31 days in Florida Itinerary

31 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
1
Orlando
— 5 nights
Drive
2
St. Augustine
— 5 nights
Drive
3
Panama City Beach
— 2 nights
Drive
4
Fort Walton Beach
— 4 nights
Fly to Miami, Shuttle to Marathon
5
Marathon
— 4 nights
Drive
6
Key West
— 5 nights
Ferry to Fort Myers Beach, FL, Taxi to Sanibel Island
7
Sanibel Island
— 2 nights
Drive
8
Treasure Island
— 3 nights
Drive

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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.
Explore hidden gems such as Beach at Daytona Beach and Angell & Phelps Chocolate Factory. Step out of Orlando to go to Daytona Beach and see Saint Demetrios Greek Orthodox Church, which is approximately 1h 5 min away. Have a day of magic on the 1st (Sat) at Walt Disney World Resort. Pack the 4th (Tue) with family-friendly diversions at Universal Orlando Resort. And it doesn't end there: get in on the family fun at Universal's Islands of Adventure, take in the architecture and atmosphere at St James Roman Catholic Cathedral, discover the magic at Disney’s Blizzard Beach Water Park, and cool off at Discovery Cove.

To find other places to visit, photos, and more tourist information, read Orlando online route planner.

Use the Route module to find travel options from your starting location 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 6th (Thu) to allow time to drive to St. Augustine.

Things to do in Orlando

Theme Parks · Historic Sites · Parks · Beaches

Side Trip

Find places to stay May 1 — 6:

St. Augustine

— 5 nights
St. Eschew the tourist crowds and head to St. Augustine Beach and Fort Clinch State Park. Your itinerary includes some good beach time at Vilano Beach and Ormond Beach. You'll find plenty of places to visit near St. Augustine: Seaside Park (in Amelia Island), Ames Park (in Ormond Beach) and TPC at Sawgrass Stadium Course (in Ponte Vedra Beach). Next up on the itinerary: identify plant and animal life at St. Augustine Alligator Farm Zoological Park, see the interesting displays at Lightner Museum, get a taste of the local shopping with High Tide Gallery Art & Gifts, and admire the landmark architecture of Old Jail.

For traveler tips, maps, reviews, and more tourist information, read our St. Augustine trip planner.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. Traveling from Orlando in May, you will find days in St. Augustine are slightly colder (83°F), and nights are about the same (67°F). Finish up your sightseeing early on the 11th (Tue) so you can go by car to Panama City Beach.

Things to do in St. Augustine

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Find places to stay May 6 — 11:

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 12th (Wed): discover the deep blue sea with a scuba or snorkeling tour, then enjoy the sand and surf at St. Andrews State Park, then do a tasting at Panama City Beach Winery, and finally browse the different shops at Pier Park. Get ready for a full day of sightseeing on the 13th (Thu): kick back and relax at Grayton Beach State Park, stroll through Santa Rosa Beach, and then immerse yourself in nature at Eden Gardens State Park.

To see other places to visit, maps, ratings, and more tourist information, go to the Panama City Beach attractions tool.

You can drive from St. Augustine to Panama City Beach in 5.5 hours. Alternatively, you can fly. Traveling from St. Augustine in May, Panama City Beach is a bit cooler at night with lows of 62°F. Wrap up your sightseeing on the 13th (Thu) to allow time to drive to Fort Walton Beach.

Things to do in Panama City Beach

Parks · Outdoors · Nature · Beaches

Side Trips

Find places to stay May 11 — 13:

Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Step off the beaten path and head to Navarre Beach and Okaloosa Island. You'll enjoy a bit of beach vacationing at Pensacola Beach and Henderson Beach State Park. Change things up with these side-trips from Fort Walton Beach: Rollins Distillery (in Gulf Breeze), Pensacola Beach (Pensacola Beach Gulf Pier, Gulf Islands National Seashore, &more) and Waterfront Gifts and Art (in Miramar Beach). There's still lots to do: contemplate the waterfront views at Destin Harbor, brush up on your military savvy at Air Force Armament Museum, and take in the waterfront at The Village of Baytowne Wharf.

Plan my day in Fort Walton Beach using traveler tips and tourist information provided by Inspirock.

