11. Deb Downing and Dennis Borner: Giving up life on land for a Caribbean sailing adventure


In the autumn of 1999, Deb Downing and Dennis Borner embarked on an atypical retirement adventure.  They sold their home and all their furniture and embarked on what was to become a twelve-year sailing adventure. In this podcast, Sue Stockdale talks to Deb and Dennis to find out how they adapted to living onboard a 49 foot ketch rig, which included learning to catch marlin, cut one another’s hair and appreciating the vibrancy of the cultures and countries they visited.

Deb Downing and Dennis Borner transcription

Sue: [00:00:00] So today on access to inspiration, I’m speaking to a remarkable  couple, Deb Downing and Dennis Borner, who spent an unusual way of enjoying their retirement. So tell us all about it.

Deb: [00:00:22] Shortly after we got married, we did like being on the water. We bought a series of smaller sailboats. Nothing too serious, but enough that we were able to teach ourselves how to sail. We still had a great deal of interest in it. So gradually the boats got a little bit larger, and then we stopped having our own boat and we actually started to charter down in the Caribbean, which is a nice thing to do if you’re in New York during the winter. We did that for about 10 years and became very friendly with the captain and his mate, they had a Morgan 49 they only made [00:01:00] 10 of them. Charlie Morgan was a big boatmaker in Florida at that time and sort of like a seed was implanted because we just enjoyed being down in the Caribbean. We enjoyed the lifestyle, the people we were meeting. It was a very healthy lifestyle. You’re in the water, you’re swimming, you’re eating well. As I said, the seed was planted, but we knew they only made 10 of them.

Dennis: [00:01:22] Can I just say something about that? The captain and crew actually have their own kind of unique story. He was a Harvard MBA who had chartered a boat, just for vacation with his buddies down in the Caribbean, and he really liked the lifestyle. So the following year he actually purchased a boat from the original owner and with his wife got together and started doing shorts. So he, in himself had this adventurous spirit and went off into that, so we were indoctrinated, I guess with his spirit, as Debbie said, being able to sail the [00:02:00] boat. We knew this was something that we could do, and then we would both enjoy.

Sue: [00:02:04] People might think a typical lifestyle when one retires is to kind of settle down and, you know, spend time with family, grandchildren. So what was the tipping point that caused you to perhaps take this different turn of events?

Dennis: [00:02:18] Well, I think the start of the tipping point was the fact that we did not have any children. All our family, younger family was living on the other coast of the U S and our other parents were all healthy. So we really didn’t have anything to anchor us, which a lot of folks too. So that was the point that we started at.

Deb: [00:02:37] And I think perhaps it was just our personalities, however you want to term it. We were always on the move. We were not going to do the conventional. We’ve saw that our life was actually in some aspects just beginning. It wasn’t the end. It was the beginning of something new.

Dennis: [00:02:54] And we had been fairly active, in our lifestyle up to that point, we had done a lot of hiking, cross country [00:03:00] skiing and camping around, so we were kind of had an interest to begin with.

Sue: [00:03:03] So this wasn’t necessarily anything too out of the ordinary,

Dennis: [00:03:06] not for us.

Our friends and family thought it was a little strange, but. In fact, my mom liked the boat and she knew the boat and stuff like that, but there were some things she just couldn’t come around to when we were getting rid of everything we had.We sold the house and the cars because actually when we retired, we retired early. I left without a pension, without health care. Dennis had retired early also, so he didn’t have a pension. So it was really depending upon our own savings and investments to keep us going. So we sold everything that we could for pocket money.

And my mom kept on reminding me, she said, where are you going to put you a living room chair? I said, mom, you don’t, put the living room chair on the boat, you know, everything is built in. You know, she just didn’t see it. So a lot of people, they’re happy for us, and maybe they weren’t surprised, but it was a lifestyle. They said, Oh no, we could never do that.

When you take a step like that. A [00:04:00] lot of people are concerned and you know, this is totally out of their realm of experience. Yeah. So they do see it as a crazy idea.

Sue: [00:04:08] And I understand that this boat wasn’t ready to go when he saw it. It wasn’t like you just stepped on it and sailed.

Dennis: [00:04:15] That’s correct.

Sue: [00:04:15] So you had to have a degree of vision to imagine what could be possible  Tell us about what it was like when you first set eyes on it.

Dennis: [00:04:22] Because we had chartered the sister ship. We knew this was a excellent boat to retire on and it had a lot of room. It was 49 feet in length. I was a Ketch rig. So it was something that two people could handle easily. It was very well founded boat and because its size, speed, it was a good, seaworthy boat, well one came up for sale. It was in rather dire condition. My self being handy and Deb being energetic and having a lot of willpower and muscle power. We found a boat. It was very good price. And  we purchased it actually six years before we left. And during that six year period I did a lot of work and fixing things up. [00:05:00] And we got a lot of personal experience sailing the boat up and down the East coast of the U S on Long Island sound. And I guess one of the big takeaways about going off sailing is having a lot of experience and experience with the vessel. That’s probably one of the key points you’d like to make to somebody. A prospective sailor is have experience with your boat. Know how to navigate and how to handle it.

