I was hoping to get some input from those of you who know these boats. I'm currently looking for either a Stiletto 27 or Macgregor 36. If I'm going to go with a cat that's not really portable and I'm willing to accept it will cost a lot more to store, I'd rather just go with the M36 (over say a S27, S30, or W29/C29). I like the idea of being able to somewhat easily disassemble the boat and trailer it without to much fuss, I think the S27 is really the only one in this group that might fit that bill. So really this leaves me with just the S27 and M36 (unless someone has other suggestions under $30k).

I realize there's a substantial difference between the S27 and M36, in more ways then one. For most reasons I like the S27 (lower initial cost, lower annual cost of ownership, construction, easier/cheaper to store (wet and dry), trailerablity, portability, and plus many other reasons). Both boats offer enough space and very basic amenities, but the M36 obviously has more real estate. Both are well constructed, the S27 being tough but light weight Nomex and the M36 being built like a tank. With the S27 I can moor it in the two pole moorings by my house (up to 30'). With the M36 I'm really not sure where I could keep it (it wont fit in those same two pole moorings), but if I have to keep it in a slip at the marina next to me it will certainly cost me at least $4k more per year over mooring the S27. Plus, I'd have to get dry storage for the M36 which I'm sure would be at least another $2k per season. With the S27 I would disassemble it and store it its trailer at my house. As you can see it would cost me a lot more to own the M36 so I'm really leaning toward the S27.

The only thing that concerns me is how the S27 will handle as you get off shore a little. Obviously this is where the M36 appeals to me much more (plus it's more spacious) over the S27. I live on the central CT shoreline and plan to take weekend trips out to the costal islands once or twice a season with whichever cat I buy. From my location in CT to Nantucket, it's about 130 miles with islands (possible stops) about every thirty miles in-between. For the most part I can hug the coastline and stay within 10 miles of land, but when (if?) I go from Martha's Vineyard to Nantucket I have to travel about 30 miles of open ocean with land being about 15 miles away when in between the islands. Having never been on a S27, I'm concerned about being this far off shore in open ocean with several friends or family on board given that the S27 is basically a light weight over-grown beach cat. So, is the S27 enough boat to safely make this trip in average conditions or should I really look harder at the M36 and deal with it being much more expensive to own/store?

There's no doubt in my mind the M36 is better suited for these trips, but it will cost about 2x as much initially, plus probably 10x as much yearly over the S27. I guess the other option is just not go from Martha's Vineyard to Nantucket... LOL.

Your input would be much appreciated!