30 days in Florida Itinerary

30 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
Taxi
1
Miami Beach
— 1 night
Drive
2
Islamorada
— 2 nights
Drive
3
Marathon
— 2 nights
Drive
4
Key West
— 4 nights
Ferry
5
Marco Island
— 2 nights
Drive
6
Naples
— 3 nights
Fly
7
Crystal River
— 2 nights
Drive
8
Orlando
— 4 nights
Drive
9
St. Augustine
— 4 nights
Drive
10
Panama City Beach
— 5 nights
Drive to Tallahassee, Fly to Miami

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Miami Beach

— 1 night

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.
Kick off your visit on the 1st (Sun): wander the streets of Lincoln Road and then get a taste of the local shopping with Aventura Mall. Get ready for a full day of sightseeing on the 2nd (Mon): kick back and relax at Hollywood Beach, get to know the fascinating history of Art Deco Historic District, and then take a stroll through Collins Avenue.

To see traveler tips, reviews, other places to visit, and other tourist information, refer to the Miami Beach trip maker.

Miami to Miami Beach is an approximately half hour car ride. You can also drive; or take a bus. In September, daily temperatures in Miami Beach can reach 90°F, while at night they dip to 77°F. Finish up your sightseeing early on the 2nd (Mon) so you can go by car to Islamorada.

Things to do in Miami Beach

Shopping · Neighborhoods · Parks · Historic Sites

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.
Start off your visit on the 3rd (Tue): discover the deep blue sea with a scuba or snorkeling tour, then head outdoors with Outdoor Activities, and then sample the tasty concoctions at Islamorada Brewery & Distillery. Get ready for a full day of sightseeing on the 4th (Wed): glide through the air with a parasailing or paragliding tour, tour the pleasant surroundings at Florida Keys Wild Bird Rehabilitation Center, then take an in-depth tour of History of Diving Museum, then take in the exciting artwork at Pasta Pantaleo Signature Gallery, and finally view the masterpieces at Lobster Trap Art Gift Shop and Gallery.

To find ratings, where to stay, photos, and other tourist information, use the Islamorada journey planning site.

You can drive from Miami Beach to Islamorada in 2 hours. Other options are to do a combination of bus and shuttle; or take a bus. In September in Islamorada, expect temperatures between 90°F during the day and 79°F at night. Finish up your sightseeing early on the 4th (Wed) so you can go by car to Marathon.

Things to do in Islamorada

Outdoors · Tours · Wildlife · Museums

Side Trip

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 5th (Thu): kick back and relax at Sombrero Beach, then tour the pleasant surroundings at The Turtle Hospital, and then stroll through Bahia Honda State Park. Get ready for a full day of sightseeing on the next day: see what you can catch with a fishing tour, stroll through Dolphin Research Center, and then take in the views from Seven Mile Bridge.

To find maps, traveler tips, other places to visit, and tourist information, read Marathon trip itinerary planning website.

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. In September, plan for daily highs up to 90°F, and evening lows to 79°F. Cap off your sightseeing on the 6th (Fri) early enough to go by car to Key West.

Things to do in Marathon

Parks · Outdoors · Wildlife · 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.
Do some cultural sightseeing at Alan S. Maltz Gallery and Key West Lighthouse and Keeper's Quarters Museum. Step off the beaten path and head to Dry Tortugas National Park and U.S. Coast Guard Cutter Ingham Maritime Museum. There's lots more to do: get outside with Outdoor Activities, stop by Isle Cook Key West, take in the exciting artwork at 7 Artists & Friends Gallery, and see the interesting displays at The Ernest Hemingway Home and Museum.

For other places to visit, reviews, where to stay, and tourist information, read our Key West trip planner.

Drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. September in Key West sees daily highs of 88°F and lows of 80°F at night. Cap off your sightseeing on the 10th (Tue) early enough to catch the ferry to Marco Island.

Things to do in Key West

Outdoors · Tours · Wildlife · Museums

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. Start off your visit on the 11th (Wed): get a dose of the wild on a nature and wildlife tour, get outside with Outdoor Activities, and then look for gifts at Keep In Touch. On the next day, cast your line with a fishing tour, then see majestic marine mammals with a dolphin and whale watching tour, and then shop like a local with Malenda Trick Art Gallery.

For more things to do, reviews, and other tourist information, read Marco Island tour builder website.

You can ride a ferry from Key West to Marco Island in 4 hours. Alternatively, you can drive. Traveling from Key West in September, Marco Island is little chillier at night with lows of 74°F. Finish your sightseeing early on the 12th (Thu) to allow enough time to drive to Naples.

