7 days in Florida Keys Itinerary

7 days in Florida Keys Itinerary

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Route & dates

7 days in Florida Keys Itinerary

Start: Orlando
Fly + shuttle:  5​h 30​min
1
Islamorada
— 1 night
Drive:  45​min
2
Marathon
— 1 night
Drive:  30​min
3
Big Pine Key
— 1 night
bus:  45​min
4
Key West
— 3 nights
Fly:  7​h 30​min
End: Orlando

1
night
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 13th (Mon): cast your line with a fishing tour.

To see photos, maps, other places to visit, and tourist information, go to the Islamorada trip itinerary planner.

Orlando to Islamorada is an approximately 5.5-hour car ride. You can also take a bus; or do a combination of train and bus. Expect a bit warmer evenings in Islamorada when traveling from Orlando in May, with lows around 77°F. Finish your sightseeing early on the 14th (Tue) to allow enough time to drive to Marathon.

Things to do in Islamorada

Outdoors Wildlife Tours

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Start off your visit on the 15th (Wed): look for all kinds of wild species at Dolphin Research Center, then identify plant and animal life at Crane Point Museum & Nature Center, then identify plant and animal life at The Turtle Hospital, and finally kick back and relax at Sombrero Beach.

To find other places to visit and more tourist information, go to the Marathon trip itinerary planner.

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. Expect a daytime high around 88°F in May, and nighttime lows around 77°F. Wrap up your sightseeing on the 15th (Wed) to allow time to drive to Big Pine Key.

Things to do in Marathon

Parks Wildlife Outdoors
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center

1
night
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. Start off your visit on the 16th (Thu): stop by Out of the Blue Gallery, look for all kinds of wild species at National Key Deer Refuge, and then enjoy the sand and surf at Bahia Honda State Park.

For other places to visit, where to stay, ratings, and tourist information, go to the Big Pine Key road trip site .

Big Pine Key is just a short distance from Marathon. Expect a daytime high around 88°F in May, and nighttime lows around 77°F. Finish up your sightseeing early on the 16th (Thu) so you can go by car to Key West.

Things to do in Big Pine Key

Parks Outdoors Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Out of the Blue Gallery ©
Out of the Blue Gallery

3
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.
Family-friendly places like Key West Butterfly & Nature Conservatory and Dolphin & Whale Watching will thrill your kids. Spend the 18th (Sat) airborne with a parasailing or paragliding tour. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, stroll the grounds of Key West Cemetery, take in the waterfront at Mallory Square, and make a trip to Duval Street.

To find reviews, other places to visit, traveler tips, and other tourist information, read our Key West trip app .

Getting from Big Pine Key to Key West by car takes about an hour. Other options: take a bus. Expect a daytime high around 85°F in May, and nighttime lows around 77°F. Finish your sightseeing early on the 19th (Sun) to allow enough time to drive back home.

Things to do in Key West

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

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