4.9/5 stars 24 reviews
  • Phone Verified
  • 20
    Years Boating

About Gary

“ASA Outstanding Sailing Instructor 2014 Sailboat deliveries North to NYC through Caribbean to Belize. ”

Aboard since 2015

From St. Petersburg, FL

Reviews of Gary (24)

  • Captain H was very informative and interesting to talk to. Even though we didn't have much wind, we had a great time!

  • Gary and the experience was great. I’ll definitely be booking with Gary again. Very responsive and a calm instructor. Good conversation as well. Thanks Gary.

  • Had a great time. It was a little stressful as it was my first time with a large sailboat but Gary was quite accommodating and helpful. The boat sailed nicely in the bay and was easy to sail under. Thanks Gary.

  • Captain H did a great job; very professional, knowledgeable, friendly, and helpful.
    I would recommend these guys without a doubt.

  • We had a good day sail on Gary's Hunter 23.5.
    It is conveniently located to sail on Tampa Bay and areas around the Sunshine Bridge in south Pinellas County.
    Gary was quite accommodating and easy to work with on our rental.
    We would rent from him again

  • Very friendly and knowledgeable owner of the Hunter the boat ran great and we had a great time out there in the bay!!!!!! Can't wait to do it again

  • Gary was very professional and accommodated my plans easily. This is a good location to sail from as several tracks are available. The boat is ok, but tired with several items not up to original equipment standards. All safety oriented equipment on the boat was fine. Sailing performance equipment more questionable.

  • A great day on the water. The Hunter sailed great; check-out was fast and simple. Price is very fair (unlike some charters on boatbound). I would definitely charter from SmarterSail again, and highly recommend it.

  • Great first experience with boatbound and Gary. Good little day boat for me and my wife on our first sail in the Tampa Bay area.

  • Great rental experience! Good introduction and briefing on boat and area. Gary walked me though the vessel and made sure I was comfortable before departure. Upon return check-in was easy and we were on our way home in no time. Great location and top-notch service!

  • Great boat and owner. Boat itself is very easy to maneuver and operate. Very wide so it's great for taking a small group out. Gary will spend time with you to ensure you're familiar with the boat. He's an instructor so takes an instructors lens on the orientation. id be happy to rent again

  • Great boat and location. Putted out to Sandy Key, anchored and walked the beach. Great family value for a day of private bay and beach enjoyment. As a beginner sailor the boat handled well and was easy single handed.

  • Gary was very easy to coordinate with. The boat was very practical and spacious if only a little stiff to steer but we had a great day out around egmont key

  • Great overview of the area from Gary. Enjoyed the boat. We had a rousing sail on Tampa Bay hitting 7 knots!

  • Great day of sailing in very windy conditions. Gary keeps his fleet in top notch condition and is a great instructor. I learned a great deal from Gary in preparation for my ASA 103/104 training. I will definitely charter from Gary again.

  • We all had a great time! Thanks!

  • We thoroughly enjoyed our day sail on Gary's sailboat on April 24, 2016. Gary was at the dock to meet us and fill us in on the details of the boat. The boat was easy to sail and handled well both under sail and with the motor. It had everything we needed for a perfect day on the bay (including a swim off the boat) with our son and daughter-in-law. Thank you Gary for making the whole process seamless.
    Chuck and Sue
    Edmonds, WA

  • Gary is a great person to lease from. I have chartered both of his vessels and they are always ready to sail. He puts you through the obligatory checkout sail before sending you on your way. As an instructor, he will be sure to give you at least one morsel of sailing knowledge in that time ;-) . I did a day sail on his 23 and an overnight with his 29.5. Both were as expected and everything was in working order and Bristol fashion. I look forward to chartering from him again and would recommend him and his boats.

  • We had a great day out on the water :)

  • What a fantastic experience! Gary was super communicative, very helpful, and most knowledgable about local conditions and sites to see. We visited from Seattle and felt right at home dealing with Gary. I would recommend checking him out and seeing what he has to offer!

    Smooth Sailing,


  • Awesome experience! A sensible briefing and sail plan. Would not hesitate to charter again.

  • Renting from Gary was a great experience, we thoroughly enjoyed the day on the Hunter 23.5, sailing the gulf along the St Pete shoreline. Gary did a nice job reviewing the boat and helping us get the route planned for the day. He was flexible when the weather turned bad on the original date, he changed it to another date that turned out to be ideal for the cruise. I would definitely like to plan another trip with one of his boats.

  • Gary is awesome. He was very helpful. He was at the boat early and had everything ready. He took the time to make sure we were familiar with this particular boat and the local area. The Hunter is amazing. It's in great shape and it's a joy to sail. I highly recommend renting from Gary.

  • Gary did a great job at communicating expectations. His knowledge of regulations made for an easy checkout process. The boat was perfect for my son and girlfriend to learn the ropes and get around Tampa Bay. The Magnusen Resort is very centrally located whether you are going to be sailing Tampa Bay, Shell island or stopping at local restaurants along the barrier islands. Looking forward to chartering from him again.