Pensacola Sailboat Charters

Two Hour Sunset Cruise:  $400

Grab your favorite beverage and anything else you’d like, kick back with some tunes and watch the sun go down while sailing around beautiful Pensacola Bay.

Half  Day (4 Hour Cruise) $600

Whether you want to watch the Blue Angels practice, just sail around and be lazy, or head out to Fort McRee and drop anchor where your party and lounge in the sun, swim or whatever you want. We can make it happen.

Note: For Blue Angel practice flights and shows, contact us for times and availability.

Full Day (8 Hour Cruise)

All the fun of the half day cruise but twice as long! Whether you want to watch the Blue Angels practice, just sail around and be lazy, or head out to Fort McRee and drop anchor where your party can lounge in the sun, swim or whatever you want. We can make it happen.



Are there age restrictions?
Yes, all passengers must be at least 6 years of age.

The times listed don’t work with our schedule.  Can we go out at a different time?
This is entirely possible depending on our schedule and other bookings.  Contact us directly before booking to see if you can customize your cruise.

Will we share the boat with other people?
No, all charters are private with a maximum of six passengers. The only other people on board are the captain and crew who are sworn to the sacred of oath of what happens on the boat stays on the boat. This is your day. Be the pirate you want to be.

Can you make special arrangements for special occasions?
Absolutely! Birthday? Proposal? Bachelorette party, Anniversary? Something else? If you have something special in mind, just connect with us well in advance of your cruise and we’ll do everything we can to make sure to make sure your special day is perfect.

Where do we get on the boat?
Passengers will be picked up and dropped off at Community Maritime Park Public Marina located next to the Blue Wahoo ballpark. Please note, that on game days you may have to pay for parking.

What to bring

  • The most important thing to bring is a great attitude! It’s time to leave your worries behind and enjoy your day on the water.
  • Sunscreen, swimwear, beach towel or anything you think you might need to survive a day in the sun.
  • While we keep snacks and a limited amount of drinks on board for our guests, if you want to bring your favorite adult beverages or food we’re happy to keep them in our cooler or freezer.

Are we going fishing?
No, while we love a good fish dinner as much as the next pirate, these are strictly sailing cruises.

Can we bring our pet?
As adorable and loveable as your pet most certainly is, we don’t allow pets.

Are there any other restrictions?
We’re glad you asked! Yes, we do have a few just to keep everyone as safe as possible.

  • If you have mobility issues, we may not be able to accommodate you. Boarding and moving around the boat will require bending and climbing , plus the motion of the boat moving through the water does require balance.
  • Alcohol – We absolutely don’t mind you drinking your favorite adult beverages if you’re of legal age, but for everyone’s safety we ask that all members of your party to keep their consumption in check.
  • The captain is in charge and makes the rules. The captain reserves the right to take the boat back to the dock for any reason he deems necessary for the safety of the crew and passengers (whether that be bad weather or mutiny).


The Pirate Professor

Captain Billy Reeder was a tenured multimedia journalism professor from Arkansas who had worked in the world of communication and journalism for more years than he cares to admit.  One fateful day, many years ago, while driving down the road he stopped at a small marina outside Little Rock that had a dock full of old neglected sailboats just floating there and desperate for some attention.  While he was wandering the docks looking at the boats and dreaming of turning to a life of piracy, the marina owner came out and during a short but productive conversation, our dear professor made a handshake deal to build a new website for the marina in exchange for a boat of his choice, sailing lessons, and a slip at the marina.  Over the next few months, he brought that little San Juan 24 back to life and taught himself to sail.  A couple of years later, he sold that boat for a 37′ sailboat down on the Gulf of Mexico and spent a few more years making Corpus Christi, TX his homeport.  There, he got a lot more salty, tan and tattooed.  In 2023, he left the world of academia and restored a classic ocean crossing 42′ sailboat to continue that life of piracy he dreamed of all those years ago. In 2024, he decided to chase the horizon and made Pensacola, FL his new homeport.  These days, instead of staring at a computer,  he’d rather spend his day hanging out with other salty souls and swapping stories.  You can call him Cap, Cap’n, Billy, Reeder, Professor, Pirate, O’ Captain My Captain, or the most common “Hey you.”

The Boat

S/V Mistress is a 1988 Tayana 42 that was built to cross oceans.  She’s big, she’s comfortable and she’s fast.  However, when the pirate found her, she was just about at the end of her days.  But, it’s amazing what a little love, and a lot of time, money and work can do.  She’s back to eating waves and chasing sunsets.