Sailing - Basics
You can join a sailing cruise, get a crewed charter or feel the breeze in your hair chartering your own vessel. The choice is yours. The benefits of a crewed charter are that you don’t have to hire the whole vessel yourself because you share it with others. The crew is supplied so you don’t have to steer, haul sails, cook or clean yourself. However getting your own charter or your own boat opens up an endless choice of seas to explore from the Mediterranean to Alaska’s North West Passage.
Sailing / Yachting - Beginners
Most beginners will probably prefer to join an organized sailing trip than drive themselves. On large vessels these are very much like floating hotels and you are generally not required to help. The skippered charters are a good intermediate step. On some of these you can help out with daily tasks or sit back and enjoy the ride.
A step up from here is to crew for someone else. Beg a seat at the local yacht club or vacation on a crewed charter which also offers personal instruction. That way you’ll be in the hands of an experienced seaman plus be learning the ropes.
From here you can rent your own sailing boat for which you will need to demonstrate experience to the outfitter and even some qualifications. A lot of companies actually provide sailing courses to provide you with the skills you need so you can set sail alone. Or they allow you to join other sailors on flotilla, whereby you can stay with the other boats as much as you like and the lead boat is always on call to assist.
For your first outing as a self-drive entity you shouldn’t venture too far or into testing waters. Do a simple "out and back" route, select a waterway you already are familiar with or one that presents no challenges. Short routes with sheltered waters, gentler winds and a multitude of anchorages, bays and islands to explore will generally be more suitable for novices.
Sailing / Yachting - Advanced
Once you’ve completed all the above steps you’ll probably want to skipper your own boat via a self-drive charter or simply buying your own. Not only can you be more flexible about where and when you travel, you can also take as long or as short as you like.
If you have already spent a fair amount of time at the helm you can select one way, long trips that take in new territory and present challenges like a sea or ocean crossing, rounding a particular cape or landing on remote islands.
Always put buying a boat down as your last step when you have plenty of skills and have proved to yourself its worth investing in the sport. If you do own your own yacht you could also consider renting it to charter companies to earn an income on it while you aren’t using it.