The Venture/Macs are an affordable entry into sailing. I bought my Venture 2-22 with trailer for $2300. Crossing to the Bahamas wasn't even a thought in my mind, only learning how to sail and it helped me on my way to achieving that goal.
It was also at a price that, since I had never sailed before, wouldn't have been a huge deal should I have decided that I hated sailing.
It did quite well on the Chesapeake and I survived to buy my next boat.