Sailing in Second Life is very different from sailing in Real Life, although with the proper amount of imagination it can also be very enjoyable.
On my second day in Second Life I found there are sail boats in Second Life and I immediately “bought” a free boat in Market Place.
Some say it is the best boat in Second Life. I wouldn’t say it since it is the only boat I own, although I sailed as a passenger in another. I can tell that she moves very beautifully and behaves in the wind as one would expect in Real Life. Speaking of wind, it is probably the most different factor that someone who is accustomed to sailing in Real Life will miss aboard a virtual sail boat. Who knows, maybe someday I will hook some fans to my computer and place them around me. For the moment, instead of air caressing my skin to indicate its whim, a small compass with an arrow must suffice.
My RL instincts lured me to acquire some virtual items that are essential for RL sailing, although certainly they are unnecessary in Second Life. The first is a life vest, something you must always carry and use when sailing.
The other item was a little more difficult to find: Boat shoes! even when sailing in the nude, it is important to prevent your feet from slipping in a wet deck and make you wish you had put the vest.
I confess. I not always wear the vest and shoes while sailing in Second Life, but that is because I don’t wear anything else either. I have found some interesting sailing areas where nudity is allowed (encouraged, even) and I can do as such, everyday.
The first place I found is The Naked Ocean. It is a small area, only 9 regions in total. It has a Marina with many boat slips to let. It is a good place to learn the basics of sailing with not too many people around mocking your failures. It also has some beautiful picnic spots as well as other accommodations for adult use. It recently changed owners and it is expanding.
The other area I found is much larger. Eden States is a residential area with hundreds of islets and islands that you can lease and “live” there. The waters among the islets are public, and nudity is allowed. However, I found that precisely the many islets constrain the sailing, because they are grouped in a way that creates channels between them and forbid sailing a region from corner to corner forcing to navigate along the edges.
 There is a free one in Market Place. https://marketplace.secondlife.com/p/PFD-Inflatable-Life-Jacket-Free/5109317
 I finally found some great shoes for only L$99 https://marketplace.secondlife.com/p/ROC-Boat-Shoes-Female/7767799