59 days in Florida Itinerary

59 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner
Make it your trip
Drive
1
St. Augustine
— 7 nights
Drive
2
Orlando
— 7 nights
Drive
3
Sarasota
— 4 nights
Drive
4
Sanibel Island
— 4 nights
Drive
5
Naples
— 5 nights
Drive
6
Marco Island
— 6 nights
Unknown
7
Everglades National Park
— 5 nights
Fly
8
Key West
— 7 nights
Drive
9
Marathon
— 5 nights
Drive
10
Islamorada
— 4 nights
Drive
11
Key Largo
— 4 nights
Fly

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St. Augustine — 7 nights

St. We've included these beaches for you: Vilano Beach and Crescent Beach Public Beach. Get some cultural insight at National Shrine of Our Lady of La Leche at Mission Nombre de Dios and Old St. Augustine Village. Get out of town with these interesting St. Augustine side-trips: Washington Oaks Gardens State Park (in Palm Coast), Gamble Rogers Memorial State Recreation Area (in Flagler Beach) and Andy Romano Beachfront Park (in Ormond Beach). Next up on the itinerary: get a dose of the wild on a nature and wildlife tour, contemplate the long history of Colonial Quarter, examine the collection at The Oldest House Museum Complex, and brush up on your military savvy at Spanish Military Hospital Museum.

To find maps, reviews, traveler tips, and more tourist information, read St. Augustine online trip itinerary builder.

Leland to St. Augustine is an approximately 7.5-hour car ride. You can also drive. Traveling from Leland in January, expect St. Augustine to be a bit warmer, temps between 65°F and 49°F. Finish up your sightseeing early on the 8th (Sun) so you can go by car to Orlando.
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Parks · Museums · Historic Sites · Outdoors
Side Trips

Orlando — 7 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.
Eschew the tourist crowds and head to Beach at Daytona Beach and Ponce de Leon Inlet Lighthouse & Museum. International Drive and Grand Bohemian Hotel Orlando are good opportunities to explore the local culture. Go for a jaunt from Orlando to Orange City to see Blue Spring State Park about 44 minutes away. There's still lots to do: get in on the family fun at Universal Orlando Resort, stroll around Lake Eola Park, and admire the natural beauty at Harry P. Leu Gardens.

To see maps, other places to visit, photos, and more tourist information, you can read our Orlando online travel route planner.

Getting from St. Augustine to Orlando by car takes about 2 hours. Other options: take a bus. While traveling from St. Augustine, expect somewhat warmer days and about the same nights in Orlando, ranging from highs of 71°F to lows of 52°F. Wrap up your sightseeing by early afternoon on the 15th (Sun) to allow enough time to drive to Sarasota.
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Parks · Theme Parks · Museums · Shopping
Side Trips

Sarasota — 4 nights

Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. You'll explore the less-touristy side of things at Crescent Beach and Legacy Trail. Marietta Museum of Art and Whimsy and The Ringling are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Sarasota: North Jetty Beach (in Casey Key) and Nokomis Beach (in Nokomis). The adventure continues: enjoy the sand and surf at South Lido Park, discover the deep blue sea with Keys Huka and Scuba, and identify plant and animal life at Save Our Seabirds.

To find maps, photos, where to stay, and tourist information, use the Sarasota visit planner.

Drive from Orlando to Sarasota in 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. January in Sarasota sees daily highs of 72°F and lows of 53°F at night. Finish up your sightseeing early on the 19th (Thu) so you can go by car to Sanibel Island.
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Outdoors · Parks · Beaches · Wildlife
Side Trips

Sanibel Island — 4 nights

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Relax by the water at Tarpon Bay Beach and Gulfside Beach. Explore hidden gems such as Sanibel Causeway and Fishing Charters & Tours. And it doesn't end there: look for all kinds of wild species at Sanibel Captiva Conservation Foundation, take in the dramatic natural features at Redfish Pass, take in the spiritual surroundings of Captiva Chapel By-The-Sea, and make a trip to St. Isabel Catholic Church.

To see maps, photos, reviews, and tourist information, read our Sanibel Island trip planning tool.

You can drive from Sarasota to Sanibel Island in 2 hours. Alternatively, you can do a combination of bus and taxi. Expect a daytime high around 75°F in January, and nighttime lows around 56°F. On the 23rd (Mon), you're off to Naples.
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Naples — 5 nights

Your cultural itinerary includes sights like Fifth Avenue South and Naples Historical Society. Step out of the city life by going to Lowdermilk Beach and Ten Thousand Islands Nwr. Venture out of the city with trips to Stand-Up Paddleboarding (in Fort Myers Beach), Koreshan State Park (in Estero) and Little Hickory Beach Park (in Bonita Springs).

To see traveler tips, where to stay, reviews, and other tourist information, refer to the Naples day trip site.

