Originally Posted by camaraderie
"In many ways, larger boats are easier to sail."...is really true. The only thing you'll really need to get used to is the additional weight when under power and pulling up to a dock. They don't stop as fast as the lighter boats...don't ask me how I found this out!
May I also suggest you expand your search a bit to look at Catalina 30's.
Nice boats and lots of 'em around at good prices...Similar to the Hunters and Beneteaus...maybe geared a bit more to comfort/space rather than speed under sail than the Bene.
If a 28 meets your needs, you should look at Sabre 28's. They have a reputation for better build and sailing qualities than many other production boats. Also, Tartan 30's are another boat you might consider for the same reasons. IMHO, both are pretty classy looking boats, but the trade off is creature comforts you get with a Cat/Hunt/Bene. It will pay you to consider your needs here carefully. In our case, we live >4 hours from the boat and ususally spend 2 nights aboard, every time we go down. For us, the need for more room overcame my attraction to the traditional appearance and superior quality of the Sabre and Tartan. After looking at a lot of Catalina's and Hunters we found and bought a really clean O'day 322 for it's roomy interior. If we lived closer to the boat, we might have chosen differently, but are very happy with our current situation.
One thing that suprised us was difficulty finding insurance. As newbies, we had a little trouble finding coverage for the O'day 322 we purchased as our first boat. From what I could gather, we would not have had an issue if we stayed under 30' and might not have been able to get coverage at all if we'd gone much bigger than our 32. You might want to call around insurance companies to see what coverage you'll be able to get before settling on a boat.
Finally, it sounds like you have more training than we've had so far, and we haven't had any problems daysailing our boat on the Cheseapeake Bay. We only took a 2 day ASA 101 class before buying the boat, but plan take private instruction on our boat once we have the basics fully assimilated.
Bill and Jill
s/v Palmetto Moon
Stingray Point, VA