14 days in Florida Itinerary

14 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner

Plan created by another user. Make it yours
Fly
1
Orlando
— 1 night
Drive
2
St. Augustine
— 3 nights
Drive
3
Naples
— 3 nights
Drive
4
Marco Island
— 1 night
Ferry
5
Key West
— 5 nights
Fly

S M T W T F S
22
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29
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31
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1
night
Orlando

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.
Start off your visit on the 29th (Sun): discover the magic at World of Disney, then don't miss a visit to Tree of Life, and then test your problem-solving skills at The Escape Game Orlando.

For where to stay, traveler tips, other places to visit, and more tourist information, you can read our Orlando road trip planning tool.

Sao Paulo, Brazil to Orlando is an approximately 12.5-hour flight. The time zone changes from Brasilia Standard Time to Eastern Standard Time, which is usually a -2 hour difference. Prepare for a bit cooler weather when traveling from Sao Paulo in December: high temperatures in Orlando hover around 29°C and lows are around 17°C. Finish up your sightseeing early on the 29th (Sun) so you can go by car to St. Augustine.

Things to do in Orlando

Theme Parks · Shopping · Fun & Games

3
nights
St. Augustine

St. Explore the numerous day-trip ideas around St. Augustine: Stetson Mansion (in DeLand) and Fort Clinch State Park (in Fernandina Beach). And it doesn't end there: get engrossed in the history at The Oldest Store Museum, gain insight at Flagler College, identify plant and animal life at St. Augustine Alligator Farm Zoological Park, and make a trip to St. George Street.

Plan my day in St. Augustine using traveler tips and tourist information provided by Inspirock.

You can drive from Orlando to St. Augustine in 2 hours. Another option is to take a bus. Expect a bit cooler weather when traveling from Orlando in December: highs in St. Augustine hover around 24°C, while lows dip to 15°C. Finish your sightseeing early on the 1st (Wed) so you can drive to Naples.

Things to do in St. Augustine

Parks · Historic Sites · Museums · Outdoors

Side Trips

3
nights
Naples

Get out of town with these interesting Naples side-trips: Speed Boats Tours (in Everglades City), Edison and Ford Winter Estates (in Fort Myers) and Bowman's Beach (in Sanibel Island).

To find ratings, reviews, photos, and more tourist information, read Naples trip itinerary maker website.

Drive from St. Augustine to Naples in 6 hours. Alternatively, you can fly; or take a bus. Traveling from St. Augustine in January, things will get somewhat warmer in Naples: highs are around 28°C and lows about 17°C. Finish your sightseeing early on the 4th (Sat) so you can drive to Marco Island.

Things to do in Naples

Parks · Wildlife · Outdoors · Museums

Side Trips

1
night
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Start off your visit on the 5th (Sun): get some thrills out on the water with a waterskiing or jet-skiing adventure, then get interesting insight from Tours, and then walk around Winterberry Park.

To find maps, where to stay, and tourist information, read our Marco Island sightseeing planner.

Marco Island is just a short distance from Naples. Traveling from Naples in January, expect slightly colder with lows of 13°C in Marco Island. Finish your sightseeing early on the 5th (Sun) to allow enough time to ride a ferry to Key West.

Things to do in Marco Island

Outdoors · Tours · Adventure · Wildlife

5
nights
Key West

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.
You'll find plenty of places to visit near Key West: Bahia Honda State Park (in Big Pine Key), Marathon (Seven Mile Bridge, The Turtle Hospital, &more) and Dolphin Research Center (in Grassy Key). Spend the 6th (Mon) exploring nature at Dry Tortugas National Park. The adventure continues: browse the exhibits of Key West Lighthouse and Keeper's Quarters Museum and examine the collection at Mel Fisher Maritime Heritage Museum.

For other places to visit, where to stay, photos, and other tourist information, use the Key West day trip planning app.

Traveling by ferry from Marco Island to Key West takes 4 hours. Alternatively, you can drive. Traveling from Marco Island in January, expect somewhat warmer with lows of 22°C in Key West. Finish up your sightseeing early on the 10th (Fri) so you can travel back home.

Things to do in Key West

Parks · Wildlife · Outdoors · Nature

Side Trips

Florida travel guide

4.3
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.