Kathleen D Sailing Catamarans

A Memorable Adventure Awaits!

Sarasota & Siesta Key, Longboat Key

and Anna Maria Island

Kathleen D Sailing Catamarans

A Memorable Adventure Awaits!

Sarasota & Siesta Key, Longboat Key

and Anna Maria Island

Your Options are endless with tours ranging from a

2-hour cruse to a Full Day Sailing Excursion.

Are you looking for an up-close wild dolphin experience?

Or do you dream of a Sunset Sail or a Moonlit evening cruse, 

With Us, you can make your dreams a reality.

 

Kathleen D Sailing Catamarans

Set Sail into Suncoast Splendor

Welcome to Kathleen D Sailing Catamarans, the crown jewel of Florida’s Suncoast sailing charters. Since setting sail in 2007, we’ve had the privilege of turning the majestic sea into a backdrop for unforgettable experiences for thousands of guests, ranging from international visitors to our cherished local community.

At Kathleen D, we believe in making the majesty of the sea accessible to everyone. That’s why we offer a variety of sailing adventures tailored to fit any schedule and budget. Choose from our exhilarating 2-hour sails, immersive 3-hour voyages, or the ultimate escapade with our half-day Adventure sails — all designed with family-friendly pricing in mind.

Discover the beauty of Florida’s coast from the unique perspective of our state-of-the-art catamarans. Whether you’re exploring our range of locations and services, booking your next adventure online, or preferring a more personal touch by calling us, we’re here to ensure your sailing experience is seamless and memorable.

Embark on a journey with Kathleen D Sailing Catamarans. Your sea adventure awaits.

See you on the water!

Our Locations & Packages

At Kathleen D Sailing Catamarans, we offer an unparalleled sailing experience across three beautiful locations: Sarasota, Longboat Key, and Anna Maria Island. Each location provides unique opportunities for public excursions and private charters.

Sarasota & Siesta Key

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Public and Private Sails Available from Here!

Longboat Key

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Private Sails, minimum 4 people.

Anna Maria Island

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Customized Sails, The Home of the AMI Adventure!

Dolphin Watch

Discover Dolphins Our Most Popular Catamaran Sail!

An enchanting 2-hour adventure aboard our spacious catamaran. Perfect for families.

Ready for an unforgettable journey?

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True Sail

True Sail Catamaran Experience: More Time, More Memories!

For those who find that a mere two hours on the water just isn’t enough, our True Sail package offers an extended 3-hour sail that combines the thrill of dolphin watching with the tranquility of the sea. Available in both morning and afternoon sessions, this package is perfect for guests who wish to immerse themselves deeper into the serenity of the ocean.

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Big Pass Adventure

The Ultimate Half-Day Family Fun!

Dive into a half-day of sailing, swimming, and kayaking with our Big Pass Adventure package, designed for family fun and aquatic enthusiasts alike. Enjoy a delicious lunch onboard as you explore the serene waters. Perfect for both morning and afternoon outings, this package includes all necessary water equipment for a hassle-free adventure.

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Sunset Sail

Glide into the Evening with Elegance

Experience the magic of the setting sun aboard our pristine sailing catamaran. Our Sunset Sail departs approximately two hours before sunset, offering a spectacular canvas of vibrant hues and tranquil waters. Perfect for romantic evenings or peaceful reflections, this sail provides an unforgettable ambiance.

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Moonrise Sail

Experience the Magic of Twilight

Once a month, experience a spectacular celestial display as the setting sun and rising moon align over the beautiful Sarasota skyline. Our exclusive Monthly Sunset / Moonrise Sail extends the enchantment with an extra hour on the water, allowing you to fully embrace the twilight transition amid stunning natural vistas. This private sail is a perfect way to celebrate special moments with those you cherish.

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Anna Maria Island Adventure

Your Customizable Escape Awaits!

Embark on a six-hour journey of fun and relaxation with our Anna Maria Island Adventure. Perfect for groups of six or more, this fully customizable trip takes you to the stunning Egmont Key and Shell Key. Enjoy swimming, kayaking, or simply unwinding on the pristine beaches as you create unforgettable memories. The adventure begins now!

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Our Sailing Catamarans

The Maine Cat 30

Maine Cat 30 - Kathleen D Sailing Catamarans

The Maine Cat 30 is a US built catamaran, built in Maine. They are equipped with 2 Yamaha Outboards each and will cruise at about 6 mph with the engines.

Each catamaran has 3 sails. a Mainsail, a Jib and a Screecher. Depending on wind speed, the Maine Cat will sail up to 10 mph.

The Maine Cat has a spacious cockpit with comfortable seating for 11 plus the captain. There is also room for a cooler. There is a spacious Galley on the Port side hull which has a refrigerator normally stocked with bottled water and space to add your drink of choice.

The galley’s are also stocked with a cutting board, eating utensils and usually plastic cups. The Starboard side hull is where we store swimming gear, pool noodles, masks, snorkels and fins. It also has a marine head. There are also working sinks on both sides.

The Maine Cat 30 also has a spacious seating area on the bow of each hull with nets stretched between the hulls. There is also a pulpit seat on the front of each hull.

We also have kayaks on board for the longer sails, there is time to stop and explore some Mangrove Tunnels or canals along the way.

The Maine Cat 30

Kathleen D Sailing Catamarans

Our second Maine Cat 30 is again a US built catamaran, built in Maine. They are equipped with 2 Yamaha Outboards each and will cruise at about 6 mph with the engines.

Each catamaran has 3 sails. a Mainsail, a Jib and a Screecher. Depending on wind speed, the Maine Cat will sail up to 10 mph.

