• Kathleen D swimming, snorkeling, shelling, kayaking on daily Dolphin Watch, Sunset Sails & day trips in Sarasota, Longboat Key & Siesta Key, Florida. Must Do Visitor Guides, MustDo.com.
  • Kathleen D swimming, snorkeling, shelling, kayaking on daily Dolphin Watch, Sunset Sails & day trips in Sarasota, Longboat Key & Siesta Key, Florida. Must Do Visitor Guides, MustDo.com. Photo by Jennifer Brinkman.

Kathleen D Sailing Catamarans

Offering daily dolphin watch, sunset sailing charters and day trips, which include sailing, swimming, snorkeling, shelling, and kayaking for up to 20 persons. The Kathleen D conveniently departs from Anna Maria Island, Longboat Key, and downtown Sarasota. Read Kathleen D’s featured blog article – click here

Treat yourself to a spectacular sailing charter experience along the beautiful shores of Anna Maria Island, Longboat Key, Sarasota, and Siesta Key, Florida aboard Kathleen D Sailing Catamarans. Unwind and relax as you feel the warm, gentle breezes while sailing the stunning turquoise waters of Florida’s Gulf coast in safety, style, and comfort.

Kathleen D offers luxurious 12 and 20 passenger sailing catamarans, making it the perfect getaway for family and friends.  A sailing charter is a terrific opportunity to see dolphins, historic landmarks, gorgeous waterfront homes and the magnificent sunset along Sarasota’s waterways while you sit back, relax and let someone else do all the work.

Affordable Sailing Experiences Starting at $55 Per Person

Sunset Sail – Pack a picnic along with your favorite wine or beer and watch a magnificent Gulf of Mexico sunset on this 2-hour sail.

Dolphin Watch – A perfect 2-hour family outing for all ages to spot these delightful creatures that abound in the area. Morning Dolphin Watch sailing tour is from 10 a.m. to 12 p.m. and Afternoon Dolphin Watch sailing tour is from 2-4 p.m.

Egmont Key Expedition – A fun 5+ hour day-time sail with swimming, snorkeling, shelling and exploring on and around the isolated Egmont Key, Florida.  Lunch is included with this trip. Sailing tour departs at 10 a.m. and returns at approximately 3:30 p.m.

True Sailing – This is a 3-hour extended Dolphin Watch sailing tour that gives you an extra hour to see and experience even more. Morning sailing tour is from 9 a.m. to 12 p.m. and the afternoon sailing tour is offered from 12:30 p.m. to 3:30 p.m.

Longboat Pass Passage – this five-hour trip sails from Harbour Square dock up the Gulf Intra-coastal Waterway to Longboat Pass. Enjoy Gulf of Mexico sailing, swimming and shelling at Beer Can Island. Lunch is included with this trip. Sailing tour departs at 10 a.m. and returns at approximately 3 p.m.

Kathleen D Sailing Catamarans also offers private charters for weddings, anniversaries, birthday parties, burials at sea, corporate outings, and family and group charters as well as monthly special event sailing trips.

Gift certificates are also available which make a terrific present!

Complimentary soft drinks, bottled water, ice offered on all excursions. Parking is also available. Don’t forget to pack your camera, towels, and sunscreen! Guests are allowed to bring wine and beer onboard for their enjoyment.

Reservations are required for all sailing charters and tours.

Three Departure Locations
Anna Maria Island – Departs from Keyes Marina on Holmes Beach, 5425 Marina Drive, Holmes Beach, FL Get Directions Map
Longboat Key – Departs mid-key at Harbour Square at the docks around back. 4134 Gulf of Mexico Drive, Longboat Key, FL Get Directions Map
Sarasota – Departs from Marina Jack, 2 Marina Plaza, E Dock, Slip 20 Sarasota, FL Get Directions Map

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