and don't regret it one bit. I sailed in a 30 foot Cape Dory starting in the late 80's and I was at the small end of the fleet. Most boats were in the 33 to 35 foot range with a few 45's tossed in. I loaded the Dory with Radar, a water maker, Satnav, a Monitor wind vane, flash hot water heater, refrigeration and every thing else that would make me more comfortable. I was comfortable and we enjoyed the entire time we were gone and only returned when we ran out of money. Now I'm sailing a 38 foot Shannon Pilot House and still on the small end of the fleet. Every where I look there are 50 foot boats. These things are wide, long and fast by our standards. I sailed on some of them from time to time and have come to the conclusion that I'll keep my 38 foot boat. Here's an example of why. A couple of years ago I helped Dan on Tropical Dance, a contributor to this thread below, deliver TD from the Rio Dulce in Guatemala to Belize. It was hot, his anchor was big, his sheets were big, his sails were big, the shade canvas was big and heavy and it was a long way to walk from one end to the other. I was surprised at the amount of work it all was. Dan's right. A larger boat is more stable in heavy weather. The down side to that is you have a long way to fall from one side to the other. The extra room was nice but I have enough room. He carried more water but I have plenty on my Shannon. There was more deck space but again, I have plenty. The extra speed was nice I'll admit that. Even an extra knot shows up on anything other then a two hour day sail out of a slip. After I added it all up, the extra knot or two wasn't worth it to me and that trip reinforced what I felt 35 years ago. You don't need a huge boat to enjoy cruising. Over the years I've managed to install just about every bell and whistle that you could possibly want on a sailboat. Forward looking Sonar would be nice. A larger generator so it could pull a larger air conditioner would be nice and maybe satellite internet so I could get some fancy weather info but that's about it. In the 19 years I've owned this boat I can remember only one time I wished I had had a larger boat. That was a Christmas party years ago while at anchor in Dana Point harbor. It was obvious from the start that we had way more people on board then we had room for. We got past it after the fifth or sixth bottle of Rum and Tequila. I knew we were in trouble when they started stuffing people into the head to see how many they could fit in... I think Dan's wife was one of them if I remember.. JMHO.