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Kathleen D Sailing Catamarans   | Call or Text Now for more information 941-896-6400

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 cruise 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 cruise, 

With Us, you can make your dreams a reality.

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.

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.

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.

The Stiletto 30

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!

Awards & Accreditations

Sail into Serenity: Sunset Cruises from Sarasota, Siesta Key, Longboat Key, and Anna Maria Island

Sail into Serenity! There’s something magical about watching the sun dip below the horizon, painting the sky in hues of orange, pink, and purple. At Kathleen D Sailing Catamarans, we offer unforgettable sunset cruises from Sarasota & Siesta Key, Longboat Key, and...

Transform Your Corporate Events with Kathleen D Sailing Catamarans

Transform Your Corporate Events with Kathleen D Sailing Catamarans Tired of the same old conference rooms and mundane board meetings? Break free from the ordinary and elevate your corporate events with an unforgettable sailing experience on Sarasota Bay. Kathleen D...

The Importance of Regular Maintenance for Our Catamarans

Regular Maintenance for Our Catamarans At Kathleen D Sailing Catamarans, we are committed to providing our guests with safe, enjoyable, and unforgettable sailing experiences. A crucial part of this commitment is the regular maintenance of our fleet to ensure that each...

Sailing Sarasota Bay: The Benefits of Northeast and Southwest Winds on a Catamaran

The Benefits of Northeast and Southwest Winds on a Catamaran Sailing Sarasota Bay in a catamaran is a remarkable experience, especially when you take advantage of the region's favorable wind directions. The geographic layout of Sarasota Bay makes it particularly...

A True Sail Adventure – The Perfect Day Trip: Exploring Sarasota’s Waters with Kathleen D Sailing Catamarans

Exploring Sarasota’s Waters with Kathleen D Sailing Catamarans Sarasota is a treasure trove of natural beauty, offering a perfect blend of vibrant marine life, stunning vistas, and tranquil waters. For those looking to experience the best of what Sarasota’s waters...

Sailing Adventures for the Whole Family: Explore Sarasota and Longboat Key with Our Pass Adventure

Sailing Adventures for the Whole Family: Explore Sarasota and Longboat Key with Our Pass Adventure When it comes to creating unforgettable memories with your family, few experiences can compare to a day spent sailing on the pristine waters of Florida's Gulf Coast. At...

Mono-Hull Sailboats vs. Catamarans: A Comparative Sailing Experience

Mono-Hull Sailboats vs. Catamarans: A Comparative Sailing Experience When it comes to choosing the perfect sailboat, the debate between a mono-hull sailboat and a catamaran is a common one among sailing enthusiasts. Both types of vessels offer unique advantages and...

Weathering the Storms: The Unyielding Spirit of Florida’s Western Coast

Weathering the Storms: The Unyielding Spirit of Florida's Western Coast Living on Florida's western coast means embracing the beauty of the Gulf of Mexico and the challenges of hurricane season. Each year, our community faces the formidable power of hurricanes and...

Experience the Magic of a Sunset Sail with Kathleen D Sailing Catamarans

Experience the Magic of a Sunset Sail with Kathleen D Sailing Catamarans There is something truly magical about watching the sun set over the horizon, painting the sky with brilliant hues of orange, pink, and purple. At Kathleen D Sailing Catamarans, we offer an...

A Magical Sunset Sail: From Gourmet Feasts to Lightning Shows

From Gourmet Feasts to Lightning Shows   If you're ever in Sarasota and looking for a memorable sailing adventure, a sunset sail from Marina Jack is a must. Recently, we embarked on a three-hour voyage aboard a 30ft Kathleen D Sailing Catamaran, and the...

The Adventure Starts Here!

Call or text us.

Phone: 941-896-6400

email: [email protected]

Phone Number

Email Address

Service required Service required Sarasota & Siesta Key Lonboat Key Anna Maria Island Private Sails Public Sails More Information Corporate Events

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

Call: 941-896-6400

You're on Lake Time.

