I loive mine....it was one of the last ones built before they made a slight change to the hull in 2003. In 2003 the boat got an interior facelift, adding teak inserts in the cabin, and backrests on the helm bench seats. The hull deadrise changed 1 degree throughout the boat if I am correct, not a huge change but it was done to keep it the same as the other sv2 hulls and not as deep as the original design. The original pre 2003 hulls were slightly more tender on the drift, but would cut a chop and laugh at it. The post 2002 hulls(2003 on) rode great, and eliminated some of the tenderness on the drift, but honestly I've been on both years and can barely notice a difference on the drift, only on the roughest days can I notice any change, I'm talking 6 ft beam sea, but there is a little less roll in the newer hull when it gets that bad, in normal conditions they are about the same. The earlier hull seems to ride better into 2-3ft chop, the newer hull rides more like a 282, with a slight bump, but still a nice ride for this size boat.
Before we purchased our 265 we test drove numerous boats from aquasport, Grady White, Boston Whaler, Pursuit, and Northcoast. The 28 whaler and the Grady were the nicest, the Pursuit wasn't far behind, the northcoast lacked and the aquasport just stinks..its really wet and pounds in anything over 3ft, I fish on a bunch of them with guys in my area and hate them, they aren't built that great either. The other boat we considered was a 28 carolina classic. It has inboards instead of outboards. Space wise compared to the 265 they are similar, but the ride on the CC blows out any of the others, but it burns the most fuel.
The 265 was designed to be a long range runner, to run the canyons of the NE and the gulfstream and lumps in the south. It had more range then most boats in its class and was designed more for day trips, but can handle overnight trips as well. It was more tailored towards fishing then the family, but does not shorthand that unless you need 50000 seats everywhere. The 265's helm is awesome...once you run a boat with a center helm it is hard to go back to a side helm. Visability is great from a center helm and gives you a great perspective, it also makes the boat feel smaller when running it due to the great visability of the whole boat, something a side helm lacks. The notched transom provided the best setup for fishing, and is no problem with standup fishing. I've backed down at 5-6kts without water coming on deck...just a slight trickle....and I mean slight. No waves have put any water in the cockpit, and I've been in 8-10's plenty of times. I've run mine 80+nm in 5-6's without turning back or thinking twice. This season we took her 110nm offshore 1 way, trolled about 6hours, overnighted, trolled 2 more hours, and ran back on 198gals.
The reason the 265 nolonger exists is due to poor planning by Grady. At the time the 265 was offered, there was also a 24/25 voyager, a 26 islander, and a 27/28 sailfish, too many boats in a small size range. Boat sales in these years slowed a slight bit as well, and the 265 was the most expensive of the bunch brand new, which emans the least sales overall of the other models. All of the models suffered overall sales due to too many boats in the size range, making profits harder to come by, something had to be eliminated and the 265 was gone. It is funny, all of those other models were changed to then fill gaps or redesigned(sailfish-to-cheseapke), I wonder how the 265 would have faired since it is one of the most popular used boats in the size range currently, they are often hard to come by, there were not a lot and most owners are very happy with them and do not sell often unless they are moving up in size.
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