39 days in Florida Itinerary

39 days in Florida Itinerary

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Route & dates

39 days in Florida Itinerary

Start: Little Rock
Fly + taxi:  6​h 15​min
1
Pensacola Beach
— 2 nights
Fly + bus:  7​h
2
Marco Island
— 3 nights
ferry:  2​h 30​min
3
Key West
— 6 nights
bus:  45​min
4
Big Pine Key
— 2 nights
Drive:  30​min
5
Marathon
— 5 nights
Drive:  45​min
6
Islamorada
— 3 nights
Drive:  45​min
7
Key Largo
— 4 nights
Drive:  1​h 15​min
8
Miami
— 5 nights
Fly:  3​h 15​min
9
Orlando
— 7 nights
Fly:  5​h 30​min
End: Little Rock

2
nights
Pensacola Beach

Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Kick off your visit on the 23rd (Thu): take in the waterfront at Pensacola Beach Gulf Pier. On the 24th (Fri), you'll have a packed day of sightseeing: steep yourself in history at Fort Pickens Area, then enjoy the sand and surf at Gulf Islands National Seashore, and then get up close to creatures of the deep with a dolphin and whale watching tour.

To find more things to do, reviews, other places to visit, and more tourist information, read Pensacola Beach trip itinerary builder .

Little Rock to Pensacola Beach is an approximately 6.5-hour combination of flight and taxi. You can also do a combination of bus, flight, and taxi; or drive. Traveling from Little Rock in May, you can expect nighttime temperatures to be somewhat warmer in Pensacola Beach, with lows of 66°F. Wrap up your sightseeing on the 25th (Sat) to allow time to travel to Marco Island.

Things to do in Pensacola Beach

Outdoors Parks Beaches

Side Trip

Navarre Beach
Highlights from your plan
Dolphin & Whale Watching
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore

3
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. Go for a jaunt from Marco Island to Everglades City to see Speed Boats Tours about 38 minutes away. There's lots more to do: see majestic marine mammals with a dolphin and whale watching tour, hunt for treasures at Marco Island Farmers Market-Wednesday- Mid November to Mid April, kick back and relax at Keewaydin Island, and tour the pleasant surroundings at South Marco Beach.

For reviews, maps, traveler tips, and tourist information, read Marco Island trip planner .

Traveling by combination of flight and bus from Pensacola Beach to Marco Island takes 7 hours. Alternatively, you can do a combination of taxi, flight, and bus; or drive. Traveling from Pensacola Beach to Marco Island, you'll lose 1 hour due to the time zone difference. In May in Marco Island, expect temperatures between 88°F during the day and 69°F at night. Finish your sightseeing early on the 29th (Wed) to allow enough time to ride a ferry to Key West.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Stand-Up Paddleboarding

6
nights
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.
Spend the 2nd (Sun) exploring nature at Dry Tortugas National Park. The adventure continues: identify plant and animal life at Key West Butterfly & Nature Conservatory, take a leisurely stroll along Mallory Square, see the interesting displays at Mel Fisher Maritime Heritage Museum, and get a new perspective on things with Boat Tours & Water Sports.

To see reviews, where to stay, more things to do, and other tourist information, go to the Key West trip itinerary builder .

Getting from Marco Island to Key West by ferry takes about 2.5 hours. Other options: drive. Plan for somewhat warmer nights when traveling from Marco Island in May since evenings lows in Key West dip to 77°F. Finish your sightseeing early on the 4th (Tue) to allow enough time to take a bus to Big Pine Key.

Things to do in Key West

Outdoors Tours Parks
Highlights from your plan
Dolphin & Whale Watching
Parasailing & Paragliding

2
nights
Big Pine Key

Big Pine Key ©
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. Kick off your visit on the 5th (Wed): identify plant and animal life at National Key Deer Refuge and then kick back and relax at Bahia Honda State Park. Get ready for a full day of sightseeing on the 6th (Thu): see some colorful creatures with a scuba or snorkeling tour and then identify plant and animal life at Blue Hole.

Ask Inspirock to suggest an itinerary and make planning a trip to Big Pine Key fast, fun, and easy.

Take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. June in Big Pine Key sees daily highs of 90°F and lows of 79°F at night. Finish up your sightseeing early on the 6th (Thu) so you can catcht the bus to Marathon.

