9 days in Florida Keys Itinerary

9 days in Florida Keys Itinerary

Created using Inspirock Florida Keys travel route builder

Make it your trip
Key Largo
— 1 night
— 2 nights
Big Pine Key
— 1 night
Key West
— 4 nights


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.
Start off your visit on the 15th (Sat): look for all kinds of wild species at Capt. Sterling's Everglades Eco-Tours and then look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center. Keep things going the next day: admire nature's wide array of creatures at Island Dolphin Care, then see some colorful creatures with a scuba or snorkeling tour, and then tour the pleasant surroundings at Spiegel Grove.

To find photos, ratings, more things to do, and other tourist information, refer to the Key Largo trip itinerary maker.

New York City to Key Largo is an approximately 7.5-hour flight. You can also drive; or take a bus. Traveling from New York City in May, things will get somewhat warmer in Key Largo: highs are around 85°F and lows about 72°F. Cap off your sightseeing on the 16th (Sun) early enough to go by car to Islamorada.

Things to do in Key Largo

Wildlife · Outdoors · Tours · Parks


— 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 17th (Mon), view the masterpieces at Old Road Gallery, then indulge your thirst for a good beer at Florida Keys Brewing Company, then take an in-depth tour of History of Diving Museum, and finally cast your line with a fishing tour. On the 18th (Tue), you'll have a packed day of sightseeing: take in the architecture and atmosphere at San Pablo Catholic Church, then enjoy the sand and surf at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and finally shop like a local with Shady Palm Art Gallery & Photography.

To find where to stay, ratings, maps, and tourist information, use the Islamorada trip planner.

Islamorada is very close to Key Largo. May in Islamorada sees daily highs of 88°F and lows of 77°F at night. Wrap up your sightseeing on the 18th (Tue) early enough to drive to Big Pine Key.

Things to do in Islamorada

Wildlife · Outdoors · Parks · Museums

Side Trip

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. Kick off your visit on the 19th (Wed): enjoy the sand and surf at Bahia Honda State Park and then see what you can catch with a fishing tour.

Start your trip to Big Pine Key by creating a personalized itinerary on Inspirock.

You can drive from Islamorada to Big Pine Key in 1.5 hours. Alternatively, you can take a bus. In May in Big Pine Key, expect temperatures between 88°F during the day and 77°F at night. Cap off your sightseeing on the 19th (Wed) early enough to go by car to Key West.

Things to do in Big Pine Key

Outdoors · Wildlife · Tours · Beaches

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.
Key West is known for wildlife, adventure, and museums. Your plan includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, don't miss a visit to Southernmost Point, stroll the grounds of Key West Cemetery, and take in the waterfront at Mallory Square.

To find photos, more things to do, where to stay, and more tourist information, you can read our Key West trip itinerary maker app.

Getting from Big Pine Key to Key West by car takes about an hour. Other options: take a shuttle; or take a bus. Expect a daytime high around 85°F in May, and nighttime lows around 77°F. Wrap up your sightseeing on the 23rd (Sun) to allow time to travel back home.

Things to do in Key West

Parks · Museums · Wildlife · Outdoors

Florida Keys travel guide

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.