Offering daily Dolphin Watches, Sunset Sails and Day Trips, which include sailing, swimming, snorkeling, shelling and kayaking for up to 20 persons. 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.
Kathleen D Sailing Catamarans offers a variety of affordable sailing experiences starting at just $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. Egmont Key Expedition – A fun 5+ hour day-time sail with swimming, snorkeling, shelling and exploring on and around the isolated Egmont Key, Florida. True Sailing – This is a 3-hour extended Dolphin Watch sailing tour that gives you an extra hour to see and experience even more. Longboat Pass Passage – this 5 hour trip sails from Harbour Square dock up the Gulf Intra-coastal Waterway to Longboat Pass.


Kathleen D 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 sails. Located in Egmont Key at the mouth of Tampa Bay is Egmont Key State Park, a Florida State Park that features many recreational activities and wildlife.
If you're vacationing on Anna Maria Island, dolphin watching is a must-do activity for kids, grandparents, and everyone in between! Our sunset cruises on the Gulf are among the most magnificent sights you will ever experience.
If you’re vacationing on Anna Maria Island, be sure to take a boat tour of the island and its surrounding areas.
Multihulls, such as these Lagoon catamarans, are very popular as bareboat charter vessels due to their spacious accommodations and stability. There are two basic types of yachts for those interested in a yacht charter vacation: bareboat charter and crewed charter. If the weather is too rough to sail, there is lightning, or there is persistent rain, we will cancel the charter or rental.


Unwind and relax as you feel the warm, gentle breezes while sailing the stunning turquoise waters of Florida’s Gulfcoast in safety, style and comfort. You don’t want to miss out on the beautiful sights that this hidden gem of an island has to offer! Kick back and relax island style with a personal cruise on the beautiful waters that surround Anna Maria Island. Captain Frank Jones has been sailing the seas for quite some time now, so rest assured, you are in good hands. But a great number of charter yachts, such as those found in bareboat fleets, will be familiar if you’re sailing them in the Indian Ocean or the Caribbean Sea.



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