Skip to main content Skip to main content

Book Direct and Save up to 25%

Only when you Click Here


Everything you need to know about the Conch Republic. Keep up on local events, nightlife and activities while in Key West.

Tips for Setting Sail in Key West

Tips for Setting Sail in Key West

May 14th, 2018 | Activities

Thinking of setting sail in Key West? There’s plenty of sailing charters around the island. Here are some tips to take into account before your trip.

Figure Out What You Want

Are you looking for a sunset cruise? Day away? Island or reef exploration? It’s important that you narrow down your options ahead of time so you know exactly what to book and what to prepare for. Sail Florida Adventures specializes in luxury sailing charters. They offer a special 24-hour sail that includes kayaking around Boca Grande, meals, stargazing, and a hot cup of coffee in the morning. Sebago Key West is another favored company that offers evening sunset sails so you can enjoy our famous Key West sunsets -- with a glass of champagne, aboard a windjammer, you name it -- Sebago has packages for all occasions. Sunset Sail Key West is also a preferred option for affordable sunset cruises. Check and compare rates in advance.

Reserve Ahead of Time

While there’s many sailing options on the island, peak seasons can cause full bookings. Don’t wait until the last minute to book your trip -- with an average of 260 days of sunshine in Key West, you have a good chance of booking the perfect day out on the water. Avoid any confusion by booking direct with charter companies, or call ahead of time for complete information that doesn’t leave you wondering the day-of.

Pack Smart

Now that you’ve decided your perfect sailing trip and booked your spot, it’s essential that you pack smart! Not only is sunblock important for some of us to apply ahead of time, but make sure to bring some with you to reapply during your excursion or after swimming. Shoes can also make or break you on a sailboat -- for those who have sailed, flip-flops are a troublesome no-no. Pack water shoes that are waterproof and can aptly grip the deck of a boat. Finally, sunglasses and a hat or head cover are important, but prepare for wind!



Booking a trip to Key West? Check out rates at The Gates Hotel