31 days in Orlando, Gainesville & Virginia Itinerary

31 days in Orlando, Gainesville & Virginia Itinerary

Created using Inspirock United States itinerary planner

Make it your trip
Fly
1
Orlando
— 6 nights
Drive
2
Gainesville
— 6 nights
Fly
3
Charlottesville
— 2 nights
Drive
4
Luray
— 1 night
Drive
5
Winchester
— 1 night
Drive
6
Arlington
— 3 nights
Drive
7
Chincoteague Island
— 2 nights
Drive
8
Williamsburg
— 5 nights
Drive
9
Virginia Beach
— 4 nights
Drive to Norfolk International Airport, Fly to Lima

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Orlando

— 6 nights

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Have a day of magic on the 29th (Thu) at Walt Disney World Resort. Pack the 30th (Fri) with family-friendly diversions at Universal Orlando Resort. Next up on the itinerary: find something for the whole family at Universal's Islands of Adventure, cool off at Discovery Cove, take in the architecture and atmosphere at St James Roman Catholic Cathedral, and discover the magic at Magic Kingdom Park.

To see maps, ratings, other places to visit, and other tourist information, read our Orlando trip planning app.

Lima, Peru to Orlando is an approximately 10-hour flight. While traveling from Lima, expect somewhat warmer days and about the same nights in Orlando, ranging from highs of 34°C to lows of 21°C. Wrap up your sightseeing on the 4th (Tue) early enough to drive to Gainesville.

Things to do in Orlando

Theme Parks · Parks · Historic Sites

Gainesville

— 6 nights
You'll find plenty of places to visit near Gainesville: Scuba & Snorkeling (in Crystal River), Ocala (Sholom Park & Farm Tours of Ocala) and Rivertown Park (in St. Johns).

For other places to visit, traveler tips, ratings, and tourist information, refer to the Gainesville road trip planning tool.

You can drive from Orlando to Gainesville in 2 hours. Alternatively, you can take a bus. Traveling from Orlando in May, you can expect nighttime temperatures to be little chillier in Gainesville, with lows of 19°C. Finish your sightseeing early on the 10th (Mon) to allow enough time to fly to Charlottesville.

Things to do in Gainesville

Wildlife · Parks · Historic Sites · Outdoors

Side Trips

Charlottesville

— 2 nights

Hoo-Ville

Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Start off your visit on the 11th (Tue): pause for some serene contemplation at Saint Francis of Assisi Catholic Church, then Head underground at Grand Caverns, and then sample some tasty brews at a beer tour and tasting. Here are some ideas for day two: look for gifts at C'ville Arts: A Cooperative Gallery, then take in nature's colorful creations at Monticello, and then contemplate the long history of The Glass Palette - Interactive Glass Art Studio.

To see more things to do, where to stay, and more tourist information, read Charlottesville trip planner.

You can fly from Gainesville to Charlottesville in 6 hours. Alternatively, you can drive; or do a combination of taxi, bus, and train. Traveling from Gainesville in May, expect Charlottesville to be slightly colder, temps between 28°C and 15°C. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Luray.

Things to do in Charlottesville

Historic Sites · Parks · Breweries & Distilleries · Tours

Side Trips

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 13th (Thu), take in nature's colorful creations at Birdsong Pleasure Garden, tour the pleasant surroundings at Stony Man Mountain Overlook, then explore the stunning scenery at Luray Caverns, and finally sample the fine beverages at River Hill Wine & Spirits.

To find where to stay, traveler tips, photos, and more tourist information, you can read our Luray tour planner.

You can drive from Charlottesville to Luray in 1.5 hours. Another option is to do a combination of bus and taxi. In May, plan for daily highs up to 28°C, and evening lows to 13°C. Cap off your sightseeing on the 13th (Thu) early enough to go by car to Winchester.

Things to do in Luray

Parks · Nature · Outdoors · Trails

Winchester

— 1 night
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Kick off your visit on the 14th (Fri): wander the wide-open spaces of Rocking S Ranch, then get engrossed in the history at Virginia Museum of Veiled History, then tee off at Shenandoah Valley Golf Club, and finally take in the exciting artwork at Shenandoah Valley Artworks.

