Our first boat was a Mac Venture 22. Great old boat to learn on and we put many new scratches in her gel coat the first year. Easy to sail with basic controls. As far as overnighting, we did many weekends our first year. As stated the v-birth is cramped for 2 people. Buy her cheap and have fun!
I fully agree with this reply...
for a first boat, get something affordable.... like the venture 21.
the 21 has a great reputation as being easy to sail, fast enough in its class to be a contender, a good weekender for 2 adventurous people, relatively cheap to outfit, its easy to rig, easy to tow, and easy to get off of a sand bar
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we had a later version of the venture and spent many 4 day weekends on it... im 6ft, and 52yrs old, and found the v-berth to be no problem at all for the 2 of us...
you will learn boat maintenance at an affordable cost, and while learning, and you will get some scuffs and scratches in it... no point in buying more boat to learn on, unless your budget allows you to not worry about a couple thousand either way....
buy a decent boat at a cheap price, learn to sail and have a blast while doing it, and when you are ready to move up to a bigger boat you will have some experience behind you to know what you want and how to take care of it....
and when you get ready to sell the first boat, you will more than likely get your initial investment back...
the venture 21 is a nicely designed hull and a fun boat to learn on... make sure it has all of its components and the sails are in usable condition.... parts can get expensive real fast.