Sailing in Key West & Florida Keys 2025
Turquoise waters, subtropical weather, and only coral-reef in the continental USA
Best time: January–April
Florida Keys archipelago is stretched for about 120 miles (193 km) and warmed by the Gulf Stream. Being a true paradise itself, sailing around it is an almost dream-like experience. That's why the opportunities to sail and explore here are unlimited.
The climate of the Florida Keys makes it possible for year-round sailing but January through April offers the strongest wind and the best sailing. June through November is the Atlantic hurricane season, so if you are sailing during it, have a well-thought-out hurricane plan. You need to be extra alert anyway as tropical storms often come and go. Monitor the weather closely no matter what time of year you visit.
Generally, the Florida Keys has unlimited sailing destinations. The ultimate are Islamorada, Big Pine Key, Key Largo, and Key West. You can book a tour to relax or a lesson to learn how to moderate winds and ocean conditions.
Practical info
What are some ideal locations to sail in the Florida Keys?
Florida Keys is home to several popular sailing destinations. Islamorada island offers a beautiful Caribbean atmosphere with crystal-clear water. Key Largo has the only living coral reef in mainland USA, among other attractions. Big Pine Key is an excellent place to spot key deer and sea turtles, while Key West offers historic sites, restaurants, and nightlife. Each of these islands is perfect for sailing, and visitors can expect to have an enjoyable experience.
When is the best time to sail in the Florida Keys?
January through April is the best time to go sailing in the Florida Keys. This is when the wind is at its peak, making the sailing experience more enjoyable. However, from June to November, the area experiences rough weather due to hurricanes and tropical storms, which makes it unsuitable for sailing. Regardless of the season, it is crucial to check the weather forecast before sailing.
Where can I book a sailing tour or lessons?
Booking sailing tours or lessons in the Florida Keys is easy. Key West and Kery Largo are the most common departure points. Popular sailing companies such as Atlantic Sailing, Fury Catamarans, and Sebago Watersports offer sailing tours, sunset cruises, and private charters in Key West. Key Largo features sunset sails, snorkeling, stargazing, and kayaking tours. Additionally, several sailing schools based in the Florida Keys offer lessons and certifications.
What measures should I take to prepare for hurricanes while sailing in Florida Keys?
It is crucial to plan for hurricanes while sailing in the Florida Keys during hurricane season. Before setting sail, monitor weather predictions carefully. Take precaution and find a safe harbor in case of severe weather or storm warning. Be sure to secure the boat correctly by anchoring it firmly with storm anchors, doubling up on lines, and removing sails, canvas, and dinghies from the boat. It is important to prioritize passenger safety at all times.
What precautions should I keep in mind while sailing around the Florida Keys?
Sailing around the Florida Keys requires special precautions to be taken. There are several marine creatures like manatees, sea turtles and dolphins, as well as fish, to watch out for. It is important to be mindful of your speed and not anchor too close to coral reefs to avoid any damage to marine life. Ensure that you check the weather forecasts regularly to prevent sailing into a thunderstorm. Proper navigation charts, compasses and acceptable sun protection are things to keep in mind too.
