Florida Keys

By admin ~ January 11th, 2012. Filed under: Destinations.

A Village Of Islands

Islamorada is a sparkling jewel in the string of

gems that comprise the Florida Keys.

By L.J. Wallace, Jr.

If you have never been to the Florida Keys, you are truly missing out on one of the most fascinating and beautiful places in the U.S. And nestled within the upper reaches of this string of delightful islands, you’ll find several that comprise Islamorada, “Village of Islands.” Islamorada has a reputation for being the “Sportfishing Capital of the World” and for two good reasons: it is said to have a larger fishing fleet per square mile than anywhere else in the world; and you can troll the deep waters offshore in the morning and be casting in the shallow flats of the ‘backcountry’ in the afternoon. But there’s so much more to this fishing paradise than just wetting a line, donning some scuba gear for a plunge down to the reef or paddling a kayak around the mangroves.

Islamorada stretches between Mile Markers (MM) 90 and 72 on storied State Highway A1A which terminates in Key West at MM- 0. It is comprised of six islands including Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of Indian Key and Lignumvitae Key, all situated between the saltwater wilderness of Everglades National Park to the north, and North America’s only coral barrier reef and the deep blue waters of the Florida Straits to the south.

Around the turn of the 19th Century, the area was home to the pioneering Pinder family who lived aboard their schooner, Island Home. Around this time, Henry Flagler was building his railroad through the Keys and track had already been laid in the area. However, the train would only stop at named towns and so the Spanish translation for Island Home—Islamorada— was adopted. However, as Islamorada Chamber of Commerce Executive Director, Judy Hull explained, “Exactly how our village got its name is still a somewhat controversial subject. Some say it’s named after the Pinder’s boat, while others will tell you that the word Islamorada is Old Spanish for Purple Isles or Village of Islands.” At any rate, in 1908 the new Islamorada train station and Post Office opened for business.

As with much of the Florida Keys, it was a docile few decades until the Labor Day hurricane of 1935 ripped through the island chain. Packing winds exceeding 200 miles per hour, the storm created turbulent seas that sent a 17-foot storm surge directly across the Keys, killing hundreds of WWI veterans working on the railroad, as well as local residents. Two years later, after the railroad ties and other debris were removed, a Hurricane monument was erected at MM-81 in Islamorada.

Fast forward to 1997. After spending its entire history as an unincorporated portion of Monroe County, on December 31st of that year, the village was incorporated. Founded in the mid-1940’s, the 42- acre Plantation Yacht Harbor Resort on Islamorada had seen better days and doing something about it was item number one for the newly installed Village Council. Although controversial, the decision was made to purchase the property and build it into a public facility. This was the beginning of Founder’s Park and PYH Marina (MM-87 bayside). “The Gem and centerpiece of our village,” is the way Director of Parks and Recreation/Public Works, John Sutter, describes it.

Construction started soon after the land was acquired and the first order of business was to tear down all the old buildings except the restaurant which became Islamorada’s first government building. But since then, the property has become “built-out” as Sutter says. It began with the athletic facilities, then a beach, then an Olympicsized pool, tennis and basketball courts, dog park (in fact, for those of you who prefer to travel with your dog, the friendly and relaxed attitude on Islamorada means that many businesses, both lodgings and restaurants, are extremely dog-friendly), golf ball hitting area, skate park, fishing jetty, marina and most recently, an open-air amphitheater. “Yea, you could say it’s a big draw,” Sutter added, tongue-in-cheekily.

Saturday and Sunday, April 2-3, brings the 20th Annual Florida Keys Island Fest, billed as “Islamorada Chamber’s best event yet!” From 10AM-5PM both days, artists, musicians and much more  will transform the park into a fun-filled family destination. New to this year’s event is the All-American Road Vintage Cruisers Car Show, featuring pre-1975 cars, trucks, motorcycles and rat rods. In addition, an array of talented musicians will also take part, appealing to music lovers of all genres, from blues to reggae. “The Florida Keys have always been known as a mecca for the performing arts, and Island Fest is the best place to experience that first hand,” says Judy. “We’re really quite lucky to have so many gifted people sharing their talents with us.” Saturday’s culinary event features a tantalizing smoked-fish dip contest, and on Sunday, don’t miss the popular “Taste of the Islands,” a delicious competition showcasing the dishes of many local restaurants. And the ever-popular “IslaMarauder” Rum Punch Contest returns as well.

It’s refreshing to see the government spend taxpayer money on a project which, in the end, everyone agrees was money well spent. “It’s because of the cohesiveness of the Chamber, the government and the businesses of our village that it all came together so successfully,” states Judy. And indeed, the park provides not only a source of recreation for Islamorada residents, but it’s also becoming an economic engine of sorts. By offering so many facilities and activities not otherwise found in the Keys, people come from far and wide and while there, spend money in the local community.

Strolling around Islamorada and chatting with the folks you quickly learn that many of them have relocated or established a winter residence here from the north. This injection of Yankee blood is likely what has had a lot to do with the Renaissance that’s occurring in Islamorada. Judy related, “We believe we have the most diverse and best dining in all the Keys.” There’s Restaurant 88, which President George H.W. Bush has frequented, or Morada Bay and its monthly Full Moon Party. But it’s not all about dining when it comes to food. “There’s just so many places to find a tasty treat,” shared frequent visitor from Long Beach Island, New Jersey, Zach Kerzner. “The Islamorada bakery has the best scones anywhere.” Kerzner went on to sum up his feelings about the Village of Islands. “Islamorada is the hot spot of the Middle Keys, maybe all the Keys. There’s just something intangible about the place; it’s happening and classy.” Interestingly, research by the Chamber also indicates that a large percentage of visitors to Islamorada—particularly shorter-term and weekend—hail from southern Florida itself. Islamorada has also seen a surge as a “Destination Wedding” location.

As far as where to stay, you have a lot to choose from. If you’ve arrived by, or trailered your boat but want to keep it safe and convenient in a dry stack, there’s Snake Creek Marina (,or for larger vessels, Plantation Yacht Harbor within Founders Park. For those flying in or arriving by car, it may be hard to decide just where to lay your head down. At the high end is what many consider to be the crown jewel of the Keys, the oceanfront Cheeca Lodge & Spa, complete with a golf course. Even if you don’t check in, it’s worth a visit to the elegant sportfishing-themed bar. If you’ve come by boat but want to spend your nights in a bed, not a bunk, then Islander Bayside Townhomes & Boatslips ( might be just the place for you with their magnificent views of the Gulf. Located on the southern tip of the islands you will find Bud N’ Mary’s Fishing Marina. Established in 1944 and home to over 40 legendary fishing captains and guides, it is the oldest and largest fishing fleet in the Florida Keys fishing industry. In addition to landside hotel accommodations at Bud N’ Mary’s, they have a pair of beautiful, custom-designed houseboats available for short- and longterm rental as well. If you arrive via a boat, dockage is available right next to them.

Islamorada has so much to offer and is so accessible, especially to those residing in the southeast, willing to make the drive, that it should be on everyone’s short-list of “must see” destinations. Islamorada Chamber of Commerce MM- 83.2; 305-664-4503; 800-FAB-KEYS; email:;

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