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Fun, Learning and Safety! 

We know that everyone requires all three to grasp the sailing fundamentals and want to come back for more.

SmarterSail is a school that specializes in private sailing lessons for solo sailors, couples, friends and families. Kids of all ages (well, greater than 4 years old) are welcome to come along as crew. Our courses are liveaboard where the instructor departs after the lessons so you can enjoy the beauty and serenity of water life entre nous – it sure beats the cost of a hotel! And, besides, you’d really rather be on a sailboat…. Right?

We are experienced sailors and ASA Outstanding Instructors who know how to tune in to each sailor’s individual learning style. A good instructor should be able to teach couples, families and children effectively. So, we teach everyone to sail together to be a team on the sailboat, not separately.

Our sailboats are well maintained and equipped with safety and navigation equipment well in excess of the requirements. Our Hunter 295s have depth sounders, DSC/AIS equipped VHFs and moving map GPS chartplotters. PFD use is mandatory on the water. We utilize checklists to ensure that nothing important is overlooked just like with the airlines.

We are a licensed Florida Yacht Brokerage and specialize in representing buyers looking for their sailboats from Maine to Texas. We can even help you if you find a sailboat that is not listed with a brokerage. We help you navigate the survey, escrow, insurance, negotiations and even delivering your sailboat. Don’t go it alone…

You’ll notice that all our pictures are of our sailboats, sailors and destination sails. We work with the reality of sailing to reach your dreams. We do have fun with dock-n-dines and you can stay aboard your sailboat. Sunset and wine in the cockpit is a great way to wind down from a day sailing. Besides, you came to get the whole experience.

We don’t need to talk about the weather. It’s the Florida West Coast and sailing is great all year. We are back at the Gulfport Municipal Marina where we started 14 years ago since our home for the last 8 years (Magnuson Marina Cove) has been sold and is under construction as The SkyBeach Hotel and Marina. Let us show you how easy, safe and fun it is to upgrade your sailing skills!

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 106, Advanced Coastal Cruising
ASA 106, Advanced Coastal Cruising
Learn to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.
ASA 111, Sailing Review
ASA 111, Sailing Review
Desire to improve or re-familiarize sailing knowledge and skills imparted during previous ASA keelboat certification course(s). Student and Instructor jointly decide on goals prior to the start of the review.
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

  • Couples Courses
  • Private Courses
  • Weekday Courses
  • Weekend Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)

Sailing School Reviews / Testimonials

  • My wife and I completed the ASA 101/103 courses with Gary. We were thoroughly impressed. From scheduling to instruction to professionalism to follow through Gary was first class. We're now getting some sailing time under our belt before we go back!

    Marcos M. - ASA 103, Coastal Cruising

  • Had a great instructor. We had private lessons on our boat and our schedule. Learned so much and has boosted our confidence level. If you need lessons the instructors at SmarterSail are patient and very knowledgeable and I highly recommend them. 

    Gina S. - SmarterSail

  • I’ve been on a few boats, but I must say that the 29.5 is the nicest! A bed I actually fit in, air conditioning, beautiful setting. It was a great way for my wife and I to spend our 25th anniversary! We just completed the ASA 103 & 104 course.

    William R. - SmarterSail

  • My husband and I celebrated our 50th anniversary earning ASA 101,103 and 104 certification with SmarterSail. Altogether it was a week that was rewarding, memorable and fun. You’ve earned an “A” from us on quality of instruction and hospitality.

    Delores T. - SmarterSail

  • My husband and I really enjoyed our weekend ASA 103 course with Gary. He's an attentive instructor with extensive experience that made the required parts much more interesting. I definitely rate Gary highly...

    Vicky Z. - ASA 103, Coastal Cruising

Contact Information


Address Gulfport Municipal Marina4630 29th Ave SGulfportFL33711United States
Phone (877) 964-7245
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