You can drive from Panama City Beach to Fort Walton Beach in 1.5 hours. You'll gain 1 hour traveling from Panama City Beach to Fort Walton Beach due to the time zone difference. In May, daytime highs in Fort Walton Beach are 81°F, while nighttime lows are 64°F. Finish up your sightseeing early on the 17th (Mon) so you can travel to Marathon.

Things to do in Fort Walton Beach

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay May 13 — 17:

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 Sombrero Beach and The Turtle Hospital. You'll enjoy a bit of beach vacationing at Bahia Honda State Park and Anne's Beach. Get out of town with these interesting Marathon side-trips: Islamorada (Islamorada Brewery & Distillery, Fishing Charters & Tours, &more), Florida Keys Wild Bird Rehabilitation Center (in Tavernier) and Island Dolphin Care (in Key Largo). And it doesn't end there: look for all kinds of wild species at Dolphin Research Center, snap pictures at Old Seven Mile Bridge, soothe aching muscles at some of the top local wellness centers, and explore the galleries of Crane Point Museum & Nature Center.

To see ratings, other places to visit, more things to do, and more tourist information, read our Marathon trip planner.

You can do a combination of flight and shuttle from Fort Walton Beach to Marathon in 6.5 hours. Alternatively, you can drive; or do a combination of bus and shuttle. The time zone difference when traveling from Fort Walton Beach to Marathon is 1 hour. Plan for somewhat warmer temperatures traveling from Fort Walton Beach in May, with highs in Marathon at 88°F and lows at 77°F. Finish up your sightseeing early on the 21st (Fri) so you can go by car to Key West.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trips

Find places to stay May 17 — 21:

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.
Eschew the tourist crowds and head to Dry Tortugas National Park and Key West Garden Club. There's still lots to do: see the interesting displays at The Ernest Hemingway Home and Museum, enjoy the sand and surf at Fort Zachary Taylor, make a trip to Duval Street, and explore the different monuments and memorials at Key West Cemetery.

To find photos, traveler tips, where to stay, and tourist information, refer to the Key West trip itinerary planner.

Getting from Marathon to Key West by car takes about 1.5 hours. Other options: take a bus. May in Key West sees daily highs of 85°F and lows of 77°F at night. Finish your sightseeing early on the 26th (Wed) so you can travel to Sanibel Island.

Things to do in Key West

Parks · Nature · Museums · Wildlife
Find places to stay May 21 — 26:

Sanibel Island

— 2 nights
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
On the 27th (Thu), enjoy the sand and surf at Captiva Beach, tour the pleasant surroundings at Blind Pass Beach Park, then kick back and relax at Bowman's Beach, and finally walk around Pond Apple Park. Get ready for a full day of sightseeing on the next day: see the interesting displays at The Bailey-Matthews National Shell Museum, take a memorable drive along Sanibel Causeway, and then take a memorable tour with Tours.

To find more things to do, traveler tips, photos, and other tourist information, use the Sanibel Island trip itinerary planning site.

You can do a combination of ferry and taxi from Key West to Sanibel Island in 5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Traveling from Key West in May, expect a bit cooler with lows of 69°F in Sanibel Island. Wrap up your sightseeing on the 28th (Fri) early enough to drive to Treasure Island.

Things to do in Sanibel Island

Outdoors · Parks · Beaches · Scenic Drive

Side Trip

Find places to stay May 26 — 28:

Treasure Island

— 3 nights
Treasure Island is a city in Pinellas County, Florida, United States. You'll enjoy a bit of beach vacationing at Treasure Island Beach and Crescent Beach. You'll discover tucked-away gems like Turtle Beach and Honeymoon Island State Park. Change things up with these side-trips from Treasure Island: Venice (Caspersen Beach & Venice Beach), Saint Pete Beach (in St. Pete Beach) and Manasota Key Beach (in Englewood).

To find where to stay, maps, more things to do, and other tourist information, use the Treasure Island day trip planner.

You can drive from Sanibel Island to Treasure Island in 3 hours. Alternatively, you can do a combination of taxi and bus. In May, daily temperatures in Treasure Island can reach 86°F, while at night they dip to 73°F. Finish up your sightseeing early on the 31st (Mon) so you can go by car back home.

Things to do in Treasure Island

Parks · Beaches · Outdoors · Nature

Side Trips

Find places to stay May 28 — 31:

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.