Chesapeake Bay South

Sailing School

Learn to Sail With SailTime!

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Unparalleled Excellence

SailTime University

SailTime Chesapeake Bay South offers some of the best sailing on the Southern Chesapeake. We are an American Sailing Association (ASA) affiliate offering unparalleled excellence in sail training.

Our goal is to give you the confidence and competence to safely skipper your own vessel, whether it’s a SailTime yacht or a keelboat. Boating lessons are geared for all experience levels, from first-time sailors to seasoned salt, we can help you take your sailing abilities to the next level.

Accelerate Skills Development

Experiential Education

We offer small class sizes (typically two to four students) to maximize helm time and accelerate your skill development. We believe that experiential education is the best way to learn, so nearly all course time is spent on the boat.

All of our instructor-captains are USCG-licensed and ASA-certified.
SailTime supports the national recreational boating education standards as recognized by the United States Coast Guard.

ASA 101 Course

Students learn to sail a boat of about 20 feet in length in moderate winds and sea conditions in familiar waters without supervision.

ASA 103 Course

Students will learn to skills to perform as skipper or crew of a 30-50 foot boat by sailing in coastal waters.

ASA 104 Course

Students will learn to pilot a 30-45′ sloop-rigged keelboat during a multi-day cruise on inland or coastal waters in moderate to heavy winds and seas.

ASA 105 Course

During this 4-day class, students will learn the theory and hands-on skills needed to safely navigate in near coastal or inland waters.

ASA 106 Course

Students will learn how to safely act as skipper and crew of a 30-50′ sailboat in near-coastal and inland waters, in any wind and weather conditions.

ASA 118 Course

This 1-day course is designed to teach docking in high wind situations, covering theory and techniques to dock and undock boats in an efficient manner.

ASA 103/104 Combo Course

The ASA 103/104 course is a 5-day, 4-night class covering the material of ASA 103 Basic Coastal Cruising and ASA 104 Bareboat Charter.

Learn to Sail

Boating Education

SailTime supports the national recreational boating education standards as recognized by the United States Coast Guard.