Around halfway between Miami and Key West, Islamorada is known as the Village of Islands. There are five keys lined up along the Overseas Highway here, and the central location makes it a good place to pause on the way to Key West.
I would be doing Islamorada a real injustice to call it a stopover though. There’s tons of things to see and do, both on the islands and in the glimmering reef-bedded waters offshore.
You can snorkel among flourishing marine life, paddle out to a ghost town on an uninhabited island, explore mangroves, study mind–boggling fossils in the walls of a quarry, and book a charter in one of the world’s sportfishing hotspots.
And really, that’s just a snapshot. You also have the option of doing nothing at all, floating at a sandbar or laying back on a beach in the shade of a palm tree.
1. History of Diving Museum
Opened in 2005, the History of Diving Museum has amassed an impressive collection of items relating to humankind’s exploration of the sea.
The museum is open daily from 10 AM to 5 PM, and guided tours are available for those who’d like an insider’s insight into the things they’re seeing.
Items on display include diving equipment, photographs, and first-hand historical accounts of significant events.
What captured my imagination most of all was the awesome display of vintage diving helmets, from more than 20 different countries. Meanwhile, among the atmospheric diving suits is an intact Iron Mike from 1930.
There’s plenty of interactivity to keep kids on board, including a fun scavenger hunt.
2. Keys History and Discovery Center
If you’re in the Keys and Islamorada for the first time, visiting the Keys History and Discovery Center would be a great way to get an overview of the area’s history, nature and culture.
At the Islander Resort, the center is spread over two floors overlooking the water.
I was engrossed by the exhibits on Flagler’s Overseas Railroad, the 1935 Labor Day Hurricane, and a 16th-century anchor salvaged from a shipwreck on the reef.
Also great is the Coral Reef Exploration Exhibit, with three aquariums showing off the marine life just offshore. This was created in partnership with the renowned Mote Marine Laboratory.
3. Robbie’s of Islamorada
I’m going to struggle to fit in everything you do with this business on Lower Matecumbe Key. Most of all, Robbie’s is a handy one-stop-shop for charters and watersports rentals.
At one of the world’s trophy fishing hotspots, you can book fishing charters on the reefs or in the backcountry of the Everglades. There are even split charters, so you can share the expense of a private charter with another party.
Added to that are kayak and paddleboard rentals, jet ski tours, parasailing, snorkeling trips, eco-cruises, or boat rentals if you want to go your own way.
But Robbie’s may be best known for the school of monster tarpon that congregate around the dock. There are more than 100, and you can buy a bucket of baitfish to feed them. Sometimes, one will even rise up and grab a fish from your hand.
4. Windley Key Fossil Reef Geological State Park
At the turn of the 20th century, when workers were quarrying limestone to build Henry Flagler’s Overseas Railroad they discovered vast fossil deposits.
The remains of a wide array of ancient coral animals are beautifully preserved in the quarry’s eight-foot walls, in a gorgeous hardwood hammock.
Windley Key is one of the few places you can see such amazing fossils in situ. Guided tours are offered December to April, but you can also look around on a self-guided visit.
I had a fantastic time on these trails, with vestiges of 120-year-old quarry machinery, and an abundance of plant and tree species in the hammock. I’d recommend getting a guidebook, with volumes of interesting detail for the various trail stops.
5. Alligator Reef Lighthouse
Whether you go by charter, wave runner, or rental boat, something that needs to be experienced off Islamorada is this historic lighthouse.
North of the namesake reef, Alligator Reef Lighthouse was built in 1873. There are no alligators in this saltwater environment, and the name comes from the USS Alligator, a schooner wrecked on the reef in 1822.
The iron skeleton frame lighthouse was decommissioned in 2015, but a group has raised millions of dollars to restore the site. When I wrote this article solar-powered lights had just been installed and illuminated.
The true joy of Alligator Reef Lighthouse comes from the astounding water clarity and abundance of marine life in the surrounding shallow waters. I can honestly say I’ve never seen water this clear, and saw a ton of barracuda.
6. Founders Park
Next to Rain Barrel Village you’ll find Islamorada’s community park, on 40 beautiful acres by the bay. One of the best things going for Founders Park is an exquisite sandy beach, on a shallow cove, with palms and mangroves at each end.
The park is a go-to for near-shore snorkeling, and on my short adventure I saw a nurse shark, rays, blue crabs, and an amazing variety of fish.
Elsewhere, Founders Park has no shortage of amenities, with an Olympic sized pool, a splash pad, a marina, a dog park, as well as baseball/softball, tennis, pickleball, soccer, and basketball facilities.
7. Rain Barrel Village
Betsy, a giant fiberglass spiny lobster has been An icon along the Overseas Highway for some 40 years. Anatomically correct, this sculpture is 400 feet long and 30 feet high.
Betsy is at the entrance to Rain Barrel Village, a famed studio and gallery complex for hundreds of local artists. In a rustic setting, shaded paths weave through lush gardens and bring you to a cluster of studios.
I doubt there’s a better place to shop for an authentic souvenir in the Keys. There’s everything from sculpture to glass, beachwear, painting, jewelry, home decor, and much more. You can also stop for a bite at the Lobster Shack Cafe, with sandwiches, snacks, fresh juices, and great coffee.
