S2 7.9 Bear Lake, UT
I know someone who lives on a 30 foot boat. I think anything from a 32-36 footer would be a fine weekend cruiser for one person or even smaller. I know a couple that cruise long chunks of the summer on a Dana 24. I think anything with a reliable diesel, and standing headroom is all you need for cruising a few days at a time. A boat in the mid 30s would give you enough space to carry what you need to cruise longer and maybe have a guest to help you sail. The smaller the boat the easier it will be to both afford and sail.Oh, I was thinking of the bigger boat since I have a 34 ft motor home and I though I could sail out somewhere, anchor down and relax like I do in the motor home.
Another question was. In my RV, I pull my pickup, I'll stop someplace for a week and jump in my truck and go play some golf. Well that doesn't look like that will work from a sailboat at anchor.
I would sign up for ASA 101 and 103. In the 103 class you will be introduced to boats in the 30 foot range and it will help you determine if you can develop the skills to single hand a boat that size. Instead of a pickup in a sailboat you carry and sometimes tow a dinghy, a small inflatable 8-10 foot boat with outboard that acts as a pickup. It can get you to and from shore where you can eat or hike or buy supplies.