21 days in Florida Itinerary

21 days in Florida Itinerary

Created using Inspirock Florida tour itinerary builder

Make it your trip
Fly
1
Fort Myers Beach
— 2 nights
Drive
2
Marco Island
— 2 nights
Drive
3
Everglades City
— 1 night
Drive
4
Miami Beach
— 2 nights
Drive
5
Key Largo
— 2 nights
Drive
6
Islamorada
— 2 nights
Drive
7
Marathon
— 2 nights
Drive
8
Key West
— 4 nights
Fly to Orlando, Bus to St. Augustine
9
St. Augustine
— 3 nights
Fly

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Fort Myers Beach

— 2 nights
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Step out of the city life by going to Corkscrew Swamp and Lovers Key State Park. Step off the beaten path and head to Bowman's Beach and Lowdermilk Beach. Explore the numerous day-trip ideas around Fort Myers Beach: Blind Pass Beach Park (in Sanibel Island), Edison and Ford Winter Estates (in Fort Myers) and Captiva Beach (in Captiva Island). There's much more to do: identify plant and animal life at Six Mile Cypress Slough Preserve, wander the streets of Fifth Avenue South, cast your line with a fishing tour, and get a taste of the local shopping with Sanibel Island Farmer's Market.

You can plan Fort Myers Beach trip in no time by asking Inspirock to help create your itinerary.

Cincinnati to Fort Myers Beach is an approximately 5-hour flight. You can also drive; or do a combination of bus, subway, and taxi. Plan for warmer temperatures traveling from Cincinnati in December, with highs in Fort Myers Beach at 80°F and lows at 62°F. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Marco Island.

Things to do in Fort Myers Beach

Parks · Outdoors · Wildlife · Beaches

Side Trips

Marco Island

— 2 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. Kick off your visit on the 23rd (Wed): take an in-depth tour of Marco Island Historical Museum, pick up some local products at Marco Island Farmers Market, enjoy the sand and surf at South Marco Beach, then indulge in some personalized pampering at some of the best spas, and finally zoom along the surf with a waterskiing or jet-skiing adventure. On the 24th (Thu), you'll have a packed day of sightseeing: stop by Keep In Touch, enjoy the sand and surf at Keewaydin Island, then contemplate the waterfront views at Capri Paddlecraft Park, then take in the exciting artwork at Malenda Trick Art Gallery, and finally stroll through Tigertail Beach.

For other places to visit, ratings, reviews, and other tourist information, read Marco Island trip itinerary app.

Traveling by car from Fort Myers Beach to Marco Island takes 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of taxi and bus. Expect a daytime high around 80°F in December, and nighttime lows around 61°F. Finish up your sightseeing early on the 24th (Thu) so you can go by car to Everglades City.

Things to do in Marco Island

Parks · Outdoors · Beaches · Shopping

Everglades City

— 1 night
Everglades City is a city in Collier County, Florida, United States, of which it is the former county seat. On the 25th (Fri), stroll through Kirby Storter Roadside Park, get a taste of the local shopping with Clyde Butcher's Big Cypress Gallery, explore the wealth of natural beauty at Ten Thousand Islands National Wildlife Refuge, then explore the activities along Chokoloskee Bay, and finally get some thrills on the water with a speed boat tour.

To find reviews, traveler tips, ratings, and more tourist information, refer to the Everglades City visit planner.

Drive from Marco Island to Everglades City in an hour. In December, daytime highs in Everglades City are 80°F, while nighttime lows are 61°F. Cap off your sightseeing on the 25th (Fri) early enough to go by car to Miami Beach.

Things to do in Everglades City

Wildlife · Parks · Outdoors · Nature

Side Trips

Miami Beach

— 2 nights

The World's Playground

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Start off your visit on the 26th (Sat): take a stroll through Lincoln Road, then get a taste of the local shopping with Britto Central, then tour the pleasant surroundings at Hollywood Beach, and finally shop like a local with Aventura Mall. On the 27th (Sun), you'll have a packed day of sightseeing: shop like a local with Collins Avenue, get to know the fascinating history of Art Deco Historic District, then stroll through South Beach, then see the interesting displays at Vizcaya Museum and Gardens, and finally enjoy the sand and surf at Bill Baggs Cape Florida State Park.

To find where to stay, photos, ratings, and more tourist information, you can read our Miami Beach driving holiday tool.

Traveling by car from Everglades City to Miami Beach takes 2 hours. Alternatively, you can fly; or do a combination of taxi and bus. Traveling from Everglades City in December, plan for somewhat warmer nights in Miami Beach, with lows around 68°F. Wrap up your sightseeing on the 27th (Sun) to allow time to drive to Key Largo.

