Sailing Instruction
Learn to Sail With SailTime!
Unparalleled Excellence
SailTime University
SailTime Annapolis sailing school invites you to discover and enjoy the finest learning experience in Chesapeake Bay sailing. We are a certified American Sailing Association (ASA) affiliate saling school offering unparalleled excellence in sail training of all abilities and skill levels.
Our goal is to give you the confidence and competence to safely skipper your own sailing vessel, whether it’s a SailTime yacht in our fleet or any keelboat. Sailing lessons are geared for all experience levels, from first-time sailors to seasoned salts, our sailing school can help you take your sailing abilities to the next level and beyond!
Experiential Education
We offer small class sizes (typically two to four students) to maximize helm time and accelerate your skills development. We believe that experiential education is the best way to learn, so nearly all our sailing school course time is spent on the sailboat.
All of our instructor-captains are USCG-licensed and ASA-certified. Learn more about each class by clicking the sailing school links below. Contact us for more info or book your sailing class time directly here.
ASA 101 Course
Sailing school students learn to sail on a Beneteau First 22, a small keelboat, in moderate winds and sea conditions in familiar waters without supervision.
ASA 102 Course
Continue growing your fundamental sailing skills. ASA 102: Keelboat 2 is the sailor’s gateway to advanced sailing skills and coastal exploration!
ASA 103 Course
ASA 104 Course
ASA 105 Course
During this 2-day class, students will learn the theory and hands-on skills needed to safely navigate in near coastal or inland waters.
ASA 106 Course
ASA 103/104 Combo Course
AB 101 Beginner Powerboating Course
AB 103 Intermediate Powerboating Course
AB 104 Advanced Powerboating Course
Learn Sailing in
Annapolis on the Chesapeake Bay
Sailing lessons in Annapolis give students the opportunity to train on the Chesapeake Bay, one of the most active and respected sailing environments in the United States. Learning in real conditions helps students understand wind patterns, navigation, and boat control faster than classroom-only instruction.
SailTime Annapolis offers structured courses for beginners and experienced sailors, focusing on hands-on training, safety, and confidence on the water. Students gain practical experience that prepares them for real-world sailing situations.
- Where do sailing lessons take place?
- Sailing lessons take place on the Chesapeake Bay in Annapolis, providing real-world sailing conditions that help students build confidence and experience on the water.
- What will I learn in sailing lessons?
- Sailing lessons cover essential skills including boat handling, sail trimming, docking, navigation, and safety procedures. Courses progress from beginner fundamentals to more advanced techniques.
- Do I need experience to start sailing?
- No experience is required. Beginner sailing courses are designed for people with no prior knowledge and focus on building skills step by step.
- What certification will I receive?
- Students can earn certifications through the American Sailing Association (ASA), which are recognized internationally and help validate sailing skills.
- How much do sailing lessons cost in Annapolis?
- Sailing lesson costs vary depending on course level and duration. Beginner lessons typically start at a few hundred dollars, while advanced certifications cost more.
- Is sailing hard for beginners?
- Sailing is easier to learn than most people expect. With proper instruction and hands-on experience, beginners can quickly gain confidence within a few sessions.
- How long does it take to learn sailing?
- Most beginners can learn the basics of sailing within a few lessons. Developing advanced skills takes more time and continued practice.