Things to do in Marco Island

Outdoors · Tours · Wildlife · Adventure

Side Trip

Naples

— 3 nights
Visiting Lowdermilk Beach and Dolphin & Whale Watching will get you outdoors. Discover out-of-the-way places like Lovers Key State Park and Miromar Outlets between Naples & Fort Myers. Step out of Naples with an excursion to Edison and Ford Winter Estates in Fort Myers--about 58 minutes away.

To see photos, traveler tips, where to stay, and more tourist information, go to the Naples road trip planning app.

Naples is just a stone's throw from Marco Island. September in Naples sees daily highs of 89°F and lows of 76°F at night. Wrap up your sightseeing on the 15th (Sun) early enough to fly to Crystal River.

Things to do in Naples

Parks · Outdoors · Wildlife · Shopping

Side Trips

Crystal River

— 2 nights

The Gem of the Nature Coast

The jewel of Florida's Nature Coast, Crystal River spreads around spring-fed Kings Bay, known for maintaining a constant 22 C (72 F) temperature all year long.
On the 16th (Mon), glide peacefully along the water with some of the best stand-up paddleboarding in the area and then see some colorful creatures with a scuba or snorkeling tour. On the next day, admire the majestic nature at Ellie Schiller Homosassa Springs Wildlife State Park.

To see other places to visit, ratings, traveler tips, and tourist information, read Crystal River sightseeing planner.

Traveling by flight from Naples to Crystal River takes 3 hours. Alternatively, you can drive; or take a bus. Plan for little chillier nights when traveling from Naples in September since evenings lows in Crystal River dip to 71°F. Cap off your sightseeing on the 17th (Tue) early enough to go by car to Orlando.

Things to do in Crystal River

Outdoors · Tours · Wildlife · Adventure

Side Trip

Orlando

— 4 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.
Your inner history buff will appreciate Ponce de Leon Inlet Lighthouse & Museum and Stetson Mansion. Your cultural itinerary includes sights like Charles Hosmer Morse Museum of American Art and Timothy's Gallery. Get out of town with these interesting Orlando side-trips: Cocoa Beach (Ron Jon Surf Shop & Cocoa Beach) and Fishing Charters & Tours (in Port Canaveral). Next up on the itinerary: take a stroll through International Drive, add some entertainment to your itinerary with Happily Ever After Fireworks, and revel in the low prices at Orlando Vineland Premium Outlets.

To find more things to do, photos, traveler tips, and other tourist information, use the Orlando trip planner.

Getting from Crystal River to Orlando by car takes about 2 hours. Other options: take a bus; or do a combination of bus and train. In September, daily temperatures in Orlando can reach 89°F, while at night they dip to 74°F. Cap off your sightseeing on the 21st (Sat) early enough to go by car to St. Augustine.

Things to do in Orlando

Shopping · Outdoors · Parks · Neighborhoods

Side Trips

St. Augustine

— 4 nights
St. You'll explore and learn at Lightner Museum and St. Augustine Pirate & Treasure Museum. You'll enjoy a bit of beach vacationing at St. Augustine Beach and Vilano Beach. Change things up with these side-trips from St. Augustine: Beach at Daytona Beach (in Daytona Beach) and Ormond Beach (in Ormond Beach). Spend the 23rd (Mon) exploring nature at Fort Matanzas National Monument. Next up on the itinerary: pause for some serene contemplation at Cathedral Basilica of St. Augustine, take in the exciting artwork at High Tide Gallery Art & Gifts, and tour the pleasant surroundings at St. Augustine Alligator Farm Zoological Park.

For traveler tips, more things to do, where to stay, and other tourist information, read our St. Augustine holiday planner.

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: take a bus. In September in St. Augustine, expect temperatures between 85°F during the day and 73°F at night. Finish up your sightseeing early on the 25th (Wed) so you can go by car to Panama City Beach.

Things to do in St. Augustine

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Panama City Beach

— 5 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.
Get outdoors at Scuba & Snorkeling and Navarre Beach. Eschew the tourist crowds and head to St. Andrews State Park and Swim with Dolphins. You'll find plenty of places to visit near Panama City Beach: Santa Rosa Beach (in Santa Rosa Beach) and Fusion Art Glass Gallery (in Seaside). Next up on the itinerary: kick back and relax at Henderson Beach State Park, take in the exciting artwork at Panama City CENTER for the ARTS, take advantage of the amenities at Panama City Beach, and do a tasting at Panama City Beach Winery.

To find other places to visit, reviews, where to stay, and more tourist information, read our Panama City Beach trip planner.

You can drive from St. Augustine to Panama City Beach in 5.5 hours. Alternatively, you can fly. In September, plan for daily highs up to 89°F, and evening lows to 70°F. Cap off your sightseeing on the 30th (Mon) early enough to travel back home.

Things to do in Panama City Beach

Outdoors · Parks · Beaches · Tours

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.