38 days in Florida Itinerary

38 days in Florida Itinerary

Created using Inspirock Florida itinerary planner

Make it your trip
Fly
1
Fort Walton Beach
— 4 nights
Drive
2
Panama City Beach
— 3 nights
Fly
3
Key West
— 6 nights
Drive
4
Big Pine Key
— 3 nights
Drive
5
Islamorada
— 5 nights
Drive
6
Key Largo
— 5 nights
Fly
7
Vero Beach
— 1 night
Drive
8
Merritt Island
— 2 nights
Drive
9
Orlando
— 6 nights
Drive
10
Tampa
— 2 nights
Fly

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Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Get out of town with these interesting Fort Walton Beach side-trips: Pensacola Beach (Chase-N-Fins, Innerlight Surf Shop, &more), Pensacola (National Naval Aviation Museum & Gulf Islands) and Beach Sand Sculptures (in Seaside). The adventure continues: tour the pleasant surroundings at Navarre Beach, get outside with Sunshine Water Sports, kick back and relax at Henderson Beach State Park, and make a trip to Destin Harbor Boardwalk.

Plan trip to Fort Walton Beach with our itinerary maker to find out where to go and what to do.

Chicago to Fort Walton Beach is an approximately 4-hour flight. You can also drive; or take a bus. In May, Fort Walton Beach is somewhat warmer than Chicago - with highs of 81°F and lows of 64°F. Wrap up your sightseeing on the 3rd (Thu) early enough to drive to Panama City Beach.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Nature

Side Trips

Panama City Beach

— 3 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.
Change things up with these side-trips from Panama City Beach: Santa Rosa Beach (Santa Rosa Beach & Blue Mountain Beach). Next up on the itinerary: fulfill a lifelong dream with a swim-with-the-dolphins experience, get up close and personal with brilliant marine life at Gulf World Marine Park, don't miss a visit to Abc Fine Wine And Spirits, and tour the pleasant surroundings at St. Andrews State Park.

Quickly create a custom-made itinerary for Panama City Beach using our trip planner.

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. In June, plan for daily highs up to 89°F, and evening lows to 72°F. Wrap up your sightseeing on the 6th (Sun) early enough to fly to Key West.

Things to do in Panama City Beach

Outdoors · Parks · Beaches · Tours

Side Trip

Key West

— 6 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.
Key West is known for museums, adventure, and wildlife. Your trip includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, head outdoors with Outdoor Activities, make a trip to Truman Little White House, and get engrossed in the history at Key West Firehouse Museum.

To see traveler tips, more things to do, other places to visit, and tourist information, read our Key West attractions planner.

Traveling by flight from Panama City Beach to Key West takes 5.5 hours. Alternatively, you can drive. Traveling from Panama City Beach in June, plan for somewhat warmer nights in Key West, with lows around 79°F. Finish up your sightseeing early on the 12th (Sat) so you can go by car to Big Pine Key.

Things to do in Key West

Parks · Museums · Outdoors · Wildlife

Big Pine Key

— 3 nights
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Step out of Big Pine Key with an excursion to Key West Angling in Sugarloaf Key--about 40 minutes away. There's still lots to do: stroll through Bahia Honda State Park, get outside with Outdoor Activities, relax and rejuvenate at SpaTerre at Little Palm Island Resort, and make a trip to Sugarloaf Key Bat Tower.

To see more things to do, maps, and other tourist information, read Big Pine Key journey planning app.

Drive from Key West to Big Pine Key in an hour. Alternatively, you can take a shuttle; or take a bus. In June, daily temperatures in Big Pine Key can reach 90°F, while at night they dip to 79°F. Cap off your sightseeing on the 15th (Tue) early enough to go by car to Islamorada.

Things to do in Big Pine Key

Outdoors · Parks · Shopping · Beaches

Side Trips

Islamorada

— 5 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.
Change things up with these side-trips from Islamorada: Marathon (Shady Palm Art Gallery & Photography, Sombrero Beach, &more). There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, appreciate the extensive heritage of Indian Key State Historic Site, stroll through Anne's Beach, and see the interesting displays at Florida Keys History & Discovery Center.

To see ratings, traveler tips, photos, and more tourist information, go to the Islamorada trip maker app.

