29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner

Make it your trip
Fly
1
Key West
— 4 nights
Drive
2
Marathon
— 3 nights
Drive
3
Key Largo
— 3 nights
Drive
4
Naples
— 6 nights
Drive
5
Sarasota
— 5 nights
Drive
6
St. Augustine
— 7 nights
Fly

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Key West

— 4 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.
Step out of the city life by going to Key West Wildlife Center and Dry Tortugas National Park. Discover out-of-the-way places like Key West Garden Club and West Martello Tower. And it doesn't end there: pause for some serene contemplation at Saint Mary Star of the Sea, don't miss a visit to US 1 Mile Marker 0, see the interesting displays at Mel Fisher Maritime Heritage Museum, and sample the fine beverages at Key West First Legal Rum Distillery.

To find traveler tips, photos, and tourist information, read Key West trip itinerary website.

Atlanta to Key West is an approximately 4-hour flight. You can also drive; or take a bus. In January, Key West is much hotter than Atlanta - with highs of 76°F and lows of 66°F. Finish your sightseeing early on the 7th (Thu) to allow enough time to drive to Marathon.

Things to do in Key West

Historic Sites · Parks · Museums · Nature

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.
Take a break from the city and head to Crane Point Museum & Nature Center and Dolphin Research Center. There's much more to do: soothe aching muscles at some of the top local wellness centers, tour the pleasant surroundings at Bahia Honda State Park, take in the views from Seven Mile Bridge, and see the top attractions with Ultimate HeliTours.

For where to stay, maps, reviews, and other tourist information, you can read our Marathon online road trip planner.

Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. January in Marathon sees daily highs of 77°F and lows of 66°F at night. Finish up your sightseeing early on the 10th (Sun) so you can go by car to Key Largo.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trip

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.
Take a break from the city and head to Anhinga Trail and Capt. Sterling's Everglades Eco-Tours. Explore hidden gems such as Molasses Reef and Robert Is Here. You'll find plenty of places to visit near Key Largo: Homestead (Losner Park & Everglades Alligator Farm). The adventure continues: take an in-depth tour of History of Diving Museum, fulfill a lifelong dream with Theater of the Sea, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, and take a tour of African Queen Canal Cruise.

To find other places to visit, photos, reviews, and other tourist information, use the Key Largo online trip maker.

Drive from Marathon to Key Largo in 1.5 hours. Alternatively, you can take a bus. Plan for a bit cooler nights when traveling from Marathon in January since evenings lows in Key Largo dip to 61°F. Wrap up your sightseeing on the 13th (Wed) early enough to drive to Naples.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Side Trips

Naples

— 6 nights
Eschew the tourist crowds and head to Captiva Beach and The Hirdie-Girdie Gallery. Visiting Barefoot Beach Preserve and Six Mile Cypress Slough Preserve will get you outdoors. Venture out of the city with trips to Lovers Key State Park (in Fort Myers Beach), Cullum’s Bonita Trail (in Bonita Springs) and Speed Boats Tours (in Everglades City).

For maps, other places to visit, more things to do, and more tourist information, use the Naples itinerary maker.

Traveling by car from Key Largo to Naples takes 3 hours. Alternatively, you can take a bus. In January, plan for daily highs up to 75°F, and evening lows to 58°F. Finish your sightseeing early on the 19th (Tue) so you can drive to Sarasota.

Things to do in Naples

Parks · Outdoors · Wildlife · Beaches

Side Trips

Sarasota

— 5 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Step out of the city life by going to Robinson Nature Preserve and Tampa Electric's Manatee Viewing Center. You'll explore the less-touristy side of things at Venice Beach and Siesta Key Rum. Get out of town with these interesting Sarasota side-trips: Fort De Soto Park (in Tierra Verde), Jungle Prada de Navarez Park (in St. Petersburg) and Punta Gorda (Peace River Wildlife Center & Fishing Charters & Tours). And it doesn't end there: steep yourself in history at Ca d'Zan, enjoy the sand and surf at Saint Pete Beach, tour the pleasant surroundings at Treasure Island Beach, and get to know the fascinating history of Marie Selby Botanical Gardens.

To find other places to visit, reviews, more things to do, and other tourist information, you can read our Sarasota trip itinerary maker website.

Traveling by car from Naples to Sarasota takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Traveling from Naples in January, plan for slightly colder nights in Sarasota, with lows around 53°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to St. Augustine.

Things to do in Sarasota

Parks · Wildlife · Outdoors · Beaches

Side Trips

St. Augustine

— 7 nights
St. Your inner history buff will appreciate National Shrine of Our Lady of La Leche at Mission Nombre de Dios and The Old Senator Tree. Explore hidden gems such as Lighthouse Point Park and Angell & Phelps Chocolate Factory. Venture out of the city with trips to Ponce de Leon Inlet Lighthouse & Museum (in Ponce Inlet), Stetson Mansion (in DeLand) and Fernandina Beach (Shrimping Museum, Fort Clinch State Park, &more). And it doesn't end there: identify plant and animal life at St. Augustine Wild Reserve, examine the collection at First Colony, admire nature's wide array of creatures at St. Augustine Aquarium, and stroll through St. Augustine Beach.

To see ratings, reviews, traveler tips, and more tourist information, use the St. Augustine day trip site.

You can drive from Sarasota to St. Augustine in 4.5 hours. Other options are to fly; or take a bus. When traveling from Sarasota in January, plan for little chillier days in St. Augustine, with highs around 65°F, while nights are about the same with lows around 49°F. Finish your sightseeing early on the 31st (Sun) so you can travel back home.

Things to do in St. Augustine

Parks · Historic Sites · Outdoors · Beaches

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.