5 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner
Make it your trip
— 2 nights
Key West
— 2 nights


Orlando — 2 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 5th (Wed) at Walt Disney World Resort. There's much more to do: get in on the family fun at Universal Orlando Resort, admire the masterpieces at Charles Hosmer Morse Museum of American Art, and make an unforgettable trip to Epcot.

To see maps, more things to do, other places to visit, and more tourist information, use the Orlando day trip planning site.

New York City to Orlando is an approximately 4.5-hour flight. You can also drive; or take a bus. Traveling from New York City in October, expect Orlando to be somewhat warmer, temps between 85°F and 69°F. Wrap up your sightseeing on the 5th (Wed) to allow time to fly to Key West.
Theme Parks · Museums
Side Trip
Find places to stay Oct 3 — 5:

Key West — 2 nights

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.
Kick off your visit on the 6th (Thu): take an in-depth tour of Fort East Martello Museum, stroll the grounds of Key West Cemetery, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, examine the collection at The Ernest Hemingway Home and Museum, then make a trip to Duval Street, and finally take in the exciting artwork at Art On Duval Key West. On the 7th (Fri), you'll have a packed day of sightseeing: steep yourself in history at Truman Little White House, view the masterpieces at 7 Artists & Friends Key West, sample the fine beverages at Papa’s Pilar Rum Distillery, Hemingway Rum Company, glide through the air with a parasailing or paragliding tour, then contemplate the long history of Curry Mansion Inn, and finally brush up on your knowledge of spirits at Key West Distilling.

To see maps, other places to visit, where to stay, and tourist information, you can read our Key West road trip planning site.

You can fly from Orlando to Key West in 3.5 hours. Other options are to drive; or take a bus. Traveling from Orlando in October, expect a bit warmer with lows of 77°F in Key West. Wrap up your sightseeing on the 7th (Fri) to allow time to fly back home.
Museums · Historic Sites · Outdoors · Adventure
Find places to stay Oct 5 — 7:

Florida travel guide

Disney Parks & Activities · Theme Parks · Beaches
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.