31 days in Florida Itinerary

31 days in Florida Itinerary

Created using Inspirock Florida trip maker

Make it your trip
Drive
1
Sanibel Island
— 1 night
Drive
2
Naples
— 4 nights
Drive
3
Marco Island
— 2 nights
Ferry
4
Key West
— 4 nights
Drive
5
Marathon
— 3 nights
Drive
6
Islamorada
— 1 night
Fly
7
Fort Walton Beach
— 4 nights
Drive
8
Panama City Beach
— 2 nights
Drive
9
St. Augustine
— 4 nights
Drive
10
Daytona Beach
— 2 nights
Drive
11
Orlando
— 3 nights

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Sanibel Island

— 1 night
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
On the 1st (Sat), examine the collection at The Bailey-Matthews National Shell Museum, then stroll through Bowman's Beach, and then see what you can catch with a fishing tour. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Captiva Beach, then tour the pleasant surroundings at Blind Pass Beach Park, and then cruise along Sanibel Causeway.

To find other places to visit, traveler tips, where to stay, and other tourist information, read our Sanibel Island online attractions planner.

Orlando to Sanibel Island is an approximately 4-hour car ride. You can also fly; or do a combination of train, bus, and taxi. In May, daytime highs in Sanibel Island are 90°F, while nighttime lows are 69°F. Cap off your sightseeing on the 2nd (Sun) early enough to go by car to Naples.

Things to do in Sanibel Island

Outdoors · Parks · Beaches · Museums

Side Trip

Naples

— 4 nights
Eschew the tourist crowds and head to Dolphin & Whale Watching and Lovers Key State Park. You'll find plenty of places to visit near Naples: Barefoot Beach Preserve (in Bonita Springs) and Fort Myers (Six Mile Cypress Slough Preserve & Edison and Ford Winter Estates).

For where to stay, maps, traveler tips, and tourist information, use the Naples driving holiday planner.

Traveling by car from Sanibel Island to Naples takes 1.5 hours. Expect a daytime high around 88°F in May, and nighttime lows around 70°F. Wrap up your sightseeing on the 6th (Thu) early enough to drive to Marco Island.

Things to do in Naples

Parks · Wildlife · Outdoors · 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 7th (Fri): enjoy the sand and surf at South Marco Beach, indulge in some personalized pampering at some of the best spas, and then take a tour by water with Boat Tours & Water Sports. On your second day here, take in the waterfront activity at Calusa Island Marina, stroll through Keewaydin Island, and then kick back and relax at Tigertail Beach.

To find reviews, where to stay, and tourist information, read our Marco Island vacation planner.

Marco Island is just a stone's throw from Naples. May in Marco Island sees daily highs of 88°F and lows of 69°F at night. Finish your sightseeing early on the 8th (Sat) to allow enough time to ride a ferry to Key West.

Things to do in Marco Island

Outdoors · Parks · Beaches · Tours

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.
Explore hidden gems such as Dry Tortugas National Park and Dolphin & Whale Watching. And it doesn't end there: take in the architecture and atmosphere at St. Paul's Episcopal Church, browse the exhibits of Key West Lighthouse and Keeper's Quarters Museum, go for a walk through West Martello Tower, and see the interesting displays at Mel Fisher Maritime Heritage Museum.

To find more things to do, reviews, photos, and tourist information, read our Key West attractions planner.

Getting from Marco Island to Key West by ferry takes about 4 hours. Other options: drive. Traveling from Marco Island in May, you can expect nighttime temperatures to be a bit warmer in Key West, with lows of 77°F. Finish up your sightseeing early on the 12th (Wed) so you can go by car to Marathon.

Things to do in Key West

Historic Sites · Parks · Nature · Museums

Marathon

— 3 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.
Eschew the tourist crowds and head to The Turtle Hospital and African Queen Canal Cruise. Change things up with a short trip to Florida Keys Wild Bird Rehabilitation Center in Tavernier (about 58 minutes away). The adventure continues: look for all kinds of wild species at Dolphin Research Center, snap pictures at Seven Mile Bridge, tour the pleasant surroundings at Sombrero Beach, and kick back and relax at Bahia Honda State Park.

For more things to do, maps, ratings, and tourist information, read Marathon trip planner.

Drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. May in Marathon sees daily highs of 88°F and lows of 77°F at night. Wrap up your sightseeing on the 15th (Sat) early enough to drive to Islamorada.

Things to do in Marathon

Parks · Outdoors · Wildlife · Beaches

Side Trips

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.
Kick off your visit on the 16th (Sun): take an in-depth tour of History of Diving Museum, then cast your line with a fishing tour, then sample the tasty concoctions at Islamorada Brewery & Distillery, and finally indulge your thirst for a good beer at Florida Keys Brewing Company.

For more things to do, photos, reviews, and more tourist information, go to the Islamorada trip maker app.

Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. In May, daily temperatures in Islamorada can reach 88°F, while at night they dip to 77°F. Cap off your sightseeing on the 16th (Sun) early enough to catch the flight to Fort Walton Beach.

Things to do in Islamorada

Breweries & Distilleries · Outdoors · Tours · Wildlife

Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Explore hidden gems such as Destin Harbor and AJ's Water Adventures. Go for a jaunt from Fort Walton Beach to Pensacola Beach to see Pensacola Beach about 54 minutes away. And it doesn't end there: stroll through Navarre Beach, take a leisurely stroll along The Village of Baytowne Wharf, don't miss a visit to Destin Harbor Boardwalk, and step off the mainland to explore Okaloosa Island.

For traveler tips, more things to do, photos, and tourist information, use the Fort Walton Beach travel route planner.

You can fly from Islamorada to Fort Walton Beach in 3.5 hours. Other options are to drive; or do a combination of shuttle and bus. The time zone difference when traveling from Islamorada to Fort Walton Beach is minus 1 hour. Expect slightly colder temperatures when traveling from Islamorada in May; daily highs in Fort Walton Beach reach 81°F and lows reach 64°F. Finish up your sightseeing early on the 20th (Thu) so you can go by car to Panama City Beach.

Things to do in Fort Walton Beach

Parks · Outdoors · Beaches · 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 21st (Fri): do a tasting at Panama City Beach Winery, then look for all kinds of wild species at Wildlife Areas, then stroll through St. Andrews State Park, and finally browse the different shops at Pier Park. Get ready for a full day of sightseeing on the 22nd (Sat): stroll through Grayton Beach State Park, tour the pleasant surroundings at Santa Rosa Beach, and then stroll through Timpoochee Trail.

To see reviews, traveler tips, where to stay, and other tourist information, read our Panama City Beach road trip tool.

You can drive from Fort Walton Beach to Panama City Beach in 1.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Fort Walton Beach to Panama City Beach. In May, plan for daily highs up to 85°F, and evening lows to 62°F. Wrap up your sightseeing on the 22nd (Sat) to allow time to drive to St. Augustine.

Things to do in Panama City Beach

Outdoors · Parks · Beaches · Nature

Side Trips

St. Augustine

— 4 nights
St. You'll discover tucked-away gems like St. Augustine Alligator Farm Zoological Park and St. Augustine Wild Reserve. Explore St. Augustine's surroundings by going to Fort Clinch State Park (in Fernandina Beach) and Jacksonville Zoo & Gardens (in Jacksonville). And it doesn't end there: enjoy the sand and surf at St. Augustine Beach, do a tasting at San Sebastian Winery, examine the collection at Lightner Museum, and take in the spiritual surroundings of Cathedral Basilica of St. Augustine.

For maps, where to stay, reviews, and other tourist information, refer to the St. Augustine driving holiday planner.

Traveling by car from Panama City Beach to St. Augustine takes 5.5 hours. Alternatively, you can fly. In May, plan for daily highs up to 83°F, and evening lows to 67°F. Finish up your sightseeing early on the 26th (Wed) so you can go by car to Daytona Beach.

Things to do in St. Augustine

Parks · Historic Sites · Wildlife · Museums

Side Trips

Daytona Beach

— 2 nights

The World's Most Famous Beach

The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
On the 27th (Thu), stop by Angell & Phelps Chocolate Factory, join the crowd at Daytona International Speedway, then tour the pleasant surroundings at Ormond Beach, and finally kick back and relax at Beach at Daytona Beach. Get ready for a full day of sightseeing on the next day: contemplate the long history of Stetson Mansion, then observe the fascinating underwater world at Marine Science Center, and then visit a coastal fixture at Ponce de Leon Inlet Lighthouse & Museum.

To see where to stay, more things to do, other places to visit, and other tourist information, go to the Daytona Beach online holiday planner.

Getting from St. Augustine to Daytona Beach by car takes about 1.5 hours. Other options: take a bus. In May in Daytona Beach, expect temperatures between 85°F during the day and 66°F at night. Finish your sightseeing early on the 28th (Fri) so you can drive to Orlando.

Things to do in Daytona Beach

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Orlando

— 3 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.
You'll discover tucked-away gems like Disney’s Blizzard Beach Water Park and Bok Tower Gardens. Explore Orlando's surroundings by going to Cocoa Beach (in Cocoa Beach) and Wild Florida Airboats (in Kenansville). There's lots more to do: don't miss a visit to Tree of Life, discover the magic at Avatar Flight of Passage, get up close and personal with brilliant marine life at SEA LIFE Orlando Aquarium, and look for gifts at World of Disney.

For maps, ratings, reviews, and tourist information, read our Orlando online tour builder.

Drive from Daytona Beach to Orlando in an hour. Alternatively, you can take a bus. In May, plan for daily highs up to 88°F, and evening lows to 69°F. Finish your sightseeing early on the 31st (Mon) to allow enough time to travel back home.

Things to do in Orlando

Parks · Outdoors · Theme Parks · Beaches

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.