Catamaran cruises

Spirit of America Catamaran Cruise

Scroll down and check out the video with Capt. Matt.  

Get ready to set sail for an unforgettable catamaran cruise and discover Branson’s natural attraction, Table Rock Lake! Join Captain Matt on a Caribbean-style adventure aboard the 48-foot  Spirit of America.  This ocean-rated vessel, operated by a coastguard-licensed captain and crew, has room for 49 passengers.  Bottled water is included, feel free to bring your cooler onboard.  Food/beverages are on a bring-your-own basis.  Alcohol onboard is limited to Beer and Wine only for those over age 21.    

Our most popular catamaran cruise is the 2-hour Sail-Swim Cruise at 1 pm, which includes large water accessories, a giant water slide, and kayaks.  

Private Sail-Swim Charters are available at 4 pm daily, book online.  Other Custom Private Charters are arranged by emailing Capt. Matt: [email protected].  Portside Pizza

Call the marina with general questions: 417.334.2628.      Book Pizza for your Charter!   Call Portside Pizza 417.263.3169 (at least 24 hr ahead) 

Life Jackets are provided for everyone before boarding and must be worn while in the water. Sailing sets your soul free—let’s get on the Spirit!

Boat Video with Capt. Matt

Things To Know

Sailing Catamaran in Beaufort, NC.

Sailing fun for the whole family.

Lookout Cruises offers daily sailing excursions departing historic Beaufort for up to 37 passengers on a 45-foot catamaran with cushioned seating, plenty of shade, and a large clean restroom on board.

Our Cruises

Cape Lookout Cruise

11:00 am – 5:00 pm

The beauty of the Cape Lookout lighthouse and its pristine surroundings is unparalleled. You’ll appreciate the stability and com fort of this 45-foot catamaran as we briskly make the six-mile ocean voyage to one of the premier anchorages in America.

Sunset Cruise

6:30 pm – 8:00 pm

The red and yellow North Carolina sunsets are some of the most beautiful in the world, and they’re yours to enjoy as we sail from the Beaufort waterfront into the gentle breezes of early evening.

Dolphin/Horse Watching Cruise

8:20 am – 10:20 am

You can watch the wild horses and dolphi ns just a few feet from the boat in their natural habitat. We join them every morning, and you can, too! This trip is great for adults and children of all ages.

Moonlight Cruise

9:00pm – 10:30pm

The Moonlight  Cruise runs only during the full moon period, so you’re guaranteed the beauty and tranquility that comes with a perfect moonlit evening. 

What a beautiful day we had. I would recommend this trip if you want to have a good time. The staff and Captain went above and beyond to make sure everything went smoothly. By far one of our favorite trips.

Pamela Hutton

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600 Front St.

Beaufort, NC 28516

United States

Opening Hours

8:30 am – 8:30 pm

+1 (252) 504-7245

[email protected]

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©2024 by Lookout Cruises

Use code BAREFOOT for 10% off Guided Tours!

Catamaran Cruises in Key West, FL

Escape the downtown crowd - cruise with billy.

Key West’s nautical history is all based on its proximity to the world’s 3rd largest living coral reef. From pirates and privateers to ship wreckers and fisherman the draw has always been the sanctuary provided by the Florida Great Barrier Reef.  Key West’s coral rock islands trace a contiguous pathway from the Atlantic Ocean & Gulf of Mexico intersect all the way to mainland Florida. To this day our primary industry, tourism, celebrates our unique natural ecosystem in the shadow of the reef. 

Whether you want to cruise a couple of hours, island-hop all day, or see our beautiful wildlife, Billy has you covered! Bring your reef-safe sunscreen, and we’ll take care of the rest!

Ticketed Tours

• Kid Friendly!
• Clock 3.5 hours
• Info Up to 36 people
• Users All ages

Dolphin Watch & Snorkel Tour

Search for wild dolphins in their natural habitat and snorkel Key West’s backcountry waters off the Seabreeze!

