31 days in Florida Itinerary

31 days in Florida Itinerary

Created using Inspirock Florida planner

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

S M T W T F S
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5

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.
Have a day of magic on the 1st (Sat) at Walt Disney World Resort. Plan for a day of cool, family-friendly fun on the 3rd (Mon) at Discovery Cove. It doesn't end there: find something for the whole family at Universal Orlando Resort and explore the world behind art at Charles Hosmer Morse Museum of American Art.

To find where to stay, photos, and more tourist information, read Orlando itinerary builder app.

Use the Route module to find suitable travel options from your home destination to Orlando. In May, daily temperatures in Orlando can reach 88°F, while at night they dip to 69°F. Wrap up your sightseeing on the 5th (Wed) to allow time to drive to St. Augustine.

Things to do in Orlando

Theme Parks · Museums

Side Trip

St. Augustine

— 4 nights
St. Eschew the tourist crowds and head to St. Augustine Alligator Farm Zoological Park and St. Augustine Beach. You'll find plenty of places to visit near St. Augustine: Jacksonville Zoo & Gardens (in Jacksonville) and Fernandina Beach (Fort Clinch State Park & Egan's Creek Park). Spend the 8th (Sat) exploring nature at Fort Matanzas National Monument. And it doesn't end there: gain insight at Flagler College, brush up on your knowledge of spirits at St. Augustine Distillery, get engrossed in the history at St. Augustine Pirate & Treasure Museum, and learn about winemaking at San Sebastian Winery.

For photos, where to stay, reviews, and other tourist information, read St. Augustine trip planner.

Drive from Orlando to St. Augustine in 2 hours. Alternatively, you can take a bus. Expect a bit cooler weather when traveling from Orlando in May: highs in St. Augustine hover around 83°F, while lows dip to 67°F. Finish your sightseeing early on the 9th (Sun) so you can drive to Panama City Beach.

Things to do in St. Augustine

Parks · Nature · Historic Sites · Museums

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 10th (Mon): learn about winemaking at Panama City Beach Winery, then see some colorful creatures with a scuba or snorkeling tour, then stroll through St. Andrews State Park, and finally make a trip to Abc Fine Wine And Spirits. Get ready for a full day of sightseeing on the next day: buy something for everyone on your list at Pier Park, tour the pleasant surroundings at Santa Rosa Beach, and then enjoy the sand and surf at Grayton Beach State Park.

To see maps, other places to visit, where to stay, and more tourist information, you can read our Panama City Beach trip itinerary builder website.

You can drive from St. Augustine to Panama City Beach in 5.5 hours. Another option is to fly. Traveling from St. Augustine in May, Panama City Beach is slightly colder at night with lows of 62°F. Finish your sightseeing early on the 11th (Tue) so you can drive to Fort Walton Beach.

Things to do in Panama City Beach

Outdoors · Parks · Beaches · Nature

Side Trip

Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. You'll explore the less-touristy side of things at Destin Harbor and Destin Harbor Boardwalk. Explore Fort Walton Beach's surroundings by going to Waterfront Gifts and Art (in Miramar Beach), Rollins Distillery (in Gulf Breeze) and Pensacola Beach (Jolly Sailing and Dolphin Cruises & Pensacola Beach). There's much more to do: enjoy the sand and surf at Navarre Beach, take a leisurely stroll along The Village of Baytowne Wharf, immerse yourself in nature at Henderson Beach State Park, and brush up on your military savvy at Air Force Armament Museum.

To find more things to do, traveler tips, other places to visit, and tourist information, you can read our Fort Walton Beach trip itinerary builder website.

You can drive from Panama City Beach to Fort Walton Beach in 1.5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Panama City Beach to Fort Walton Beach. Expect a daytime high around 81°F in May, and nighttime lows around 64°F. Finish up your sightseeing early on the 15th (Sat) so you can travel to Key Largo.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Nature

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.
On the 16th (Sun), meet the residents at Island Dolphin Care, fulfill a lifelong dream with a swim-with-the-dolphins experience, then get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, and finally identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center. On your second day here, take a tour of Spiegel Grove, pause for some serene contemplation at Key Largo Baptist Church, and then step aboard African Queen Canal Cruise.

