ASA Courses

Take a sailing vacation!

Learn to sail in one of the most beautiful sailing grounds in the world, 
while enjoying a fun-filled sailing vacation in the US Virgin Islands

Each individual and combination course is flexible schedule based, allowing us the freedom to schedule our classes based on your needs. Beginner through advanced sailors are welcomed. Those seeking a sailing vacation, as well as adventure seekers with no sailing experience are invited aboard. All of our sailing instructors are licensed by the United States Coast Guard, and are certified by the American Sailing Association after an evaluation process. You will learn from experienced instructors.

Combination Course 1

7 Day

$3,295


Prerequisite: Basic Sailing (ASA 101) or equivalent experience

Not required, but highly recommended


This class is fast paced. The more boating experience you have prior to the class, the more you will get out of the training. The class will be very challenging for the student without any prior boating experience. The student will learn to cruise safely in local and regional waters—as both skipper and crew—on an auxiliary sailboat of about 20 to 30 feet in length, in moderate winds and sea conditions. This course includes knowledge about gear and equipment, safety, weather, duties of skipper and crew, and seamanship. You will learn skills in boat handling under power and sail, crew overboard recovery, docking, anchoring, reefing, and heaving to. Upon completion you will be certified to bareboat charter in hundreds of locations worldwide.


We limit the class size to four students, unless special arrangements have been made. This allows everyone sufficient hands-on time to become confident and competent in each skill.

Combination Course 2

5 Day

$2,795


ASA 101 required


This is the intermediate cruising standard for individuals with basic cruising experience. The student will act as skipper or crew of a 30 to 50 foot boat sailing by day in coastal waters. This course includes knowledge about gear and equipment, safety, weather, and seamanship. You will learn skills in boat handling under power and sail, crew overboard recovery, docking, anchoring, reefing, and heaving to. You will gain knowledge of boat systems (engine cooling, fuel, electrical, marine head), maintenance procedures, and emergency situations. You will plan and provision for your cruise, learn more about weather and radio communications, plot and sail a course to a destination, anchor overnight, and dock in a transient slip or pick up a mooring. You will also learn more about sail trim. During the class you will be expected to cook underway and at anchor as well as doing clean-up chores. 


Combination Course 3 

6 Day

$3,195


ASA 101 required


The student will act as skipper on an auxiliary-powered sailing cruising catamaran of approximately 30 to 45 feet in length during a multi-day live-aboard cruise on inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions. You will gain knowledge of catamaran structure, components and features, performance under sail and power, boat systems, seamanship and safety, heavy weather operation, and emergency response. This course includes learning boat systems (engine cooling, fuel, electrical, marine head), maintenance procedures, and emergency situations. You will plan and provision for your cruise, learn more about the weather and radio communications, plot and sail a course to a destination, anchor overnight, and dock in a transient slip or pick up a mooring. You will also learn more about sail trim. During the class you will be expected to cook underway and at anchor, as well as do clean-up chores.


Coastal Navigation 

$275


Online Study



The student will demonstrate the navigational theory required to safely navigate a sailing vessel in coastal or inland waters. No sailing skills are included in this standard. The practical application of this sailing knowledge is found in the advanced coastal cruising standard. This course includes topics on compass corrections, chart reading, course plots, fixes and bearings, current and tide calculations, and navigation corrections for leeway and current.


Cruising Catamaran

2 Day

$1,495


ASA 101, 103, 104 required


The student will learn to skipper an auxiliary-powered sailing cruising catamaran of approximately 30 to 45 feet in length during a multi-day live-aboard cruise on inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions. You will gain knowledge of catamaran structure, components and features, performance under sail and power, boat systems, seamanship and safety, heavy weather operation, and emergency response.



Basic Celestial Navigation

$195


Online Study



The student will learn basic celestial navigational theory and will study the parts of the sextant. Much of the course is devoted to reducing a noon sun sight to establish a fix and a Polaris sight to obtain a latitude. The student will use this information to set up a Universal Plotting Sheet and plot the sights. The student will write the written exam for ASA certification. You will have one year from the date of registration to complete the classwork.



ASA Challenges

The American Sailing Association (ASA) allows experienced students to challenge the ASA 101, 103, and 104 level courses. To challenge a particular level, the student must register for the challenge course, pay the fee, and then will be scheduled to take the ASA written exam for that level. Once the exam is passed, the student will then take the water skills examination and demonstration. The 101 and 103 level challenges are one day in length, the 104 requires two days.




For more information, please contact the school.
101 Challenge – 1 day  $470
103 Challenge – 1 day  $400
104 Challenge – 2 days  $750


ASA Veterans

At ASA we recognize the sacrifices made by the men and women who have served or are serving in our country’s armed forces. As a token of our appreciation for your service, we are inviting veterans, active military personnel, and reservists to share our passion for sailing by offering a 10% discount on our ASA 101-104 ASA Courses. Join us on the water with the wind in your sails! ASA and Sandy Toes Sailing say thank you for your service and want to show our appreciation to veterans, active military personnel and reservists.



The Learning Experience



Sandy Toes Sailing

Sandy Toes Sailing is affiliated with R&R Charters and Sail School located in Chester, Maryland. and follows the curriculum set forth by ASA Sailing and R&R Sailing School. R&R Charters and Sail School is owned and operated by Dave and Penny Renoll, who both hold USCG licenses and have been sailing on the Chesapeake Bay for 30+ years. They have also sailed in Greece, Italy, and the British Virgin Islands.  

“It’s fun, it’s an adventure, and it’s a wonderful way of life!”


We are professional educators who delight in sharing our passion for sailing. Each student will enjoy a personal learning experience as they master the knowledge and skills to feel confident in their sailing abilities. Advance your skills with some individual instruction, or learn as a small group with friends and family. Our maximum of four students per boat gives all students the greatest amount of boat handling experience on the water.


Additional ASA Classes

R&R Charters and Sail School and R&R Sailing School North offer several more advanced ASA classes including ASA 106 Advanced Coastal Cruising, ASA 107 Celestial Navigation, ASA 108 Offshore Passage Making, ASA 117 Basic Celestial Navigation, ASA 118 Docking Endorsement, ASA 119 Weather Endorsement and ASA 120 Radar Operator Endorsement.


The Possibilities

When your classes draw to a close, how about some hands on sailing fun? Check out our charter options. You can charter SV Gloria for a few hours to hone your sailing skills, and just have fun without the pressure of an instructor aboard. Or perhaps you would like to really cruise. How about a crewed charter aboard Great Adventure for a day, weekend, or week? Sandy Toes Sailing and R&R are here for you!


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