Dec. 20, 2017: Hurricane Irma damaged many buildings in Islamorada and some will not open for months. Among places closed in Islamorada at this writing are the Postcard Inn, La Siesta, Chesapeake Beach Restort, Islander Resort and the Cheeca Lodge. At this point, only 35 percent of the pre-storm accommodations have re-opened, according to the Monroe County Tourism Development Agency. This pre-storm article references only places that have re-opened.
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
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.
One brewery, Islamorada Beer Company, 82229 Overseas Highway, is right on the highway 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. (The beer company has since opened a distillery too.)
One mile away in the Morada Way Art and Cultural District, you’ll find the Florida Keys Brewing Company, the first craft brewery in the Upper Keys.
Its taproom is decorated in a colorful Keys-worthy way — with mosaics made from thousands of bottle caps from breweries worldwide – and it offers board games that keep kids (or adults) occupied. Here too there are always a variety of beers you can try as flights.
On the night we visited, the brewery’s large community space next to the taproom was filled with people engrossed in a painting class.
The brewery has live music some nights and actively participates in the Morada Way ArtWalks on the third Thursday of each month.
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.
With its embrace of the off-beat, the Florida Keys have always appealed to artists, and Islamorada (like all the Florida Keys) is home to many artists and craftsmen. Key West is well-known for its arts scene; now the Upper Keys are working to be recognized.
The liveliest time to visit the district is 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
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 and has completed about half of its permanent exhibits. It’s located on the grounds of the classic resort, The Islander, 82100 Overseas Highway.
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
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
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
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.
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.
2017 programs at Florida Keys History & Discovery Center
- Thursday, Oct. 26 Haunted History: Robert the Doll Returns (just in time for Halloween)
- Wednesday, Nov. 16 Florida is a Land Remembered with Rick Smith Jr.
- Wednesday, Nov. 29 History of Biscayne Bay with authors Jim Kushlan and Kirsten Hines
- Wednesday, Dec. 13 Oh Florida! How America’s Weirdest State Influences the Rest of the Country with Author and Reporter Craig Pittman.
- Details at the museum website.
Resources for planning a Florida Keys vacation:
- Mile marker guide with dozens of stops to help make the most of your drive south.
- Florida Keys wildlife: Places to see animals
- Tiki bars: Soak up the Keys atmosphere
- 12 great kayak outings in the Keys
- Top 10 pit stops on Overseas Highway
- Free beaches in the Florida Keys
- Original African Queen boat in Key Largo
- Florida Keys Wild Bird Center
- John Pennekamp Coral Reef State Park