29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida journey planner

Make it your trip
Fly to Miami, Shuttle to Marathon
1
Marathon
— 2 nights
Drive
2
Islamorada
— 1 night
Drive
3
Key Largo
— 2 nights
Drive
4
Key West
— 3 nights
Ferry
5
Marco Island
— 3 nights
Drive
6
Fort Myers Beach
— 2 nights
Drive
7
Sarasota
— 3 nights
Fly
8
Fort Walton Beach
— 4 nights
Drive
9
Panama City Beach
— 2 nights
Drive
10
St. Augustine
— 6 nights
Fly

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Marathon

— 2 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 Sombrero Beach and The Turtle Hospital. Attractions like Dolphin Research Center and Crane Point Museum & Nature Center make great kid-friendly stops. There's lots more to do: snap pictures at Old Seven Mile Bridge, kick back and relax at Bahia Honda State Park, take a memorable tour with Tours, and shop like a local with Shady Palm Art Gallery & Photography.

For where to stay, more things to do, ratings, and other tourist information, read Marathon travel route builder tool.

Lisbon, Portugal to Marathon is an approximately 14-hour combination of flight and shuttle. Traveling from Lisbon to Marathon, you'll gain 5 hours due to the time zone difference. Plan for a bit warmer temperatures traveling from Lisbon in June, with highs in Marathon at 38°C and lows at 30°C. Wrap up your sightseeing on the 7th (Mon) early enough to drive to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trip

Islamorada

— 1 night

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.
Start off your visit on the 8th (Tue): get close to the beloved marine mammals with Theater of the Sea, take an in-depth tour of History of Diving Museum, then stop by Bass Pro Shops, and finally see the vivid underwater world at Alligator Reef Light House.

To see other places to visit, maps, photos, and other tourist information, read Islamorada trip itinerary maker app.

Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. In June, daytime highs in Islamorada are 38°C, while nighttime lows are 30°C. Finish your sightseeing early on the 8th (Tue) so you can drive to Key Largo.

Things to do in Islamorada

Wildlife · Tours · Outdoors · Museums

Key Largo

— 2 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.
On the 9th (Wed), look for all kinds of wild species at Everglades Alligator Farm and then look for all kinds of wild species at Anhinga Trail. On the 10th (Thu), you'll have a packed day of sightseeing: fulfill a lifelong dream with a swim-with-the-dolphins experience, step aboard African Queen Canal Cruise, then identify plant and animal life at Molasses Reef, and finally look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center.

For more things to do, photos, where to stay, and tourist information, go to the Key Largo day trip website.

Key Largo is just a stone's throw from Islamorada. In June, daytime highs in Key Largo are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 10th (Thu) early enough to drive to Key West.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Trails

Side Trips

Key West

— 3 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.
Take a break from the city and head to Dolphin & Whale Watching and Dry Tortugas National Park. Family-friendly places like Florida Keys Eco-Discovery Center and Spas will thrill your kids. There's still lots to do: take in the pleasant sights at Key West Garden Club, tour the pleasant surroundings at Audubon House & Tropical Gardens, take in the waterfront at Key West Historic Seaport, and pause for some photo ops at Key West AIDS Memorial.

To see where to stay, traveler tips, photos, and more tourist information, use the Key West trip itinerary planner.

You can drive from Key Largo to Key West in 2.5 hours. Another option is to take a bus. In June, daytime highs in Key West are 36°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 13th (Sun) to allow time to ride a ferry to Marco Island.

Things to do in Key West

Parks · Nature · Historic Sites · Museums

Marco Island

— 3 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. Kids will appreciate attractions like Keewaydin Island and Spas. Take a break from the city and head to South Marco Beach and Tigertail Beach. Next up on the itinerary: get some thrills out on the water with a waterskiing or jet-skiing adventure, kick back and relax at Hideaway Beach, look for all kinds of wild species at Briggs Nature Center, and stroll around Winterberry Park.

To find traveler tips, photos, where to stay, and more tourist information, refer to the Marco Island travel route planning app.

Getting from Key West to Marco Island by ferry takes about 4 hours. Other options: drive. Traveling from Key West in June, plan for a bit cooler nights in Marco Island, with lows around 27°C. Wrap up your sightseeing on the 16th (Wed) early enough to drive to Fort Myers Beach.

Things to do in Marco Island

Parks · Outdoors · Beaches · Wildlife

Fort Myers Beach

— 2 nights
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. On the 17th (Thu), tour the pleasant surroundings at Blind Pass Beach Park, then tour the pleasant surroundings at Captiva Beach, and then tour the pleasant surroundings at Bowman's Beach. Keep things going the next day: enjoy the sand and surf at Barefoot Beach Preserve, then admire the majestic nature at Lovers Key State Park, and then see majestic marine mammals with a dolphin and whale watching tour.

