Try sailThree Hour Try Sail

Have you always wanted to try sailing, but didn’t know where to start? Are you looking for a low cost and minimal commitment way to get on the water and experience sailing? Even if you have sailing experience, the Try Sail is a great way to grow your knowledge and hone your skills. It’s only $199 and it’s the easiest way to go sailing in Annapolis.

How Does Try Sail Work?

Call J World Annapolis at (410) 280-2040 to purchase a Try Sail for $199, and we’ll email your certificate. During our sailing season (April 1 to October 31), call to schedule either a weekday or weekend session and join us in Annapolis for a custom tailored sailing experience. It’s that easy!

What will the on-the-water experience be like?

We take sailing education seriously. This three-hour session is a condensed version of our award-winning education program. Your will really be sailing, not just “riding along”. From the moment you leave the dock, the tiller and sheets will be in your hands. With top-flight coaching staff quietly teaching and encouraging each student. We keep the class size small (a limit of four students per boat) so everyone is engaged in steering, trimming sails, learning right-of-way rules, tacking, gybing and more.

We want everyone to have the best three-hour sailing experience possible, so we will be offering both weeknight and weekend options. Make a day of it exploring Annapolis, or kick off date night in the most special way. You might sail by some Wednesday or Thursday night racing out on the Bay, or sail around the Annapolis harbor on a busy Saturday and then enjoy an afternoon exploring the sights, sounds and all that Annapolis has to offer. If conditions are right, we might even be able to sneak a spinnaker up!

Each session will cruise to wherever the wind is best.  We hope to give everyone a tour of Annapolis Harbor and peek out into the Bay. Sights include the Bay Bridge, the Naval Academy, Ego Alley YP Boats, crab pots and more!

I am giving/received this as a gift. How do they/I redeem the certificate?

Simply fill out the J World Registration Form, indicate what date you would like to schedule your sail for, and we will be in touch to verify your certificate and complete the scheduling process!

What if the person I give the certificate to wants to bring a friend?

That’s no problem. Anyone with a gift certificate can add folks to their trip for just $199 per person. Sailing is a social sport, and this is certainly designed to be a social “mixer”. We encourage individuals to come and meet other sailors to start their own “sailing buddy” networks, or come as an intact group and start your sailing adventures together.

I still have some questions.

The best thing to do is pick up the phone and give us a call. Again, that number is (410) 280-2040. Or shoot us an email at We’ll be happy to help you with any questions you may have.

Try Sail 2