39 days in Florida Itinerary

39 days in Florida Itinerary

Created using Inspirock Florida route planner

Plan created by another user. Make it yours

Route & dates

1
Marathon
— 3 nights
2
Key West
— 6 nights
3
Marco Island
— 2 nights
4
Sanibel Island
— 2 nights
5
Orlando
— 6 nights
6
St. Augustine
— 5 nights
7
Panama City Beach
— 4 nights
8
Pensacola
— 6 nights
9
Key Largo
— 4 nights

3
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
We've included these beaches for you: Bahia Honda State Park and Sombrero Beach. Explore hidden gems such as The Turtle Hospital and Dolphin Research Center. There's much more to do: see what you can catch with a fishing tour, get all the information you need at Pigeon Key Foundation, examine the collection at Crane Point Museum & Nature Center, and take in the views from Seven Mile Bridge.

To find ratings, traveler tips, other places to visit, and more tourist information, go to the Marathon trip itinerary app.

San Juan, Puerto Rico to Marathon is an approximately 7.5-hour flight. You'll gain 1 hour traveling from San Juan to Marathon due to the time zone difference. In July, daily temperatures in Marathon can reach °C, while at night they dip to °C. Wrap up your sightseeing on the 7th (Sun) to allow time to drive to Key West.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trip

Big Pine Key
Highlights from your plan
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center
Bahia Honda State Park ©
Bahia Honda State Park

6
nights
Key West

Key West ©
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.
Escape the urban bustle at Dry Tortugas National Park and Waterskiing & Jetskiing. You'll visit kid-friendly attractions like Dolphin & Whale Watching and Stand-Up Paddleboarding. And it doesn't end there: see some colorful creatures with a scuba or snorkeling tour, get engrossed in the history at Key West Lighthouse and Keeper's Quarters Museum, view the masterpieces at 7 Artists & Friends Gallery, and examine the collection at The Ernest Hemingway Home and Museum.

For other places to visit, traveler tips, maps, and other tourist information, read our Key West tour itinerary planner.

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. July in Key West sees daily highs of °C and lows of °C at night. Finish up your sightseeing early on the 13th (Sat) so you can catch the ferry to Marco Island.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
Dolphin & Whale Watching
Stand-Up Paddleboarding

2
nights
Marco Island

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 14th (Sun): look for all kinds of wild species at Wildlife Areas and then see what you can catch with a fishing tour. On the 15th (Mon), you'll have a packed day of sightseeing: take a memorable tour with Tours, thenget interesting insight from Tours, and then take a tour by water with Boat Tours & Water Sports.

To find more things to do, maps, ratings, and other tourist information, read our Marco Island trip itinerary planner.

You can ride a ferry from Key West to Marco Island in 3.5 hours. Another option is to drive. Expect a bit cooler evenings in Marco Island when traveling from Key West in July, with lows around °C. Finish up your sightseeing early on the 15th (Mon) so you can go by car to Sanibel Island.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trip

Nature & Wildlife Tours
Highlights from your plan
Nature & Wildlife Tours
Dolphin & Whale Watching
Waterskiing & Jetskiing

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kick off your visit on the 16th (Tue): look for all kinds of wild species at J.N. "Ding" Darling National Wildlife Refuge and then admire the natural beauty at Edison and Ford Winter Estates. On the 17th (Wed), you'll have a packed day of sightseeing: examine the collection at The Bailey-Matthews National Shell Museum, kick back and relax at Bowman's Beach, and then kick back and relax at Captiva Beach.

For ratings, traveler tips, maps, and more tourist information, read Sanibel Island day trip planning app.

You can drive from Marco Island to Sanibel Island in 2 hours. In July, plan for daily highs up to °C, and evening lows to °C. Wrap up your sightseeing on the 17th (Wed) early enough to drive to Orlando.

Things to do in Sanibel Island

Parks Outdoors Beaches

Side Trips

Captiva Beach, Edison and Ford Winter Estates
Highlights from your plan
The Bailey-Matthews National Shell Museum ©
The Bailey-Matthews National Shell Museum
Bowman's Beach ©
Bowman's Beach
Captiva Beach ©
Captiva Beach

6
nights
Orlando

Orlando ©
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.
Get a sense of the local culture at Ponce de Leon Inlet Lighthouse & Museum and Madame Tussauds Orlando. Get in touch with nature at Discovery Cove and Fishing Charters & Tours. Pack the 20th (Sat) with family-friendly diversions at Universal's Islands of Adventure. Have a day of magic on the 18th (Thu) at Walt Disney World Resort. Next up on the itinerary: make an unforgettable trip to Happily Ever After Fireworks, laugh and play at World of Disney, make a splash at Disney's Typhoon Lagoon Water Park, and test your problem-solving skills at popular escape rooms.

For maps, traveler tips, and more tourist information, go to the Orlando road trip planner.

