Destination: Key West

The Keys as lively as ever after 2017's string of hurricanes and there's still time to take advantage of the peak season. Hoist your sails and use this guide to navigate the best of the Conch Republic, from mooring fields to offshore regattas.

Hurricane Irma’s fierce winds and storm surges roared into the Florida Keys as a Category 4 hurricane in September of 2017. Contrary to the popular rumor that all of the Florida Keys suffered absolutely devastating damage, the islands are rebounding, and some of them already look as if they were untouched by the storm. Key West is one of those islands, and the end of spring is a great time to experience it because it’s less crowded than usual.

Stretching from the southern tip of Florida to the Dry Tortugas National Park, the Florida Keys dot a 220-mile arc across incredibly beautiful turquoise waters. Key West is the southernmost island connected by the Overseas Highway. The Dry Tortugas are about 70 nautical miles west of Key West and accessible only by boat or seaplane.

The clear waters surrounding this unique string of tropical islands are home to the Great Florida Reef, the only living coral barrier reef in the continental United States. One of the largest barrier reef systems in the world, this Florida reef tract begins near Miami and extends 300 miles southwest to the Dry Tortugas. Its vast coral reef system is teaming with fish and wildlife, and visitors from all over the world come to experience the world-renowned ocean excursions it provides, including fishing, snorkeling, and scuba diving.

Sailing to Key West via Hawk Channel

The Keys run parallel to the Florida barrier reef, and Hawk Channel separates the two. Hawk Channel is good for sailing, as it is protected from ocean swells but still has great wind. Running from Biscayne National Park to Key West, Hawk Channel is the preferred route to the southernmost Florida Keys for many. Stay within the channel, and watch out for variable depths. Cruising through Hawk’s Channel at night requires attentive sailors, especially during crab and lobster seasons when there are typically lots of traps in the channel.

Hawk’s Channel offers so many beautiful places to swim and so many interesting islands to stop at long the way that zigzagging between the reef and the islands is a great way to experience this beautiful archipelago.

Avoiding the shallows around Key West

Some of the waters surrounding Key West are notoriously shallow and full of seagrass beds and boat-crunching coral. Even for the most experienced sailors, navigating these waters can be a challenge. You can incur major fines and fees by running aground in the Florida Keys, so take extra precautions to avoid damaging the valuable Keys habitat and your boat. Always use-up to-date charts and familiarize yourself with the water you plan to sail through. Use marked channels where they exist, and stay in deeper water to avoid damaging shallow-water habitats. Use extra caution when sailing at low tide.

Locals’ tip: Avoid the “Bubba sticks.” Locals have marked some really shallow spots and sunken objects most often with a PVC pipe and sometimes with a flag, too.

Best seasons

The subtropical climate of the Florida Keys allows for year round sailing, but different seasons offer different opportunities. Typically, the best time for strong wind and good sailing is January through April. The water visibility during the heart of the summer is extraordinary and makes for some amazing fishing and diving, but June through November is also the Atlantic hurricane season. The 2017 Atlantic hurricane season was a good example of how intense hurricane season can be. If you are sailing in the Florida Keys during hurricane season, have a realistic, well-thought out hurricane plan. Even without hurricanes, you need to be extra alert because tropical storms frequently come and go. Year-round, the wind and weather can change quickly in the Florida Keys, so monitor the weather closely no matter what time of year you come down.

Best mooring fields

The Garrison Bight Mooring Field is the only official mooring field in Key West. It is located north of City Marina, between Fleming Key and Sigsbee Park. Garrison Bite offers dinghy docks, shower and laundry facilities, and a parking lot adjacent to the docks, and it is free if you’re on a mooring ball. The dinghy docks are further away from the famous Key West action than you might think, about a 20-minute walk to the historic seaport and a 20-minute walk to Duval Street. Bicycling is very popular on the island and will cut your transit time in half. Bike rentals are readily available.

The down side of the Garrison Bight Mooring Field is that it is exposed to the wind and the seas from the north (north/northeast is the prevailing wind pattern in the winter). And since this is the only official mooring field in Key West, it can be completely full at times, so have a back-up plan.

Best sailing club

The Key West Community Sailing Center is a small nonprofit sailing club with lots of heart and soul. It’s on a big mission to make the sailing experience accessible to all the people of Key West, regardless of their gender, age, financial situation, etc. The Center hosts a free women's sailing class on the weekends, races on Wednesdays and Sundays, and a kid’s sailing summer camp. It also hosts the “Around The Island Race,” a fun race loved by the locals.

Best inshore race

The Schooner Wharf Bar Wrecker’s Cup Race Series (Wrecker’s Race) is a race series that takes place on the last Sunday of the month from January through April. The seven-mile course runs from Key West Harbor to Sand Key. Wrecker’s Races reenact traditions of the Key West wreckers of the 1800’s. Vessels full of treasure from the ports of the Caribbean and Gulf of Mexico frequently crashed into Key West’s unmarked reefs, and the first wrecker to reach the scene won the right to salvage the ship’s cargo (and the responsibility to save the crew!). Now the first boat to make it to the reef wins a trophy and a bottle of rum! This all-in-fun event is enjoyed by Key West charter boats and private boats. There are six classes, and prizes are awarded at the Schooner Wharf Bar after party.

Best offshore race

The Conch Republic Cup is a regatta from Key West to Havana, Cuba, that draws racers and cruisers from around the world. The race offers long-distance offshore racing and inshore buoy racing. A balance of race days and lay days makes it possible for participants to exercise their sailing skills, sail with and against Cuban racers, and enjoy the lively local culture of Havana and Key West. The schedule is also designed to highlight the sailing education programs of the Key West Community Sailing Center. The goal of the Conch Republic Cup is to support the Cuban and American people as they return to sailing and racing between Cuba and the southernmost point of the U.S. and to bring about cultural exchange through the sport of sailing.

Best bar

Located right on the docks of the historic seaport, the Schooner Wharf Bar is an authentic slice of old Key West. This laid-back, open-air bar has live music day and night and is always full of local boaters and tourists alike. The Wharf is also host to most of the island’s captain’s meetings and regatta award ceremonies. Whether you’re there for a sailing event or to relax and watch the island’s fleet of schooners make their way in and out of the harbor, don’t miss this historic watering hole.