I agree with Bob Austin; there are endless boats out there that will make a trip to the Caribbean or anywhere around North America if you just turn the key and go. Some may be more comfortable than others, but if you don't go you won't know. I cruised my Alura 30, now Mainship Pilot 30, to Tortola, down through the Bahamas and then straight from Grand Turk to San Juan. It was an older boat that I picked up for less than 30k in 1993, and had less than 40k in it when I sold it. Had a wonderful trip and would do it again if anyone asked me to go. My wife and I, with our two daughters (pre-teen), cruised that boat all over the northern Caribbean for six years and often had family come join us. Sure, it was camping some times, but we went places in that boat we can now only reminisce about given the much deeper draft of our 60 footer. Back in my younger days, mid to late 30's, I used to go camping in the Bahamas and the Keys in my 20' center console. Plenty of trips across the Gulfstream and out to Tortugas in that boat; its what I had and I wanted to go. My parents cruised their 62' trawler by them selves out of Vancouver right up until Dad died at 76, so age shouldn't be a deterrent; you just don't push it beyond your capabilities and comfort level. Updating electronics is just buying two or three hand held GPS's, new charts, a good set of dividers and a parallel rule, a couple of hand held VHF's, cell phone, all you need for 1K or less. Don't get caught in the trap of trying to make it "perfect", or you'll never go anywhere. Oh ya, a case of filters is always nice. There are incredible deals out there right now and more will be around when prepaid storage charges run out in the spring. Even if you can't do the work your self, there are lots of marginally employed "boat" people willing to moonlight for a reasonable rate. You could probably even trade boat time for labor. But the key is you have to do it! Stop dreaming / talking about it and just jump in and do it! Bob Phillips, Another Asylum, Tortola, BVI