How would you recommend that someone prepares to cruise?
Begin by doing a lot of reading about cruising. You can learn a lot from the many books written by cruisers about their boats and what is involved. Nowadays you can find this info by "cruising the WWW including blogs of sailors who have done it and are in the process. There are sailing forums to learn all sorts of things. You take it in and then go for what suits you - your budget and so forth. Things WILL change so be prepared.
Is there a place you visited where you wish you could have stayed longer?
Most places offer more if you invest the time and penetrate into the culture and ... land. Hanging on the hook gives one a limited perspective on the place you are at. My favorite place was Antiqua and Guadeloupe. The Canaries were interesting (culture) by not the greatest for snug harbors.
Show respect and consideration. Anchor with lots of room and try to be invisible (audibly) to your neighbors. As you are part of the scenery, try to keep your boat in a good appearance.
How has cruising affected your personal relationships?
If you have a sailing mate, it's the cat's meow. Very close (working) relationship - mutual dependence. Landlubber mates simply don't get it nor care to. They prefer to let others do it for them.
Describe your first sailing experience
It came when I was in my mid to late 30s and I was fascinated by the clever little boats and how they were a world unto themselves. A world that intersected the world I lived in and most people do. These compact efficient, modern yet ancient vessels have the potential to take a single person anywhere on the planet that touches the sea - and that's a lot of the world. I sailed with a friend on my inauguration down Long Island Sound.
Are you attracted more to sailing itself or cruising-as-travel and has that changed over time?
Sailing can be many things. When you have time and money you are free to go explore and move about. When you are stuck on land it is a delicious escape you never tire of, despite the work required to maintain a sailing boat. Don't like planes anymore, and much prefer to sail if I could... Like a turtle who takes him shelter (home) with him wherever he goes.
Over 25 years I have spent only a few weeks in total tied to a dock (except winter wet storage). A few days in Bermuda following the Marion Bermuda Race in 91 and one night in Portland ME when my wife took the bus up to join me for a ME cruise. I use a seasonal mooring when I am land based and when I leave it I am on the hook. Anchoring is where I spend most of my time when I am not making way.
How do you fund your cruise?
My 4 year cruising was funded by a combination of savings, selling my home and a small inheritance. When it was all spent I came back broke and began to work again. Kept the boat.
How did you secure your valuables (in and on your vessel) while going ashore?
I don't have anything valuable except money itself and the boat and gear. I don't lock usually (only the dink) and only sometimes. Only been robbed when I wintered in water in a marina and someone stole my running rigging. And your dinghy? We lost a new RIB and OB several yrs ago in RI. It was either tied to the boat, or not well tied as my wife probably assumed I would tend to this and I may have simply assumed she secured it. We don't recall. But it was gone in the AM and nowhere to be found in the area. If it was found the finder decided to keep it. And if it was stolen, that was the intent. We use a stainless steel chain and padlock, but anyone with a smallish bolt cutter could easily defeat this.
What question do you wish I would have asked you besides the ones I've asked you and how would you answer it?
How do you get hands on experience?
I was sort of dumped in the water and forced to sail. I got the sailing bug from a friend who induced me into a partnership and then backed out. So I went to the broker and asked for a smaller boat.. after having taken a 3 day sailing course. So, in short order I purchased the boat I would cruise on, live and and still own 25 years later. I pressured my friend to help me sail the boat out to a summer mooring and then to come with me for the first few sails. Then I was on my own and worse I had a wife at the time who was not a sailor. So the first 5 years of ownership I sailed the boat as much as I could, even in the snow one Fall. During my learn to sail period I fitted the boat out with the gear and upgrades to go offshore and live aboard. My final tests were to sail to Maine (1000 mile trip) and to do the Marion Bermuda race with a crew of experienced sailors including, you guessed it, the friend who got me into it all.l Once I got to Bermuda I was ready to go. So the total learn to sail from absolute novice to sailing solo about the Caribbean was just under 6 years. Key to my experience was the notion that I had to do everything myself and alone if need be and that turns out to be the case 98% of the time. I've set the boat up for single handing and it's the only way I can imagine being comfortable on a sailboat - knowing everything about the vessel. Because... you never know when you need to know.
How do you know when you have enough?
When your confidence exceeds your fear you have reached the level where you can go for it, whatever that "it" is. You always need to be prudent and have a healthy bit of fear about what could happen and so running all the what ifs... book learning, some trials and so forth and preparation will give you the necessary confidence that dominate the fear. Fear is basically the absence of experience and so the more experience you have both practical and books the better off you are. But you can waste your life in preparation and there comes a time when you just have to go or it and accept the risks and that you have taken reasonable measures to mitigate risk.
How do you prepare for the bad stuff?
There's two kinds of bad stuff. Stuff you could have prevented by preparation and maintenance and the stuff that mother nature hurls at you. It's hard to practice hurricanes or lee shores. But you can read and apply lesser experiences to when the shit hits the fan. Each one of those build confidence and it's mostly in the boat which will take it a lot better than you will. When I think about the conditions I sailed in in my early years either weather has moderated or I am just not sailing in what I cut my teeth on back then. But every once in a while you find yourself in nasty weather and the only thing about it is, you've been there before and you know you and the boat can make it. So you need to go out in heavy weather close to shore if you plan to deal with it offshore... where at least there are no lee shores!
How do you cope with fear?
Experience is the only way. You need to fall back on your training and experience and the knowledge that others have faced far worse with far less. You don't dwell on it and instead take care of business and the mission to get thru to the other side. This keeps you pretty busy. Shiva's a great boat and a lot tougher than I am. I take care of her and she takes care of me. That's the deal.