The Fleet

The Simple Sailing fleet is the most well-maintained group of charter sailboats in St. Petersburg. Simple Sailing Charters prides itself on our fleet, and promises every charter customer will be given a clean, like-new sailboat for their sailing adventure.

In addition to Simplicity, our flagship, Simple Sailing has an extensive fleet of charter sailboats in St. Petersburg to meet any charter needs. In addition to the boats shown here, Simple Sailing has standing arrangements with many other charter companies for sailboats of all sizes and types - just ask, we can arrange the perfect charter for you! Whether you want a sunset cruise, a day sail around Tampa Bay, or a multi-night charter to any of our featured destinations, Simple Sailing's sailboat fleet in St. Petersburg will meet your needs.

Check out the Simple Sailing fleet below:


Andiamo Sailboat: Catalina 28

Sandy: Duffy 21

Futura: Catamaran 39

Believe Sailboat: Hunter 27 

Salty: Duffy 21

Lorikeet: Jeanneau 38

Excitement Sailboat: Hunter 22

Buster: Duffy 21 

Bella: Hunter 36

Explorer: Fishing Boat

Dream: Hunter 36

KarAmour: Swift Trawler

Our sailing fleet is based on boats from Hunter Marine, chosen for their reliability as well as their sailing capabilities, and complemented by our Leopard luxury catamaran. Many of our customers enjoy their sails on a Hunter sailboat so much, they consider purchasing a Hunter boat or joining our boat club for continuing sails.

For 2012, Simple Sailing Charters will be adding a 2nd luxury catamaran to our fleet as well as additional Hunter monohull sailboats. Simple Sailing continues to expand and upgrade our fleet on a constant basis to ensure our customers have a wonderful sailing experience. To schedule a charter sail, call us at (727) 362-4732