You can drive from Sanibel Island to Naples in 1.5 hours. In January, daytime highs in Naples are 75°F, while nighttime lows are 58°F. Finish your sightseeing early on the 28th (Sat) so you can drive to Marco Island.
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Side Trips

Marco Island — 6 nights

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. Your cultural itinerary includes sights like Marco Island Historical Museum and San Marco Catholic Church. Discover out-of-the-way places like Native Guided Fishing Charters and Keewaydin Island. There's lots more to do: kick back and relax at South Marco Beach, stroll through Tigertail Beach, look for all kinds of wild species at Otter Mound Preserve, and grab your bike and head to Island Bike Shop & Bicycle Rentals.

To see more things to do, ratings, photos, and tourist information, read Marco Island visit planning tool.

Marco Island is just a stone's throw from Naples. Expect little chillier evenings in Marco Island when traveling from Naples in January, with lows around 53°F. Cap off your sightseeing on the 3rd (Fri) early enough to travel to Everglades National Park.
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Parks · Outdoors · Beaches · Tours

Everglades National Park — 5 nights

Largest Subtropical Wilderness in the United States

A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S. Overflow from Lake Okeechobee into the Florida Bay formed these wetlands, which are home to manatees, American crocodiles, Florida panthers, and an array of wading birds, land birds, and birds of prey.
Get outdoors at Anhinga Trail and Gumbo Limbo Trail. Get some cultural insight at Flamingo and Nike Missile Site HM-69. Next up on the itinerary: stroll through 99 Mile Wilderness Waterway, contemplate the waterfront views at Eco Pond, take in the waterfront at West Lake Trail, and look for all kinds of wild species at Nine Mile Pond Canoe Trail.

To find other places to visit, reviews, ratings, and tourist information, go to the Everglades National Park day trip planning app.

Explore your travel options from Marco Island to Everglades National Park with the Route module. Expect a bit warmer evenings in Everglades National Park when traveling from Marco Island in February, with lows around 68°F. Finish your sightseeing early on the 8th (Wed) to allow enough time to fly to Key West.
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Parks · Trails · Outdoors · Nature

Key West — 7 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.
Eschew the tourist crowds and head to Saint Mary Star of the Sea and Stand-Up Paddleboarding. Do some cultural sightseeing at St. Paul's Episcopal Church and West Martello Tower. There's still lots to do: brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum, examine the collection at The Ernest Hemingway Home and Museum, take a leisurely stroll along Key West Historic Seaport, and browse the exhibits of Truman Little White House.

To see more things to do, maps, ratings, and tourist information, you can read our Key West online travel planner.

Traveling by flight from Everglades National Park to Key West takes 2.5 hours. Alternatively, you can take a bus; or take a bus. In February in Key West, expect temperatures between 78°F during the day and 68°F at night. Finish up your sightseeing early on the 15th (Wed) so you can go by car to Marathon.
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Parks · Historic Sites · Outdoors · Museums

Marathon — 5 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.
Get outdoors at The Turtle Hospital and Bahia Honda State Park. Satisfy your inner culture vulture at Crane Point Museum & Nature Center and San Pablo Catholic Church. There's much more to do: enjoy the sand and surf at Sombrero Beach, admire the majestic nature at Curry Hammock State Park, snap pictures at Old Seven Mile Bridge, and look for all kinds of wild species at Sombrero Reef.

Use Inspirock's suggestions to plan your Marathon trip and find the best activities and attractions for your vacation.

You can drive from Key West to Marathon in 1.5 hours. Another option is to take a bus. Expect a daytime high around 79°F in February, and nighttime lows around 68°F. Finish up your sightseeing early on the 20th (Mon) so you can go by car to Islamorada.
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Parks · Outdoors · Beaches · Wildlife
Side Trips

Islamorada — 4 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
We've included these beaches for you: Library Beach Park and Anne's Beach. Get some cultural insight at Indian Key State Historic Site and Lobster Trap Art Gift Shop and Gallery. And it doesn't end there: take a tour by water with Boat Tours & Water Sports, look for all kinds of wild species at Alligator Reef Light House, take in the exciting artwork at Old Road Gallery, and soothe aching muscles at some of the top local wellness centers.

To find traveler tips, photos, reviews, and more tourist information, go to the Islamorada day trip website.

You can drive from Marathon to Islamorada in an hour. Another option is to take a bus. In February in Islamorada, expect temperatures between 79°F during the day and 68°F at night. Finish your sightseeing early on the 24th (Fri) to allow enough time to drive to Key Largo.
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Parks · Outdoors · Museums · Shopping

Key Largo — 4 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.
Explore hidden gems such as Capt. Sterling's Everglades Eco-Tours and Key Largo Baptist Church. Get a sense of the local culture at Boca Chita Key and Keys' Meads. There's still lots to do: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, enjoy the sand and surf at Harry Harris Park, take a memorable tour with Conch Republic Divers, and explore the gorgeous colors at Grecian Rocks.

Discover how to plan a Key Largo trip in just a few steps with Inspirock's itinerary builder.

Key Largo is just a stone's throw from Islamorada. Traveling from Islamorada in February, expect a bit cooler with lows of 62°F in Key Largo. Finish your sightseeing early on the 28th (Tue) so you can fly back home.
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Parks · Wildlife · Historic Sites · Outdoors
Side Trip

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.
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