To plan Fort Myers Beach vacation without wasting time, ask Inspirock to design an itinerary.

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. In June, plan for daily highs up to 38°C, and evening lows to 27°C. Finish your sightseeing early on the 18th (Fri) so you can drive to Sarasota.

Things to do in Fort Myers Beach

Parks · Outdoors · Beaches · Wildlife

Side Trips

Sarasota

— 3 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Escape the urban bustle at Fort De Soto Park and Stand-Up Paddleboarding. You'll enjoy a bit of beach vacationing at Treasure Island Beach and Nokomis Beach. Venture out of the city with trips to Venice (Venice Beach & Caspersen Beach), Stump Pass Beach State Park (in Englewood) and St. Pete Beach (in St. Pete Beach). Next up on the itinerary: enjoy the sand and surf at Crescent Beach.

To see ratings, reviews, traveler tips, and tourist information, use the Sarasota trip maker tool.

Drive from Fort Myers Beach to Sarasota in 2 hours. Alternatively, you can take a bus. In June, daily temperatures in Sarasota can reach 37°C, while at night they dip to 28°C. Finish your sightseeing early on the 21st (Mon) to allow enough time to fly to Fort Walton Beach.

Things to do in Sarasota

Outdoors · Parks · Beaches · Nature

Side Trips

Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. You'll discover tucked-away gems like Pensacola Beach and AJ's Water Adventures. Escape the urban bustle at Henderson Beach State Park and Navarre Beach. Venture out of the city with trips to Waterfront Gifts and Art (in Miramar Beach) and Pensacola Beach (Gulf Islands National Seashore & Fort Pickens Area). Next up on the itinerary: stroll through Okaloosa Island, don't miss a visit to Destin Harbor Boardwalk, learn about all things military at Air Force Armament Museum, and take a leisurely stroll along The Village of Baytowne Wharf.

To find maps, traveler tips, where to stay, and more tourist information, read our Fort Walton Beach route builder.

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 (EST) to Central Standard Time (CST), which is usually a -1 hour difference. June in Fort Walton Beach sees daily highs of 35°C and lows of 26°C at night. Wrap up your sightseeing on the 25th (Fri) to allow time to drive to Panama City Beach.

Things to do in Fort Walton Beach

Outdoors · Beaches · Parks · Nature

Side Trips

Panama City Beach

— 2 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.
Start off your visit on the 26th (Sat): buy something for everyone on your list at Pier Park, then don't miss a visit to Abc Fine Wine And Spirits, then kick back and relax at St. Andrews State Park, and finally take a memorable tour with Tours. On the 27th (Sun), you'll have a packed day of sightseeing: enjoy the sand and surf at Santa Rosa Beach, then enjoy the sand and surf at Grayton Beach State Park, and then explore the landscape on two wheels at Timpoochee Trail.

For traveler tips, ratings, where to stay, and other tourist information, refer to the Panama City Beach attractions planner.

Drive from Fort Walton Beach to Panama City Beach in 1.5 hours. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In June in Panama City Beach, expect temperatures between 37°C during the day and 26°C at night. Finish up your sightseeing early on the 27th (Sun) so you can go by car to St. Augustine.

Things to do in Panama City Beach

Outdoors · Parks · Beaches · Nature

Side Trips

St. Augustine

— 6 nights
St. Relax by the water at Ormond Beach and St. Augustine Beach. Visiting St. Augustine Alligator Farm Zoological Park and Nature & Wildlife Tours will get you outdoors. Change things up with these side-trips from St. Augustine: Fernandina Beach (Shrimping Museum & Fort Clinch State Park), Daytona Beach (Angell & Phelps Chocolate Factory, Beach at Daytona Beach, &more) and Fernandina Beach (in Amelia Island). Spend the 1st (Thu) exploring nature at Fort Matanzas National Monument. The adventure continues: take a tour by water with Boat Tours & Water Sports, examine the collection at Lightner Museum, get engrossed in the history at St. Augustine Pirate & Treasure Museum, and gain insight at Flagler College.

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

Traveling by car from Panama City Beach to St. Augustine takes 5.5 hours. Alternatively, you can fly. In June in St. Augustine, expect temperatures between 36°C during the day and 26°C at night. Finish up your sightseeing early on the 3rd (Sat) so you can catch the flight back home.

Things to do in St. Augustine

Parks · Historic Sites · Outdoors · Nature

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.