Learn to Sail in Siesta Key

Few shorelines are as picturesque as Siesta Key. And the clear, turquoise water is perfect for swimming, fishing, and watersports of all kinds. But there really is no better way than to enjoy the Gulf waters than with a leisurely sail! Even if you have never sailed before, Siesta Key is the perfect place to start. 

catamaran on the water

About Sara Bay Sailing

Sara Bay Sailing and Charters is located on Longboat Key with a stunning view of Sarasota Bay. With almost 20 years of charter and instruction experience, it is just the place to help you achieve the skills to make sailing a safe and enjoyable activity. Their skilled instructors provide beginners lessons and assist novice sailors on their path to seeking ASA certifications. 

Course Options 

Sara Bay offers a wide range of courses for all levels: 

In ASA 101 Basic Keelboat Sailing, students learn the knowledge of basic sailing terminology, parts and functions, helm commands, and basic navigation rules to avoid collisions. You will learn to skipper a sloop-rigged keelboat of approximately 20 to 27 feet by day in sea conditions. 

ASA 103, Basic Coastal Cruising teaches you to skipper a sloop-rigged auxiliary powered keelboat. You will learn cruising sailboat terminology, basic boat systems, auxiliary engine options, docking procedures, and more. At least 24 hours of previous sailing experience is a recommended prerequisite. 

ASA 104, Bareboat Cruising focuses on skippering a sloop-rigged auxiliary powered keelboat of approximately 30 to 45 feet during a multi-day cruise upon inland or coastal waters in moderate to heavy winds and sea conditions. At least 80 on-sailing hours are a prerequisite. 

To improve or refresh your sailing skills, take ASA 111, Sailing Review, which allows you to decide on goals prior to the lessons, seminars, or webinars. This course allows additional flexibility for students to establish personal goals with their teachers. ASA 101, Basic Keelboat Sailing is a prerequisite of the course. 

mother and daughter

The ASA 114, Cruising Catamaran is a more advanced course, in which students will learn to skipper an auxiliary-powered sailing cruising catamaran of approximately 30 to 45 feet in length during a multi-day liveaboard cruise upon inland or coastal water in moderate to heavy winds and sea conditions. ASA 101, ASA 103, and ASA 104 are prerequisites. 

To improve your docking skills, ASA 118, Docking Endorsement is designed to help. In this course, you will learn to safely and efficiently dock an auxiliary-powered sailboat. 

All of the courses available can be counted towards progressive certification programs. Each certification requires participations to satisfy knowledge and skills standards through a written exam and on-the-water practical exam. The length of each course varies, depending on skill requirements. 

After You’re Certified

For those who complete the ASA 103, Basic Coastal Cruising class and those who demonstrate sufficient sailing skills, Sara Bay offers a Catalina 22’ to charter for a day of sailing. The cost is $200 per day with a $750 damage deposit. For those who would like to sail but aren’t confident in their abilities, captained charters are available for a day on the water. 

Alternatively, Key Sailing and Latitude Sailing provide a variety of charter options for individuals and private groups. With Key Sailing, choose between 2, 3, and 4-hour tours. You’ll be provided with comfortable pillows, cushions, and back rests, snack and soft drinks, chocolates, photos – even sailing lessons can be arranged. Latitude Sailing offers multi-day bareboat tours, sunset cruises, and more. 

When back on land, consider our Siesta Key vacation rentals when looking for places to stay. All rentals are within walking distance from Siesta Key Village, centrally located, and close to the beach. Guests even receive beachfront access to Crescent Beach.

Plan Your Vacation

For a truly memorable vacation, close to the sand and waves, there is no better place to find yourself than Siesta Key! Check out our amazing rentals and book your dream vacation…


Our Location

Crystal Sands Condominiums
6300 Midnight Pass Road
Siesta Key, FL 34242

Toll-Free: 888-419-1446
Local: 941-349-7007

Fax: 941-346-1963

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