For where to stay and tourist information, read Key Largo trip builder tool.

Traveling by flight from Fort Walton Beach to Key Largo takes 5.5 hours. Alternatively, you can drive; or do a combination of bus and shuttle. Due to the time zone difference, you'll lose 1 hour traveling from Fort Walton Beach to Key Largo. Traveling from Fort Walton Beach in May, expect a bit warmer with lows of 72°F in Key Largo. Wrap up your sightseeing on the 17th (Mon) early enough to drive to Islamorada.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

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 18th (Tue): take an in-depth tour of History of Diving Museum, sample the tasty concoctions at Islamorada Brewery & Distillery, then see what you can catch with a fishing tour, and finally sample the tasty concoctions at Florida Keys Brewing Company. Here are some ideas for day two: get outside with Contagious Charters, then stop by Bella Sol Fragrance Bar and Gifts, and then get outside with A Lil' Tail Charters.

For ratings, where to stay, traveler tips, and other tourist information, use the Islamorada tour planner.

Islamorada is just a stone's throw from Key Largo. In May, daily temperatures in Islamorada can reach 88°F, while at night they dip to 77°F. Wrap up your sightseeing on the 19th (Wed) to allow time to drive to Marathon.

Things to do in Islamorada

Outdoors · Breweries & Distilleries · Wildlife · Tours

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.
You'll discover tucked-away gems like The Turtle Hospital and Dolphin Research Center. Next up on the itinerary: snap pictures at Seven Mile Bridge, kick back and relax at Bahia Honda State Park, tour the pleasant surroundings at Sombrero Beach, and shop like a local with Shady Palm Art Gallery & Photography.

To find maps, photos, more things to do, and other tourist information, use the Marathon holiday maker tool.

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In May, daily temperatures in Marathon can reach 88°F, while at night they dip to 77°F. Finish your sightseeing early on the 22nd (Sat) to allow enough time to drive to Key West.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trip

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.
Discover out-of-the-way places like Dry Tortugas National Park and Key West Cemetery. Next up on the itinerary: see the interesting displays at The Ernest Hemingway Home and Museum, make a trip to Truman Little White House, learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum, and look for all kinds of wild species at Key West Butterfly & Nature Conservatory.

To see maps, ratings, reviews, and tourist information, you can read our Key West trip planner.

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. May in Key West sees daily highs of 85°F and lows of 77°F at night. Wrap up your sightseeing on the 27th (Thu) to allow time to ride a ferry to Marco Island.

Things to do in Key West

Parks · Museums · Nature · Wildlife

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 28th (Fri): go for a stroll along the water at Marco Island Marina, see majestic marine mammals with a dolphin and whale watching tour, and then relax and rejuvenate at some of the best spas. Get ready for a full day of sightseeing on the next day: kick back and relax at South Marco Beach, then look for gifts at Keep In Touch, then enjoy the sand and surf at Keewaydin Island, and finally explore the activities along Capri Paddlecraft Park.

To see where to stay, maps, reviews, and other tourist information, go to the Marco Island itinerary planning tool.

You can ride a ferry from Key West to Marco Island in 4 hours. Another option is to drive. Plan for a bit cooler nights when traveling from Key West in May since evenings lows in Marco Island dip to 69°F. Wrap up your sightseeing on the 29th (Sat) to allow time to drive to Sanibel Island.

Things to do in Marco Island

Parks · Outdoors · Wildlife · Beaches

Sanibel Island

— 2 nights
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kick off your visit on the 30th (Sun): see the interesting displays at The Bailey-Matthews National Shell Museum, browse the eclectic array of goods at Sanibel Island Farmer's Market, then kick back and relax at Bowman's Beach, and finally get interesting insight from Tours. Here are some ideas for day two: kick back and relax at Captiva Beach, then stroll through Blind Pass Beach Park, then cruise along Sanibel Causeway, and finally walk around Pond Apple Park.

Plan a trip to Sanibel Island easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by car from Marco Island to Sanibel Island takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In May in Sanibel Island, expect temperatures between 90°F during the day and 69°F at night. Cap off your sightseeing on the 31st (Mon) early enough to go by car back home.

Things to do in Sanibel Island

Outdoors · Parks · Beaches · Wildlife

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.