newsletter sign up
cruising and chartering
Skip to content
/ ADVERTISE WITH US
Cruising and Chartering
Destination: The Florida Keys
Can the Florida Keys really be better than the Bahamas?
George Sass Sr.
November 6, 2014
Cruising along at 20 knots, we can clearly see the sandy bottom 6 feet below. The azure-blue water off to starboard stretches for miles with scattered mangrove outcroppings interrupting the far horizon. We’re passing one island after another to port, and if it weren’t for the endlessly long, elegant bridge structures connecting these islands, we could mistake our surroundings for the Bahamas. No, we’re not in the Sea of Abaco. We’re in Florida Bay, cruising the Florida Keys. Until our recent two-month exploration of this 126-mile tropical archipelago, we agreed with others who have rated it “almost as good as being in the Bahamas.” But as we near the end of our extended cruise from one end of the island chain to the other, we’re upgrading our view. In our humble opinion, cruising the Florida Keys is not only as good as the Bahamas; in some ways, it’s better. We begin our wintertime foray into the Keys at Plantation Yacht Harbor in Islamorada, located at Mile Marker 87. For reference, the southernmost point of the Florida Keys is at MM 0 in Key West. Key Largo is the largest and northernmost key, with MM 110 marking Jewfish Creek and the gateway into the Keys. Heading southwest from Key Largo, the most popular areas are Tavernier, Islamorada, Marathon, Big Pine and finally Key West.
George Sass, Sr.
fishing key west
Whether one is approaching by land or sea from Florida’s mainland, the incredible color of the water creates a lasting first impression. The bright aqua-blue seas are as crystal clear as they are in the Bahamas. As one travels south, commercial development gives way to a more natural environment, punctuated by exotic flora and fauna, white-sand beaches and funky roadside attractions: one-of-a-kind cafes, dive museums, exotic art and furnishings, turtle hospitals, charter boats, resorts and motels. And one’s sense of leaving the everyday world behind intensifies. Locals seem less interested in what others think, and within reason it’s simply “live and let live.” It’s the universal island attitude. Hey, mon, even the local Winn-Dixie carries Kalik, and getting dressed for dinner means putting on a clean T-shirt. Of course, none of this laid-back attitude would be possible without the latitude, which ensures warm temperatures even in the dead of winter. Back home in Annapolis, Maryland, it was 7 degrees Fahrenheit. In Jacksonville, Florida, it was 50. In Key Largo, 78. With Islamorada as our base, we slowly acclimate to Keys time. An afternoon cruise to Little Basin on Upper Matecumbe Key brings us to Bayside Marina and the two-story World Wide Sportsman store. Even if you’re not an avid angler, you’ll enjoy the replica of Ernest Hemingway’s Pilar sport-fish boat and the huge selection of fishing gear and apparel. Overlooking the anchorage while enjoying a fresh fish sandwich upstairs in the Zane Grey bar, it’s 82 degrees with a cloudless sky. The coming weekend brings a flurry of activity at Islamorada’s Founders Park with the annual Gigantic Nautical Flea Market, which features more than 200 vendors displaying tons of new and used boating gear, apparel, nautical art and boat stuff of all kinds. As one local described it, “If you can’t find it here, you don’t need it.” I was still recovering from the sheer size and madness of visiting the Miami International Boat Show, so the relaxed, festive atmosphere of this event was a welcome relief.
After a couple of unsuccessful fishing trips in the backcountry (either our old hot spots were unproductive or we had lost our touch) we decided to go exploring and run our boat to Flamingo, part of Everglades National Park. From Islamorada, the 45-mile route follows the Intracoastal Waterway (ICW) in Florida Bay until Long Key, where it runs northwest 20 miles to East Cape and then turns east 10 miles to Flamingo. Overall, the inside, or bay side, of the Keys is quite shallow. Boats with drafts exceeding 5 feet find much of it inaccessible and instead travel on the outside, or ocean side, following the well-marked Hawk Channel that leads from Biscayne Bay to Key West. But Florida Bay’s calmer waters offer so many attractions whether fishing or cruising that a shoal-draft boat — even a rented one — is the best choice for getting the most out of the Keys. This is center-console territory, with good reason. We thread our way through the channel that leads to the Flamingo Marina and tie up along the concrete wall near the visitor center. That afternoon and evening we attend two fascinating park ranger presentations about the wildlife and history of Flamingo and Everglades National Park. The marina actually has two basins (one for salt water and one for fresh water), and seeing a 7- to 10-foot-long alligator basking in the sun on the freshwater side explains why the ranger discourages swimming. The next day we head west 12 miles following the shoreline past East Cape and drop our hook in 6 feet of water off a beautiful, white-sand beach near Middle Cape. Landing our dinghy, we are amazed to be the only humans on the pristine beach, which stretches for miles and miles. And suddenly we realize why: Following us as we walk is a pair of fins above two dark shadows 50 feet from the shoreline. Yes, the beach is beautiful, but it’s probably not the best place to bring the kids to splash around and make sand castles. After a few days in the wild, we are ready for a change of pace and head south to Key West. Because we’ve run the outside route several times in the past, we choose the inside route, following the ICW and stopping for the night at Bahia Honda State Park. With the boat anchored between the old railroad bridge and the highway bridge, we land our dinghy in the small-boat basin and hit the beach, ranked among the top 25 beaches in the United States. And yes, here you can swim safely in the protected area. Complete with pavilions, picnic tables and a snack bar, the state park also features an attractive campground overlooking the water. Climbing the steps to the old railroad bridge, we are treated to a spectacular view.