Things to do in Big Pine Key

Parks Wildlife Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Blue Hole ©
Blue Hole

5
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.
Marathon is known for wildlife, beaches, adventure, nature, and shopping. Your plan includes some of its best attractions: get all the information you need at Pigeon Key Foundation, look for all kinds of wild species at The Turtle Hospital, cast your line with a fishing tour, and enjoy the sand and surf at Sombrero Beach.

To find ratings, maps, where to stay, and other tourist information, read Marathon travel planner.

Marathon is very close to Big Pine Key. In June, plan for daily highs up to 90°F, and evening lows to 79°F. Wrap up your sightseeing on the 11th (Tue) to allow time to drive to Islamorada.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trip

Sunset Park Beach
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Crane Point Museum & Nature Center ©
The Turtle Hospital ©
The Turtle Hospital

3
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Islamorada is known for wildlife, adventure, museums, beaches, and breweries & distilleries. Your plan includes some of its best attractions: see what you can catch with a fishing tour, indulge your thirst for a good beer at Islamorada Beer Company, find your balance on the water with some of the best stand-up paddleboarding in the area, and see some colorful creatures with a scuba or snorkeling tour.

To find reviews, maps, traveler tips, and more tourist information, read Islamorada online trip itinerary maker .

Drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. In June, plan for daily highs up to 90°F, and evening lows to 79°F. Finish your sightseeing early on the 14th (Fri) to allow enough time to drive to Key Largo.

Things to do in Islamorada

Outdoors Tours Wildlife
Highlights from your plan
Fishing Charters & Tours
Stand-Up Paddleboarding
Scuba & Snorkeling

4
nights
Key Largo

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.
Get out of town with these interesting Key Largo side-trips: Homestead (Everglades Alligator Farm & Coral Castle) and Anhinga Trail (in Everglades National Park). The adventure continues: get up close and personal with brilliant marine life at Island Dolphin Care, look for all kinds of wild species at Wildlife Areas, explore and take pictures at USCG Duane, and immerse yourself in nature at John Pennekamp Coral Reef State Park.

For more things to do, traveler tips, other places to visit, and more tourist information, read our Key Largo trip planner .

Drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. In June, daytime highs in Key Largo are 88°F, while nighttime lows are 75°F. Finish your sightseeing early on the 18th (Tue) to allow enough time to drive to Miami.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trips

Homestead, Anhinga Trail
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Dolphins Plus Marine Mammal Responder ©

5
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Venture out of the city with trips to R.F. Orchids (in Homestead), Everglades National Park (Shark Valley & Gumbo Limbo Trail) and iFLY Indoor Skydiving - Fort Lauderdale (in Davie). There's much more to do: enjoy the sand and surf at South Beach, steep yourself in history at Barnacle State Historic Site, zoom along the surf with a waterskiing or jet-skiing adventure, and identify plant and animal life at Loggerhead Marinelife Center.

To see other places to visit, where to stay, traveler tips, and other tourist information, you can read our Miami trip planning tool .

Getting from Key Largo to Miami by car takes about 1.5 hours. Other options: take a bus. June in Miami sees daily highs of 89°F and lows of 77°F at night. Finish your sightseeing early on the 23rd (Sun) so you can travel to Orlando.

Things to do in Miami

Parks Outdoors Shopping

Side Trips

Miami Beach, Everglades National Park, iFLY Indoor Skydiving - Fort Lauderdale, Palm Beach Zoo & Conservation Society, Loggerhead Marinelife Center
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Gumbo Limbo Trail ©
Gumbo Limbo Trail
South Beach ©
South Beach

7
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.
Have a day of magic on the 30th (Sun) at Walt Disney World Resort. Have a day of magic on the 24th (Mon) at Magic Kingdom Park. There's much more to do: get in on the family fun at Universal Orlando Resort, discover the magic at Epcot, laugh and play at Disney's Animal Kingdom, and add some entertainment to your itinerary with Happily Ever After Fireworks.

To find where to stay, reviews, photos, and tourist information, you can read our Orlando itinerary maker site .

Traveling by flight from Miami to Orlando takes 3.5 hours. Alternatively, you can drive; or do a combination of train and flight. In June, daytime highs in Orlando are 91°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 30th (Sun) to allow time to travel back home.

Things to do in Orlando

Theme Parks Parks Wildlife
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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