50 days in Florida Itinerary
Created using Inspirock Florida route builder
Start: Cartagena
Fly
1
Key West
— 5 nights
Drive
2
Marathon
— 4 nights
Drive
3
Islamorada
— 4 nights
Drive
4
Key Largo
— 5 nights
Drive
5
Marco Island
— 4 nights
Drive
6
Fort Myers Beach
— 3 nights
Drive
7
Captiva Island
— 1 night
Drive
8
Sanibel Island
— 2 nights
Drive
9
Sarasota
— 4 nights
Fly
10
Fort Walton Beach
— 5 nights
Drive
11
Panama City Beach
— 4 nights
Drive
12
St. Augustine
— 5 nights
Drive
13
Cocoa Beach
— 3 nights
Drive to Orlando International Airport, Fly to Cartagena
End: Cartagena
Thu, Jun 20 - Thu, Aug 8
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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.Shop till you drop at Alan S. Maltz Gallery and Collections Key West Gallery. Explore hidden gems such as Dolphin & Whale Watching and Florida Keys Eco-Discovery Center. Spend the 23rd (Sun) exploring nature at Dry Tortugas National Park. There's still lots to do: see the interesting displays at The Ernest Hemingway Home and Museum, explore the world behind art at Key West Museum of Art & History at the Custom House, stop by We Cycle, and identify plant and animal life at Vandenberg Wreck.
To find photos, other places to visit, ratings, and tourist information, read Key West holiday builder site.
Cartagena, Colombia to Key West is an approximately 9.5-hour flight. In June, daily temperatures in Key West can reach 36°C, while at night they dip to 30°C. Cap off your sightseeing on the 25th (Tue) early enough to go by car to Marathon.
Highlights from your trip
Marathon — 4 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.Explore hidden gems such as Bahia Honda State Park and Crane Point Museum & Nature Center. Step out of the city life by going to Sombrero Beach and The Turtle Hospital. Step out of Marathon to go to Florida City and see Everglades National Park, which is approximately 1h 10 min away. And it doesn't end there: identify plant and animal life at Dolphin Research Center, get a taste of the local shopping with Paradise Produce, snap pictures at Seven Mile Bridge, and see what you can catch with a fishing tour.
To find reviews, ratings, photos, and tourist information, go to the Marathon sightseeing planner.
You can drive from Key West to Marathon in 1.5 hours. Another option is to take a bus. June in Marathon sees daily highs of 38°C and lows of 30°C at night. Finish your sightseeing early on the 29th (Sat) to allow enough time to drive to Islamorada.
Side Trips
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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.Step off the beaten path and head to History of Diving Museum and Lobster Trap Art Gift Shop and Gallery. Your cultural itinerary includes sights like Pasta Pantaleo Signature Gallery and Indian Key State Historic Site. There's still lots to do: look for all kinds of wild species at Alligator Reef Light House, get outside with Pelican Cove Resort, fulfill a lifelong dream with Theater of the Sea, and shop like a local with Michelle Nicole Lowe Art Gallery.
Take the guesswork out of planning a Islamorada vacation by using our trip itinerary maker.
Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. June in Islamorada sees daily highs of 38°C and lows of 30°C at night. Wrap up your sightseeing on the 3rd (Wed) to allow time to drive to Key Largo.
Highlights from your trip
Key Largo — 5 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 some cultural sightseeing at Keys' Meads and Homestead Historic Town Hall Museum. Escape the urban bustle at Swim with Dolphins and Molasses Reef. Venture out of the city with trips to Anhinga Trail (in Everglades National Park) and Everglades Alligator Farm (in Homestead). There's still lots to do: stroll through Spiegel Grove, stop by Shell World Florida Keys, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, and explore the gorgeous colors at Key Largo Dry Rocks.
To see more things to do, ratings, where to stay, and more tourist information, you can read our Key Largo travel site.
Key Largo is very close to Islamorada. Traveling from Islamorada in July, expect little chillier with lows of 28°C in Key Largo. Finish up your sightseeing early on the 8th (Mon) so you can go by car to Marco Island.
Side Trips
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Marco Island — 4 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. Head to Clyde Butcher's Big Cypress Gallery and Keep In Touchfor some retail therapy. Escape the urban bustle at Keewaydin Island and South Marco Beach. Change things up with these side-trips from Marco Island: Ochopee (Kirby Storter Roadside Park & Nature & Wildlife Tours). And it doesn't end there: get a new perspective on things with Boat Tours & Water Sports, enjoy the sand and surf at Tigertail Beach, take in the exciting artwork at Malenda Trick Art Gallery, and relax and rejuvenate at some of the best spas.
Plan trip to Marco Island with our itinerary maker to find out where to go and what to do.
You can drive from Key Largo to Marco Island in 3 hours. Other options are to do a combination of bus and taxi; or do a combination of bus and ferry. In July, plan for daily highs up to 38°C, and evening lows to 28°C. Finish up your sightseeing early on the 12th (Fri) so you can go by car to Fort Myers Beach.
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Plan trip to Marco Island with our itinerary maker to find out where to go and what to do.
You can drive from Key Largo to Marco Island in 3 hours. Other options are to do a combination of bus and taxi; or do a combination of bus and ferry. In July, plan for daily highs up to 38°C, and evening lows to 28°C. Finish up your sightseeing early on the 12th (Fri) so you can go by car to Fort Myers Beach.
Side Trip
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Fort Myers Beach — 3 nights

Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Your itinerary includes some good beach time at Bonita Springs Public Beach and Fort Myers Beach. Do some cultural sightseeing at Fifth Avenue South and Edison and Ford Winter Estates. Get out of town with these interesting Fort Myers Beach side-trips: Barefoot Beach Preserve (in Bonita Springs), Fishing Charters & Tours (in Punta Gorda) and Lowdermilk Beach (in Naples). There's still lots to do: admire the majestic nature at Lovers Key State Park.
Start your trip to Fort Myers Beach by creating a personalized itinerary on Inspirock.
Traveling by car from Marco Island to Fort Myers Beach takes 1.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of bus and taxi. July in Fort Myers Beach sees daily highs of 38°C and lows of 28°C at night. Finish up your sightseeing early on the 15th (Mon) so you can go by car to Captiva Island.
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Start your trip to Fort Myers Beach by creating a personalized itinerary on Inspirock.
Traveling by car from Marco Island to Fort Myers Beach takes 1.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of bus and taxi. July in Fort Myers Beach sees daily highs of 38°C and lows of 28°C at night. Finish up your sightseeing early on the 15th (Mon) so you can go by car to Captiva Island.
Side Trips
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Captiva Island — 1 night

Start off your visit on the 16th (Tue): enjoy the sand and surf at Captiva Beach, view the masterpieces at 2 Islands Gallery, and then glide through the air with a parasailing or paragliding tour.
To find reviews, where to stay, maps, and more tourist information, read Captiva Island day trip planning app.
You can drive from Fort Myers Beach to Captiva Island in an hour. July in Captiva Island sees daily highs of 38°C and lows of 28°C at night. Wrap up your sightseeing on the 16th (Tue) to allow time to drive to Sanibel Island.
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To find reviews, where to stay, maps, and more tourist information, read Captiva Island day trip planning app.
You can drive from Fort Myers Beach to Captiva Island in an hour. July in Captiva Island sees daily highs of 38°C and lows of 28°C at night. Wrap up your sightseeing on the 16th (Tue) to allow time to drive to Sanibel Island.
Highlights from your trip
Sanibel Island — 2 nights

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.Kick off your visit on the 17th (Wed): kick back and relax at Blind Pass Beach Park, stroll through Bowman's Beach, and then examine the collection at The Bailey-Matthews National Shell Museum. Here are some ideas for day two: stroll around Pond Apple Park, glide peacefully along the water with some of the best stand-up paddleboarding in the area, then cruise along Sanibel Causeway, and finally stop by Three Crafty Ladies.
To find where to stay, reviews, and more tourist information, read our Sanibel Island tour itinerary planning tool.
Sanibel Island is very close to Captiva Island. July in Sanibel Island sees daily highs of 38°C and lows of 28°C at night. Finish your sightseeing early on the 18th (Thu) so you can drive to Sarasota.
Highlights from your trip
Sarasota — 4 nights

Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Give yourself a bit of retail therapy at Beach Market and St. Armands Circle. Get in touch with nature at Treasure Island Beach and Crescent Beach. Venture out of the city with trips to Venice (Caspersen Beach & Venice Beach), Nokomis Beach (in Nokomis) and Stump Pass Beach State Park (in Englewood). There's still lots to do: identify plant and animal life at Myakka River State Park, kick back and relax at St. Pete Beach, immerse yourself in nature at Fort De Soto Park, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.
To find reviews, traveler tips, and other tourist information, read Sarasota road trip planning app.
Getting from Sanibel Island to Sarasota by car takes about 2 hours. Other options: do a combination of taxi and bus. July in Sarasota sees daily highs of 38°C and lows of 28°C at night. Finish your sightseeing early on the 22nd (Mon) so you can fly to Fort Walton Beach.
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To find reviews, traveler tips, and other tourist information, read Sarasota road trip planning app.
Getting from Sanibel Island to Sarasota by car takes about 2 hours. Other options: do a combination of taxi and bus. July in Sarasota sees daily highs of 38°C and lows of 28°C at night. Finish your sightseeing early on the 22nd (Mon) so you can fly to Fort Walton Beach.
Side Trips
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Fort Walton Beach — 5 nights

Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Get outdoors at AJ's Water Adventures and Henderson Beach State Park. Your cultural itinerary includes sights like Pensacola Lighthouse & Maritime Museum and Fort Pickens Area. Get out of town with these interesting Fort Walton Beach side-trips: Pensacola Beach (Gulf Islands National Seashore & Innerlight Surf Shop), CHROMA/ Kathleen Broaderick Studio & Gallery (in Santa Rosa Beach) and Pensacola (Room Escape Games & National Naval Aviation Museum). The adventure continues: step off the mainland to explore Okaloosa Island, take in the waterfront at The Village of Baytowne Wharf, make a trip to Destin Harbor Boardwalk, and enjoy the sand and surf at Navarre Beach.
For maps, where to stay, ratings, and tourist information, read Fort Walton Beach trip itinerary builder website.
Traveling by flight from Sarasota to Fort Walton Beach takes 4.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In July, daily temperatures in Fort Walton Beach can reach 37°C, while at night they dip to 27°C. Finish your sightseeing early on the 27th (Sat) to allow enough time to drive to Panama City Beach.
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For maps, where to stay, ratings, and tourist information, read Fort Walton Beach trip itinerary builder website.
Traveling by flight from Sarasota to Fort Walton Beach takes 4.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In July, daily temperatures in Fort Walton Beach can reach 37°C, while at night they dip to 27°C. Finish your sightseeing early on the 27th (Sat) to allow enough time to drive to Panama City Beach.
Side Trips
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Panama City Beach — 4 nights

World's Most Beautiful Beaches
Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.Eschew the tourist crowds and head to St. Andrews State Park and Saint George Island State Park. Do your shopping at Pier Park and The Blue Giraffe. You'll find plenty of places to visit near Panama City Beach: St. Joseph Peninsula State Park (in Port Saint Joe), Grayton Beach State Park (in Grayton Beach) and Florida Caverns State Park (in Marianna). There's much more to do: enjoy the sand and surf at Santa Rosa Beach, test your team's savvy at popular escape rooms, discover the deep blue sea with a scuba or snorkeling tour, and learn about winemaking at Panama City Beach Winery.
To see where to stay, photos, more things to do, and more tourist information, refer to the Panama City Beach trip planner.
Traveling by car from Fort Walton Beach to Panama City Beach takes 1.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Fort Walton Beach to Panama City Beach. Expect a daytime high around 38°C in July, and nighttime lows around 27°C. Finish your sightseeing early on the 31st (Wed) so you can drive to St. Augustine.
Side Trips
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St. Augustine — 5 nights

St. Step out of the city life by going to St. Augustine Alligator Farm Zoological Park and Fort Matanzas National Monument. Relax by the water at St. Augustine Beach and Beach at Daytona Beach. Explore the numerous day-trip ideas around St. Augustine: Ponce Inlet (Ponce de Leon Inlet Lighthouse & Museum & Marine Science Center) and Fort Clinch State Park (in Fernandina Beach). There's much more to do: take an in-depth tour of St. Augustine Pirate & Treasure Museum, take in the spiritual surroundings of Cathedral Basilica of St. Augustine, examine the collection at Lightner Museum, and brush up on your military savvy at Spanish Military Hospital Museum.
Find out how to plan St. Augustine trip without stress by asking Inspirock to help create an itinerary.
Traveling by car from Panama City Beach to St. Augustine takes 5.5 hours. Alternatively, you can fly. Expect a daytime high around 38°C in July, and nighttime lows around 28°C. Cap off your sightseeing on the 5th (Mon) early enough to go by car to Cocoa Beach.
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Find out how to plan St. Augustine trip without stress by asking Inspirock to help create an itinerary.
Traveling by car from Panama City Beach to St. Augustine takes 5.5 hours. Alternatively, you can fly. Expect a daytime high around 38°C in July, and nighttime lows around 28°C. Cap off your sightseeing on the 5th (Mon) early enough to go by car to Cocoa Beach.
Side Trips
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Cocoa Beach — 3 nights

Situated in one of Florida's busiest vacation areas, Cocoa Beach burst onto the world scene in the 1960s, when it became a popular setting for parades honoring the nation's "Apollo" astronauts.You'll get in some beach time at Cocoa Beach and Sebastian Inlet State Park. Explore hidden gems such as Fishing Charters & Tours and Canaveral National Seashore. When in Cocoa Beach, make a side trip to see Merritt Island National Wildlife Refuge in Merritt Island, approximately Merritt Island away. Next up on the itinerary: stop by Ron Jon Surf Shop, explore the engaging exhibits at The Wizard of Oz Museum, and test your team's savvy at popular escape rooms.
To find photos, more things to do, and other tourist information, go to the Cocoa Beach online travel planner.
Traveling by car from St. Augustine to Cocoa Beach takes 2.5 hours. Alternatively, you can do a combination of bus and car. In August, plan for daily highs up to 36°C, and evening lows to 30°C. Cap off your sightseeing on the 8th (Thu) early enough to travel back home.
Side Trips
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Florida travel guide
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.