41 days in Florida Itinerary

41 days in Florida Itinerary

Created using Inspirock Florida sightseeing planner

Make it your trip
Fly
1
Key Largo
— 3 nights
Drive
2
Islamorada
— 2 nights
Drive
3
Marathon
— 4 nights
Drive
4
Key West
— 5 nights
Ferry
5
Marco Island
— 2 nights
Drive
6
Fort Myers Beach
— 2 nights
Drive
7
Sanibel Island
— 2 nights
Drive
8
St. Pete Beach
— 2 nights
Fly
9
Fort Walton Beach
— 4 nights
Drive
10
Panama City Beach
— 2 nights
Drive
11
St. Augustine
— 5 nights
Drive
12
Daytona Beach
— 2 nights
Drive
13
Orlando
— 5 nights
Fly

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Key Largo

— 3 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.
You'll explore the less-touristy side of things at Anhinga Trail and Swim with Dolphins. Deepen your sense of the past at sights like Key Largo Baptist Church and Saint Justin Martyr Catholic Church. When in Key Largo, make a side trip to see Robert Is Here in Homestead, approximately Homestead away. And it doesn't end there: get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, stroll through Florida Keys Wild Bird Rehabilitation Center, step aboard Spiegel Grove, and admire the majestic nature at John Pennekamp Coral Reef State Park.

Plan a trip to Key Largo easily and quickly by telling Inspirock to suggest an itinerary.

San Juan, Puerto Rico to Key Largo is an approximately 6-hour flight. The time zone difference when traveling from San Juan to Key Largo is minus 1 hour. In May, daily temperatures in Key Largo can reach 34°C, while at night they dip to 26°C. Finish your sightseeing early on the 24th (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 25th (Wed): get close to the beloved marine mammals with Theater of the Sea, view the masterpieces at Rain Barrel Village, and then take an in-depth tour of History of Diving Museum. Get ready for a full day of sightseeing on the 26th (Thu): head off the coast to Windley Key, then steep yourself in history at Pasta Pantaleo Signature Gallery, then kick back and relax at Anne's Beach, and finally get outside with Satisfaction Charters Inc..

For reviews, ratings, traveler tips, and tourist information, read Islamorada online holiday planner.

Islamorada is very close to Key Largo. In May, plan for daily highs up to 36°C, and evening lows to 29°C. Finish your sightseeing early on the 26th (Thu) so you can drive to Marathon.

Things to do in Islamorada

Museums · Outdoors · Shopping · Parks

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 Everglades National Park and Dolphin Research Center. When in Marathon, make a side trip to see Shark Valley Visitor Center in Everglades National Park, approximately Everglades National Park away. The adventure continues: tour the pleasant surroundings at The Turtle Hospital, see the interesting displays at Crane Point Museum & Nature Center, cast your line with a fishing tour, and get up close and personal with brilliant marine life at Florida Keys Aquarium Encounters.

To find more things to do, reviews, and more tourist information, use the Marathon trip itinerary builder site.

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In May, daily temperatures in Marathon can reach 36°C, while at night they dip to 29°C. Finish up your sightseeing early on the 30th (Mon) so you can go by car to Key West.

Things to do in Marathon

Parks · Wildlife · Nature · Outdoors

Side Trips

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.
Get some historical perspective at St. Paul's Episcopal Church and Key West Garden Club. Satisfy your inner culture vulture at U.S. Coast Guard Cutter Ingham Maritime Museum and Key West Historic Seaport. Spend the 31st (Tue) exploring nature at Dry Tortugas National Park. And it doesn't end there: examine the collection at The Ernest Hemingway Home and Museum, explore the different monuments and memorials at Key West Cemetery, explore the gorgeous colors at Vandenberg Wreck, and enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum.

To see photos, where to stay, and tourist information, use the Key West vacation planning app.

Drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 34°C in May, and nighttime lows around 29°C. Wrap up your sightseeing on the 4th (Sat) to allow time to ride a ferry to Marco Island.

