Freelance Captains For Hire
Experienced local captains you can hire for your rental day. Each one is independent, so you contact them and pay them directly.
Independent Local Captains
How Hiring a Captain Works
Our captains are experienced and vetted for your safety. Although not a requirement, we encourage you to hire a captain if you don't have boating experience.
Every captain below is an experienced freelancer running their own business. Each one keeps their own schedule and sets their own rates, so you call the one you want, check they are free on your date, and settle up with them on the day.
That two-part booking is what a bareboat arrangement is. We rent you the 2026 TriToon, and separately you engage a captain to run it. How the two halves fit together is broken down under the pontoon rental with a captain, which is also where you start the booking.
Read this first
Two Rules That Apply to Every Captain
01
You can hire any captain you wish. You must contact them directly.
02
You will pay your captain directly on the day of your rental. Gratuities are appreciated.
No captain fee runs through our booking system. Ask about rates and availability when you call them.
The Captains
Experienced and vetted. Call any of them to check availability for your date.
Captain James
Capt. James Lowe is a lifelong Florida outdoorsman, licensed captain, and experienced marine professional with extensive knowledge of Florida's Gulf Coast. A former fishing charter captain and current Certified Marina Operator (CMO), James brings years of experience in vessel operations, navigation, marine safety, and boat handling. When he is not working on the water, you will likely find him fishing, boating, hunting, or enjoying Florida's outdoors.
Available Saturdays
(727) 515-1526
Captain Paul
As a Tampa Bay native, I grew up on the water and have spent much of my life enjoying all that the area's waterways have to offer. From powerboating and sailing to waterskiing and jet skiing, boating has always been an integral part of my life. This firsthand experience has given me an in-depth knowledge of the waters throughout Tampa Bay, along with a deep appreciation for the region's boating community and coastal lifestyle.
Available 7 Days a Week
(727) 310-4300
Captain Joe
Captain Joe started boating on these waters in 1972, well over 50 years of experience on the Gulf of America. Since 2010 he has been teaching boating safety for Freedom Boat Club, and he is well versed in different types of boating, inshore and offshore. He knows these waters from Louisiana to Key West, and will teach boating safety as well.
Available 7 Days a Week
(910) 520-0010
Captain Ray
Captain Ray has spent more than 25 years on the water, enjoying Florida's waterways and sharing great experiences with family, friends, and guests. His focus is simple: safety, reliability, and making every trip a memorable one.
Available 7 Days a Week
(813) 363-0477
Captain Brian
A true Florida native and lifelong St. Petersburg local, he grew up on the water and has years of experience operating everything from 55-foot sportfishing boats to Carolina Skiffs, and even a hot dog boat. Whether exploring local islands and sandbars, bar hopping along the Intracoastal, or catching a Florida sunset, his goal is to provide a safe, fun and memorable experience while showing you Tampa Bay like a local.
Available Monday to Thursday
(727) 688-1886
Captain Amanda
Hi! I'm Captain Amanda. I was born and raised in Boston, Massachusetts. Growing up I loved being on my family boat and on the water. After moving to Florida in 2017 I fell in love with the natural beauty of the state. I became a captain at age 25 and I am passionate about sharing my love for the water and marine life with everybody. My top priority is keeping you all safe while you let loose or have a relaxing boat day! I can't wait to set sail with you!
Available Wednesdays & Thursdays
(978) 500-3132
Captain Justin
St. Pete, FL native. Former first responder with two decades of water rescue experience. Water is my passion, and with beach boy vibes your boat day will be one of the highlights of your trip to the Tampa Bay area with Capt Justin behind the helm.
Available 7 Days a Week
(727) 776-6397
Captain Scott
As a retired Sheriff's Deputy from the Marine Unit, I am very familiar with the Tampa Bay waterway area. I have had extensive training in boat operations and safety. I currently hold a USCG 100 ton license and I'm all about safety, while having a great time.
Available Monday to Friday
(813) 477-3041For questions about the boat itself, call us at (813) 445-7223.
Top reasons
Why Groups Hire a Captain
Skip the debate over who drives
Drinking and driving - Yep, the authorities are just as bad on the water as they are on land when it comes to this. Sit back, have a cold one, and let your Captain do the driving.
Local knowledge of these waters
Are you familiar with the Gulfport and Tampa Bay waterways? It's not rocket science, but it is very easy to get turned around and lose your bearings if you're not familiar with the area. Our captains are all local, and know these waters very well.
Nobody in your group has driven a boat
No one in your group has ever driven a boat before. Enough said.
A guide who knows where to go
Our Captains make great tour guides. If you're not familiar with our area, these guys can make suggestions on where to go, and make sure you hit the spots that interest you the most.
Booking the Boat and the Captain
Reserve the pontoon first, because that is the date that has to be locked in. Then pick a captain from the list, call them, and agree on a departure time and roughly where you want to go. Everyone meets at the slip inside the City of Gulfport Municipal Marina.
Captain rates typically run about $50 to $75 per hour, though each captain sets their own and it varies, so confirm it when you call. You pay your captain dockside on the day, and gratuities are appreciated. If you would rather drive yourself instead, a self-drive pontoon rental is the same 2026 TriToon with you at the helm, subject to the Florida age and safety education rules in our boat rental FAQ.
Captained days tend to range further than self-drive days, because the person driving already knows the water. Ask about the sandbars near Bunces Pass, Shell Key Preserve, or the run north toward Madeira Beach and John's Pass.
Lock In the Boat, Then Call Your Captain
Book the boat first, then call a captain to check they are free that day.