| (877) 964-7245 |

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

101, 103, 104, 105, 106, 111, 118

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, Basic 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, Basic Coastal Cruising

Contact Information


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