Package Rates

Key Sailing Charters off Longboat Key on      the Gulf of Mexico in Sarasota Florida

6′ 5″ of Headroom, 2 Private Heads and Showers.  Many open ports that enhance lighting and ventilation

Prime vendor of Ritz Carlton, Longboat Key Club, Lido Beach Resort, Turtle Beach Resort, Hyatt Sarasota, Hyatt Siesta, Hotel Indigo, Siesta Key Bungalows and more!

A true sailing experience, competing in several regattas, and winning the SYC Regatta. Official educational vessel by Sarasota County proclamation.


One to Six guests may enjoy a PRIVATE charter for $330 for 2 hours or $450 for 3 Hours. Ask us about longer charters or larger groups.

YOU may also join a GROUP of no more than 6 strangers (new friends) for $55 per person for 2 hours or $75 per person for 3 hours. Never more than three couples on your date night with us.   

 Other options are available as we personalize the guest list, route and snacks for each cruise.

 Gift certificates can be e-mailed to you the day they are ordered!

As winner of the Sarasota Chamber of Commerce 2012 International Business of the Year, Key Sailing is, “Sarasota’s International Ambassador from the Water.” 

We want to make YOUR cruise as enchanting as possible.  

In the last 5 years, the majority of Key Sailing guests have chosen PRIVATE charters for 6 or fewer guests. 

Although this is not your only option, we especially enjoy this type of customized charter.  

A larger boat with fewer guests means more “room to roam in sun and shade,” and more personal attention for YOU.  

 Personalized group charters and customized private charters means: “Never a crowded boat ride.”

We make sure that “Date Night” for mom never includes a sail with someone else’s children and we personalize every group sail as if it was a private sail.

We treat your sail as if it was our only sail.


We never require a deposit and reserve with just your name and phone number. Snacks and soft drinks are included in all packages, as well as free sailing lessons, photos and EVERYTHING but voluntary gratuity. We are also happy to offer local ideas to cater lunch or dinner for your special anniversary celebration. Each charter is customized for your needs. We have bubbles, silly bands and comfortable life jackets for your children, microfiber snuggies for Grandma to enjoy a winter sunset, and temper-pedic pillows and chocolate for everyone! If you come in the morning, Jan can even make a Starbucks run for your family if you ask her in time! 

Enjoy either music or the quiet of the lapping waves. We will even personalize your route, although the journey IS the destination.

Payment is by check or cash, but not credit card. 

We never charge extra for extra services like wedding ceremonies, marriage proposals on board, or even memorial services. 

(US Coast Guard Master Captain Tim is also a licensed and ordained minister.) 


Life can be stressful, so Key Sailing wants to make your time away on the water as relaxing as possible. 
It is our pleasure to serve you, “fresh air, fine chocolates, and a few hours of peace on earth.”

Choose the Package which best accommodates your Sailing Desires

THE MANATEE -Two hour MANATEE bay charters are great for families in the morning, for a taste of true sailing in the afternoon, or for a spectacular sunset cruise at the edge of the Gulf of Mexico! Perfect for wildlife sightings and for the budget. Our promise to you: We do not have a “quota” and do not cancel our group charters if the boat isn’t full…In fact, we DO usually have a waiting list, so please book your sailing choice as early as possible!

THE DOLPHIN -Three hour DOLPHIN day or sunset charters are our most popular choice to give you that extra hour for dolphin sighting or venturing to the edge of the Gulf of Mexico, or as many guests prefer, heading under the John Ringling Causeway (The Key Breeze is the tallest sailing vessel in Sarasota that fits under the bridge!) toward the Ringling Mansion in the North Bay. You and the captain will plan your route right from the yacht on the day of sail!

THE PELICAN -Four hour PELICAN charters give you enough time for the option of true Gulf sailing. In addition, for those who choose to take the helm, a sailing certificate is provided as the US Coast Guard counts four hours as a full day of sailing instruction! These exclusive sails are offered as private charters only.

Key Sailing in the Gulf of Mexico off the coast of Siesta Key in Sarasota Florida Key Sailing in the Gulf of Mexico off the coast of Siesta Key in Sarasota FloridaCreate your own private Sailing Adventure

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Gift Certificates make a perfect present
for Weddings, Anniversaries, Holidays, Birthdays, Office Employee Rewards, and Real Estate Closings

Just call anytime, 24/7
1-941-346-sail (7245)

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