About Dalton Charters

We are a small family business. As lifelong natives of North West Florida, we have spent our lives on the waters of the Emerald Coast.

OrieAnna’s Sunset Cruise is the perfect way to watch a beautiful sunset from your Private sailing vessel! This “cruise to nowhere” allows us time for pure sailing with no hurry to get anywhere. Our destination is the best view of the changing watercolors of sunset cruising through the bay!

OrieAnna is a Maxim 38 sailing catamaran built in Durban, South Africa built by Maxim Yachts. She is 36’ long with a beam of 20’6” and boasts a mast height of 56’! OrieAnna has 3 berths, two bathrooms, a large salon, a spacious cockpit, and a beautiful forward deck with a 360 vista.

OrieAnna has sailed the Indian Ocean from South Africa to Madagascar, continuing to South America into the Amazon! After her stay in South America, she made her way to the Caribbean and on to the Florida and Georgia coasts. Since her Ocean crossings, she has made her current port of call Two Georges Marina on the Choctawhatchee Bay, but when she pines for open blue waters, OrieAnna makes trips from Destin, Florida, to the Keys, and onwards to the Caribbean and Tortugas before returning home.

Meet Captain Jacob

An excellent sailor, years of experience, and a qualified United States Coast Guard 100-ton Master Captain with sailing endorsement. Captain Jacob just loves sailing and the water with a passion. His knowledge of the local waterways, marine life, and Emerald Coast is never-ending. His infectious humor, with the biggest smile, will certainly entertain you. A real people person, loves looking after his guests and will ensure everyone is safe and has the most memorable time of their vacation. When he finds the time,  he is an avid diver and fisherman and is always ready to conjure up some amazing fishy tales!