Private Sailing Cruise (2 hrs) from $295 . Extra time available @ $100 per additional hour.
Price includes: Captain, crew, and non-alcoholic beverage.
ImportantPlease 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.
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” 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
"It doesn’t get any better than Captain Cliff and Always For Sail!! This was our second sail with Captain Cliff and once again we had a wonderful time, Charley’s First is an incredible boat, Captain and the crew are always so attentive, you literally want for nothing once you’re onboard except for maybe more hours of sailing!! A must do for anyone visiting or locals who are looking for the most relaxing, safe, fun sail ever!! Thank you! Thank you!! Visited June 2016"
"You could not have a better time on the water than to sail with Cliff and his crew on Charlie’s First. We had a 10-month old baby with us and everything went smoothly. We learned a lot about the area, local waters, and about sailing in general. We would heartily recommend this experience to anyone who has a special occasion or just wants to enjoy another slice of St. Augustine life! Thanks, Cliff."
"My husband surprised me with a chartered sunset sailboat ride out into the ocean. It was so quiet and was such a beautiful experience, one I’ll never forget. We sailed east onto the ocean, and then back into the inlet to sail around in the intercostal. The lighthouse was always in view and we loved seeing that since it relates to our wedding night. The captain made a point to take us to where we wanted to go. I really wanted to feel what it was like to be on the ocean and we wanted a picture with the lighthouse behind us from the sailboat. He took us by the Fort and along the streets of downtown St. Augustine. His crew had knowledge to my random questions and left us to enjoy each other while we cuddled on the loveseat at the front of the boat, to soak in this lavish experience. I’d highly recommend this for everyone to try! It was so amazing!
The captain made a point to take us to where we wanted to go. I really wanted to feel what it was like to be on the ocean and we wanted a picture with the lighthouse behind us from the sailboat. He took us by the Fort and along the streets of downtown St. Augustine. His crew had knowledge to my random questions and left us to enjoy each other while we cuddled on the loveseat at the front of the boat, to soak in this lavish experience. I’d highly recommend this for everyone to try! It was so amazing!"
"You have to do this if you visit St Augustine! Charlie’s First Captain Cliff’s boat was impressive. She was roomy, clean and sailed beautifully. Her crew, Captain Cliff and first mate Peter had complete command of her and made sailing her look effortless. We just sat back and enjoyed the breeze, sea and sunshine. Peter looked after us and made sure we wanted for nothing, We enjoyed cold drinks, informative tid bits of the history of the area and lots of laughs too. They worked together well. We felt safe and confident that all was well. After a great sail off shore we finished our trip with a cruise past the city’s downtown swinging by the Bridge of Lions, the waterfront and the Castillo de San Marcos Fort. The crew made sure we got pictures of our whole group together with the city in the background. We finished our trip where we started at the Conch House Marina. The seamanship and experience of Captain Cliff and Peter was impressive as we docked perfectly despite the crowded marina on the labor day weekend. Great job guys! Thanks for a memorable day! Visited September 2014."
"What an amazing time!!! Captain’s Cliff, Melissa and crew were so personable and really know their stuff. We had such a beautiful sunset cruise creating memories that will last forever. Such a beautiful sailboat too!!
We will definitely be booking them again.Being from the St Augustine area it was so nice to see this beautiful city from a different perspective. We started out at the marina and headed out to the ocean for a bit where we saw several dolphins, and then headed back in for a tour of the city from the water. We had beautiful weather and a view of the sunset we’ll never forget."
"I found Always for Sail while I was researching sunset sail cruises for our anniversary celebration in St. Augustine. I was really interested in a private charter for my wife and I in order to avoid being crammed in a sail boat with a bunch of other tourists and take away from the intimacy and romance of the moment and occasion. After calling another local sail charter and gasping at their ridiculous price for a private charter, I came across Always for Sail….WHAT A LIFESAVER! Cliff, Melissa, and Greg engaged us in friendly conversation, and really made us feel like we were sailing with long-time friends. We were treated like family, but made to feel like VIP’s. I can’t say enough about Always for Sail."