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Private Sailing Cruise (2 hrs) from $295 . Extra time available @ $100 per additional hour.

Price includes: Captain, crew, and non-alcoholic beverage.

Please click link below to read more and view pricing. Price is for 4 guests in your party. $25 extra for each additional person up to a maximum of 6.


Click here to read more and view pricing

Departure time is at 4pm. If you prefer to depart earlier or later than 4pm you’ll need to let us know before or right after you book and we’ll do our best to accommodate.   

 Welcome to Always for Sail

We are committed to giving you the very best sailing experience.  We are located in Saint Augustine, Florida.  We offer a variety of sailing charters including: harbor cruises, offshore cruises and inland waterway cruises. Whether you are planning a romantic cruise for two, or a fun-filled family getaway vacation, our sailing charter is what you are looking for.  

An unforgettable experience…

Always For Sail Charters offers several private sailing cruises to choose from including a variety of harbor cruises like a romantic sunset harbor cruise, afternoon harbor cruise and a offshore cruise.

Any one of these Cruise Packages gives you a taste for the beauty of downtown Saint Augustine by water. Depending on the length of charter and wind conditions you will enjoy the scenic waters of Saint Augustine from offshore, inshore or both. Call now to reserve your cruise!

Charley’s First

“Charley’s First” is a 51′ Morgan Out Island Ketch hull #1. She was designed by Charley Morgan himself and manufactured by The Morgan Yacht company, the Rolls Royce of sailing Yachts. She has a center cockpit above decks and weighs in at 48,000 pounds which ensures for a smooth and comfortable ride. Down below there is a large aft stateroom with a separate head (bathroom) and a large V birth with a separate head, a large spacious galley and salon area. She is well equipped with all the comforts of home including air conditioning , fans, color TV, DVD, stereo with CD player and i Pod, ice box, blender, microwave, coffee maker and much more.

We have a good selection of DVDs, books and games. We keep an ample supply of snorkeling gear and fishing tackle. Of course, the boat has all of the safety equipment and state of the art electronics like Global Positioning System, Chart plotter, autopilot, Marine VHF radio, 2000 watt power inverter backed by a total of four 4d batteries
51 Out Island Morgan

Customer’s Testimonials