5 days in Florida Keys Itinerary

5 days in Florida Keys Itinerary

Created using Inspirock Florida Keys travel planner

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Route & dates

5 days in Florida Keys Itinerary

Start: Philadelphia
Fly:  6​h 30​min
1
Key West
— 2 nights
Bus:  1​h 15​min
2
Marathon
— 1 night
Drive:  45​min
3
Islamorada
— 1 night
Shuttle + Fly:  7​h 15​min
End: Philadelphia

2
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.
Kick off your visit on the 12th (Tue): find your balance on the water with some of the best stand-up paddleboarding in the area. Keep things going the next day: paddle through the water with a kayaking and canoeing tour, then enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum, and then pause for some serene contemplation at Saint Mary Star of the Sea.

To see traveler tips, more things to do, and tourist information, read our Key West trip planner .

Philadelphia to Key West is an approximately 6.5-hour combination of train and flight. You can also fly; or drive. Plan for much hotter temperatures traveling from Philadelphia in February, with highs in Key West at 78°F and lows at 68°F. Finish your sightseeing early on the 14th (Thu) to allow enough time to drive to Marathon.

Things to do in Key West

Outdoors Tours Adventure
Highlights from your plan
Stand-Up Paddleboarding
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea
Kayaking & Canoeing

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 (Fri): identify plant and animal life at Dolphin Research Center, then identify plant and animal life at Crane Point Museum & Nature Center, then tour the pleasant surroundings at Sombrero Beach, and finally take in the views from Seven Mile Bridge.

For where to stay, more things to do, traveler tips, and tourist information, you can read our Marathon planning tool .

Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. In February, daytime highs in Marathon are 79°F, while nighttime lows are 68°F. Wrap up your sightseeing on the 15th (Fri) early enough to drive to Islamorada.

Things to do in Marathon

Parks Wildlife Outdoors
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Crane Point Museum & Nature Center ©
Sombrero Beach ©
Sombrero Beach

1
night
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Kick off your visit on the 16th (Sat): discover the deep blue sea with a scuba or snorkeling tour, then identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, and then take in the exciting artwork at Old Road Gallery.

To find out how to plan a trip to Islamorada, use our trip itinerary maker.

Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. February in Islamorada sees daily highs of 79°F and lows of 68°F at night. Finish your sightseeing early on the 16th (Sat) so you can travel back home.

Things to do in Islamorada

Wildlife Outdoors Tours

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
Old Road Gallery ©
Old Road Gallery
Scuba & Snorkeling

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