38 days in Florida Itinerary

38 days in Florida Itinerary

Created using Inspirock Florida route planner

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Route & dates

38 days in Florida Itinerary

Start: Fort Lauderdale
Fly:  3​h 30​min
1
Orlando
— 5 nights
Drive:  2​h 15​min
2
Sarasota
— 4 nights
Drive:  2​h 30​min
3
Marco Island
— 3 nights
ferry:  2​h 30​min
4
Key West
— 5 nights
bus:  45​min
5
Big Pine Key
— 3 nights
Drive:  30​min
6
Marathon
— 4 nights
Drive:  45​min
7
Islamorada
— 4 nights
Drive:  45​min
8
Key Largo
— 4 nights
Drive:  1​h 15​min
9
Miami
— 5 nights
bus:  45​min
End: Fort Lauderdale

5
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 10th (Fri) at Walt Disney World Resort. Pack the 12th (Sun) with family-friendly diversions at Universal's Islands of Adventure. There's lots more to do: find something for the whole family at Universal Orlando Resort, enjoy the sand and surf at Discovery Cove, get your game on at Nomadic, and discover the magic at Happily Ever After Fireworks.

For other places to visit, maps, traveler tips, and more tourist information, go to the Orlando online trip itinerary planner .

Fort Lauderdale to Orlando is an approximately 3.5-hour flight. You can also drive; or take a bus. Traveling from Fort Lauderdale in May, expect a bit cooler with lows of 69°F in Orlando. Wrap up your sightseeing on the 15th (Wed) to allow time to drive to Sarasota.

Things to do in Orlando

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

4
nights
Sarasota

Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Get out of town with these interesting Sarasota side-trips: Clearwater Beach (in Clearwater), Parasailing & Paragliding (in Madeira Beach) and Tampa (Busch Gardens & Fishing Charters & Tours). There's much more to do: add some adventure to your tour with a kayaking and canoeing tour, explore the different monuments and memorials at Sarasota National Cemetery, admire the masterpieces at The Ringling, and get your game on at Outerlife Studios - Escape Room St. Pete.

To find photos, traveler tips, where to stay, and other tourist information, go to the Sarasota sightseeing planner .

Drive from Orlando to Sarasota in 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In May in Sarasota, expect temperatures between 87°F during the day and 68°F at night. Finish your sightseeing early on the 19th (Sun) so you can drive to Marco Island.

Things to do in Sarasota

Outdoors Tours Theme Parks

Side Trips

Tampa, Parasailing & Paragliding, Clearwater Beach, Outerlife Studios - Escape Room St. Pete
Highlights from your plan
Stand-Up Paddleboarding
Fishing Charters & Tours
Parasailing & Paragliding

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. Take a break from Marco Island with a short trip to Speed Boats Tours in Everglades City, about 38 minutes away. And it doesn't end there: see majestic marine mammals with a dolphin and whale watching tour, look for gifts at Keep In Touch, cast your line with a fishing tour, and fly like a bird with a parasailing or paragliding tour.

For photos, reviews, where to stay, and more tourist information, you can read our Marco Island sightseeing planning website .

Traveling by car from Sarasota to Marco Island takes 2.5 hours. Alternatively, you can take a bus. May in Marco Island sees daily highs of 88°F and lows of 69°F at night. Finish your sightseeing early on the 22nd (Wed) so you can ride a ferry to Key West.

Things to do in Marco Island

Tours Outdoors Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Parasailing & Paragliding

5
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.
Spend the 25th (Sat) exploring nature at Dry Tortugas National Park. The adventure continues: see the interesting displays at The Ernest Hemingway Home and Museum, make a trip to Duval Street, cast your line with a fishing tour, and take a tour by water with Boat Tours & Water Sports.

For reviews, photos, where to stay, and other tourist information, use the Key West road trip planner .

Traveling by ferry from Marco Island to Key West takes 2.5 hours. Alternatively, you can drive. Traveling from Marco Island in May, Key West is a bit warmer at night with lows of 77°F. Finish up your sightseeing early on the 27th (Mon) so you can catcht the bus to Big Pine Key.

