Dawn at the pier at the Islander Resort, a classic Islamorada hotel.
Dawn at the pier at the Islander Resort, a classic Islamorada hotel. (Photo: Bonnie Gross)

July 2018: Hurricane Irma damaged many buildings in Islamorada and some accommodations will not reopen until the winter season of 2018.

Visiting the Florida Keys does not mean visiting Key West. There are excellent reasons to stop well short of the end of the road.

One of my favorite destinations is Islamorada.  Located in the Upper Keys, Islamorada is only two hours from Miami and is developing an interesting cluster of cultural attractions.

Islamorada, long known for its fishing, has added several new features to the local scene: The Morada Way Arts and Cultural District,  two fun craft breweries bursting with Keys flavor, a top-quality museum and new historic walking tours.

In addition, Islamorada has terrific recreational opportunities, including a section of the Florida Keys Overseas Heritage Trail that provides scenic and safe bicycling and my favorite kayak trip in the Keys – kayaking out to historic Indian Key. It’s also home to many classic Florida Keys spots.

Here’s a guide to some of the best things to do in Islamorada, with an emphasis on the recent additions.

Two local breweries open

The Florida Keys Brewing Company in Islamorada
The Florida Keys Brewing Company in Islamorada. (Photo: Bonnie Gross)

Exploring the Florida Keys means heat and sun, and two local breweries have opened in the last three years to quench the inevitable thirst of visitors.

The Florida Keys Brewing Company was the first craft brewery in the Upper Keys opening in 2015 and in 2018 it moved to a new taproom with a beer garden right off the Overseas Highway at MM 81.6 (81611 Overseas Highway.)

Its taproom is decorated in a colorful Keys-worthy way — with mosaics made from thousands of bottle caps from breweries worldwide. There are always a variety of locally brewed beers you can try as flights.


Mosaic made of beer caps inside tasting room at Florida Keys Beer Company. (Photo: Bonnie Gross)

The brewery has a variety of programs scheduled including live music some nights.

The other brewery, Islamorada Beer Company, 82229 Overseas Highway, is only blocks away and is popular with visitors who like trying flights of their 10 different drafts with names like Sandbar Sunday, No Wake Zone and Card Sound Brown. The brewery sells lots of merchandise folks love to buy as souvenirs. In an adjoining space, the beer company has opened a rum distillery .

The Morada Way Arts and Cultural District

The Morada Way district’s center is the historic 1935 Hurricane Monument and the nearby iconic Green Turtle Inn. It stretches along the half-mile section of the Old Highway, which was the only road when the railroad ran down the middle of what is now the Overseas Highway.

There is now a tour of Islamorada available as a free app. Walk Historic Islamorada is available through Florida Stories, at the Florida Humanities Council, the Google Play Store or iStore.

The ten-stop tour starts at the Green Turtle Inn. It is a one-mile journey that tells stories of early pioneers, the most powerful hurricane to ever strike North America, the hurricane or Red Cross Houses built for survivors, the memorial built to honor the hundreds of victims, and one of the few bona fide pirate stories connected to the island chain. The tour ends at the Pioneer Cemetery located on the picturesque beach of the Cheeca Lodge, at one time the heart of this historic community.

Hurricane Monument in Islamorada. Be sure to stop and look at the tile mosaic at the base of the plinth. It’s a map of the Keys affected by the 1935 storm. (Photo:Bonnie Gross)

Along with celebrating its rich history, Islamorada is working to recognize the many working artists and craftsmen who create a rich art scene. The Morada Way district is liveliest on the evening of the third Thursdays each month, when there is an Art Walk with live music and performance artists.

Restaurants grouped in the district include the No. 1-rated restaurant in Islamorada, Chef Michael’s, and the popular Ma’s Fish Camp.

The new Florida Keys History & Discovery Center

Florida Keys History & Discovery Center in Islamorada.
Florida Keys History & Discovery Center in Islamorada is on the grounds of the Islander Resort. (Photo: Bonnie Griss)

Despite their small size and population, the Upper Keys are full of colorful history – from shipwrecks, hurricanes, pirates, and sunken treasure to vacationing movie stars. It’s where presidents go to fish, where classic movies have been filmed and where the Key Lime pie first became a must-have regional specialty.

The Florida Keys History & Discovery Center, 82100 Overseas Highway , Islamorada, is committed to telling those stories in an entertaining way.  The museum opened in 2014. It’s located on the grounds of the classic resort, The Islander, 82100 Overseas Highway.

Exhibit at Florida Keys History & Discovery Center in Islamorada. (Photo: Bonnie Gross)
Exhibit at Florida Keys History & Discovery Center in Islamorada. (Photo: Bonnie Gross)

The Florida Keys History & Discovery Center is not like a lot of local history museums – small dusty rooms inside a public library. It’s a two-story 7,500 square foot oceanfront museum with a state-of-the-art theater and exhibits designed by the same firm that did the interior of the Salvador Dali Museum in St. Petersburg.

