The Venture is a lake boat. The Pearson 22 is probably an Ensign, which has is not a cruiser, and would be like sailing a stone coming off a J22. If not an Ensign, 22 is still too small.
If you want to sail the islands, up your budget to $3-6000 and get a decent condition 25 footer (Cal, Catalina, C&C, for example). You will enjoy a nice sailing boat and be able to experience the cruising life. When oyu sell it, you'll get the money back. Plan to spend $1-2000 a year on maintenance and expenses, that's the way it goes.