Superior Sailing Lessons in Sunny Key West

Learn To Sail By Day / Enjoy Key West By Night

ASA Certified Training Facility



Southernmost Sailing School offers various packakges to meet your needs. All our classes have a 3 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 to good to be true.

Click on each tab below to learn more about our courses.

Package Discounts Available!


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Bareboat Express to the Bahamas!

Southernmost Sailing School  Opens a New Bare boat Express Adventure To Bimini in the Bahamas.

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Bareboat Express to the Dry Tortugas!

Southernmost Sailing School Opens a New Bare boat Express Adventure To The Dry Tortugas!

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$475/person + tax
(minimum 2 students) for 16 hours of instruction over 2 days.

ASA-Certification-101 Learn to skipper a 26′ 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 26′ 1994 Hunter sloop rigged sail boat with a tiller is the perfect boat to learn in, it also has a 10hp out board.

This beautiful boat can also serve as your room for the night. For just $100.00 a night, you can stay right at the marina, Sunset Marina, on Stock Island (2 miles from down town Key West). Additional folks staying in the boat are only an additional $20.00 per night up to 3 max. This rate is only for our students sorry! and is done on a first come basis.

We can also provide a Beach Cruiser Bike with a basket, lights and a lock for $25.00 for 2 days and an additional $10.00 for each additional day. We also have maps of the area and some discount coupons from time to time.

We try to have 2 students at a time, so if you’re by your lonesome, we need to charge 675.00 for private lessons.

101 Keel Boat is done in light to moderate winds, (oh and by the way the hunter will NOT tip over). 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.

$450/person + tax
(minimum 2 students private lesson $650.00) for 16 hours of instruction over 2 days.

ASA-Certification-103 Learn to skipper a sloop-rigged auxiliary powered 26′ 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 and 2 students, 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.

$550/person + tax
(minimum of 2 people and 2 days) and includes an over night stay at sea.


Private lessons are $950 for 1 person + tax

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 Last Call, this class is also a minimum of 2 days and includes an over night stay at sea. This class covers the information on the different systems on board such as electrical, heads, holding tanks, water systems, minor diesel engine maintenance. Also included is provisioning, cooking plus more on docking and mooring, which is preparing you for the cruising adventure of your life. The price of this trip is flexible depending on the food and lodging. There is a ASA 100 question test as well, but by now we know you can sail!


$425/person + tax

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.

1 student here is fine. for 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!!!

$60/student per hour + tax
(3 hour minimum, limit 4 passengers) on Last Call

Once you have passed all of these tests and exams, you are qualified to Bare Boat “Last Call.” You will be able to take her out, cruise around Key West and have some time to really practice what you have learned.

Southernmost Sailing Perks:

Your class comes with a set of Placard Cards that remind you of the tasks involved to sail safely

  • Flotilla Members (Repeat Customers w/ Certification) get discounts.
  • Stay on sailboat for only $100 a night with any lesson package by reservation only. Additional person only $20 a night. (Staying aboard “Last Call” 26′ Hunter is on a space available basis.)
  • Bike rentals $25 for 2 days. Bikes available are single speed beach cruisers with basket, lights and locks. Each additional day is $10 per bike.