Meet the YOLO crew – A mix of locals and transplants that help make your Anna Maria Island adventure an unforgettable one. From our USGC Licensed captains, to our knowledgeable crew members and our resident water dog the YOLO crew wants you to feel safe and comfortable when exploring the skies and waters of AMI.



A true Florida Native with a lifetime of boating experience, Ryan is an international parasail trainer, licensed as officer in charge of navigational watch, able to operate commercial towing vessels, and captain a vessel 100 gross tons. He is certified in CPR, first aid, and basic boating safety. During Operation Enduring Freedom, as a member of the military police, Sergeant Davis was assigned to water patrol security for Central Command and was trained in diesel mechanics. Ryan has also captained boats for URS construction surveyors during the building of the Gulf Stream Pipeline. Growing up with the water as his back yard he can tell you all you need to know about the area and its wildlife.


Parasail Captain

Nate was born and raised on Anna Maria Island. He grew up on the water and spent plenty of days at the local Marina his father ran. Today he is able to share his love for the water with his daughters and wife. When Nate is not enjoying the water, he is a full time Fire Fighter at the station down the street. So if you ever have Captain Nate as your captain know that you are in the best of hands!


Tour Captain

Captain Mark has been living on this beautiful Island for over 35 years (which is 5 years longer than he’s been alive if you believe him). Originally from Ohio he moved south and forgot the way home. He has held a Masters 50 ton license for over 20 years and has more knowledge of the local wildlife and environment than anyone we know. Before he joined us at YOLO he operated a 40ft Charter vessel, delivering boats to and from the Caribbean, Miami and the Keys, educated the youth of today as a teacher for over 15 years and even moonlighted as a super hero at weekends! He now works with us as our Sight Seeing Captain and we are lucky to have him.


Sailboat & Shuttle Captain

John loves a good adventure. Previous to coming to Anna Maria Island, John was a white water rafting master guide. He has done over 1000 trips and is an expert on the water. But now he has fallen in love with the tropical weather of Bradenton. John is an excellent shuttle captain making sure your trip out into the gulf is informative and exciting!


Parasail Crew & Fishing Captain


Fishing Captain

Scott lives and breaths anything related to fishing. He is so confident in his fishing ability his tag line is “He guarantees to catch at least 1 fish”. Scptt grew up in Bradenton but originally hails from Tennessee. His southern roots run deep, country music, hunting, and comfort foods are some of his favorite things.


Parasail Crew

Kayleen is another Bradenton Native. She loves any out of door activity and usually brings a fishing pole to cast in the water after her parasailing crew shift. Currently finishing up her nursing degree, Kayleen has one of the kindest hearts you will meet.


Parasail Crew & Office Mate

Morgan has lived in the AMI area for 20 years now. She loves anything to do with being on the water & soaking up sunshine! While she’s not in our office taking reservations or crewing on the parasail boat, you can find her in her classroom teaching 5th graders!