Affordable Membership Sailing with SailTime Annapolis
Enjoy Affordable Hassle-Free Sailing and Sailing Instruction on the Chesapeake Bay!
Welcome to SailTime Annapolis
SailTime Annapolis offers the best experience available in fractional sailing, and a cost effective, hassle free alternative to ownership. SailTime is similar to joining an athletic club (but you will actually use it!). You choose the boat that you want to become a member on, and then you schedule your time to sail on the online calendar. When you show up for your SailTime the boat is ready to sail. You sail, we take care of the rest. When all you want to do is sail, SailTime Annapolis is the right choice for you.
SailTime Annapolis has a variety of sizes of boats available: Colgate 26 (day sailor), 2009 Hunter 33, 2009 Hunter 36, 2012 Hunter 39, and a 2012 Gemini Catamaran. We are actively looking for owner/members to add another Gemini Catamaran and any size Hunter to the fleet. If you are interested in becoming an owner/member please contact us at 443-376-7245. All of our boats are in top condition and have membership spots available. All boats are limited to 8 members to guarantee equal time to each member.
We are located in the Port Annapolis Marina in Back Creek. This allows you to be out in the open waters of the Chesapeake Bay in less than 10 minutes. Many popular destinations are within a day sail: Annapolis City Dock, Baltimore’s Inner Harbor, St. Michaels, Rock Hall, Kent Island, Herrington Harbor. In addition to sailing a high quality yacht with SailTime Annapolis, you will be able to take advantage of the Port Annapolis Marina facilities while on your SailTimes. Cool off in the marina pool or send the kids for a swim while you are loading your gear onto the boat.
OK, so you are ready to go, but, your skills are a little rusty. No problem! SailTime is an American Sailing Association (ASA) Certification Facility. We will help you become the sailor you have always dreamed of being. You will learn to safely sail on the boat that you will be sailing with your membership. After you practice and master the skills of ASA 101 Basic Keelboat and 103 Basic Coastal Cruising (required for SailTime membership) you can take the upper level classes: 104 Bareboat Chartering, 105 Coastal Navigation, and 106 Advanced Coastal Cruising. When you are finished you will be more than qualified to charter anywhere in the world, or even sail around it! But first, you should schedule a time to stop by the SailTime Annapolis office and take a look at the boats and the facilities.
To set up your appointment call Gordon at 443-376-7245 or email gbennett@sailtime.com.
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Sailing Lessons in the Chesapeake Bay
SailTime Annapolis is an ASA Certified Training Facility
Click HERE to view the SailTime Annapolis Sailing Academy website.
SailTime Annapolis welcomes members and non-members to come discover sailing in the Chesapeake Bay. SailTime Annapolis provides excellence in sail training in conjunction with the American Sailing Association (ASA).
Our goal at SailTime Annapolis is to teach you the skills and decision making required to safely and confidently command your own SailTime yacht or bareboat charter. Whether you are a first time sailor or you have a few seasons under your belt, we can help you take your sailing to the next level with the following courses…
ASA Courses:
101 – Basic Keelboat Sailing ($650)
103 – Basic Coastal Cruising ($775)
104 – Bareboat Chartering ($995)
105 – Coastal Navigation ($495)
Non-Certification Classes:
Introduction to Sailing – 1 day ($225 per person) 2 person minimum to make class active
Introduction to Sailing – 2 days ($395 per person) 2 person minimum to make class active
Learning to sail well takes quality instructors and time on the water, period. That’s why at SailTime Annapolis our classes limited to four students. Our instructors have USCG captain’s licenses and ASA instructor certifications. Captain Gordon is also a certified teacher by the state of Maryland with years of classroom and on the water teaching experience.
Customer Comment
“Gordon, we want to thank you so much for the best vacation ever. We learned so much from you. You are an exceptional teacher.” Tom and Mary T.
“Thank you for being a great instructor and for the time on the Bay. I thoroughly enjoyed being on the water. Your low-key, high-encouragement teaching style helped me regain my sailing confidence, and I am looking forward to more sailing.” – Leslie F.
“I spent the weekend with Captain Gordon learning the basics. Coming from someone who never sailed, his approach was phenomenal: simple, challenging, and fun. I had a great time and look forward to learning and experiencing more with the rest of his courses over the next year or so. I cannot overstate the fun and ease of the experience Captain Gordon provides. Serious thumbs up!” – Eric W.
“Thanks for a fun week. We learned a lot and feel confident about heading out on our own. We’ll see you out there.” – Matt L.
Please call (443) 376-7245 for class times and availability or visit www.annapolissailinginstruction.com
Frequently Asked Questions

