First, the web stuff to do
The FIRST thing you should do to sell your sailboat is place an ad here on Sailing Texas; it's free, it's easy, and it gets results! Each boat gets it's own webpage which you can refer to in other ads.
SECOND, go to the pages listed below and find the sites that let you post a free ad or message. Post your message on as many sites as you can WITH the url for your ad on Sailing Texas. Most of these places don't let you post a picture, but with the url for your ad on Sailing Texas everyone can see your boat, and a picture is worth a thousand words! So with 3 or 4 pictures...
On my Texas classified links page you will find many other places on the net in Texas that have sailboat classified ads, and many of them you can also post on for free!
On our Classifieds by State page you will find website classifieds from most states. Some of them you can post on for free, so place an ad on sites in a state near your state.
And lastly, our Classifieds by Model page has classifieds dedicated to each particular make or model, so if your model is listed place an ad on the appropriate site.
For hints on what to include in your ad see
Build a better ad
The non web stuff to do
Clean and shiny, get out there and clean that boat, inside and out! It doesn't cost much to clean a boat, but it makes it worth a lot more money. Not only will people pay more, but often a dirty boat will make people walk away without even giving you an offer.
Make any repairs you can, if needed. The fewer things wrong with a boat the easier it is to sell.
Make sure the trailer has good tires that hold air, fix the trailer lights. Grease the wheel bearings. It really helps to sell a boat if you can honestly say the trailer is ready to go on a long trip. I've sold several boats to people that pulled them several hundred miles to get them home, but if they didn't know the trailer was ready they would not have come to look, much less bought them!
Price the boat right. Not too low, but not too high either. Especially not too low! Check the Sailing Texas Photo Gallery and see what your boat model has been selling for. You can't always go by the price people are ASKING for their boat, because they often sell for less! Look to see which ads expired and which ones sold the boat.
Boats do depreciate. Their value goes down as they get older, and yours will to. You can price yours fairly at $50,000, but if it doesn't sell for 6 months it won't be worth $50,000 any more, so to sell your boat reduce the price on your boat faster than it is depreciating.
Decide what you think is a fair price for your boat, then get the word out quick and wide. If it doesn't sell in a month, lower the price and repost your ads. If you have wide exposure and it is not selling, you are probably too high. You want the highest price you can get, and if you wait too long to sell, depreciation will hurt you as the boat gets older.
Posting ads on several sites, all with a url pointing to your ad here on Sailing Texas, helps a lot more than you think. It takes time for ads to get on the search engines, and this is THE one thing I have found that works!!
Lastly, in your ad be sure to mention your boats GOOD points, every boat has some. New sails, "doesn't leak a drop", stereo, outboard just serviced, etc. People have no way of knowing if you don't tell them!