Things to do in Miami Beach

Shopping · Parks · Neighborhoods · Beaches

Side Trips

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.
Kick off your visit on the 28th (Mon): look for all kinds of wild species at Anhinga Trail, then identify plant and animal life at Everglades Alligator Farm, then take a memorable tour with Capt. Sterling's Everglades Eco-Tours, and finally step aboard African Queen Canal Cruise. Keep things going the next day: identify plant and animal life at Molasses Reef, explore the gorgeous colors at Spiegel Grove, fulfill a lifelong dream with a swim-with-the-dolphins experience, then indulge in some personalized pampering at Prana, and finally identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center.

For maps, traveler tips, ratings, and more tourist information, read Key Largo online road trip planner.

Traveling by car from Miami Beach to Key Largo takes 1.5 hours. Alternatively, you can take a bus; or take a bus. In December, plan for daily highs up to 79°F, and evening lows to 66°F. Finish your sightseeing early on the 29th (Tue) to allow enough time to drive to Islamorada.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Side Trips

Islamorada

— 2 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.
Kick off your visit on the 30th (Wed): get a taste of the local shopping with Lobster Trap Art Gift Shop and Gallery, look for gifts at Zero Dress Code Boutique, then get close to the beloved marine mammals with Theater of the Sea, and finally steep yourself in history at Indian Key State Historic Site. On the next day, immerse yourself in nature at Lignumvitae Key Botanical State Park, take in the exciting artwork at Pasta Pantaleo Signature Gallery, explore the striking landscape at Windley Key Fossil Reef Geological State Park, then get engrossed in the history at History of Diving Museum, and finally sample the tasty concoctions at Islamorada Brewery & Distillery.

To see maps, photos, traveler tips, and other tourist information, use the Islamorada travel planner.

Islamorada is just a stone's throw from Key Largo. December in Islamorada sees daily highs of 80°F and lows of 71°F at night. Finish up your sightseeing early on the 31st (Thu) so you can go by car to Marathon.

Things to do in Islamorada

Shopping · Wildlife · Nature · Parks

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.
Kick off your visit on the 1st (Fri): take a tour by water with Boat Tours & Water Sports, enjoy the sand and surf at Sombrero Beach, then identify plant and animal life at The Turtle Hospital, then get a taste of the local shopping with Shady Palm Art Gallery & Photography, and finally enjoy the sand and surf at Bahia Honda State Park. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at National Key Deer Refuge, examine the collection at Crane Point Museum & Nature Center, then look for all kinds of wild species at Dolphin Research Center, and finally take in the architecture and atmosphere at San Pablo Catholic Church.

To find more things to do, reviews, and more tourist information, refer to the Marathon trip planner.

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. In December, daytime highs in Marathon are 80°F, while nighttime lows are 71°F. Finish your sightseeing early on the 2nd (Sat) so you can drive to Key West.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trip

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.
Get outdoors at Dolphin & Whale Watching and Dry Tortugas National Park. Key West Lighthouse and Keeper's Quarters Museum and Saint Mary Star of the Sea will appeal to history buffs. Next up on the itinerary: take in the architecture and atmosphere at St. Paul's Episcopal Church, see the interesting displays at The Ernest Hemingway Home and Museum, indulge in some personalized pampering at some of the best spas, and look for all kinds of wild species at Key West Butterfly & Nature Conservatory.

For more things to do, traveler tips, reviews, and more tourist information, use the Key West online holiday planner.

Getting from Marathon to Key West by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 76°F in January, and nighttime lows around 66°F. Finish your sightseeing early on the 6th (Wed) so you can travel to St. Augustine.

Things to do in Key West

Parks · Historic Sites · Nature · Museums

St. Augustine

— 3 nights
St. Museum-lovers will get to explore Ponce de Leon Inlet Lighthouse & Museum and The Ximenez-Fatio House. You'll get in some beach time at Ormond Beach and St. Augustine Beach. Explore the numerous day-trip ideas around St. Augustine: Beach at Daytona Beach (in Daytona Beach) and Lighthouse Point Park (in Ponce Inlet). There's much more to do: see majestic marine mammals with a dolphin and whale watching tour, examine the collection at Lightner Museum, take in the architecture and atmosphere at Cathedral Basilica of St. Augustine, and admire the architecture and history at National Shrine of Our Lady of La Leche at Mission Nombre de Dios.

To find other places to visit, where to stay, traveler tips, and tourist information, refer to the St. Augustine route planner.

Do a combination of flight and bus from Key West to St. Augustine in 7 hours. Alternatively, you can drive; or take a bus. In January, St. Augustine is little chillier than Key West - with highs of 65°F and lows of 49°F. Finish up your sightseeing early on the 9th (Sat) so you can travel back home.

Things to do in St. Augustine

Parks · Outdoors · Beaches · Historic Sites

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.