• Most Popular Cruise
• Clock 2 hours
• Info Up To 38 People

Key West Sushi & Sunset Cruise

Dine on fresh sushi while taking in the famous Key West sunset. You will cruise past the southernmost point of the U.S., tropical beaches and a Civil War era Fort Zachary Taylor Historic Sate Park.

Private Experiences

• Our Newest Boat
• Clock 2 to 8 hours
• Info 1-6 People

Barefoot Private Charters

Create the perfect outing for up to 6 with a custom charter! Cast off from the island and explore the unique nature surrounding the Florida Keys!

• Clock 3 Hours
• Info 1 to 40 people

Morning Island Charter

Spend your morning at the sandbar and experience the turquoise waters surrounding Key West at a slower pace on this private charter.

• Clock Varies

Seabreeze Charters

Snorkel, see Dolphin, or visit a sandbar with an open-air cruise for up to 40 people. Create the perfect escape with a private adventure aboard our 45-foot Corinthian catamaran!

Hilton Head Catamaran Tour

Quick details.

• Hour Glass Duration: 2.5 hours
• User Ages: Must be 5+ to ride
• Users Passengers: Maximum 2 passengers per boat
• Ticket Adult Price: $135 per person (Ages 13+)
• Ticket Child Price: $110 per person (Ages 5-12)

Clock   Tour Time: YOU MUST SHOW UP 45 MINUTES BEFORE SHEDULED TOUR TIME

Star Outline Cancellations: Read our cancellation policy carefully. There is a $50.00 dollar minimum Cancelation Fee assessed to all cancelled bookings, regardless of whether or not you cancel 72 hours prior to your scheduled booking/tour time. Again, a minimum $50.00 Cancelation Fee will be assessed to all cancellations. No Cancellations by Email – Phone call only. No Exceptions.

Adult Ages 13+

Priced per person, child ages 5-12, adventure awaits you on our hilton head catamaran tour.

Drive your own two-seat boat on Hilton Head’s family-owned catamaran tour and have a blast on the water! Our amazing 2.5-hour adventure around the beautiful marshlands of Hilton Head Island is unlike any other.

After a safety briefing, experience the excitement of being on the water at speeds up to 30 miles per hour with our local captains, who share their knowledge of the area with you. Slow down to see dolphins, manatees, and other marine life. This adventure is great for kids and adults alike, so bring the whole family. It’s sure to be the best part of your Hilton Head vacation!

We offer this tour seven days a week, year-round. Join us for a morning, afternoon, or sunset tour.

What to Wear

Beach attire with water shoes, sandals, or flip-flops is appropriate. A light jacket is optional when the weather is below 75 degrees. Although you shouldn’t get soaked, a towel is recommended due to minor splashing. Sunscreen, sunglasses, and hats are also recommended.

Important Information

• You must be 18 or older and hold a valid driver’s license to operate the catamaran.
• You must arrive 30 minutes before your scheduled tour; this gives us ample time to brief you.
• Each boat has a maximum weight limit of 500 lbs.
• A cooler of ice and water is provided for each boat. You may bring other drinks and snacks if needed.
• A 15% gratuity is customary, but only if your trip was exceptional.
• There is a small dry storage area on each boat for cell phones, cameras, keys, wallets, and small purses. No large beach bags or backpacks, please.

Backwater Adventure's CraigCat Tours of the Ten Thousand Island

Ages 8+ (18+ to Drive) • Top Ranked Marco Island Tour since 2011!

Quick Details

• User Ages: 8+ (18+ to Drive)
• Hour Glass Duration: 1.5 or 2.5 hour

2.5 Hour Tour

1.5 hour tour, go on a craigcat adventure in marco island and the ten thousand islands.

• 2.5 Hour Tour: Most Popular Choice. About midway through the trip, the tour stops at a secluded barrier island for shelling and swimming. The entire trip will cover up to 30 miles of the most beautiful waterways in Southwest Florida.
• 1.5 Hour Tour: THIS TOUR DOES NOT STOP AT AN ISLAND LIKE OUR 2 1/2 HOUR TOUR! The entire tour will cover roughly 15-20 miles of our favorite waterways around the backwaters of Marco Island and the 10,000 Islands.