Things to do in Key West

Parks · Historic Sites · Museums · Nature

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 5th (Sun): relax and rejuvenate at some of the best spas, then see majestic marine mammals with a dolphin and whale watching tour, and then enjoy the sand and surf at South Marco Beach. Here are some ideas for day two: explore the activities along Capri Paddlecraft Park, then tour the pleasant surroundings at Keewaydin Island, and then kick back and relax at Tigertail Beach.

To find maps, traveler tips, other places to visit, and other tourist information, you can read our Marco Island holiday planner.

You can ride a ferry from Key West to Marco Island in 4 hours. Alternatively, you can drive. Plan for a bit cooler nights when traveling from Key West in June since evenings lows in Marco Island dip to 27°C. Finish your sightseeing early on the 6th (Mon) so you can drive to Fort Myers Beach.

Things to do in Marco Island

Outdoors · Parks · Beaches · Wildlife

Fort Myers Beach

— 2 nights
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Kick off your visit on the 7th (Tue): immerse yourself in nature at Lovers Key State Park, kick back and relax at Barefoot Beach Preserve, and then admire the natural beauty at Edison and Ford Winter Estates. Get ready for a full day of sightseeing on the next day: wander the streets of Fifth Avenue South, then kick back and relax at Lowdermilk Beach, then indulge in some personalized pampering at some of the best spas, and finally see majestic marine mammals with a dolphin and whale watching tour.

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

You can drive from Marco Island to Fort Myers Beach in 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 8th (Wed) so you can drive to Sanibel Island.

Things to do in Fort Myers Beach

Parks · Wildlife · Outdoors · Beaches

Side Trips

Sanibel Island

— 2 nights
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kick off your visit on the 9th (Thu): enjoy the sand and surf at Captiva Beach, choose your vessel at Boat Rentals, and then enjoy the sand and surf at Blind Pass Beach Park. On the 10th (Fri), you'll have a packed day of sightseeing: cruise along Sanibel Causeway, then see the interesting displays at The Bailey-Matthews National Shell Museum, and then stroll through Bowman's Beach.

For where to stay, other places to visit, and other tourist information, you can read our Sanibel Island road trip tool.

Sanibel Island is just a short distance from Fort Myers Beach. June in Sanibel Island sees daily highs of 38°C and lows of 27°C at night. Finish up your sightseeing early on the 10th (Fri) so you can go by car to St. Pete Beach.

Things to do in Sanibel Island

Outdoors · Parks · Beaches · Tours

Side Trip

St. Pete Beach

— 2 nights
St. Kick off your visit on the 11th (Sat): tour the pleasant surroundings at St. Pete Beach, wander the streets of Pass-a-Grille Beach, Florida, and then kick back and relax at Treasure Island Beach. On the 12th (Sun), you'll have a packed day of sightseeing: paddle through the water with a kayaking and canoeing tour, appreciate the extensive heritage of Marie Selby Botanical Gardens, and then steep yourself in history at Ca d'Zan.

To see traveler tips, ratings, photos, and tourist information, read St. Pete Beach day trip app.

Drive from Sanibel Island to St. Pete Beach in 3 hours. Alternatively, you can do a combination of taxi and bus. June in St. Pete Beach sees daily highs of 36°C and lows of 29°C at night. Finish your sightseeing early on the 12th (Sun) so you can fly to Fort Walton Beach.

Things to do in St. Pete Beach

Outdoors · Parks · Beaches · Historic Sites

Side Trips

Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. You'll explore and learn at Pensacola Lighthouse & Maritime Museum and Air Force Armament Museum. Explore hidden gems such as Pensacola Beach and Henderson Beach State Park. Explore the numerous day-trip ideas around Fort Walton Beach: Gulf Islands National Seashore (in Pensacola Beach) and National Naval Aviation Museum (in Pensacola). There's much more to do: stroll through Navarre Beach, take a leisurely stroll along The Village of Baytowne Wharf, head off the coast to Okaloosa Island, and get close to the beloved marine mammals with AJ's Water Adventures.

For maps, other places to visit, traveler tips, and other tourist information, go to the Fort Walton Beach trip builder website.

