By Tom Scherberger

Want to explore the cultural, historical, and architectural treasures of Islamorada, Fla.?

Just go to Florida Stories Walking Tours, and download the app created by the Florida Humanities Council.

With this app you can learn, at your own pace and on your own schedule, what some of Florida’s most unique towns and cities have to offer.

Here’s an overview of what you can experience via the Islamorada app:

Where: Historic Islamorada, Florida Keys
of stops: 10
time: 40
: Historic Islamorada, Florida Keys
: The Green Turtle Inn


Just 90 minutes south of Miami, Islamorada claims to be the sport fishing capital of the world, boasting the world’s largest fishing fleet per square mile.

The village is spread across six islands (or “keys”) but the walking tour is concentrated on a one-mile stretch of Upper Matecumbe Key along U.S. 1, which ties the keys together and leads to Key West, the southernmost point of the U.S.

The tour covers the beginnings of the Overseas Highway, the devastation of the 1935 Hurricane that toppled Henry Flagler’s Overseas Railroad and the stories of pioneer settlers.


The Green Turtle Inn has been an Islamorada icon for seven decades, the building a survivor of the Labor Day 1935 hurricane and its menu famous for turtle steaks, turtle stew, and turtle chowder.

The Fern Inn, which once occupied the building, made key lime pie famous. Fern Butter didn’t invent the dessert but she was the first to make it a commercial success, and her fans included Thomas Edison, radio and TV personality Arthur Godfrey, and President and Mrs. Harry Truman.

The Red Cross House is one of 28 hurricane-proof houses built in the Upper Keys after the 1935 hurricane, all built of 18-inch thick poured concrete. The building known today as Villa Properties was one of the first rebuilt after the hurricane, and housed a school before becoming the Over-Seas Inn among others, including the Key Inn Restaurant.

The Kaiyo Grill features a 20-ft. replica of the Alligator Lighthouse a few miles to the east of you, so it’s a convenient place for a real Islamorada pirate story.

The 1935 hurricane runs through many of the stories in this tour and is the subject of the Florida Keys Memorial, more commonly known as the Hurricane Monument. It was dedicated on Nov. 14, 1937 to commemorate the hundreds of victims the storm and features an 18-ft obelisk, representing the 18-ft. storm surge the storm wrought.

Notable characters

Baseball legend Ted Williams retired to an Islamorada home near the famed Cuban restaurant Manny and Isa’s, where customers would stop just to sit in his seat and order his favorite, a Cuban sandwich.

Fun Fact

In 1907, William Krome named a new subdivision Islamorada, or Island Home, and the name caught on.

Things To Do

Fishing is the main draw but water choices abound, including windsurfing, kiteboarding, waverunners and parasailing. You can charter a boat to dive, snorkel or fish the close-in shallows.

Enjoy a dolphin encounter at Theater of the Sea.

Explore the tropical forest at Lignumvitae Key Botanical State Park.

There’s more history to explore at Indian Key Historic State Park, a tiny island with 1800s ruins.

Lorelei Restaurant & Cabana Bar is a rustic spot on the water specializing in fresh seafood and spectacular sunsets. Try Pierre’s for a touch of fine dining, with rack of lamb, octopus tiradito and key lime tart.




Places to Go

5 Fun Things to Do in Islamorada

  • 4 minute read

By Kara Franker Measuring only 20 miles long and, in some places, barely 150 feet wide, Islamorada is a collection of islands located in the Florida...