Find places to stay Jun 24 — 29:
Highlights from your trip
Shenandoah National Park — 4 nights

Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.Escape the urban bustle at Grand Caverns and Appalachian Trail. Discover out-of-the-way places like Dark Hollow Falls and Old Rag Mountain Hike. There's much more to do: take your sightseeing to a higher altitude at Hawksbill Mountain, take a memorable drive along Skyline Drive, trek along Dickey Ridge Trail, and explore the different monuments and memorials at Dean Cemetery.
To see more things to do, traveler tips, and more tourist information, you can read our Shenandoah National Park trip itinerary maker website.
You can drive from Williamsburg to Shenandoah National Park in 3 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of train, bus, and taxi. In June, daytime highs in Shenandoah National Park are 34°C, while nighttime lows are 20°C. Finish your sightseeing early on the 3rd (Mon) so you can drive to Luray.
Side Trips
Find places to stay Jun 29 — Jul 3:
Highlights from your trip
Luray — 5 nights
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.Eschew the tourist crowds and head to Shenandoah Caverns and Stony Man Mountain Overlook. Get outdoors at Zipline and Skyline Caverns. Venture out of the city with trips to Harrisonburg (Shenandoah Heritage Market & White Oak Lavender Farm & The Purple WOLF Tasting Room), Frontier Culture Museum (in Staunton) and Bryce Resort (in Basye). There's lots more to do: get engrossed in the history at The Car and Carriage Caravan Museum, admire the sheer force of Crabtree Falls, trek along Luray Hawksbill Greenway, and surround yourself with nature on Raptor Hill Falconry.
To see other places to visit, more things to do, and other tourist information, use the Luray trip planner.
Traveling by car from Shenandoah National Park to Luray takes 1.5 hours. In July, plan for daily highs up to 35°C, and evening lows to 22°C. Finish up your sightseeing early on the 8th (Sat) so you can catch the flight to Cherokee.
Side Trips
Find places to stay Jul 3 — 8:
Highlights from your trip
Cherokee — 6 nights
Trails of Legends and Adventures
The center of Cherokee culture in the eastern part of the country, the town named after this Native American tribe serves as a base camp for hiking in the Great Smoky Mountains.Step out of the city life by going to Mingo Falls and Soco Falls. You'll visit kid-friendly attractions like Mountain Farm Museum and Oconaluftee Islands Park. Change things up with these side-trips from Cherokee: Sapphire (Whitewater Falls & Gorges State Park), River Rafting & Tubing (in Bryson City) and Highlands (Sunset Rock and Ravenel Park & Glen Falls). There's still lots to do: take in the awesome beauty at Whiteside Mountain, see the interesting displays at Wheels Through Time Transportation Museum, look for gifts at Mast General Store, and trot along with a tour on horseback.
To find photos, where to stay, more things to do, and more tourist information, go to the Cherokee trip planner.
Traveling by flight from Luray to Cherokee takes 3.5 hours. Alternatively, you can drive; or do a combination of car, train, bus, and taxi. July in Cherokee sees daily highs of 33°C and lows of 19°C at night. Finish up your sightseeing early on the 14th (Fri) so you can travel back home.
Side Trips
Find places to stay Jul 8 — 14:
Highlights from your trip
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Virginia travel guide
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.