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

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 1st (Sat) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: find something for the whole family at Universal Orlando Resort, cool off at Discovery Cove, take in the architecture and atmosphere at St. James 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.
Theme Parks · Parks · Historic Sites

Gainesville — 6 nights

Get out of town with these interesting Gainesville side-trips: Ocala (Sholom Park & Farm Tours of Ocala), Scuba & Snorkeling (in Crystal River) and Rivertown Park (in St. Johns).

To see reviews, traveler tips, ratings, and more tourist information, use the Gainesville trip planner.

You can drive from Orlando to Gainesville in 2 hours. Alternatively, you can take a bus. Traveling from Orlando in May, expect slightly colder with lows of 19°C in Gainesville. Wrap up your sightseeing on the 10th (Mon) early enough to fly to Charlottesville.
Parks · Wildlife · Historic Sites · Museums
Side Trips

Charlottesville — 2 nights

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.
Historic Sites · Parks · Breweries & Distilleries · Tours
Side Trips

Luray — 1 night

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.
Kick off your visit on the 13th (Thu): take in nature's colorful creations at Birdsong Pleasure Garden, trek along Stony Man Mountain Overlook, then Head underground at Luray Caverns, and finally sample the fine beverages at River Hill Wine & Spirits.

To find reviews, more things to do, photos, and tourist information, read our Luray trip builder.

Getting from Charlottesville to Luray by car takes about 1.5 hours. Other options: do a combination of bus and taxi. May in Luray sees daily highs of 28°C and lows of 13°C at night. Finish up your sightseeing early on the 13th (Thu) so you can go by car to Winchester.
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.
Museums · Outdoors · Shopping · Golf
Side Trips

Arlington — 3 nights

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: Steven F. Udvar-Hazy Center (in Chantilly), St George's Episcopal Church (in Fredericksburg) and National Museum of the Marine Corps (in Triangle). There's much more to do: get to know the fascinating history of The Tomb of the Unknown Soldier, contemplate the long history of Arlington National Cemetery, pause for some serene contemplation at The Basilica of Saint Mary, and explore the landscape on two wheels at Mount Vernon Trail.

To find other places to visit, traveler tips, maps, and more tourist information, you can read our Arlington holiday builder app.

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 bus. Expect a bit warmer evenings in Arlington when traveling from Winchester in May, with lows around 17°C. Finish your sightseeing early on the 17th (Mon) so you can drive to Chincoteague Island.
Historic Sites · Parks · Museums · Outdoors
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: stroll through 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.
Wildlife · Parks · Nature · Outdoors
Side Trip

Williamsburg — 5 nights

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). And it doesn't end there: get engrossed in the history at Colonial Williamsburg, don't miss a visit to Jamestown Glasshouse, contemplate the long history of Bassett Hall, and pause for some serene contemplation at Saint Bede Catholic Church.

For more things to do, reviews, other places to visit, and tourist information, read our Williamsburg trip itinerary planning website.

Getting from Chincoteague Island to Williamsburg by car takes about 3 hours. Other options: take a bus; or take a bus. When traveling from Chincoteague Island in May, plan for a bit warmer days in Williamsburg, with highs around 30°C, while nights are about the same with lows around 17°C. Cap off your sightseeing on the 24th (Mon) early enough to go by car to Virginia Beach.
Historic Sites · Theme Parks · Museums · Parks
Side Trips

Virginia Beach — 4 nights

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: sample the fine beverages at Tarnished Truth Distilling Company, pause for some photo ops at Naval Aviation Monument, step aboard Battleship Wisconsin at Nauticus, and take a leisurely stroll along Virginia Beach Boardwalk.

For other places to visit, photos, more things to do, and tourist information, read our Virginia Beach trip planner.

You can drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In May, daily temperatures in Virginia Beach can reach 29°C, while at night they dip to 18°C. Cap off your sightseeing on the 28th (Fri) early enough to catch the flight back home.
Parks · Museums · Outdoors · Beaches
Side Trip

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.