To find more things to do, ratings, traveler tips, and tourist information, read Winchester trip maker.

You can drive from Luray to Winchester in 1.5 hours. In May, daytime highs in Winchester are 26°C, while nighttime lows are 13°C. Finish your sightseeing early on the 14th (Fri) so you can drive to Arlington.

Things to do in Winchester

Museums · Golf · Outdoors · Shopping

Side Trips

Arlington

— 3 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.
Explore the numerous day-trip ideas around Arlington: St George's Episcopal Church (in Fredericksburg), Steven F. Udvar-Hazy Center (in Chantilly) and National Museum of the Marine Corps (in Triangle). There's lots more to do: appreciate the extensive heritage of The Tomb of the Unknown Soldier, steep yourself in history at Arlington National Cemetery, take in the architecture and atmosphere at The Basilica of Saint Mary, and don't miss a visit to John F. Kennedy Grave Site.

For where to stay, more things to do, traveler tips, and tourist information, read our Arlington trip planning tool.

Traveling by car from Winchester to Arlington takes 1.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi, train, and subway. Traveling from Winchester in May, you can expect nighttime temperatures to be a bit warmer in Arlington, with lows of 17°C. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Chincoteague Island.

Things to do in Arlington

Parks · Historic Sites · Museums · Nature

Side Trips

Chincoteague Island

— 2 nights
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Kick off your visit on the 18th (Tue): examine the collection at Chincoteague Bay Field Station, then grab your bike and head to Bike Depot, and then get up close to creatures of the deep with Captain Dan's Around the Island Tours. On the 19th (Wed), you'll have a packed day of sightseeing: look for all kinds of wild species at Chincoteague National Wildlife Refuge.

To see reviews, where to stay, other places to visit, and other tourist information, refer to the Chincoteague Island visit planning tool.

Drive from Arlington to Chincoteague Island in 4 hours. Alternatively, you can do a combination of flight and bus; or do a combination of subway, train, bus, and taxi. In May, daily temperatures in Chincoteague Island can reach 26°C, while at night they dip to 16°C. Cap off your sightseeing on the 19th (Wed) early enough to go by car to Williamsburg.

Things to do in Chincoteague Island

Wildlife · Parks · Nature · Outdoors

Side 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.
Change things up with a short trip to The Noland Trail in Newport News (about 36 minutes away). Plan for a day of cool, family-friendly fun on the 22nd (Sat) at Busch Gardens Williamsburg. Next up on the itinerary: contemplate the long history of Colonial Williamsburg, explore the striking landscape of Colonial National Historical Park, pause for some serene contemplation at Saint Bede Catholic Church, and make a trip to Jamestown Glasshouse.

To find reviews, photos, other places to visit, and tourist information, go to the Williamsburg tour itinerary maker.

Traveling by car from Chincoteague Island to Williamsburg takes 3 hours. Alternatively, you can take a bus; or take a bus. Expect somewhat warmer weather when traveling from Chincoteague Island in May: highs in Williamsburg hover around 30°C, while lows dip to 17°C. Wrap up your sightseeing on the 24th (Mon) to allow time to drive to Virginia Beach.

Things to do in Williamsburg

Historic Sites · Theme Parks · Museums · Parks

Side Trips

Virginia Beach

— 4 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.
Go for a jaunt from Virginia Beach to Norfolk to see Weyanoke Bird and Wildflower Sanctuary about 38 minutes away. There's still lots to do: brush up on your knowledge of spirits at Tarnished Truth Distilling Company, take a pleasant ride with a tour on horseback, admire the masterpieces at Chrysler Museum of Art, and admire the natural beauty at Norfolk Botanical Garden.

To see more things to do, maps, other places to visit, and more tourist information, read Virginia Beach trip app.

Traveling by car from Williamsburg to Virginia Beach takes 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect a daytime high around 29°C in May, and nighttime lows around 18°C. Wrap up your sightseeing on the 28th (Fri) early enough to fly back home.

Things to do in Virginia Beach

Parks · Museums · Outdoors · Beaches

Side Trip

Virginia travel guide

4.6
Historic Sites · Wineries & Vineyards · Gardens
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.