Pontoon Rental With a Captain in Gulfport
Rent the 2026 TriToon and hire an experienced local captain from our list, so nobody in your group has to drive.
Gulfport, Florida
How A Bareboat Rental Works
A bareboat rental is two arrangements that happen on the same day. You rent the boat from us, and you hire an experienced captain separately from a list of local freelancers. Here is exactly how it works.
You book the boat through our booking system. Then you choose from the freelance captains for hire, contact that captain directly, and pay them on the day of your rental. Gratuities are appreciated.
Step By Step
How the Two Bookings Fit Together
Here it is in four steps. You are not buying a charter with a captain included. You are renting a boat from us, and hiring a captain yourself.
You Rent The Boat
Reserve the 2026 TriToon through our booking system.
You Hire A Captain
Choose from our experienced captains for hire. Every name on that list is vetted, and each one works independently.
You Contact Them Directly
Agree on your departure time and where you want to go. The captain plans the day around your group.
You Pay Them Dockside
Payment goes to your captain directly on the day of the rental. Gratuities are appreciated.
Why Hire a Captain
Every captain on the list is experienced and vetted for your safety, however, you can hire any captain you wish. Reach out to the captain you choose, agree on a departure time, and settle up dockside on the day you go out.
Hiring a captain makes sense for two reasons. Drinking is the first. The authorities treat impaired operation on the water as seriously as they treat it on land, so if anyone in your group plans to have a drink, someone else should be running the boat. Sit back, have a cold one, and let your captain do the driving.
Local knowledge is the second. Boca Ciega Bay, the Intracoastal Waterway and the passes near Shell Key are easy places to lose your bearings if you have never run them. Every captain on the list is local and knows these waters well. They also make great tour guides, and they can point the day toward the sandbars, beaches and waterfront stops your group wants most.
Captained days often run north up the Intracoastal toward Madeira Beach and John's Pass, or south to Fort De Soto and Egmont Key. Groups looking at boat rentals in Madeira Beach can reach it from our dock in the same afternoon.
PINELLAS CAPTAINS WHO KNOW THE PASSES
Local Captains, One Home Dock in Gulfport
The captains on our list run these exact waters week after week. They know which sandbar near Bunces Pass still has water under it at low tide, and which one to leave until the tide turns.
They also know the manatee zones through the Intracoastal Waterway, the current at the passes, and where the shade sits at midday. Ask about the downtown St. Petersburg waterfront, Pass-a-Grille or Shell Key Preserve and they will tell you where to go. Our pontoon rentals in Gulfport start close to all of it, and the pontoon boat gallery shows what those days look like on the water.
Read The Room
When Hiring a Captain Makes Sense
Serving
Captained Days Across Pinellas County
Where the day goes depends on your group and the tide.
Captained Rental Questions
You rent the boat from Tampa Bay Pontoon Rentals and you hire the captain separately. Two arrangements, one day on the water. We provide the 2026 TriToon, and the captain you choose provides the operation.
You contact the captain directly, and you pay the captain directly on the day of your rental.
You pay your captain directly on the day of your rental, and gratuities are appreciated.
Each captain sets their own terms, so ask when you contact them to confirm your date.
Yes. Our captains are experienced and vetted for your safety. Hiring one is not a requirement, though we encourage it if you do not have boating experience.
You can hire any captain you wish from the list. Availability varies by date, so reaching out to two of them is a smart move on a busy weekend.
In the event of inclement weather prior to boarding, your tour can either be rescheduled or refunded. If the Captain has already left the dock and must return prior to the completion of the tour, a discount will be applied in increments of 25%, 50%, 75% depending on length of voyage.
The full weather, refund and dog policies sit in our rental FAQ.
Fishing and watersports are not offered at this time. Captained days are cruising days: sandbars, beaches, the Intracoastal Waterway and the bay.
Our Tampa Bay boating blog covers where local groups tend to go and what to bring.
Let a Local Captain Take the Helm
Reserve the boat first, then reach out to a captain from the list. Most groups have both locked in within a day.
Still deciding? Weigh this rental against the pontoon rental (no captain).