39 days in Florida Itinerary

39 days in Florida Itinerary

Created using Inspirock Florida route planner

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Route & dates

39 days in Florida Itinerary

Start: San Juan, Puerto Rico
Fly + shuttle:  7​h 45​min
1
Marathon
— 3 nights
bus:  1​h 15​min
2
Key West
— 6 nights
ferry:  2​h 30​min
3
Marco Island
— 2 nights
Drive:  1​h 45​min
4
Sanibel Island
— 2 nights
Drive:  3​h 45​min
5
Orlando
— 6 nights
Drive:  2​h
6
St. Augustine
— 5 nights
Drive:  5​h 30​min
7
Panama City Beach
— 4 nights
Drive:  2​h 15​min
8
Pensacola
— 6 nights
Fly + shuttle:  5​h 30​min
9
Key Largo
— 4 nights
shuttle + Fly:  7​h
End: San Juan, Puerto Rico

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.
Escape the urban bustle at Fishing Charters & Tours and Sombrero Beach. Kids will appreciate attractions like Dolphin Research Center and Crane Point Museum & Nature Center. Go for a jaunt from Marathon to Big Pine Key to see National Key Deer Refuge about 34 minutes away. There's much more to do: identify plant and animal life at The Turtle Hospital, kick back and relax at Bahia Honda State Park, snap pictures at Seven Mile Bridge, and get answers to all your questions at Pigeon Key Foundation.

To see other places to visit, more things to do, and tourist information, refer to the Marathon day trip planner.

San Juan, Puerto Rico to Marathon is an approximately 8-hour combination of flight and shuttle. You can also do a combination of flight and bus; or do a combination of car, flight, and shuttle. The time zone difference when traveling from San Juan to Marathon is minus 1 hour. In July, daily temperatures in Marathon can reach 39°C, while at night they dip to 32°C. Finish your sightseeing early on the 7th (Sun) to allow enough time to take a bus 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.
Do some cultural sightseeing at U.S. Coast Guard Cutter Ingham Maritime Museum and Mel Fisher Maritime Heritage Museum. Kids will appreciate attractions like Key West Butterfly & Nature Conservatory and Fort Zachary Taylor. Spend the 9th (Tue) exploring nature at Dry Tortugas National Park. There's still lots to do: glide peacefully along the water with some of the best stand-up paddleboarding in the area, make a trip to Truman Little White House, get a new perspective on things with Boat Tours & Water Sports, and explore the different monuments and memorials at Key West Cemetery.

To find more things to do, ratings, where to stay, and more tourist information, use the Key West tour itinerary planner.

Getting from Marathon to Key West by bus takes about 1.5 hours. Other options: drive. In July in Key West, expect temperatures between 37°C during the day and 32°C at night. Finish your sightseeing early on the 13th (Sat) to allow enough time to ride a 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
Scuba & Snorkeling

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. On the 14th (Sun), surround yourself with nature on a nature and wildlife tour and then cast your line with a fishing tour. Get ready for a full day of sightseeing on the 15th (Mon): get up close to creatures of the deep with a dolphin and whale watching tour, get interesting insight from Tours, and then take a tour by water with Boat Tours & Water Sports.

To plan Marco Island vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by ferry from Key West to Marco Island takes 2.5 hours. Alternatively, you can drive. Traveling from Key West in July, plan for little chillier nights in Marco Island, with lows around 28°C. Cap off your sightseeing on the 15th (Mon) early enough to go by car to Sanibel Island.

Things to do in Marco Island

Tours Outdoors Wildlife

Side Trip

Nature & Wildlife Tours
Highlights from your plan
Nature & Wildlife Tours
Dolphin & Whale Watching
Fishing Charters & Tours

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Start 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 all the interesting features of Edison & Ford Winter Estates. Get ready for a full day of sightseeing on the 17th (Wed): see the interesting displays at The Bailey-Matthews National Shell Museum, then kick back and relax at Bowman's Beach, and then kick back and relax at Captiva Beach.

To find ratings, traveler tips, and more tourist information, you can read our Sanibel Island holiday planner.

Getting from Marco Island to Sanibel Island by car takes about 2 hours. In July, daytime highs in Sanibel Island are 38°C, while nighttime lows are 28°C. Cap off your sightseeing on the 17th (Wed) early enough to go by car to Orlando.

Things to do in Sanibel Island

Parks Outdoors Beaches

Side Trips

Edison and Ford Winter Estates, Captiva Beach
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Captiva Beach ©
Captiva Beach
Edison and Ford Winter Estates ©
Edison and Ford Winter Estates

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.
Satisfy your inner culture vulture at Ponce de Leon Inlet Lighthouse & Museum and Madame Tussauds Orlando. Get outdoors at Fishing Charters & Tours and Discovery Cove. Have a day of magic on the 18th (Thu) at Walt Disney World Resort. Pack the 20th (Sat) with family-friendly diversions at Universal's Islands of Adventure. And it doesn't end there: make an unforgettable trip to World of Disney, make a splash at Disney's Typhoon Lagoon Water Park, test your team's savvy at popular escape rooms, and try out the rides at Happily Ever After Fireworks.

