Kathleen D Sailing Catamarans Launches New Website for Sarasota-Area Sailing Adventures

Kathleen D Sailing Catamarans has launched a completely redesigned website that makes it easier for residents and visitors to explore the waters surrounding Sarasota, Siesta Key, Longboat Key and Anna Maria Island.

The new website, developed and managed by Sande Caplin & Associates, can be viewed at kathleend.net.

The updated site gives visitors a clearer, more visual way to compare sailing experiences, learn about the company’s fleet and experienced captains, select a departure location, check current availability and begin planning a public sail or private charter.

Sailing the Florida Suncoast Since 2007

Kathleen D Sailing Catamarans has welcomed local residents, vacationers, families, couples and groups aboard its boats since 2007. The Sarasota-based company combines authentic sailing with knowledgeable captains, comfortable American-built catamarans and a variety of experiences designed around the natural beauty of Florida’s Gulf Coast.

The company offers public departures from Sarasota, private charters from Sarasota and Longboat Key, and customizable six-hour adventures departing from Anna Maria Island. Each trip provides guests with an opportunity to see the Suncoast from an entirely different perspective—away from traffic, crowded attractions and the distractions of everyday life.

For more context on sailing in the region, see the Sarasota Sailing Squadron story in the Suncoast Post.

Depending on the experience selected, a day on the water can include sailing, dolphin watching, swimming, kayaking, visiting a sandbar, beachcombing or simply relaxing aboard the catamaran while enjoying the scenery.

Six Ways to Experience the Gulf Coast

The new website organizes Kathleen D’s six principal sailing experiences by duration, helping guests choose the outing that best fits their interests and schedule.

The two-hour Dolphin Watch is a family-friendly sailing experience that offers guests an opportunity to search for wild dolphins and learn more about the marine environment. Because dolphins are wild animals, sightings cannot be guaranteed—but that is also what makes every encounter special.

Guests seeking more time under sail can select the three-hour True Sail, while the four-hour Big Pass Adventure combines sailing with opportunities for swimming, kayaking and visiting a sandbar. Lunch and water equipment are included with the Big Pass Adventure.

Kathleen D also offers a two-hour Sunset Sail, a limited three-hour Sunset and Moonrise Sail, and a customizable six-hour Anna Maria Island Adventure that can include destinations such as Egmont Key or Shell Key, depending on weather, water conditions and the group’s preferences.

Public Sails, Private Charters and Special Events

Guests may reserve individual seats on selected public sails or book an entire catamaran for a private experience.

Private charters are available for birthdays, anniversaries, proposals, reunions, bachelor and bachelorette outings, corporate gatherings, client entertainment and other celebrations. Longer private charters provide additional flexibility, allowing the captain and guests to create a day that may combine dolphin watching, sailing, swimming, kayaking, sandbar time and a Gulf Coast sunset.

Guests are welcome to bring a picnic along with beer, wine or champagne where permitted. Hard liquor is not allowed. Routes and activities are always subject to weather and safe boating conditions, with the captain making the final decision when conditions change.

Three Suncoast Departure Areas

Kathleen D Sailing Catamarans serves three of Southwest Florida’s most popular waterfront destinations:

Sarasota and Siesta Key: Public and private sails depart from Marina Jack at 2 Marina Plaza, Dock E, Slip 20, in downtown Sarasota.

Longboat Key: Private sails can be reserved online, while public sail availability may be requested directly from the company. Departures are from the docks behind Harbour Square at 4134 Gulf of Mexico Drive.

Anna Maria Island: Custom six-hour group adventures depart from the Holmes Beach Boat Ramp and may include swimming, kayaking, beachcombing and time at nearby islands.

Visitors interested in other Gulf Coast destinations can also read the Suncoast Post guide to Gulf Coast attractions.

A Fleet Designed for Comfortable Sailing

Kathleen D operates three sailing catamarans: two Maine Cat 30 vessels and a Stiletto 30. The American-built catamarans provide generous deck space and a stable sailing platform, giving guests room to move around, relax and enjoy unobstructed views of the water.

Online reservations are available for groups of up to six guests on the Maine Cat vessels. Parties of seven to eleven can contact the company directly to discuss availability and arrangements.

The crew is led by owner and operator Captain Kraig L. Stull, a USCG Master Captain with a 100-ton license, sailing and towing endorsements, and extensive experience on West Florida waters. The team also includes booking agent Jil Penkava and licensed captains Thomas Stull, Fred Means and Charles Alexander Jenkins.

Kathleen D Sailing Catamarans has received Tripadvisor Travelers’ Choice recognition in 2023, 2024 and 2025. The company is also connected with Visit Sarasota County, the Longboat Key Chamber of Commerce and the Siesta Key Chamber of Commerce.

A New Website Built Around the Guest Experience

The redesigned website allows visitors to compare trips, explore sailing locations, meet the captains, view the fleet, read guest reviews and access live booking calendars from a computer, tablet or mobile phone.

Rather than requiring visitors to search through multiple pages for basic information, the new design places trip duration, departure location, public or private availability and booking options at the center of the experience.

Visitors can begin planning their adventure at kathleend.net and follow Kathleen D Sailing Catamarans on Facebook.

For questions, private-charter requests or assistance selecting the right sailing experience, call or text 941-896-6400 or email kathleendsailingcatamarans@gmail.com.

Whether the goal is spotting dolphins, celebrating a special occasion, enjoying a Sarasota sunset or spending an unhurried day exploring the islands, Kathleen D Sailing Catamarans offers an inviting way to leave the shoreline behind and experience the Florida Suncoast from the water.

Related Stories

• Sarasota Sailing Squadron Set to Host 50th World Sunfish Championship
• 10 Tourist Traps on Florida’s Gulf Coast That Are Actually Worth Visiting
• Discover Your Dream Vacation at Siesta Key Bungalows

Photos from Kathlene D Website