12 days in Florida Keys Itinerary

12 days in Florida Keys Itinerary

Created using Inspirock Florida Keys trip itinerary planner
Make it your trip
Key West
— 3 nights
— 3 nights
— 2 nights
Key Largo
— 3 nights


Key West — 3 nights

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.
Key West is known for sightseeing, wildlife, and adventure. Your trip includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, stroll the grounds of Key West Cemetery, and make a trip to Truman Little White House.

To find maps, where to stay, and tourist information, refer to the Key West trip tool.

Boston to Key West is an approximately 7-hour flight. You can also drive; or do a combination of train and bus. Plan for warmer temperatures traveling from Boston in February, with highs in Key West at 78°F and lows at 68°F. Finish your sightseeing early on the 10th (Fri) so you can drive to Marathon.
Museums · Historic Sites · Parks · Outdoors

Marathon — 3 nights

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 SpaTerre at Little Palm Island Resort in Little Torch Key, approximately Little Torch Key away. There's still lots to do: look for all kinds of wild species at National Key Deer Refuge, enjoy the sand and surf at Bahia Honda State Park, tour the pleasant surroundings at Sombrero Beach, and get close to the beloved marine mammals with Dolphin Connection.

To see more things to do, traveler tips, maps, and tourist information, you can read our Marathon online itinerary planner.

Getting from Key West to Marathon by car takes about 1.5 hours. Other options: take a bus. In February, plan for daily highs up to 79°F, and evening lows to 68°F. Wrap up your sightseeing on the 13th (Mon) to allow time to drive to Islamorada.
Parks · Wildlife · Outdoors · Beaches
Side Trips

Islamorada — 2 nights

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 14th (Tue): get to know the fascinating history of Indian Key State Historic Site and then get close to the beloved marine mammals with Theater of the Sea. Get ready for a full day of sightseeing on the next day: examine the collection at Florida Keys History & Discovery Center, then tour the pleasant surroundings at Anne's Beach, then sample the tasty concoctions at Florida Keys Brewing Company, and finally sample the tasty concoctions at Islamorada Brewery & Distillery - MM82.

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

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can 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 15th (Wed) so you can drive to Key Largo.
Outdoors · Historic Sites · Breweries & Distilleries · Tours

Key Largo — 3 nights

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 Key Largo's surroundings by going to Anhinga Trail (in Everglades National Park) and Robert Is Here (in Homestead). The adventure continues: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, take a tour of African Queen Canal Cruise, observe the fascinating underwater world at Island Dolphin Care, and fly like a bird with a parasailing or paragliding tour.

To see where to stay, reviews, traveler tips, and more tourist information, go to the Key Largo sightseeing website.

Key Largo is just a short distance from Islamorada. Traveling from Islamorada in February, you can expect nighttime temperatures to be a bit cooler in Key Largo, with lows of 62°F. Wrap up your sightseeing by early afternoon on the 18th (Sat) to allow enough time to fly back home.
Parks · Outdoors · Wildlife · Tours
Side Trips

Florida Keys travel guide

Scuba & Snorkeling · Parasailing & Paragliding · Landmarks
An archipelago of about 1,700 islands extending in a gentle arc south and southwest of Florida's mainland, the Florida Keys divide the Atlantic from the Gulf of Mexico. Many visitors on vacation come to scuba dive in the coral reefs, fossilized and exposed as sea levels declined over thousands of years. In addition to being one of the world's top diving and fishing spots, the Keys feature hundreds of shops, restaurants, bars, and various tourist attractions, most of them crowded all year long with visitors on vacation. To soak up the Keys' atmosphere and discover writer Ernest Hemingway's former haunts, drive from one island to the other all the way to Key West, located just 140 km (90 mi) from Cuba.