14 days in Florida Keys Itinerary

14 days in Florida Keys Itinerary

Created using Inspirock Florida Keys itinerary builder

Make it your trip
Fly to Miami International Airport, Drive to Marathon
— 4 nights
— 2 nights
Key Largo
— 3 nights
Key West
— 4 nights



— 4 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kids will enjoy Fishing Charters & Tours and National Key Deer Refuge. The adventure continues: enjoy the sand and surf at Bahia Honda State Park, admire nature's wide array of creatures at Florida Keys Aquarium Encounters, take in the views from Old Seven Mile Bridge, and relax and rejuvenate at some of the top local wellness centers.

For reviews, photos, ratings, and tourist information, go to the Marathon road trip tool.

Cedar Rapids to Marathon is an approximately 11.5-hour combination of flight and car. You can also do a combination of flight and car; or drive. Traveling from Cedar Rapids to Marathon, you'll lose 1 hour due to the time zone difference. While traveling from Cedar Rapids, expect somewhat warmer days and much warmer nights in Marathon, ranging from highs of 88°F to lows of 77°F. Finish your sightseeing early on the 20th (Thu) to allow enough time to drive to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trip


— 2 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 21st (Fri), get engrossed in the history at History of Diving Museum, see what you can catch with a fishing tour, then soothe aching muscles at Island Flow Yoga, and finally kick back and relax at Anne's Beach. Get ready for a full day of sightseeing on the next day: take in the exciting artwork at Lobster Trap Art Gift Shop and Gallery, then get outside with Takedown Charters, and then see what you can catch with A Lil' Tail Charters.

To see ratings, maps, where to stay, and other tourist information, go to the Islamorada trip itinerary planning app.

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. In May, daytime highs in Islamorada are 88°F, while nighttime lows are 77°F. Finish up your sightseeing early on the 22nd (Sat) so you can go by car to Key Largo.

Things to do in Islamorada

Outdoors · Tours · Wildlife · Museums

Key Largo

— 3 nights

Diving Capital of the World

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.
You'll visit kid-friendly attractions like Island Dolphin Care and Florida Keys Wild Bird Rehabilitation Center. And it doesn't end there: see some colorful creatures with a scuba or snorkeling tour, see the vivid underwater world at Spiegel Grove, admire the majestic nature at John Pennekamp Coral Reef State Park, and step aboard African Queen Canal Cruise.

To find reviews, ratings, traveler tips, and more tourist information, read our Key Largo trip itinerary tool.

Key Largo is just a stone's throw from Islamorada. Traveling from Islamorada in May, expect little chillier with lows of 72°F in Key Largo. Finish your sightseeing early on the 25th (Tue) to allow enough time to drive to Key West.

Things to do in Key Largo

Wildlife · Parks · Tours · Outdoors

Key West

— 4 nights

Conch Republic

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.
Attractions like The Ernest Hemingway Home and Museum and Truman Little White House make great kid-friendly stops. The adventure continues: identify plant and animal life at Key West Butterfly & Nature Conservatory, explore the different monuments and memorials at Key West Cemetery, kick back and relax at Fort Zachary Taylor, and admire the natural beauty at Audubon House & Tropical Gardens.

To see ratings, more things to do, traveler tips, and tourist information, refer to the Key West journey planner.

You can drive from Key Largo to Key West in 2.5 hours. Another option is to take a bus. Expect a daytime high around 85°F in May, and nighttime lows around 77°F. Finish your sightseeing early on the 29th (Sat) so you can travel back home.

Things to do in Key West

Parks · Wildlife · Museums · Historic Sites

Florida Keys travel guide

Scuba & Snorkeling · Landmarks · Parasailing & Paragliding
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.