15 days in Florida Keys Itinerary

15 days in Florida Keys Itinerary

Created using Inspirock Florida Keys trip planner

Make it your trip
Fly
1
Key West
— 7 nights
Drive
2
Marathon
— 2 nights
Drive
3
Islamorada
— 2 nights
Drive
4
Key Largo
— 3 nights
Drive

S M T W T F S
5
6
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10
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12
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15
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25

Key West

— 7 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.
You'll get in some beach time at Higgs Beach and Fort Zachary Taylor. Step out of the city life by going to Waterskiing & Jetskiing and Smathers Beach. Next up on the itinerary: sample the fine beverages at Key West First Legal Rum Distillery, identify plant and animal life at Key West Butterfly & Nature Conservatory, see the interesting displays at The Ernest Hemingway Home and Museum, and brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum.

For photos, maps, where to stay, and other tourist information, go to the Key West holiday maker site.

Regina, Canada to Key West is an approximately 12-hour flight. You can also drive; or do a combination of bus and train. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. While traveling from Regina, expect a bit warmer days and much warmer nights in Key West, ranging from highs of 37°C to lows of 32°C. Finish your sightseeing early on the 17th (Fri) to allow enough time to drive to Marathon.

Things to do in Key West

Parks · Outdoors · Beaches · Museums

Marathon

— 2 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.
On the 18th (Sat), enjoy the sand and surf at Bahia Honda State Park and then kick back and relax at Sunset Park Beach. Get ready for a full day of sightseeing on the next day: take in the exciting artwork at Shady Palm Art Gallery & Photography, see the vivid underwater world at Sombrero Reef, and then see some colorful creatures with a scuba or snorkeling tour.

For other places to visit, maps, photos, and other tourist information, read our Marathon road trip tool.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. July in Marathon sees daily highs of 39°C and lows of 32°C at night. Finish your sightseeing early on the 19th (Sun) so you can drive to Islamorada.

Things to do in Marathon

Outdoors · Parks · Beaches · Wildlife

Side Trips

Islamorada

— 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 20th (Mon), take in the exciting artwork at Old Road Gallery, see what you can catch with a fishing tour, then enjoy the sand and surf at Anne's Beach, and finally indulge your thirst for a good beer at Islamorada Brewery & Distillery. Get ready for a full day of sightseeing on the next day: get outside with A Lil' Tail Charters and then head outdoors with Takedown Charters.

Plan a Islamorada trip in moments using our itinerary builder.

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. July in Islamorada sees daily highs of 39°C and lows of 32°C at night. Cap off your sightseeing on the 21st (Tue) early enough to go by car to Key Largo.

Things to do in Islamorada

Outdoors · Wildlife · Tours · Parks

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.
On the 22nd (Wed), trek along Anhinga Trail and then see some colorful creatures with a scuba or snorkeling tour. Keep things going the next day: kick back and relax at Harry Harris Park, then look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, and then explore the gorgeous colors at Grecian Rocks.

For where to stay, maps, ratings, and more tourist information, read our Key Largo trip itinerary builder website.

Key Largo is just a short distance from Islamorada. Plan for slightly colder nights when traveling from Islamorada in July since evenings lows in Key Largo dip to 28°C. On the 24th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Side Trip

Florida Keys travel guide

4.3
Scuba & Snorkeling · Landmarks · Wildlife Areas
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.