This is an interactive adventure where you will experience wildlife, sea life, adventure and beauty. This is not your everyday guided tour at all because you get to DRIVE YOUR OWN BOAT! Your guide is driving his boat in front of you to guide you safely around the Ten Thousand Islands and pointing out the sights! The backwaters of Marco Island have many dolphin, manatees, shore birds and other sea life that can be seen along the way.

The Craig-Cat is an exceptionally unique watercraft! This two-seat catamaran with 30 Horsepower outboard engine driven speed boat allows our guests to go up to speeds nearing 30 mph. The boat allows for a much more intimate ride than similar watercraft such as wave runners or jet skis for our guests. Sit back and relax with your guests on a CraigCat tour from Marco Island with comfortable seats placed side-by-side to make conversation easy.

The CraigCat is known for being very stable and very safe as well as easy to operate. After a short 10 minute instructional speech, you will have all the know how needed to operate the vessel.

The CraigCat offers a space for a complimentary cooler provided by us filled with bottled water and ice already. The CraigCat also has a small dry box built on the boat to place your belongings safe from any splashes!

Important information

• Must be 18 y/o with a valid driver’s license to drive and 8 y/o and up to be a passenger.
• Visitors with disabilities or limitations must call to see if we can accommodate.
• There is a weight capacity maximum of 250 lbs. / person.
• No alcohol or illegal drugs are permitted on the tour.
• No person under the influence of alcohol or illegal drugs may participate in the tour. Refunds will not be given for any party if a participant shows up under the influence.
• Participants will be required to sign a liability/hold harmless waiver prior to “making way”.

CraigCat Catamaran Tours

Be the Captain of your own adventure on a backwater tour of Amelia Island and it’s surrounding areas. Experienced guides will lead you on an adventure through the waterways of Amelia Island as you travel on your own CraigCat Tour boat. There are  various places to explore by water such as Downtown Fernandina Beach, Fort Clinch, Tiger Island, Cumberland Island , Fort George, and many more! These tour locations are treasured for their rich history and natural charm.

Fast Fun & Adventure

Our CraigCat catamarans are quick, roomy and exceptionally well-built water vehicles. They deliver a unique experience with the performance of a sports boat and the ability to drift across the water ( speeds up to 25 mph! ) and the genuine comfort of a runabout. These mini boats offer high-speed stability and comfort with unmatched horsepower and high-tech handling. CraigCat sets the standard in aquatic excitement and you will not be disappointed in the fun!

Dolphins, Manatee, Horses, Oh my!

On this journey, you also have the opportunity to see various wildlife unique to this area. Will you see a dolphin playing in the water? A manatee passing by your boat? Or maybe some majestic wild horses running free on the shores of Cumberland Island. Our guides are local naturalists with plenty of interesting facts about the area that will keep you entertained for hours.

Family Fun for Everyone

Each CraigCat can carry 2 people, one driver and one passenger. Drivers must be over 18, but the passenger can be 5 or above, so this is a great family water tour .  We can also accommodate one passenger in the tour guide’s CraigCat, so a family of 5 can enjoy this amazing tour, too. Larger family? No problem, you could also book our pleasure boat “Ms. Elvira” so you can sit back and let our Captain do all the work while you watch the CraigCats glide across the water.

Questions? Call: 904-891-5687

Minimum Age: Drivers - 18, Passenger - 5 Equipment: Supplied by Riptide. Experience Needed: Beginners welcome.

Captain your own CraigCat with top speeds of 25 mph.

Note: If born after January 1, 1988 you must complete a online temporary boaters' safety course prior to driving/operating the Craigcats. Visit https://www.boat-ed.com/floridarental for your quick Online Florida State–Approved Boat Rental Course .

24 hours notice for cancellations required.

Private Boat Tours

Kayak Tours

Stand Up Paddle Board Tours