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Here is a list of some of the more interesting sailing and marine simulators:

Virtual Sailor, by Ilan Papini. Very adaptable, allowing users to create their own add-on boats and scenery. Much detail is possible, and the user can roam around the interiors of the boats, and look out the windows. Sailboats with multiple sails, motorboats, and even submarines are possible. Hundreds of freeware downloads are available. Full weather, tide, wave effects are adjustable... by far the most complete marine simulator available. The simulator is up to version 7 now.

The weak points of this sim are that it is very resource draining, it is hard to set it up for racing, and the AI is not believable. But the strong points are the addon ability, because this is hard or impossible to do with any other sim. You can use the sim to simply cruise around, too, which is not possible with other sailing simulators.
Virtual Skipper: A very well done racing simulator, with believable AI. The graphics are very detailed, including some fast traffic you have to avoid while racing. You have three boats and a half-dozen racing circuits to chose from.  But  compared to the latest versions of this sim, it looks sort of "arcade like", and much less realistic.

This title is out of print, but you can find copies on eBay, and on the close out racks at Babbage's and E&B's software. I would look for Version 3 or above, shown below, rather than this first version.

Virtual Skipper2: The amazing update to VSK (above). The graphics seem to have been improved to a great extent. Check out the site to see the screenshots... you would think they are shots from real racing footage!

Virtual Skipper3:  I finally got a copy of this version 3 on ebay, as in 2007 it is a couple of years old now. I am very impressed. It runs very smoothly on my old 500mhz CPU PC! So if you have a slower machine, and can't run version 4 (not shown here) or the latest version 5 (below), this might be for you.

You can play against the computer AI boats, which are very good. There is a challenge option, where you can learn to sail the boats through progressivily harder stages. And as of December 2007, I still see people on the multiplayer server!


OMG I need a faster computer. Virtual Skipper 4. Click on the image for a stunning screenshot.

Virtual Skipper 5: No, that is not a photograph to the left. Go to the site and see the screenshots of the game for yourself. If you can run this version, why wait? Click on the image for a larger version. Or click here for another stunning shot.
Sail Simulator 4.0, by Stentec. Another racing sim... this one has many adjustments for crew weight, halyards, sheets, adn so on. Graphics is not it's forte. The crew is very articulated and active. I think the sim runs fast... it's sort of skittish, and the dynamics are not realistic. More of an arcade level sim.
Posey Sailing Simulators. I think that this is an older generation simulator... I remember them from several years ago, when the demo was offered at AOL downloads. The price has not come down to meet it's archaic look, however... I think it's still around $60. It comes in several versions, including racing and cruising.
Interactive Sailing: I have a warm place in my heart for this early attempt at a racing simulator. I've spent many pre-VS winter nights racing the "enemy" across it's plastic, whitecapped waters. It's been made fun of whenever I mention it, but I wonder if they have tried it. There is something appealing about the layout and gameplay, and the graphics, although only a series of 2D images, are surprisingly immersive. It is also possible to over-write the graphics, which I did at one point... and put pictures of your own boat in place of the J/105! But the included 30 minutes of actual racing film clips alone make this disk worth purchasing, the next time you see one sitting on a tag sale table... no more than $5, though, I think.
Man of War II, by Strategy First: The best age of sail gameplay I've seen... and the graphics may be crude, but this serves a purpose: The low processor demands, and low "lag time", allow HUGE multiplayer games. Dozens of players meet twice weekly to battle it out in classic duels. Very detailed ship damage, weapons ranges and effectiveness, and sailing characteristics, all give a full sense of the logistics involved in fighting such a battle. 
Age of Sail II, by Talonsoft. Now we're talking! This age of woodenwarships sim is quite complete, both with graphics and gameplay. Well, so I hear... but I have yet to get my copy. I think I will get lost in it, when I finally grab one.

By the way, Talonsoft's original version of Age of Sail  is still quite an entertaining "top down view" simulator. It can be found at tag sails and online for under $5.

Sail 2000, by Vivid Simulations: this seems to be a re-work of "Interactive Sailing" (see above), with similar 2D graphics and gameplay. However, it was given a bit of a facelift, and multiplayer was added. There was a Sail 95, but I cannot find any copies of it. I'm not sure if Vivid Simulations is still in business, as thier site appears to be down. But Landfall Navigation still sells the sim.
21st Century Sailing Simulator: This sim also has strong similarities to the old Interactive Sailing... most notably the control panel. The graphics are 2D... I once downloaded the demo, and it was obivous the graphics were not the selling point. 

I think the incredible sucess of these "graphic poor/gameplay rich" simulators shows that the market is wide open for a simulator which combines graphics, AI, good multiplayer, and ability to create add-ons. Well, except for the addon abiltiy, Virtual Skipper blows them all away.