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I think the two types of charters you are mentioning are two types of audiences. (Though like cv said, I would cross both sides of that. This was the best vacation I ever had: 8 days/7 nights I notice the stops are a bit different now but the stops were villages and starting point for hikes into tinier villages or good views or historical spots. It was much more of the crew doing it for us but it was by no means stop and go shopping like the big cruises. 10 cabins total. We ported (is that the word?) in a different village port every night and sailed off in the am to the next destination. A few times we stopped in random coves mid day to leap off into the water for a swim before ouzo filled afternoon sails. The crew partied every night with us in little open air restaurants, the crew provided breakfast on the boat before setting sail and it had a honor bar. How freaking cool is THAT? At that time it was about $ each person 2 person cabins with your own "shower" (I could sit on the toilet and "shower" at the same time if I wanted. :) including tours and breakfast everyday. Lunch was available for extra cost. They threw in extras now and again such as a bottle of ouzo and plate of cheese and olives for the afternoon snacktime. You even want to check in with the company as they have tours in the US. We had a tour guide on the boat with us who took us on (optional) hikes at every port, told us the best places to eat or shop, historical and natural sites nearby, etc. That's all beside your point I guess, but the more research the better for your adventure. Anyhow, I think you would be safer in a bigger boat and far more comfortable. I don't heat a "creature comfort" I it a necessity! I would think a shower is a HUGE difference when trying to charter. I would want access to a shower for sure if it was overnight. If you can charter the bigger boat, then could that pay for the extra payments? An 84 yo wow! Then I guess it cannot be too hard to handle. Sounds like it has good juju. Follow your "dream"!

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