9 days in Disney, Florida Keys & Siesta Key Itinerary

9 days in Disney, Florida Keys & Siesta Key Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
Fly to Tulsa International Airport, Drive to Disney
— 2 nights
Key Largo
— 2 nights
Siesta Key
— 3 nights



— 2 nights
Disney is a town in Mayes County, Oklahoma, United States. You'll find plenty of places to visit near Disney: Natural Falls State Park (in West Siloam Springs), Bowling Ball Yard Art (in Nowata) and Totem Pole Park (in Foyil). And it doesn't end there: get a taste of the local shopping with Zena Suri Alpacas, see human ingenuity at work at Pensacola Dam, see the interesting displays at Darryl Starbird's National Rod & Custom Hall of Fame Museum, and tee off at Shangri-La.

To see ratings, reviews, photos, and tourist information, use the Disney road trip planning app.

Chicago to Disney is an approximately 6.5-hour combination of flight and car. You can also drive. While traveling from Chicago, expect a bit warmer days and about the same nights in Disney, ranging from highs of 78°F to lows of 57°F. Wrap up your sightseeing on the 16th (Sun) to allow time to travel to Key Largo.

Things to do in Disney

Outdoors · Golf · Parks · Museums

Side Trips

Key Largo

— 2 nights

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
On the 17th (Mon), get up close and personal with brilliant marine life at Island Dolphin Care and then identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center. On the 18th (Tue), you'll have a packed day of sightseeing: look for gifts at florida keys key lime products, take an in-depth tour of History of Diving Museum, then cast your line with a fishing tour, and finally soothe aching muscles at Island Flow Yoga.

For where to stay, reviews, ratings, and more tourist information, use the Key Largo road trip planning website.

Drive from Disney to Key Largo in 22 hours. Alternatively, you can drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect a bit warmer temperatures when traveling from Disney in May; daily highs in Key Largo reach 85°F and lows reach 72°F. Wrap up your sightseeing on the 19th (Wed) to allow time to drive to Siesta Key.

Things to do in Key Largo

Parks · Nature · Wildlife · Tours

Side Trip

Siesta Key

— 3 nights
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Family-friendly places like Siesta Beach and Turtle Beach will thrill your kids. Explore the numerous day-trip ideas around Siesta Key: St. Pete Beach (Pass-a-Grille Beach, Florida & Saint Pete Beach). There's much more to do: glide peacefully along the water with some of the best stand-up paddleboarding in the area, indulge in some personalized pampering at some of the best spas, stop by Silver City Sarasota, and meet the residents at Mote Marine Laboratory & Aquarium.

To see ratings, where to stay, traveler tips, and tourist information, use the Siesta Key trip planner.

Drive from Key Largo to Siesta Key in 5 hours. Alternatively, you can take a bus; or take a bus. In May, plan for daily highs up to 87°F, and evening lows to 68°F. Wrap up your sightseeing on the 22nd (Sat) to allow time to travel back home.

Things to do in Siesta Key

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trips

Florida Keys travel guide

Scuba & Snorkeling · Landmarks · Wildlife Areas
An archipelago of about 1,700 islands extending in a gentle arc south and southwest of Florida's mainland, the Florida Keys divide the Atlantic from the Gulf of Mexico. Many visitors on vacation come to scuba dive in the coral reefs, fossilized and exposed as sea levels declined over thousands of years. In addition to being one of the world's top diving and fishing spots, the Keys feature hundreds of shops, restaurants, bars, and various tourist attractions, most of them crowded all year long with visitors on vacation. To soak up the Keys' atmosphere and discover writer Ernest Hemingway's former haunts, drive from one island to the other all the way to Key West, located just 140 km (90 mi) from Cuba.