The new museum is blessed with a $1 lease for 50 years for its space inside the Florida Keys Conference Center on the grounds of the Islander.  With grants from the Monroe County Tourist Development Council and the help from the area’s pioneer families, the museum is collecting historic artifacts and completing its exhibits.

“People think Key West is where all the Florida Keys history happened, but what they don’t realize is the incredible amount of history in the Upper Keys,” said Brad Bertelli, the museum’s curator and historian. “There are so many untold stories.”

With the first floor devoted to permanent exhibits on topics like Indian Key, the original native American people, sunken treasure fleets and the tradition of sport fishermen, the museum’s upstairs houses changing exhibits and the 35-seat surround-sound theater.

The theater plays a loop of historic documentaries and interviews. In one, the oldest living survivor of the great Labor Day hurricane of 1935 is interviewed at age 101 about his experience during the storm that killed more than 400 and blew away Henry Flagler’s Over Sea Railway.  It was the strongest hurricane to ever make landfall in the United States or Caribbean.


The Florida Keys Overseas Heritage Trail

The Florida Keys Overseas Heritage Trail in Islamorada.
The Florida Keys Overseas Heritage Trail in Islamorada. (Photo: David Blasco)

A bike trail extends from Key Largo to Key West, but it’s not finished and some sections put cyclists next to highway traffic in a narrow shoulder.

In Islamorada, however, this trail takes the Old Highway and this section makes a delightful, scenic and safe 20-mile roundtrip.

Here are details about biking in Islamorada on the Florida Keys Overseas Heritage Trail.

Feed the tarpon at Robbie’s Marina

The dock at Robbie's Marina in the Florida Keys
The dock at Robbie’s Marina in the Florida Keys. (Photo: Bonnie Gross

I can’t drive down the Overseas Highway without stopping at Robbie’s Marina, bayside at Mile Marker 77.

The big draw at Robbie’s is the chance to see 50 to 100 enormous tarpon swimming around the dock in clear water only a few feet deep. You pay $1 to go out on the dock and it’s another $3 for a bucket of fish pieces to toss to them. It might be the most entertainment you’ll find in the Keys for a few bucks. The tarpon splash and lunge; the pelicans try to steal the bait fish and the macho guys (sorry, it is always guys) try to hand-feed the tarpon at the risk of ending up with tarpon teeth up to their wrists.

Kayak to Indian Key

This model of how Indian Key appeared in its heyday is at the Florida Keys History & Discovery Center in Islamorada. (Photo: Bonnie Gross)
This model of how Indian Key appeared in its heyday is at the Florida Keys History & Discovery Center in Islamorada. (Photo: Bonnie Gross)
Kayaking to Indian Key in Islamorada
Kayaking to Indian Key in Islamorada. (Photo: Bonnie Gross)

One of those little green islands you see from the Overseas Highway is actually the former county seat of Dade County.

Now a ghost town, Indian Key is a state park accessible only by boat that preserves a community that thrived in the 1830s until an Indian attack in 1840 ended its development. It’s a beautiful and fascinating place, and a perfect destination for kayaking through the shallow clear waters.

More about kayaking to Indian Key.

Lorelei Cabana Bar and Restaurant

Lorelei, MM 82 Bayside, Islamorada, has decks, chickee huts, palm trees and a sandy waterfront that create an expansive and outstanding place to watch the sunset. Hundreds gather nightly, lining the beach and filling every space, to watch. It’s as pure a Florida Keys experience as you can have.

Here’s a guide to the best Keys tiki bars, which includes Lorelei.

More information on things to do in Islamorada

Florida Keys History & Discover Center, 82100 Overseas Highway, on the grounds of the Islander Resort, Islamorada. Hours: Thursday to Sundays, 10 a.m. to 5 p.m. Admission is $12 adults, $10 seniors and children 13 and under free.

Historic Upper Keys Walking Tours: Happy Hour History Tour, $18, including first beer. Indian Key Tour: $13.

The Florida Keys Brewing Company , 200 Morada Way, Islamorada, 300 yards east of Mile Marker 81.6  oceanside. Open noon to 10 p.m. daily.

Islamorada Beer Company, 82229 Overseas Highway, Islamorada. Open noon to 9 pm. Monday to Saturday and noon to 6 p.m. Sunday.

The Florida Keys Overseas Heritage Trail. Florida Rambler report

Indian Key Historic State Park kayaking guide from Florida Rambler.

Lorelei Cabana Bar, MM 82 Bayside, Islamorada

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Updated July 11, 2018