Sailing School


The perfect all-inclusive sailing package awaits! Stay at the Blockade Runner Hotel, walk down to our private Soundside docks, and begin your sailing experience aboard our fleet of J/22s. Our Soundside offers calm waters and steady sea breezes, ideal for both beginner and intermediate sailing instruction. A complete compliment of sailing conditions surround the resort hotel.

Try Sailing
Test the waters with a one hour fun sail with a certified instructor to see if an ASA course is right for you.

Discover Sailing
Gain confidence, with an instructor, through one hour of classroom and a three hour sailing session that counts towards ASA 101 Certification.

ASA 101 Certification- Basic Keelboat Sailing

ASA 101 basic keelboat sailing is the first step in the ASA sailing progression. The course is family-friendly and welcomes all ages over 13, with no previous boating experience required. The course is completed over two full days and covers basic skills such as preparation of the boat, hoisting sails, rules of the road, points of sail, man overboard drill, heaving to and much more. This course is six to eight hours a day shared between our waterfront training gazebo and our J/22 vessels. Hands-on training includes open water sailing, docking, anchoring, etc. Each day begins at 8:30 am and ends around 5 pm. Upon graduation you will receive ASA certification, and you will be ready to safely and confidently skipper boats of 20 ft. Former students are encouraged to rent the same J/22 boat used for their course to further develop their skills and confidence. All inclusive packages for the 101 course are available with big savings throughout the year.

ASA 103 Certification – Basic Coastal Cruising

After finishing ASA 101 and exhibiting mastery of the skills, the ASA 103 Coastal Cruising Course is the next step in ASA’s sailing progression. We want you to have a strong foothold in the basics so you can come in and expand your knowledge and sailing abilities in the ASA 103 course. After completing this two-day course you will receive ASA certification enabling you to cruise safely in local and regional waters as both skipper and crew on a sailboat of about 33 to 44 ft in length, in moderate winds and sea conditions. Our practical hands-on instruction will show you safety requirements, maneuvering in and out of marina slips and along docks, and basic navigation for both inland and offshore ocean sailing techniques. This course will be taught on board either S/Y Allana (Freedom 44 Cat Ketch) or S/Y Maidona (38′ Custom Sloop).

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“The staff was amazing!! Everyone is so helpful and friendly, the resort itself is simply beautiful.. we had an wonderful time…”

Shana, Facebook