5 days in Florida Itinerary

5 days in Florida Itinerary

Created using Inspirock Florida sightseeing planner

Make it your trip
Fly
1
Key West
— 1 night
Fly
2
Orlando
— 3 nights
Drive

S M T W T F S
12
13
14
15
16
17
18
19
20
21
22
23
24
25

Key West

— 1 night

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
On the 15th (Wed), admire the masterpieces at Fort East Martello Museum, glide through the air with a parasailing or paragliding tour, stroll the grounds of Key West Cemetery, then see the interesting displays at The Ernest Hemingway Home and Museum, then tour the pleasant surroundings at Key West Butterfly & Nature Conservatory, and finally brush up on your knowledge of spirits at Key West First Legal Rum Distillery. On the 16th (Thu), you'll have a packed day of sightseeing: get a taste of the local shopping with Alan S. Maltz Gallery, sample the fine beverages at Papa’s Pilar Rum Distillery, Hemingway Rum Company, and then get a taste of the local shopping with 7 Artists & Friends Gallery.

For where to stay, maps, and tourist information, read our Key West trip maker app.

Jacksonville to Key West is an approximately 5-hour flight. You can also drive; or do a combination of train and bus. Traveling from Jacksonville in September, plan for a bit warmer nights in Key West, with lows around 80°F. Finish your sightseeing early on the 16th (Thu) to allow enough time to fly to Orlando.

Things to do in Key West

Museums · Shopping · Breweries & Distilleries · Adventure

Orlando

— 3 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.
Pack the 19th (Sun) with family-friendly diversions at Universal Orlando Resort. Pack the 18th (Sat) with family-friendly diversions at Universal's Islands of Adventure. There's more to do: find something for the whole family at SeaWorld and discover the magic at Magic Kingdom Park.

To see maps, reviews, and other tourist information, refer to the Orlando visit planner.

Fly from Key West to Orlando in 3 hours. Alternatively, you can drive; or take a bus. Expect a bit cooler evenings in Orlando when traveling from Key West in September, with lows around 74°F. Finish your sightseeing early on the 19th (Sun) so you can drive back home.

Things to do in Orlando

Theme Parks

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.