Custom Charters

We have an excellent selection of large and small craft to cover almost any of your boating needs. The most popular packages are the sunset cruise, half-day cruise, and the full-day cruise. We also offer multi-day charters and weekend getaway packages (which can include hands-on ASA sailing lessons). - If you have a more specific destination in mind, our knowledgeable and friendly staff can help you create the perfect trip.

Planning a party or other special occasion? Simple Sailing can help with that too! The Simplicity serves as a unique setting for your event, and we can arrange meals for your guests, arrange transportation, or provide for other special needs. Just ask! - If you'd like more extensive planning assistance for your meeting, wedding, memorial, or another gathering, we can recommend a St. Petersburg Meeting Planner to handle all the arrangements.

Popular Single Day Packages



Sunset Cruise

Nothing is quite as romantic as watching a sunset next to someone you love. Tampa Bay is known for its world famous sunsets and there's no better place to be than on the water. 

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.


Half-Day Cruise

If you're in town for a visit then taking a half-day cruise one of the absolute best ways to see the city. We have many beautiful destinations like Egmont Key, along with some great waterfront restaurants, beaches, and ports catering to boaters.


Full Day Cruise

Tampa Bay is a wonderful area to experience by boat. We have some incredible water-front restaurant and locals between Tampa and Sarasota that cater to boaters. We also have some gorgeous tropical locations like Egmont Key, that have beautiful white sandy beaches, reefs, and historic forts to explore.




Multi-Day Charter

Ready for an adventure on the high seas while experiencing a true taste of tropical bliss? Journey port to port to sample Southern Florida's waterfront cities, or just a relaxing while you vacation in tropical paradise... Florida has some amazing destinations to enjoy. Start by journeying port to port to sample which area has the best waterfront food and entertainment. Or simply kick back and enjoy the tropical splendor of Southern Florida. -


Multi-Day ASA Onboard Class - Want to Whats cooler than enjoying a multi-day sailing adventure... How about learning to sail with onboard sailing lessons too! You may be captaining your next charter!





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.

Your wedding can take place under sail, at dockside or even on a quiet beach. Whatever you decide, Simply Sailing can arrange it all, from a professional to perform the ceremony to catering and photography.


Teambuilding Events



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

  • We can organize a tightly structured event or provide a less structured event. Sailing allows your team to enjoy themselves and spend quality time together away from the stresses of the office. A sample itinerary might look like this: Sample Itinerary
  • Sailing on Tampa Bay is an excellent way to build all aspects of your team.
  • A perfect way to strengthen relationships with key clients.
Simply Sailing can provide Corporate Sailing Charters on The Simplicity or the other boats in our fleet or regattas which include a combination of sailing instruction, team-building, and competition. We know all of the other charter boats on Tampa Bay and work to arrange the best boats and captains for your event.


Boat Club Membership

Simple Sailing offers a Sailing Club for frequent charterers. Membership benefits include:

  • Unlimited sailing on select yachts*.
  • Discounted charter fees.
  • Discounted ASA Sailing Lessons.
  • Social events, seminars and more for members!

*Unlimited sailing available on yachts which are not otherwise chartered. Captain's fees not included, if applicable. 


Yacht Share Program


Through Simple Sailing's Simple Share program, you can enjoy sailing a luxury catamaran on your schedule, without the expense and hassle of maintenance and upkeep. Contact us today to find out more about this exciting program!


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.