Deb: [00:05:23] Because the boat is, we often told ourselves when we got caught in a storm or conditions weren’t as favorable as it like, the boat will take care of itself. Just don’t do something stupid. You know, but that only came about because we had spent a lot of time with the boat.

Sue: [00:05:41] So when you saw that boat and you’d been sailing it for six years and you’d been presumably improving it from its state of disrepair, did you have that vision at the outset that this was where you were going to end up or did that evolve over that six year period?

Deb: [00:05:55] I think we knew we wanted to live on it and cruise, [00:06:00] but we didn’t know exactly when would be the time.

Dennis: [00:06:03] I think it was more of a fuzzy idea in your background and the other good thing for us, I think, is that we both kind of shared that vision, which is pretty important. But anyhow, it worked out very well for us, but it was kind of fuzzy first. yeah. And it didn’t come in focus until later on.

Sue: [00:06:20] So when you then took that plunge that step to say, okay, we are going to go off on this boat. We’re going to sell our worldly possessions and this is going to be our adventure. How did you plan where to go? Because the world’s a big place. You could go anywhere on that boat.

Deb: [00:06:34] That’s true. That is true. We were in the Chesapeake at that point in time, and of course Bermuda is like the sailors Mecca. So we said, all right, that’ll be our first stop. We’ll do Bermuda, and then from there we naturally thought of the Caribbean. It was within reach. Of course, we were quite familiar with the sailing grounds because we had chartered down there.

But to our delight, after some time in the Eastern Caribbean, we [00:07:00] discovered the Western Caribbean and that really made a big difference because it was new, it was different. And then we started traveling a lot more off the boat. We spent time in Peru and Venezuela  you know, you were there. Some one would watch over your boat and you just take off and it was great.  I know we just felt more and more comfortable in the cultures and the environment and the people we were meeting if we weren’t on the boat, our transportation was either the local bus, taxis, Taxis in central America are different from what you would expect, but they were always fun. We really enjoyed all those experiences.

Dennis: [00:07:33] We had traveled down to the Eastern Caribbean. We thought it’d be nice to go back and revisit on our own set of keel. And also the sister ship that gentleman was still chartering his boat, and I believe he was down in Antigua at the time, so we thought it would be quite fun to have a little race, which we did.

Sue: [00:07:53] And who won?

Dennis: [00:07:54] Well, it was a series of races and it was very evenly matched since the boats are identical.

[00:08:00] Deb: [00:08:00] I think we nosed them out at the end. Yeah.

Dennis: [00:08:03] But again, we had planned out the first season, and when you’re sailing, your life is kind of dictated, where you go is dictated by the seasons. So we knew we would go down the Eastern Caribbean chain to Grenada.

And then from there we would decide. Well we ended up in Trinidad, which is all the way down at the end of that Eastern and spent the rainy season there and then the following season we went back up to Martinique because the food was excellent,

Deb: [00:08:31] but you become very fluid. One of our friends always describe any sailors plans as made in jello because it just is. It’s constantly changing. You take advantage of the opportunities that come up and the weather and the weather,

Sue: [00:08:45] I am imagining that there might be quite a community of people who tend to be sailing in the Caribbean, it wasn’t a completely solo activity.

Dennis: [00:08:52] No. In fact, the whole environment of going off on your own and stuff is kind of a filtering media. So when [00:09:00] you go into the sailing community and you find it a very diverse set of people that all kind of have a common traits. So yes, there was a whole subculture community of sailing folks. And we were introduced to that in December, 23rd down in the American Virgin islands, St John, where they were setting up a Christmas gathering. They call it a gam in sailing. So initially we went down there knowing nobody finding that we actually did know a couple of people because they came from the Chesapeake and met, I don’t know, hundreds of other folks right off from the get go.

Deb: [00:09:37] One of the most enjoyable aspects of sailing. There were quite a few of them. The people you met when you are living on land or dirt dweller, as we referred to the people living on land because of your income perhaps, or your religion or your ethnicity or your interests, it kind of dictates where you [00:10:00] live, in your career. But when you want a water, you share that water with the multimillion dollar yacht. And then on the other side of you and maybe a 28 foot folk boat that came from Holland. So that diversity was just absolutely incredible and different people and the perspectives that you got. I found it extremely enjoyable. We met people that we would have never met. If we were still on land, and yet, as Dennis said, that multimillion dollar yacht when everybody would get together and the topic was anchors. Everybody was talking about anchors. So I think, I guess the important takeaway is people are much more similar. Then different. But a lot of times we don’t have the opportunity to see that.

Sue: [00:10:45] And what you’re saying is when you have that shared interest that allows that diversity to shine, whilst having that common interest,

Dennis: [00:10:53] And it’s much more social than we’ve found in other situations in that your only mode of transportation when you’re anchored [00:11:00] is a dinghy and you find yourself immediately either going around and saying hello to other folks, or what is typical is they would come over and say hello to you if they hadn’t seen you. Or if you’ve met them before, it’s like an old homecoming. Yeah.