key west bar
We continue to travel the inside route, which takes us northwest up Big Spanish Channel through the backcountry wilderness to the Gulf of Mexico. As is sometimes the case, the weather report isn’t accurate, and as we turn the corner into the Gulf, the winds pick up to a nasty 30 knots. The low-lying mangroves give us little protection, and when we turn south into Northwest Channel, which leads to Key West, we get smacked with stacked head seas that have been building from the endless fetch of the Atlantic Ocean. Our final approach to Key West is a long, slow, wet slog. We’ve made reservations at the Galleon Marina downtown, which offers floating docks, resort amenities and an unobstructed view of the harbor. It’s a perfect place to lick our wounds and make things shipshape after our rough passage. While most people seem to love or hate Key West, my wife and I love it for its aesthetics and creative atmosphere. We’ve discovered some of the best fine art on the East Coast in its galleries, and live music seems to be coming from everywhere. While the increased cruise ship activity fills downtown with gawking day-trippers, we’ve learned to avoid this daily surge of humanity. We search for restaurants that are off the cruise ships’ itinerary, and we walk the residential side streets and alleys that have no tourist attractions. Our first discovery this trip is El Siboney, a homestyle Cuban restaurant on Catherine Street, about a mile from the harbor. Its garlic chicken and roast pork dishes are memorable, and the friendly, cozy setting attracts mostly locals. Our most impressive dining experience, however, is at Santiago’s Bodega in the neighborhood of Bahama Village, a 16-block area named for its original residents of Bahamian ancestry. The neighborhood is a bit rough around the edges, but it’s free of tourist traps. Santiago’s is a tapas restaurant, and we found ourselves “oohing and aahing” at every surprising, savory dish. Of course, whenever we’re in Key West we watch street performers as the sun sets on Mallory Square or take a self-guided “Duval pub crawl” on Duval Street. As we head back up the Keys, we discover new anchorages and revisit old favorites. We spend a night tucked inside Little Crawl Key at Curry Hammock State Park and then run out to Alligator Reef for an afternoon of spectacular snorkeling. And to make our Keys adventure complete, we book a day of backcountry fishing. Yes, cruising is all about attitude and latitude. And it’s all right here in the good ol’ USA.
Fishing for Shark in the Florida Keys
Fishing Reports from Islamorada:
Fishing in this part of the Keys falls into two basic categories: offshore and backcountry. Whether you choose to go deep- sea fishing or explore the shallow waters of Florida Bay, Islamorada's reputation as the Sport Fishing Capital of the World is well deserved. There's no shortage of quality charter boats and highly experienced captains, and for the best results you'll want to book some time with one of these experts. If you have your own boat or you're going out with a friend, be sure to get a fishing license by visiting
or by calling 888-347-4356 (888-FISH-FLORIDA). You'll also want to make sure you understand the recreational limits and regulations for each species. With regard to offshore angling, late winter and early spring can bring rapid changes in weather and water temperatures that will challenge even the most experienced captains. March and April are transitional months when both winter and summer fish can be caught. Out on the reef, yellowtail snapper can usually be found. Grouper season opens May 1, and you’ll find them waiting for you on the bottom. King mackerel can usually be found around the wrecks too. In deeper water, you’ll chase blackfin tuna and dolphin (mahi), and for a real thrill you might want to try shark fishing. For a more exotic challenge, give deep-drop swordfishing a shot. The best time to catch a sailfish starts in October, but some can be caught in the summer. For backcountry-fishing fans, Florida Bay’s flats hold a wide variety of fish that can be caught in a number of different ways by both beginners and pros. As the water warms up, the most consistent and arguably exciting fishing will be for tarpon; those silver kings sure do fight. Live shrimp on spinning gear will land 30- to 150-pounders. No experience necessary. You can cast a fly as well. Some charters specialize in night tarpon fishing. Also for beginners, mangrove snappers can be caught in the channels in and under the mangrove root structures. Mud minnows or live shrimp on a light leader with a little weight and a small hook work best. Spotted trout can be found on the mud flats using live shrimp and light jigs. Snook and redfish will also be running, but when all else fails, any old bloody fish head will attract a shark bite. Some of the best charter captains in the Keys work out of Bud N' Mary's Marina at MM 79.8 on the ocean side. Visit
Fairline’s Cozy Cruiser
Benetti Yachts Launches the Diamond 145
Meet The Pardo 38
Reviewed: Riviera 6000 Sport Yacht Platinum Edition
New Season, New Yachts
Denting the Marine-Communications Universe
Denting the Marine-Communications Universe
Consulting Digital Clouds
A Rogue Wave, a Rescue at Sea, then Reunited
/ ADVERTISE WITH US