For reviews, ratings, other places to visit, and tourist information, refer to the Orlando day trip planning website .

You can drive from Sanibel Island to Orlando in 4 hours. Other options are to fly; or do a combination of bus and train. In July, plan for daily highs up to 38°C, and evening lows to 28°C. Finish your sightseeing early on the 23rd (Tue) to allow enough time to drive to St. Augustine.

Things to do in Orlando

Theme Parks Outdoors Beaches

Side Trips

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

5
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Eschew the tourist crowds and head to Dolphin & Whale Watching and Catty Shack Ranch Wildlife Sanctuary. Visit Fort Matanzas National Monument and Cathedral Basilica of St. Augustine for their historical value. Explore St. Augustine's surroundings by going to Beach at Daytona Beach (in Daytona Beach) and Ormond Beach (in Ormond Beach). There's still lots to do: examine the collection at St. Augustine Pirate & Treasure Museum, steep yourself in history at Colonial Quarter, look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park, and kick back and relax at St. Augustine Beach.

To see traveler tips, more things to do, where to stay, and tourist information, use the St. Augustine online driving holiday planner .

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. July in St. Augustine sees daily highs of 38°C and lows of 28°C at night. Wrap up your sightseeing on the 28th (Sun) early enough 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 Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

4
nights
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.
You'll explore the less-touristy side of things at Santa Rosa Beach and St. Andrews State Park. You'll enjoy a bit of beach vacationing at Henderson Beach State Park and Panama City Beach. Step out of Panama City Beach with an excursion to Florida Caverns State Park in Marianna--about 1h 30 min away. Next up on the itinerary: fulfill a lifelong dream with a swim-with-the-dolphins experience, do a tasting at Panama City Beach Winery, get up close to creatures of the deep with a dolphin and whale watching tour, and buy something for everyone on your list at Pier Park.

For other places to visit, more things to do, and more tourist information, go to the Panama City Beach online vacation planner .

You can drive from St. Augustine to Panama City Beach in 5.5 hours. Other options are to do a combination of bus and flight; or do a combination of bus, flight, and taxi. In July in Panama City Beach, expect temperatures between 38°C during the day and 27°C at night. Finish your sightseeing early on the 1st (Thu) to allow enough time to drive to Pensacola.

Things to do in Panama City Beach

Outdoors Parks Beaches

Side Trips

Destin, Santa Rosa Beach, Florida Caverns State Park
Highlights from your plan
Dolphin & Whale Watching
Swim with Dolphins
Henderson Beach State Park ©
Henderson Beach 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.
Fort Morgan State Historic Site and Pensacola Lighthouse and Museum will appeal to history buffs. You'll get in some beach time at Gulf State Park Fishing Pier and Navarre Beach. Explore Pensacola's surroundings by going to Orange Beach (Dolphin & Whale Watching, Fishing Charters & Tours, & more) and Gulf State Park (in Gulf Shores). There's much more to do: kick back and relax at Pensacola Beach, tour the pleasant surroundings at Gulf Islands National Seashore, and learn about all things military at National Naval Aviation Museum.

To find maps, other places to visit, more things to do, and tourist information, read Pensacola trip itinerary maker website .

Traveling by car from Panama City Beach to Pensacola takes 2.5 hours. You'll gain 1 hour traveling from Panama City Beach to Pensacola due to the time zone difference. In August, daytime highs in Pensacola are 38°C, while nighttime lows are 28°C. Finish up your sightseeing early on the 7th (Wed) so you can travel to Key Largo.

Things to do in Pensacola

Outdoors Beaches Parks

Side Trips

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

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 Parasailing & Paragliding and Florida Keys Wild Bird Rehabilitation Center. Get in touch with nature at Scuba & Snorkeling and Fishing Charters & Tours. Get out of town with these interesting Key Largo side-trips: Everglades Alligator Farm (in Homestead) and Anhinga Trail (in Everglades National Park). The adventure continues: explore the gorgeous colors at Spiegel Grove, look for all kinds of wild species at Grecian Rocks, and immerse yourself in nature at John Pennekamp Coral Reef State Park.

To find other places to visit, more things to do, and more tourist information, use the Key Largo trip planner .

Traveling by combination of flight and shuttle from Pensacola to Key Largo takes 5.5 hours. Alternatively, you can do a combination of taxi, flight, and shuttle; or drive. You'll lose 1 hour traveling from Pensacola to Key Largo due to the time zone difference. In August, daily temperatures in Key Largo can reach 38°C, while at night they dip to 29°C. 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, Anhinga Trail, Everglades Alligator Farm
Highlights from your plan
Fishing Charters & Tours
Anhinga Trail ©
Anhinga Trail
Scuba & Snorkeling

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