22 days in Florida Itinerary

22 days in Florida Itinerary

Created using Inspirock Florida route planner

Make it your trip
Fly
1
Orlando
— 4 nights
Drive
2
Kissimmee
— 1 night
Fly
3
Key West
— 5 nights
Drive
4
Big Pine Key
— 2 nights
Drive
5
Marathon
— 3 nights
Drive
6
Key Largo
— 3 nights
Drive
7
Miami
— 3 nights
Fly

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Orlando

— 4 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.
Get some cultural insight at Stetson Mansion and Franklin Anderson Gallery. Take a break from Orlando with a short trip to Scuba & Snorkeling in Crystal River, about 1h 45 min away. There's still lots to do: explore the world behind art at Charles Hosmer Morse Museum of American Art, make an unforgettable trip to Walt Disney World Resort, take in the architecture and atmosphere at St James Roman Catholic Cathedral, and try out the rides at Happily Ever After Fireworks.

For ratings, photos, more things to do, and more tourist information, go to the Orlando trip planner.

Norfolk to Orlando is an approximately 4-hour flight. You can also drive; or take a train. Traveling from Norfolk in December, you will find days in Orlando are much hotter (77°F), and nights are a bit warmer (59°F). Wrap up your sightseeing on the 31st (Tue) early enough to drive to Kissimmee.

Things to do in Orlando

Theme Parks · Outdoors · Tours · Shopping

Side Trips

Kissimmee

— 1 night

Gateway to Fun

A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.
Start off your visit on the 1st (Wed): look for gifts at Black Market Minerals, find something for the whole family at Old Town, and then cozy up to a beverage at Island Grove Wine Company at Formosa Gardens.

For ratings, traveler tips, and other tourist information, read Kissimmee sightseeing planner.

Traveling by car from Orlando to Kissimmee takes an hour. Alternatively, you can take a train; or take a bus. In December in Kissimmee, expect temperatures between 76°F during the day and 59°F at night. Finish your sightseeing early on the 1st (Wed) so you can travel to Key West.

Things to do in Kissimmee

Theme Parks · Fun & Games · Nightlife · Wineries

Key West

— 5 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.
Your cultural itinerary includes sights like The Ernest Hemingway Home and Museum and Truman Little White House. Do your shopping at 7 Artists & Friends Gallery and Alan S. Maltz Gallery. The adventure continues: look for all kinds of wild species at Key West Butterfly & Nature Conservatory, see the vivid underwater world at Vandenberg Wreck, see some colorful creatures with a scuba or snorkeling tour, and see the interesting displays at Mel Fisher Maritime Heritage Museum.

For maps, ratings, reviews, and tourist information, refer to the Key West trip builder app.

Fly from Kissimmee to Key West in 4.5 hours. Alternatively, you can drive; or take a bus. Traveling from Kissimmee in January, you can expect nighttime temperatures to be somewhat warmer in Key West, with lows of 66°F. Finish up your sightseeing early on the 6th (Mon) so you can go by car to Big Pine Key.

Things to do in Key West

Wildlife · Outdoors · Tours · Museums

Big Pine Key

— 2 nights
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. On the 7th (Tue), enjoy the sand and surf at Calusa Beach and then tour the pleasant surroundings at Bahia Honda State Park. Here are some ideas for day two: stop by Out of the Blue Gallery, look for all kinds of wild species at National Key Deer Refuge, and then get a taste of the local shopping with Artists in Paradise Gallery.

To see more things to do, maps, ratings, and tourist information, read Big Pine Key online trip itinerary planner.

Traveling by car from Key West to Big Pine Key takes an hour. Alternatively, you can take a shuttle; or take a bus. January in Big Pine Key sees daily highs of 77°F and lows of 66°F at night. Finish your sightseeing early on the 8th (Wed) so you can drive to Marathon.

Things to do in Big Pine Key

Parks · Outdoors · Beaches · Shopping

Marathon

— 3 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Crane Point Museum & Nature Center and Shady Palm Art Gallery & Photography will appeal to museum buffs. Your itinerary includes some good beach time at Sombrero Beach and Sunset Park Beach. Explore the numerous day-trip ideas around Marathon: Islamorada (Indian Key State Historic Site & Florida Keys Brewing Company). It doesn't end there: look for all kinds of wild species at The Turtle Hospital and take a tour by water with Boat Tours & Water Sports.

Plan my trip to Marathon with suggested itineraries provided by Inspirock.

Marathon is very close to Big Pine Key. In January, daily temperatures in Marathon can reach 77°F, while at night they dip to 66°F. Wrap up your sightseeing on the 11th (Sat) to allow time to drive to Key Largo.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trips

Key Largo

— 3 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.
Do your shopping at Pasta Pantaleo Signature Gallery and Michelle Nicole Lowe Art Gallery. You'll explore and learn at Old Road Gallery and Homestead Historic Town Hall Museum. Step out of Key Largo with an excursion to Anhinga Trail in Everglades National Park--about 56 minutes away. There's lots more to do: take a tour by water with Boat Tours & Water Sports, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, see some colorful creatures with a scuba or snorkeling tour, and get interesting insight from Tours.

To see ratings, maps, other places to visit, and more tourist information, you can read our Key Largo online vacation maker.

Traveling by car from Marathon to Key Largo takes 1.5 hours. Alternatively, you can take a bus. Traveling from Marathon in January, expect slightly colder with lows of 61°F in Key Largo. Finish your sightseeing early on the 14th (Tue) so you can drive to Miami.

Things to do in Key Largo

Wildlife · Outdoors · Tours · Parks

Side Trips

Miami

— 3 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
For shopping fun, head to Lincoln Road or Aventura Mall. You'll explore and learn at The Wolfsonian - Florida International University and Lock & Load Museum. Explore Miami's surroundings by going to Panther Ridge Conservation Center (in Wellington) and Shark Valley Visitor Center (in Everglades National Park). Next up on the itinerary: enjoy the sand and surf at South Beach, wander the streets of Collins Avenue, and appreciate the extensive heritage of Art Deco Historic District.

To find maps, more things to do, reviews, and more tourist information, use the Miami travel route planning site.

Traveling by car from Key Largo to Miami takes 1.5 hours. Alternatively, you can take a bus. In January, daily temperatures in Miami can reach 77°F, while at night they dip to 63°F. Finish up your sightseeing early on the 17th (Fri) so you can travel back home.

Things to do in Miami

Parks · Shopping · Neighborhoods · Outdoors

Side Trips

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.