Key West Sailing Tours

There's no question about it: sailing is the most unique way of exploring the seas off the coast of Key West Florida. Sailing is an experience on its own, unlike any other type of vessel that cuts through the waters. Sailing is not the high speeds of a jet ski, nor is it the loud noise of a motorized catamaran. Sailing is the relaxed way of fully appreciating the beauty and tranquility of nature and the Florida Keys. On these sailing expeditions, you and your group will get to experience Key West the way it was meant to be experienced: in the most relaxing, enjoyable, and memorable ways.

When you climb on board a sailboat, and you see the crew lift the boat's massive sails (on many trips you even get to help the crew raise the sails), you will understand why people are so passionate about sailing. It is a much more engaging and down-to-basics type of way to head out to sea. Unlike catamarans, that oftentimes feel like a big party boat, sailboats are smaller and offer a more intimate ride. Sure, they are not as fast as catamarans, but the point of a sailing expedition is not speed. The point of sailing is to completely and fully enjoy the experience of being on the calm blue waters off the coast of Key West Florida.

The experience of sailing harks back to the time of pirates, explorers, and navy men. These are all figures who have been monumental in the development and growth of the small southernmost island of Key West. There are various types of sailboats in Key West from the massive schooner sailboats that are the most reminiscent of the 18th and 19th century ships to the smaller and more intimate 6-person sailboats.

With the various Key West sailing excursions we offer, you will have the opportunity of jumping aboard one of the island's best sailboats for a memorable journey on the calm clear-blue waters of the Gulf of Mexico. Immerse yourself in our sailing excursions as you feel the balmy sea breeze of Key West. Any time of the day is a great time for a sailing excursion. So whether you join us for the famous Mimosa Morning Sail or one of the excellent sunset sailing excursions, you can expect a journey that is sure to become one of the highlights of your time in Key West.