Postcards from Nowhere

Cruising in the Keys and Islamorada reveals many lesser-known gems.

October 4, 2007

It is good that so many yachtsmen are wandering the world in search of paradise, for there is a spot in South Florida that natives have been coveting for years. I will certainly be shunned for telling you that just 69 miles from Miami, Islamorada in the Florida Keys is more than a world away. The Keys are unique to the United States, and Islamorada is unique to the Keys. The Keys’ subtropical environment is home to the only living reef in North America, and Islamorada is a blend of old and new, traditional tourist tacky and upscale fare. It is a premium slice of real estate positioned between the reef and the fertile shallow waters of Florida Bay.

Once just islands in the stream, the Keys were united by Florida’s developer/pioneer Henry Flagler, of Standard Oil fame. The last leg of his Florida East Coast Railroad, the Key West extension, stretched from Miami to Key West and was completed 1912. A bit more than a year later, Flagler died at age 83. Its construction had been his dream, an engineering feat few thought possible at the time. Today, the seven-year effort ranks as one of the greatest engineering achievements in history. After the area was devastated by the 1935 hurricane, the track, including more than 18 miles of open-water bridgework, was converted to roadway. Though Islamorada is about a 11/2-hour drive from Miami, it is best explored by boat.

Yachtsmen on the eastern coast of Florida have several options for reaching Islamorada from the mainland. The best route depends on the specifics of your vessel and the sea conditions. If you are running offshore, it is best to run inside the edge of the Gulf Stream when headed south to avoid the strongest current. Past Miami, Hawk Channel runs between the reef and the Keys.


If the wind is strong, and Hawk Channel is stirred up, you can pass into Biscayne Bay via Government Cut and the Port of Miami or at Cape Florida. From here, it is a simple matter to follow the Intracoastal Waterway down the bay side of the Keys. There is an occasional wait for an opening at the Jewfish Creek Bridge. Once in Islamorada, vessels may pass between the ocean and bay at Snake Creek-the bridge has been known to open on demand. Proper charts are essential, and a cruising guide can be useful, although one I spotted for sale recently was an antique and a waste of money. Make certain you check for updates. A general note of caution: While most areas are well marked, navigation in the Keys is precise, and bumping into the reef or damaging sea grasses is a taxable offense. If you have any concerns regarding this, contact the Florida Keys National Marine Sanctuary at (305) 853-0877.

For dockage, my choices fall into two categories. For the young and restless, Holiday Isle Resort & Marina (ocean side) offers three meals a day in multiple restaurants, live entertainment and a flock of drinking options, including the “world-famous” Tiki Bar. The marina has 19 transient slips for vessels up to 110 feet. On weekends, this place is hoppin’ and can be rather loud.

For those seeking peace of mind, Plantation Yacht Harbor (bay side) is now part of Founders Park, a 48-acre recreational area with walking paths, a beach, ball fields, tennis courts and an Olympic-class pool and dive facility. It is one of the quietest berths I have found in the Keys. Currently, the property has no restaurant, but dining is a short walk away. There are 15 transient slips for vessels up to 80 feet. For those who prefer to swing on the hook, locals and some transients have adopted an anchorage adjacent to town on the bay side.


While Islamorada has taxi services, the best way to indulge in the area’s cuisine is by tender or skiff. My favorites include Marker 88 for casual fine dining. You might try Smugglers Cove for simple local flavor, Islamorada Fish Company for the obvious and the Lorelei Restaurant & Cabana Bar for breakfast. Hog Heaven, a waterfront sports bar and grill, is not a bad spot for lunch.

By land, breakfast is served local-style at Mangrove Mike’s. Squid Row serves some of the freshest seafood in town and has a pleasant family atmosphere. The truly adventurous will ultimately uncover Woody’s. This is more a warning than a recommendation-its house band delivers blues, verbal abuse and foul jokes. What might have been referred to in more tasteful times as burlesque is also a house specialty, so leave the kids at home. At the other end of the spectrum, Morada Bay offers upscale sunset cocktails and dining on the beach-don’t miss the full-moon party. Pierre’s, next door, is worth a jacket and tie. If you’re in the mood for sushi, try Kaiyo.

Islamorada is, of course, known as the sportfishing capital of the world. It was a passion for fishing that drew President Bush’s dad to the area, and you can find his autographed image all over town. Dolphin, wahoo, tuna and billfish can be found offshore, but it is the flats and backcountry that are the major attraction. Good luck; the bonefish in these waters are big, but rather smart. Tarpon are massive (up to 200 pounds) and not so smart. If you receive help from a guide, tarpon are almost a sure thing in spring and early summer. Check with the dockmaster for a recommendation. I have fished endless hours with Capt. Matt Bellinger of Bamboo Charters, and he has been a victim in Telltales on numerous occasions. If you want to catch fish and like to laugh, he’s the best ticket in town.


Diving and snorkeling also are major attractions in this area, and while Bahamas veterans may pooh-pooh, missing the opportunity is their loss. Visibility is often more than 60 feet, and there is a variety of challenges, from shallow snorkeling reefs to deep wrecks. Lobster season extends from August 6 through March 31. There is also a frantic two-day mini sport season (the last Wednesday and Thursday of July) that, in my opinion, is worth avoiding. Check current regulations and be advised that Islamorada recently adopted its own rules regarding this popular crustacean. Popular dive sites are well marked on the water, and local charts are available at dive centers.

If you must play golf, the Cheeca Lodge & Spa has a nine-hole pitch-and-putt, as well as fine dining of its own. Kids will enjoy Theater of the Sea, a small but interesting aquarium with marine-mammal shows. Eco-tours are becoming quite popular in the backcountry, and bird-watchers will find more than an eyeful. If you must shop, traditional Keys roadside opportunities abound, and fisherman shouldn’t miss Worldwide Sportsman. It is something of a cross between a tackle store and a theme park. Upstairs, the plush Zane Grey Lounge is a must-see.

There is a reason more than one cruising buddy begged me to not write this story. Islamorada is simply one of the most pleasant, laid-back spots I have found on the chart.



Holiday Isle Dockmaster Keith Bell (305) 664-2321 Plantation Yacht Harbor Dockmaster Scott Parker (305) 852-2381


Squid Row, (305) 664-9865 Pierre’s, (305) 664-3225 Morada Bay, (305) 664-0604 Uncles, (305) 664-4402 Kaiyo, (305) 664-5556 Green Turtle Inn, (305) 664-9031 Bentleys, (305) 664-9094 Mangrove Mike’s, (305) 664-8022 Papa Joes, (305) 664-8109


Marker 88, (305) 852-9315 Islamorada Fish Company, (305) 664-9271 Smugglers Cove, (305) 664-5564 Lorelei, (305) 664-4656 Hog Heaven, (305) 664-9669


Cheeca Lodge & Spa, (305) 664-4651 Theater of the Sea, (305) 664-2431 Worldwide Sportsman, (305) 664-4615 Windley Key Fossil Reef State Geological Site, (305) 664-2540 Robbies (where you can hand-feed tarpon), (305) 664-9814


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