Superior Sailing Lessons in Sunny Key West

Learn To Sail By Day / Enjoy Key West By Night

ASA Certified Training Facility



Mother, mother Ocean I have heard your call,
Ive wanted to sail upon your waters,
since I was 3 feet tall.
Now is the time to make the call!
I hope to be sailing with you soon!
Captain Brad

Overnight trips to the Marquesas and Boca Grande

Southernmost Sailing School opens a new overnight adventure to The Marquesas Key and Boca Grande!

ASA Keel Boat 101 Class
(maximum class size 4 students) for 16 hours of instruction over 2 days.

2 Person Deal: $1750.00

ASA-Certification-101 Learn to skipper a 30′ sailboat 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.

Our 30′ Catalina boat has an electric motor, steering wheel and is air conditioned.

We try to have at least 2 students at a time, so if you’re by your lonesome, we need to charge $1270.00 for private lessons.

101 Keel Boat is done in light to moderate winds. Our practice area is only 1 mile from Beautiful Sunset Marina and is protected on 3 sides by land, so even if, there is a lot of wind, we are pretty well protected and its only 10 feet deep in the whole area and we never lose sight of land.

Easy Peasee, and it’s really fun. Through my training, you will be able to pass the ASA 100 question Test and on the water sailing exam.

Call to book today at 305-407-4141.

ASA Coastal Cruising 103 Class

(maximum class size 4 students) for 16 hours of instruction over 2 days.

2 Person Deal: $1800.00

Private Lesson: $1176.50

ASA-Certification-103 Learn to skipper a sloop-rigged auxiliary powered 30′ 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. This class is also minimum 2 days, about 4 hours in the class room and 12 to 14 sailing on a course, usually to a Beautiful Reef for a lunch break and snorkel. You are going to know Chart Navigation with all the fun tools and a GPS, more sailing and boat handling, sail trim safety, and communications at sea, will prepare you for the ASA 100 question test and on the water sailing exam.

Call to book today at 305-407-4141.



ASA Bare Boat 104 Class

2 days and includes an overnight stay at sea and includes all meals

2 Person Deal: $2200.00

ASA-Certification-104Private lessons are $1800.00 for 1 person

Learn how to sail a sloop-rigged, auxiliary powered 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.

On Obsession, this class is also a minimum of 2 days and includes an overnight stay at sea. This class covers the information on the different systems on board such as electrical, heads, holding tanks, water systems, minor electric motor maintenance. Also included is provisioning, cooking plus more on docking and mooring, which is preparing you for the cruising adventure of your life. There is a ASA 100 question test as well, but by now we know you can sail!

Call to book today at 305-407-4141.


ASA Docking Endorsement 118 Class

$900 per day

*Additional rates apply for docking course on personal vessel

ASA-Endorsement-118Learn basic docking skills for boats with single inboard or outboard engines. Discover the basic theory and hands-on techniques needed to dock and undock boats in an efficient manner and without damage or injury. 16 hours of instruction over 2 days learning how to get on and off the dock like a pro in all different situations understanding the forces that affect the single engine vessel and how to control them. There is a 33 question test at the conclusion of the class and a certification for your log book. We can also provide extra time to work on docking with any other class at an hourly rate. Help stamp out DAD, Docking Anxiety Disorder!!!

Call to book today at 305-407-4141.

ASA 111 Sailing Refresher Class

Full day – $900.00 for 7 hours (student only)
Ride along fee for up to 3 additional people – $200.00 

Half day – $600.00 for 4 hours (student only)
Ride along fee for up to 3 additional people – $200.00 

Half to full day on-water skills review clinic is targeted to meet the needs of ASA certified sailors who either need a “refresher” or those who sail more regularly that wish to get focused instruction in a few areas (e.g., docking, sail trim, etc.).

Call to book today at 305-407-4141.

Discover Sailing Cruise

Half day – $600.00 

Not sure if you are serious about learning to sail? Come aboard our vessel for 1/2 a day and see if sailing is for you. Get a taste of basic sailing skills before signing up for a class.  Meet the captain/instructor, drive the boat, listen to some good music, relax and even watch the sunset.

Call to book today at 305-407-4141.

Additional Sailing Hours - $150.00 per hour
Additional Day of Sailing - $900 per day

If you are a student and would like to add another day of sailing its $900.00 per day for the boat the captain and fuel etc. So take an extra day to go out after completing your course to hone your skills and bring the whole family.

Southernmost Sailing Perks:

Your class comes with a set of Placard Cards that remind you of the tasks involved to sail safely. So that after you’re back home you can use this waterproof set of 8 informational business card size placards which cover safety, raising and setting all sails, man over board recovery, getting underway and much more. See them in our shop.

  • Flotilla Members (Repeat Customers w/ Certification) get discounts.
  • All our prices are all inclusive and do not include any additional fees.
  • Ask about our live aboard experience during your sailing class


Package Discounts Available!


Southernmost Sailing School offers various packakges to meet your needs. All our classes have a 4 person maximum in order to ensure personal attention to get the most out of your class. If you prefer to learn on your own, we also offer private lessons.

Our day begins at 9:30 AM in the boat. We recommend bringing the following:

  • Lunch
  • Sun screen
  • Hat
  • Sun glasses (polarized work the best on these sunny waters)
  • Jacket
  • Camera
  • Snorkel gear (if you have it)

We will be back at the docks by 4pm,  so you have time to clean up and go out for the evening on the bikes. LEARN by day and PARTY by night in Key West!

 I know it sounds too good to be true