You can drive from Sanibel Island to Orlando in 4 hours. Other options are to fly; or do a combination of taxi, bus, and train. In July, plan for daily highs up to °C, and evening lows to °C. Finish up your sightseeing early on the 23rd (Tue) so you can go by car to St. Augustine.

Things to do in Orlando

Theme Parks Outdoors Beaches

Side Trips

Ponce de Leon Inlet Lighthouse & Museum, Fishing Charters & Tours
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Fishing Charters & Tours
Ponce de Leon Inlet Lighthouse & Museum ©
Ponce de Leon Inlet Lighthouse & Museum

5
nights
St. Augustine

St. Augustine ©
St. Take a break from the city and head to Beach at Daytona Beach and Fort Matanzas National Monument. Get some cultural insight at St. Augustine Pirate & Treasure Museum and Colonial Quarter. Change things up with these side-trips from St. Augustine: Ormond Beach (in Ormond Beach) and Catty Shack Ranch Wildlife Sanctuary (in Jacksonville). There's much more to do: identify plant and animal life at St. Augustine Alligator Farm Zoological Park, visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., stroll through St. Augustine Beach, and pause for some serene contemplation at Cathedral Basilica of St. Augustine.

Take the guesswork out of planning a St. Augustine vacation by using our trip itinerary maker.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around °C in July, and nighttime lows around °C. Finish your sightseeing early on the 28th (Sun) to allow enough time to drive to Panama City Beach.

Things to do in St. Augustine

Parks Historic Sites Outdoors

Side Trips

Beach at Daytona Beach, Ormond Beach, Catty Shack Ranch Wildlife Sanctuary
Highlights from your plan
St. Augustine Alligator Farm Zoological Park ©
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

4
nights
Panama City Beach

Panama City Beach ©
Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Get in touch with nature at St. Andrews State Park and Florida Caverns State Park. You'll explore the less-touristy side of things at Henderson Beach State Park and The Village of Baytowne Wharf. Step out of Panama City Beach with an excursion to Santa Rosa Beach in Santa Rosa Beach--about 46 minutes away. There's lots more to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, do a tasting at Panama City Beach Winery, buy something for everyone on your list at Pier Park, and take a memorable tour with Tours.

To see where to stay, ratings, and more tourist information, refer to the Panama City Beach travel itinerary planner.

You can drive from St. Augustine to Panama City Beach in 5.5 hours. Another option is to fly. July in Panama City Beach sees daily highs of °C and lows of °C at night. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Pensacola.

Things to do in Panama City Beach

Outdoors Parks Beaches

Side Trips

Destin, Florida Caverns State Park, Santa Rosa Beach
Highlights from your plan
Henderson Beach State Park ©
Henderson Beach State Park
Swim with Dolphins
St. Andrews State Park ©
St. Andrews State Park

6
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Pensacola Lighthouse and Museum and National Naval Aviation Museum will appeal to museum buffs. Bring the kids along to Pensacola Beach and Fishing Charters & Tours. Explore the numerous day-trip ideas around Pensacola: Navarre Beach (in Navarre), Orange Beach (Dolphin & Whale Watching, Parasailing & Paragliding, &more) and Fort Morgan State Historic Site (in Fort Morgan). There's still lots to do: enjoy the sand and surf at Gulf Islands National Seashore, tour the pleasant surroundings at Gulf State Park, and take in the waterfront at Gulf State Park Fishing Pier.

To find ratings, more things to do, where to stay, and more tourist information, refer to the Pensacola attractions tool.

Getting from Panama City Beach to Pensacola by car takes about 2.5 hours. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In August, daily temperatures in Pensacola can reach °C, while at night they dip to °C. Cap off your sightseeing on the 7th (Wed) early enough to travel to Key Largo.

Things to do in Pensacola

Outdoors Parks Beaches

Side Trips

Orange Beach, Pensacola Beach, Gulf Shores, Navarre Beach, Fort Morgan State Historic Site
Highlights from your plan
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Dolphin & Whale Watching

4
nights
Key Largo

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.
Explore hidden gems such as Fishing Charters & Tours and Parasailing & Paragliding. Visiting Anhinga Trail and Everglades Alligator Farm will get you outdoors. There's lots more to do: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, see the vivid underwater world at Grecian Rocks, immerse yourself in nature at John Pennekamp Coral Reef State Park, and tour the pleasant surroundings at Spiegel Grove.

To see maps, more things to do, where to stay, and tourist information, you can read our Key Largo holiday builder site.

Getting from Pensacola to Key Largo by flight takes about 5.5 hours. Other options: drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Pensacola to Key Largo. August in Key Largo sees daily highs of °C and lows of °C at night. Finish your sightseeing early on the 11th (Sun) so you can travel back home.

Things to do in Key Largo

Wildlife Parks Outdoors

Side Trips

Islamorada, Everglades Alligator Farm, Anhinga Trail
Highlights from your plan
Fishing Charters & Tours
Anhinga Trail ©
Anhinga Trail

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