8. Islamorada Brewery & Distillery
This spot opened in 2014, initially with a craft brewery and then adding Islamorada first and only distillery in 2017.
The Islamorada Brewery & Distillery is right by the Overseas Highway in the heart of the action on Upper Matecumbe Key.
When it comes to beer, the essentials are Sandbar Sunday (American Wheat Ale), Channel Marker IPA, and Islamorada Ale, which has a citrus twist.
Meanwhile, with a 100-gallon still and oak barrels for aging, the distillery produces a highly-rated lineup of rums, gins and vodka. One standout is the Dark Barrel aged Rum, and there are flightable cocktails if you can’t decide on one.
I can’t get enough of the food truck here, available Thursday through Monday and serving burgers, wraps, and pub-style small plates with a Keys twist.
9. Islamorada Sandbar
Tantalizing, about a mile out on the oceanside, is one of the most famous sandbars in Florida. You can only get there by water, but this is Islamorada after all, and there’s no lack of options.
You can do it by paddleboard, kayak, wave runner, or any number of private or semi-private excursions from the likes of Robbie’s and Key Largo Adventures. What I found was a slice of paradise, with glistening shallow waters, perfect for swimming, snorkeling or just floating.
Come on a hot weekend in summer and the sandbar is hopping, with 300+ boats anchored here. There’s a party vibe to this place on these days with music pumping and boats selling food.
10. Indian Key Historic State Park
Another of the remarkable places to discover by water from Islamorada is a ghost town on a tiny island. Indian Key was in fact the very first seat for Dade County. At that this was a community of ‘wreckers’, salvaging materials from shipwrecks on the reefs.
That was in 1836, in the middle of the Second Seminole War. A few years later, a raid by the Native Americans led to the island’s abandonment.
Scraps of the town remain, and for lovers of history, there’s no better place to get an interesting look into the past. For me the ideal way to discover Indian Key is by kayak.
It’s an easy paddle from spots like Robbie’s, and you can spend a couple of hours snorkeling or exploring the ruins.
11. Anne’s Beach
The Overseas Highway passes right next to this beach at the southwestern tip of Lower Batecumbe Key. Named for the local environmentalist Anne Eaton, Anne’s Beach has a small but enticing patch of sand on waveless waters.
For me, it’s not so much a place to hang out for a day as somewhere to discover on a walk, or a picnic. There’s a boardwalk through the mangroves parallel to the highway for about a ¼ mile.
This is a great spot for wildlife encounters, with fish clearly visible in the waters, and a profusion of crabs and wading birds like ibises. The predictable breezes and large swath of tranquil shallow water also makes this a prime location for kiteboarding.
12. Florida Keys Brewing Company
When the Florida Keys Brewing Company was established in 2012 it became the first production brewery in the Florida Keys.
Even now, when craft breweries are almost everywhere, this is the only brewery to brew and package its beer locally in Islamorada. If you spend any time in bars or restaurants around the Keys, FKBC may be a name familiar to you.
When I checked out the tasting room there were 20 beers on tap, with a lot of refreshing IPAs and Lagers, perfect for the tropical climate. The beer garden is also something special, with beautiful vegetation, yard games, and a stage for live music.
The permanent food truck here serves excellent tacos and burritos. You can order at the window, and your food will be brought to your table.
13. Library Beach Park
The name of this beach isn’t coincidental, as it sits directly behind the Monroe County Public Library. Greeting you at this unfrequented spot is a sliver of sandy shoreline on a mangrove channel.
That doesn’t sound like much, but I loved Library Beach Park. The waters are clear and have a pool-like quality that parents with smaller children will appreciate. Although, a current does flow through the channel, so this is something to be aware of.
Behind is a basic but attractive park area with a grassy space, playground equipment and a chickee hut with two picnic tables.
14. The Florida Keys Overseas Heritage Trail
If you wanted you could hop on a bicycle and ride way from Lower Matecumbe Key to Key Largo.
The Village of Islands is on the longest completed stretch of the Florida Keys Overseas Heritage Trail.
Partly using existing paved paths and sidewalks, and partly on the railbed of the Overseas Railroad, this state trail will soon connect Key Largo with Key West, 106 miles away. In Islamorada it means you can leave the car behind and get to most places with a bicycle.
One of the sights not included in my list is The Florida Keys Memorial. Carved from coral limestone quarried at Windley Key, this memorial remembers the 400+ people killed in the 1935 Labor Day Hurricane.
15. Whale Harbor Restaurant and Seafood Buffet
I’m not ashamed to say that a trip to the Florida Keys means indulging in a lot of seafood. The Whale Harbor Restaurant and Seafood Buffet is the perfect place to do just that.
This local icon has been around for more than a century, and is renowned for its Seafood Feast Buffet.
The price when I came was $39.95, and laid out before you is a scarcely imaginable bounty of seafood. From grilled mahi mahi to shucked live oysters, ceviche, crab cakes, crab legs, grilled salmon, shrimp and much more, everything is prepared by a dedicated in-house team.
Leave space for the dessert station, with its delicious tres leches cake and Cuban-style flan.