I have played quite a few games of Cutlass and like it quite a bit. As mentioned above, it's a skirmish game of pirates on land, raiders on the island sort of thing. The rules are detailed, but only okay in their organization. It took us a long time to figure out what the long range of a musket was, for example. Has a chart section in the back that I photocopied, cut apart and rearranged (and added in a few tables because it worked better) to suit us. We put that down to the language difference caused by the ocean separating us. The rule book fell apart after two weeks so I just put all the pages into sheet protectors and went forward from there. No biggee.
Combat works pretty well for a skirmish level game. Detailed enough to have a good skirmish feel but not crazy detailed to slow down the game. We especially like the ability to do things with or to figures that are down, or 'taken out' as the game says. You can pick them up and try and get them off the board (worth it due to the campaign system), stomp them a la Orks to really eliminate them from the crew list, or raise them as undead by the undead player, which is really evil as that figure / character now shows up in future games as part of the undead crew. Messes with your mind.
Each of the crew lists is different enough to give a good flavor to the various races. And each list has some different crew skills allowing even more flavor. Though gaining crew skills is difficult and makes new crew much weaker than old crew, unnecessarily so IMO.
Where Cutlass does very well is in the various missions the crews can undertake. Players can generate missions based on 'stance', offensive, defensive and then matrixed with whether you're famous or infamous. Adds a nice factor to the campaign. I think there are nine or so missions. My particular favorite is the barfight one. Simple and loads of fun.
Worth the money to buy, and you can use your own figures for crews. I have used a bunch of old Grenadier figures of Vikings as a crew (hey, it's fantasy, right!). One of my daughters fielded an ancient Eqyptian undead dog headed Anubi crew, which makes for a very surreal tabletop, let me tell you. I also have a large force of Frogs, armed with muskets, pikes, spears and more, that the players will end up running up against when they don't feel like beating on each other for once. Got to love the crazies over at Eureka Miniatures.
Hope this helps
Kevin in Albuquerque