8 days in Florida Keys Itinerary

8 days in Florida Keys Itinerary

Created using Inspirock Florida Keys tour itinerary maker

Make it your trip
Fly to Key West, Bus to Big Pine Key
1
Big Pine Key
— 1 night
Drive
2
Islamorada
— 1 night
Drive
3
Key Largo
— 1 night
Drive
4
Key West
— 4 nights
Fly

S M T W T F S
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Big Pine Key

— 1 night
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 17th (Mon): stroll through Bahia Honda State Park and then see what you can catch with a fishing tour.

To find photos, ratings, other places to visit, and more tourist information, you can read our Big Pine Key trip planner.

Chicago to Big Pine Key is an approximately 6-hour combination of flight and bus. You can also drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Big Pine Key. While traveling from Chicago, expect a bit warmer days and much warmer nights in Big Pine Key, ranging from highs of 88°F to lows of 77°F. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Islamorada.

Things to do in Big Pine Key

Outdoors · Wildlife · Tours · Parks

Islamorada

— 1 night

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.
Kick off your visit on the 18th (Tue): look for all kinds of wild species at Dolphin Research Center, take an in-depth tour of History of Diving Museum, then look for gifts at Bella Sol Fragrance Bar and Gifts, and finally take a memorable tour with Tours.

To see reviews, where to stay, ratings, and tourist information, refer to the Islamorada travel itinerary planner.

Traveling by car from Big Pine Key to Islamorada takes 1.5 hours. 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 18th (Tue) to allow time to drive to Key Largo.

Things to do in Islamorada

Wildlife · Parks · Tours · Outdoors

Side Trip

Key Largo

— 1 night

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 19th (Wed), observe the fascinating underwater world at Island Dolphin Care, then identify plant and animal life at Wildlife Areas, and then stroll through Spiegel Grove.

To see more things to do, ratings, photos, and other tourist information, you can read our Key Largo trip itinerary builder.

Key Largo is just a stone's throw from Islamorada. Expect a bit cooler evenings in Key Largo when traveling from Islamorada in May, with lows around 72°F. Finish your sightseeing early on the 19th (Wed) so you can 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.
Bring the kids along to The Ernest Hemingway Home and Museum and Scuba & Snorkeling. Next up on the itinerary: look for all kinds of wild species at Key West Butterfly & Nature Conservatory, take in the waterfront at Mallory Square, don't miss a visit to Duval Street, and see the vivid underwater world at Vandenberg Wreck.

For photos, reviews, where to stay, and tourist information, read Key West online trip itinerary planner.

You can drive from Key Largo to Key West in 2.5 hours. Another option is to take a bus. In May, daytime highs in Key West are 85°F, while nighttime lows are 77°F. Wrap up your sightseeing on the 23rd (Sun) to allow time to fly back home.

Things to do in Key West

Parks · Museums · Wildlife · Historic Sites

Florida Keys travel guide

4.3
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.