Traveling by car from Big Pine Key to Islamorada takes 1.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 90°F, and evening lows to 79°F. Finish up your sightseeing early on the 20th (Sun) so you can go by car to Key Largo.

Things to do in Islamorada

Parks · Outdoors · Wildlife · Museums

Side Trip

Key Largo

— 5 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.
Key Largo is known for wildlife, nature, and adventure. Your trip includes some of its best attractions: see some colorful creatures with a scuba or snorkeling tour, tour the pleasant surroundings at Spiegel Grove, see the vivid underwater world at North Dry Rocks, and step aboard SS Benwood.

To find where to stay, traveler tips, photos, and other tourist information, read Key Largo trip itinerary app.

Key Largo is very close to Islamorada. June in Key Largo sees daily highs of 88°F and lows of 75°F at night. Cap off your sightseeing on the 25th (Fri) early enough to catch the flight to Vero Beach.

Things to do in Key Largo

Parks · Wildlife · Nature · Spas

Vero Beach

— 1 night
Vero Beach is a city in, and the seat of Indian River County, Florida, United States. Kick off your visit on the 26th (Sat): walk around Riverside Park, discover the deep blue sea with Shark Bait Beach Gear Rentals, and then indulge in some personalized pampering at White Orchid Spa.

For more things to do, traveler tips, maps, and more tourist information, read our Vero Beach sightseeing planner.

Getting from Key Largo to Vero Beach by flight takes about 3 hours. Other options: drive; or do a combination of bus and taxi. In June, daytime highs in Vero Beach are 89°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 26th (Sat) early enough to drive to Merritt Island.

Things to do in Vero Beach

Tours · Outdoors · Adventure · Spas

Merritt Island

— 2 nights
On the 27th (Sun), take an unforgettable tour with a helicopter tour, then look and learn at NASA Kennedy Space Center Visitor Complex, and then get outside with Local Lines Guide Service. On the 28th (Mon), you'll have a packed day of sightseeing: tour the pleasant surroundings at Merritt Island National Wildlife Refuge, then see the interesting displays at Parker Brothers Concepts, then get up close to creatures of the deep with Time and Tide Tours, and finally soothe aching muscles at Beach Pole Fitness.

To see where to stay, reviews, other places to visit, and other tourist information, read Merritt Island travel planning site.

Getting from Vero Beach to Merritt Island by car takes about 1.5 hours. Other options: do a combination of bus and taxi. June in Merritt Island sees daily highs of 87°F and lows of 76°F at night. Finish your sightseeing early on the 28th (Mon) so you can drive to Orlando.

Things to do in Merritt Island

Outdoors · Museums · Wildlife · Childrens Museums

Side Trips

Orlando

— 6 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.
Pack the 29th (Tue) with family-friendly diversions at Universal Orlando Resort. Have a day of magic on the 30th (Wed) at Walt Disney World Resort. There's much more to do: get in on the family fun at Universal's Islands of Adventure, cool off at Discovery Cove, look for gifts at M&M'S World Disney Springs, and make an unforgettable trip to Magic Kingdom Park.

To find maps, reviews, and more tourist information, read our Orlando online vacation builder.

You can drive from Merritt Island to Orlando in 1.5 hours. Alternatively, you can take a shuttle. Expect a daytime high around 91°F in June, and nighttime lows around 73°F. Wrap up your sightseeing on the 4th (Sun) to allow time to drive to Tampa.

Things to do in Orlando

Theme Parks · Shopping

Tampa

— 2 nights

Big Guava

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
Kick off your visit on the 5th (Mon): enjoy the sand and surf at Clearwater Beach, then stroll through Seaside Seabird Sanctuary, and then glide through the air with a parasailing or paragliding tour. On the next day, find something for the whole family at Busch Gardens Tampa Bay and then appreciate the history behind 9/11 Fallen Heroes Memorial.

For ratings, traveler tips, photos, and more tourist information, read Tampa trip planning app.

Traveling by car from Orlando to Tampa takes 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 91°F in July, and nighttime lows around 77°F. Finish your sightseeing early on the 6th (Tue) so you can fly back home.

Things to do in Tampa

Theme Parks · Outdoors · 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.