The Maine Cat has a spacious cockpit with comfortable seating for 11 plus the captain. There is also room for a cooler. There is a spacious Galley on the Port side hull which has a refrigerator normally stocked with bottled water and space to add your drink of choice.

The galley’s are also stocked with a cutting board, eating utensils and usually plastic cups. The Starboard side hull is where we store swimming gear, pool noodles, masks, snorkels and fins. It also has a marine head. There are also working sinks on both sides.

The Maine Cat 30 also has a spacious seating area on the bow of each hull with nets stretched between the hulls. There is also a pulpit seat on the front of each hull.

We also have kayaks on board for the longer sails, there is time to stop and explore some Mangrove Tunnels or canals along the way.

The Stiletto 30

Longboat Key
The Stiletto 30 – Our Sportier Number!

It is also a US built catamaran built here in Sarasota Florida. 30 feet long and 16 ft wide. It has one Yamaha outboard engine and cruises at 6 mph. The stiletto has tiller steering.

The Stiletto has 3 sails. The Mainsail, Jib and a Spinnaker. We normally will only fly the spinnaker with an experienced crew on board. Depending on wind speed, the Stiletto will sail up to 20 mph. The manufacturer will boast it is capable of more and I would not argue the point. The Stiletto is quite fast and agile.

The cockpit has comfortable seating for 6 plus a captain. Each hull is primarily used for storage of the cooler, swimming gear, pool noodles, masks, snorkels, fins, life jackets and kayak paddles. It also has a marine head.

The Stiletto 30 also has a spacious trampoline stretched between the 2 hulls in the front and another aft the cockpit where we typically store 2 kayaks.

Some returning customers will request the Stiletto as it is a very memorable experience.

Florida Suncoast’s Premier Catamaran Sailing Charter

Established in 2007 we have created lasting memories for thousands of visitors and our local friends! We provide 2 hour, 3 hour, and 1/2 day Adventure sails at family friendly pricing. Explore our locations and services, book online or give us a call to discuss our many sailing options.
See you on the water!

Reviews

Rexann Cecil
Rexann Cecil
2024-07-07
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We had a wonderful time with Captain Craig! We saw dolphins, sea horses, and sting rays. It was so beautiful! We’ll definitely be going on another trip!
Martin Camargo
Martin Camargo
2024-07-07
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Our experience with Kathleen D Sailing was absolutely amazing. Thomas was incredibly kind and supportive throughout our trip. The boat ride was wonderfully peaceful, with relaxing music that enhanced the atmosphere perfectly. It was exactly as we had imagined and we wholeheartedly recommend Kathleen D Sailing. This enjoyable experience has even sparked my interest in learning how to navigate a sailboat myself.
Eric Rogers
Eric Rogers
2024-07-06
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Went out with Thomas and had an amazing time! Highly recommended and very toddler friendly!
Andi F
Andi F
2024-06-30
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I had the pleasure of boarding one of the stunningly beautiful catamarans with a group of friends this evening. I couldn’t have imagined a better captain than Captain Kraig. He was very welcoming to everyone on board even my tween. He ensured smooth sailing both figuratively and literally. His knowledge of sailing, the waters, the local history, and his years of experience were displayed beautifully along our voyage. I cannot wait for another trip and memory aboard the beautiful catamaran with Captain Kraig!
Asher Winkle
Asher Winkle
2024-06-29
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Great photography
Paul Bates
Paul Bates
2024-06-11
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With rain threatening, we had the perfect sail, with dolphin sightings, hint of the sunset and a flashing light show to end the night. Our captain was the perfect host.
Hunter Scalf
Hunter Scalf
2024-06-11
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Kevin F
Kevin F
2024-05-25
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Captain Charlie was great. Saw some dolphins on the trip, as well as a beautiful sunset. Boat is clean and comfortable with great seating for a unique sunset sail experience!
n holt
n holt
2024-05-21
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Captain Charlie exceeded our expectations. The boat was clean and comfortable for all, from age 17 to 80. He found dolphins playing, so that was an unexpected treat. He pointed out homes of interest and positioned us for perfect sunset views. Highly recommend as fun for all ages.
Tyler Geyen
Tyler Geyen
2024-05-03
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Captain Craig gave us a great boating experience. Our two young girls said he is nice and caring- he even answered all of our questions, which was a LOT! We couldn’t believe the dolphins came and swam with our boat. Thank you so much for the lovely day! 🐬

Awards & Accreditations

Trip Advisor Award 2023 - Kathleen D Sailing Catamarans
Trip Advisor Award 2024 - Kathleen D Sailing Catamarans

Blog Posts

Sailing Adventure in Sarasota: A Memorable Day on the Water

Sailing Adventure in Sarasota: A Memorable Day on the Water

Sailing Adventure in Sarasota: A Memorable Day on the Water Ahoy, adventure seekers and sailing enthusiasts! Captain Kraig here, recounting an exhilarating journey aboard the Maine Cat 30 with Kathleen D Sailing Catamarans. On June 19th, 2024, amidst the sunny shores...

Kathleen D Sailing Catamarans

The Adventure Starts Here!

Call or Text Us

Phone: 941-896-6400

Email

Email

Address

Marina Plaza (Dock E, Slip 20)
Sarasota, FL 34236

15 + 5 =

Sarasota & Siesta Key

Longboat Key

Anna Maria Island

Kathleen D Sailing Catamarans

2 Marina Plaza (Dock E, Slip 20)
Sarasota, FL 34236

email: [email protected]

Call: 941-896-6400