Sail away with us!

Our competent team is looking forward to helping you build your sailing skills.

About Charisma Sailing

Learn to sail or earn advanced sailing certifications through our US Sailing Accredited School with locations in Key West and Miami, Florida.

At Charisma Sailing, we are passionate about helping clients discover the mind-altering beauty and tranquility of sailing and the feeling of freedom on the open water.  From learning to sail to bareboat charter certification, we offer personalized pathways to sailing proficiency.

We have made it our mission to teach environmental protection through experiential marine education. Our operations are following ocean-safe procedures and we are in the process of seeking certification through the Blue Star Diving program that promotes responsible diving and snorkeling practices to enhance visitor appreciation and understanding of the marine ecosystems within the Florida Keys National Marine Sanctuary. 

From novices to advanced sailors, our individualized programs are designed to help improve our clients’ sailing skills safely and with confidence. Students of all levels learn under the guidance of experienced US Sailing certified instructors, who have a passion for teaching and sharing their knowledge.

We specifically train and certify new yacht owners and those who are planning to charter or own a yacht in the future. In addition, boat owners can place their boat in the capable care of the highly qualified staff and crew of our Yacht Management division at any of the Key West marinas. We are always looking for business partnerships!

Captain Robert Gardner

Charisma Sailing was founded by Captain Robert Gardner to offer personalized pathways to achieve sailing proficiency and certification with US Sailing instruction, courses, and certifications in both Key West and Miami.

Captain Rob was born and raised in Chicago, where he owned and operated a commercial construction and real estate management firm, but traveled and sailed all over the world during the Chicago winters. 

He has been sailing the Great Lakes and inland waters since the age of seven, and is a USCG Masters-Licensed Captain, US Sailing-Certified Instructor, and holds NOLS/WMI and American Red Cross Medical Certifications.

Rob’s experience includes both command and crew on sailing and motor yachts ranging from 30’ to 70’ throughout the Great Lakes, Mediterranean Sea, Atlantic Ocean, Caribbean Sea, and the Gulf of Mexico. He has worked as a Charter Captain, Delivery Captain, and Sailing Instructor, and is skilled in all aspects of boat operations, maintenance, and fleet management. He also has a great deal of personal experience from 4 years living aboard his own Dufour 450.  

Although always an avid sailor, he is also passionate about environmental protection, teaching, experiential education, and youth development. His past experience included Wilderness Adventure Expedition Leadership and Outdoor Instructor for youth and adults. 

He genuinely loves meeting new students and will be happy to share his sailing experience, local and environmental knowledge.

Captain Rob is available for individualized sailing and boating instructions, including basic cruising, bareboat cruising with catamaran endorsement, and coastal navigation.