Sailing School Overview and Pricing

SailTime welcomes members and non-members to discover the enjoyment of sailing the Chesapeake Bay.

SailTime Annapolis provides excellence in sail training in conjunction with the American Sailing Association (ASA).

Our goal at SailTime Annapolis is to teach you the skills and decision-making required to safely and confidently command your own SailTime yacht or bareboat charter. Whether you are a first-time sailor or you have a few seasons under your belt, we can help you take your sailing to the next level with the following courses…

Non-Certification Classes: Call 443-376-7245 or email This email address is being protected from spambots. You need JavaScript enabled to view it. to schedule. 

 Introduction to Sailing – 1 day ($245) - Beneteau First 22


Take your "First Sail" free by clicking HERE

This online introductory to sailing course provides basic knowledge for the ASA 101 certification.


Learning to sail well takes quality instructors and time on the water, period. That’s why at SailTime Annapolis our classes are limited to four students. Any ASA 101, 103, or 104 class can be taught as a private two-person class. Our instructors have USCG captain’s licenses, ASA instructor certifications, and are trained to teach using multiple methods. We have the best instructors!

Prices below are per-person for open enrollment courses; private lessons are also available.

ASA 101 - Basic Keelboat Sailing $650


Learn to skipper a sloop-rigged keelboat of approximately 20 feet (6.1 m) to 27 feet (8.23 m) in length by day in light to moderate winds (up to 15 knots) and sea conditions.

ASA 101 Basic Keelboat Sailing lessons build knowledge of basic sailing terminology, parts & functions, helm commands, basic sail trim, points of sail, buoyage, seamanship, and boating safety including basic navigation rules to avoid collisions and hazards. Auxiliary power operation is not required.

Once you have completed the ASA 101 course, you will be eligible to skipper the First 22 by joining the SailTime membership program!


Click here for additional info at the ASA website



ASA 103 - Basic Coastal Cruising $775

Learn to skipper a sloop-rigged auxiliary powered (inboard or outboard engine) keelboat of approximately 25 feet (7.62 m) to 35 feet (10.67 m) long by day in moderate winds (up to 20 knots) and sea conditions.

ASA 103 Basic Coastal Cruising lessons build knowledge of cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather interpretation, boating safety, and seamanship.

Once you have completed the ASA 103 course, you will be qualified to join the SailTime membership program. The SailTime program gives you access to a larger boat to use throughout the season without the expense and commitment of buying your own boat. You will be able to sail a late model Beneteau or Hunter yacht all season long for less than the cost of the slip.



ASA 104 - Bareboat Cruising $995

Able to skipper a sloop-rigged, auxiliary-powered keelboat of approximately 30 feet (9.14 m) to 45 feet (13.72 m) in length during a multi-day cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions.

ASA 104 Bareboat Cruising lessons builds knowledge of provisioning, galley operations, boat systems, auxiliary engine operation, routine maintenance procedures, advanced sail trim, coastal navigation including basic chart plotting and GPS operation, multiple-anchor mooring, docking, health & safety, emergency operations, weather interpretation, and dinghy/tender operation.

Click here for additional info at the ASA website



ASA 105 - Coastal Navigation $495


ASA 105 - Coastal Navigation lessons focus on learning how to apply the navigational theory and practices for safe navigation of a sailing-vessel in coastal and inland waters.

On-water coastal navigation skills elements are contained in the ASA103 Basic Coastal CruisingASA 104 Bareboat Cruising, and ASA 106 Advanced Coastal Cruising, in progressively increasing levels of detail.


Click here for additional info at the ASA website


ASA 106 - Advanced Coastal Cruising $1395





ASA 106 Advanced Coastal Cruising lessons improve your ability to safely act as skipper and crew of a sailing-vessel about 30 feet (9.14 m) to 50 feet (15.24 m) in length in coastal and inland waters, in any conditions.


Click here for additional info at the AA website


ASA 114 - Cruising Catamaran $695


ASA 114 Cruising Catamaran lessons focus on advanced cruising standards for individuals with existing cruising experience.

The individual can act as skipper and crew of a 30-50 foot multihull sailboat by day in coastal waters. The standard includes skills unique to a 30-50 foot multihull.

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ASA 118-Docking Endorsement $375

This course is designed to teach basic docking skills for boats with single inboard or outboard engines. It covers the basic theory and hands-on techniques needed to dock and undock boats in an efficient manner and without damage or injury.


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4 Hour Introduction to Sailing - TravelZoo/LivingSocial Deal

Bring a printed copy of your TravelZoo or Living Social offer.  

The following schedules are available only for the TravelZoo and LivingSocial 4-Hour Introduction to Sailing special offer.  

There is a maximum of 4 people per trip.  Select your preferred time on the calendar and use your voucher number to make the total due $0.  Please make a reservation for each person that has a voucher.  Do not request a reservation for a person that has not yet purchased a voucher.  

On the day of your sail plan to arrive promptly at the scheduled time.  

We are located at the Port Annapolis Marina - 7082 Bembe Beach Road Suite 204, Annapolis, MD.  

If you are using a GPS to find the marina, it will take you past the entrance so keep an eye out for the Port Annapolis Marina sign on the left side of the road just after the sharp left-hand bend in the road.  You will want to dress for full weather exposure (rain or shine) including hats, sunglasses, sunscreen, loose-fitting clothing, CLOSED TOED NON-MARKING SHOES, raincoat and rain pants.   We will provide the PFD (personal floatation device).  You may also bring non-alcoholic drinks and lite snacks. 

Bring a printed copy of your TravelZoo or Living Social offer.



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