Featured Packages | Sailboat Charters | St. Petersburg

Simple Sailing can arrange any charter you need - below are examples of some of our most popular packages for our sailboat charters:


Corporate Teambuilding

Simply Sailing will tailor your teambuilding charters or sailing event to the needs of your team

Sailboat Weddings

As classically romantic as it sounds, intimate sailboat wedding charters are perfect for the couples who want a private ceremony. The Simple Sailing wedding package includes space for just the two of you and up to four friends on board a beautiful Catamaran sailboat.

Sunset Cruises

Cruise the shores of St. Petersburg as you watch a dramatic Florida sunset. Departing approximately 2 hours before sunset, this relaxing journey can be shared by up to six passengers or can be a romantic experience for two.

Weekend Getaways

What better way to “get away from it all” than to leave land entirely? Relax aboard the Simiplicity, a luxury catamaran. Simple Sailing offers 2-day and 3-day weekend packages, with optional catering packages available.

Learn to Sail

The best way to learn to sail is by sailing! Our experienced sailing school instructors will guide you in every aspect of operating a monohull or catamaran, from launching and all the way back to port. Contact us today to arrange lessons or a learning cruise, or learn more about our classes below.