Things to do in Key West

Tours Outdoors Wildlife
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

3
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. Big Pine Key is known for nature, wildlife, adventure, nightlife, and shopping. Your plan includes some of its best attractions: admire the majestic nature at Bahia Honda State Park, explore and take pictures at Grimal Grove, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and get a new perspective on things with Boat Tours & Water Sports.

For more things to do, other places to visit, maps, and other tourist information, go to the Big Pine Key planner .

Traveling by bus from Key West to Big Pine Key takes an hour. Alternatively, you can drive. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Wrap up your sightseeing on the 30th (Thu) to allow time to take a bus to Marathon.

Things to do in Big Pine Key

Wildlife Parks Outdoors
Highlights from your plan
National Key Deer Refuge ©
National Key Deer Refuge
Bahia Honda State Park ©
Bahia Honda State Park
Fishing Charters & Tours

4
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.
When in Marathon, make a side trip to see Fishing Charters & Tours in Cudjoe Key, approximately 42 minutes away. And it doesn't end there: get answers to all your questions at Pigeon Key Foundation, kick back and relax at Sombrero Beach, take in the views from Seven Mile Bridge, and get a new perspective on things with Boat Tours & Water Sports.

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

Marathon is very close to Big Pine Key. In May, daily temperatures in Marathon can reach 88°F, while at night they dip to 77°F. Cap off your sightseeing on the 3rd (Mon) early enough to go by car to Islamorada.

Things to do in Marathon

Wildlife Outdoors Tours

Side Trip

Fishing Charters & Tours
Highlights from your plan
Crane Point Museum & Nature Center ©
Pigeon Key Foundation ©
Pigeon Key Foundation
San Pablo Catholic Church ©
San Pablo Catholic Church

4
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: cast your line with a fishing tour, take an in-depth tour of History of Diving Museum, glide through the air with a parasailing or paragliding tour, and appreciate the extensive heritage of Indian Key State Historic Site.

To find other places to visit, traveler tips, maps, and tourist information, read our Islamorada online vacation builder .

Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. Expect a daytime high around 90°F in June, and nighttime lows around 79°F. Finish up your sightseeing early on the 7th (Fri) so you can go by car to Key Largo.

Things to do in Islamorada

Outdoors Tours Wildlife
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Indian Key State Historic Site ©
Indian Key State Historic Site

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.
Take a break from Key Largo with a short trip to Anhinga Trail in Everglades National Park, about 48 minutes away. There's much more to do: get up close and personal with brilliant marine life at Island Dolphin Care, immerse yourself in nature at John Pennekamp Coral Reef State Park, see some colorful creatures with a scuba or snorkeling tour, and get some thrills out on the water with a waterskiing or jet-skiing adventure.

Plan my trip to Key Largo with suggested itineraries provided by Inspirock.

You can drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. In June, daily temperatures in Key Largo can reach 88°F, while at night they dip to 75°F. Cap off your sightseeing on the 11th (Tue) early enough to go by car to Miami.

Things to do in Key Largo

Parks Outdoors Wildlife

Side Trip

Anhinga Trail
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Dolphins Plus Marine Mammal Responder ©
Scuba & Snorkeling

5
nights
Miami

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Get out of town with these interesting Miami side-trips: Everglades National Park (Shark Valley & Gumbo Limbo Trail), JP Outfitters Inc. (in Hollywood) and City Church (in Homestead). And it doesn't end there: admire the natural beauty at Fairchild Tropical Botanic Garden, get the lay of the land with Walking tours, examine the collection at Lock & Load Museum, and take a stroll through Art Deco Historic District.

To see traveler tips, maps, photos, and other tourist information, go to the Miami road trip website .

Traveling by car from Key Largo to Miami takes 1.5 hours. Alternatively, you can take a bus. In June in Miami, expect temperatures between 89°F during the day and 77°F at night. Wrap up your sightseeing by early afternoon on the 16th (Sun) to allow time for the car ride back home.

Things to do in Miami

Parks Outdoors Trails

Side Trips

Miami Beach, Everglades National Park, Fairchild Tropical Botanic Garden, JP Outfitters Inc., City Church
Highlights from your plan
Walking tours
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Fairchild Tropical Botanic Garden ©
Fairchild Tropical Botanic Garden

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