Southern Most Sailing School
Key West, Florida Keys
| (305) 407-4141 |

When you come to KeyWest to take your sailing classes you will be in a Tropical or subtropical area of Florida. Our prevailing winds are from the South East and we separate the Gulf of Mexico and the Atlantic Ocean with our narrow peninsula. This means we can get the benefit of the Ocean Breeze but not the big waves on the Gulf side.  When you’re trying to learn how to sail you can concentrate on just that and not be tossed around by 4 to 6  foot waves like you might be if you were sailing on the Atlantic Ocean side of KeyWest.

We are located at Sun Set Marina in Sunny Key West a modern marina with floating docks and great amenities.

We are 1.5 miles from the Key West Airport classes begin at 9 am and end at 4 pm so you can Learn by Day and explore Key West at Night.

We use a 30′ Catalina Obsession MkII with an electric motor – the perfect boat to learn on.

American Sailing Certifications Offered

ASA 101, Keelboat Sailing 1
ASA 101, Keelboat Sailing 1
Learn to skipper a 20' - 27' sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards.
ASA 103, Coastal Cruising
ASA 103, Coastal Cruising
Learn to skipper a sloop-rigged auxiliary powered 25'-35' keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety and seamanship.
ASA 104, Bareboat Cruising
ASA 104, Bareboat Cruising
Learn how to sail a sloop-rigged, auxiliary powered 30'-45' sailboat during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring / mooring, docking, emergency operations, weather, and more.
ASA 118, Docking Endorsement
ASA 118, Docking Endorsement
The successful sailor will have the knowledge and skills to safely and competently dock and maneuver a sailboat under auxiliary power in a variety of conditions. Includes knowledge of steering and propulsion theory, wind and current, single and double-rudder monohulls, catamarans, safety precautions, knots and line handling, fixed and floating docks.

Other Services Available

  • Women Only Courses
  • Couples Courses
  • Private Courses
  • Weekday Courses
  • Weekend Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)
  • Sunset Cruises


ASA Veterans Sailing Education Program - Sign Up Now >>

At ASA we recognize the sacrifices made by the brave men and women who have served or are serving in our country's armed forces. As a token of our appreciation, and our way of saying thank you, we are inviting veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Basic Keelboat Sailing course. Southern Most Sailing School is offering a minimum of $50.00 or 10% off their ASA 101 Basic Keelboat Sailing course.

Contact Information

Southern Most Sailing School

Address 5555 College RdKey WestFL33040United States
Phone (305) 407-4141
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