Traveling by flight from St. Pete Beach to Fort Walton Beach takes 4.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Traveling from St. Pete Beach in June, Fort Walton Beach is slightly colder at night with lows of 26°C. Finish your sightseeing early on the 16th (Thu) so you can drive to Panama City Beach.

Things to do in Fort Walton Beach

Outdoors · Parks · 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.
Kick off your visit on the 17th (Fri): see some colorful creatures with a scuba or snorkeling tour, then kick back and relax at St. Andrews State Park, and then kick back and relax at Panama City Beach. On the 18th (Sat), you'll have a packed day of sightseeing: kick back and relax at Grayton Beach State Park, then stroll through Santa Rosa Beach, and then browse the different shops at Pier Park.

To see traveler tips, reviews, other places to visit, and more tourist information, use the Panama City Beach holiday website.

You can drive from Fort Walton Beach to Panama City Beach in 1.5 hours. You'll lose 1 hour traveling from Fort Walton Beach to Panama City Beach due to the time zone difference. June in Panama City Beach sees daily highs of 37°C and lows of 26°C at night. Finish your sightseeing early on the 18th (Sat) to allow enough time to drive to St. Augustine.

Things to do in Panama City Beach

Outdoors · Parks · Beaches · Nature

Side Trip

St. Augustine

— 5 nights
St. Popular historic sites such as Fort Clinch State Park and Fort Matanzas National Monument are in your itinerary. Step off the beaten path and head to St. Augustine Beach and Cathedral Basilica of St. Augustine. Get out of town with these interesting St. Augustine side-trips: Amelia Island Historic District (in Amelia Island) and Jacksonville Beach (in Jacksonville Beach). There's much more to do: get engrossed in the history at St. Augustine Pirate & Treasure Museum, contemplate the long history of Old Jail, examine the collection at Lightner Museum, and brush up on your military savvy at Spanish Military Hospital Museum.

For traveler tips, reviews, other places to visit, and more tourist information, read our St. Augustine trip site.

You can drive from Panama City Beach to St. Augustine in 5.5 hours. Alternatively, you can fly. In June, daytime highs in St. Augustine are 36°C, while nighttime lows are 26°C. Finish your sightseeing early on the 23rd (Thu) to allow enough time to drive to Daytona Beach.

Things to do in St. Augustine

Historic Sites · Parks · Nature · Outdoors

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.
Start off your visit on the 24th (Fri): stroll through Equestrian Adventures of Florida, admire the landmark architecture of Stetson Mansion, then observe the fascinating underwater world at Marine Science Center, and finally see the interesting displays at Ponce de Leon Inlet Lighthouse & Museum. Get ready for a full day of sightseeing on the 25th (Sat): get a dose of the wild on Blue Heron River Tours Inc, tour the pleasant surroundings at Ormond Beach, and then kick back and relax at Beach at Daytona Beach.

To find reviews, maps, ratings, and more tourist information, read Daytona Beach road trip planner.

Traveling by car from St. Augustine to Daytona Beach takes 1.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Daytona Beach can reach 37°C, while at night they dip to 26°C. Finish your sightseeing early on the 25th (Sat) to allow enough time to drive to Orlando.

Things to do in Daytona Beach

Outdoors · Parks · Museums · Beaches

Side Trips

Orlando

— 5 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 Boat Tours & Water Sports. Have a day of magic on the 26th (Sun) at Walt Disney World Resort. Plan for a day of cool, family-friendly fun on the 30th (Thu) at Discovery Cove. The adventure continues: find something for the whole family at Universal Orlando Resort and discover the magic at Epcot.

For other places to visit, traveler tips, where to stay, and other tourist information, read our Orlando trip planning site.

Drive from Daytona Beach to Orlando in an hour. Alternatively, you can take a bus. In June, plan for daily highs up to 38°C, and evening lows to 26°C. Finish up your sightseeing early on the 30th (Thu) so you can catch the flight back home.

Things to do in Orlando

Theme Parks · Tours · Outdoors

Side Trip

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.