Deb: [00:11:15] The other cruisers became your family.

Sue: [00:11:17] I can imagine that now. You’re making it to be a wonderful experience. You’re giving us all the upsides here, but I bet there are also some challenging times. I wonder if you could share with us some of those difficulties that you faced and how you overcame them.

Dennis: [00:11:31] It’s a bit of work. It’s like a little house on the Prairie and that you have to get up every day and chop the wood cause you’re going chop wood. There’s maintenance on the boat. You’re actually constantly on watch because you’re, we were an anchor. So if the weather changed or shifted, you had to make sure that you weren’t dragging anchor. There’s always repairs on a boat.

Deb: [00:11:52] We would provision for quite awhile when we us the big canvas bags, we call them ice bags, the heavy duty LL bean, [00:12:00] and you would go into town, hop on the local bus. Get to a supermarket, try to put everything you needed into those two bags, then hop back on to the bus, and that would take almost the entire day.

Sometimes there were a lot of tasks like that, but if it’s something that you want, you’re going to do it.  I think that’s the key thing. We knew quite a few cruisers that their marriages were not going to survive if they continu cruising. They got along okay on land. More space, but not on a boat.

Sue: [00:12:32] So that close proximity, I’m imagining it takes a special type of couple to be able to operate well in that environment.

Dennis: [00:12:39] It does. And some people who can be that closely coupled on land because of the outside  forces, and your  responsibilities they’re stressed, and when they get in that environment where they’re stressed, they just don’t do well. So remove the stress and they’re fine. Yeah. [00:13:00] But the stress on like all of a sudden the wind starts costing 30 miles an hour and your canvases flapping, making huge amount of noises and people are dragging around you and yelling. That can be very stressful for some folks and they don’t do well and they don’t find that out until they actually experience it.

Sue: [00:13:17] So it’s almost about stress management as a skill, whether it’s on dry land or on a boat. That ability to be calm under pressure sounds like that’s an important characteristic to have.

Deb: [00:13:30] I think it is. And an important aspect of that is how much you trust your partner. When we, sailed overnight, we always maintained a watch. There was always someone upon deck and we maintained a three hour on three hour off. It would not do well for us if I was fearful when Dennis was up or vice versa. You don’t have to trust the other person and it’s not something that you sit down and spell it out and it’s just like an implicit. [00:14:00] Whenever you are going to do is going to be a good decision. If we’re both up, then we’ll mutually come up with a decision making, but you do have to trust the other person

Dennis: [00:14:10] And your responsibilities are for sailing the boat, navigating the boat, keeping a watch for other vessels. And keeping a watch on the boat itself to make sure that it’s secure. So it’s all the things you need to learn. You do need to trust your partner

Deb: [00:14:25] and just the corollary to that, it was difficult to find a hairdresser on the anchorages where we were at. In fact, we usually seek out anchorages where  there weren’t any towns around. So. Especially from a female perspective. To me, that’s the ultimate test of trust. When your mate, your husband has the scissors in hand and he’s going to cut your hair. What’s interesting is that we still, even though we’re land dwellers, is now. We still cut each other’s hair. I haven’t found a hairdresser liked Dennis. So he continues [00:15:00] doing it.

Dennis: [00:15:00] Mr. Dennis. Mr. Dennis, to you!

Sue: [00:15:03] What a skill to learn, Dennis

Deb: [00:15:05] and we, actually did.No, because that was one thing we had not thought about, and we certainly didn’t have any books to learn and there was no, at that time, YouTube. So we just kind of started doing it.

Dennis: [00:15:17] And which brings up another point. That there are a lot of skills you think you know all about cause you’ve read all the books and studied all the charts and went to the seminars. There’s a whole gamut of information that you just learn and the only way to learn it is by experience. That was kind of fun.

Sue: [00:15:35] Well, as you said, this isn’t the end of your life. It’s the beginning of another adventure. I’m imagining there’s a lot of learning to be done. Yes. So you say, now that you’re back on land, what caused you to then finish doing your sailing and have some other part of your life?

Deb: [00:15:51] Well, we had always agreed from the onset if either one of us had had enough for whatever reason, that we both agreed to, [00:16:00] give it up. And we were faced with another major retrofit of the boat. The boat was built in 76. It was completely upgraded before we left. But usually you’re thinking every. 10 to 15 years while we were sailing, we were still doing maintenance and repairs, and in fact, we were in Venezuela and remember, we, we rigged the entire boat ourselves. We were really faced with a lot we would have had to get new sales. So we started thinking about it. Dennis, you expressed some interest. You wanted to go camping up in Alaska. I think you wanted a, I’m a little bit more of a change, so we decided that’s it. We kept the boat in the Chesapeake and we did the car camping in Alaska and that was great fun. We came back, we were sailing around the Chesapeake. First winter comes  we get through that second winter comes, I turn to Dennis and say, I’m getting too old for this, because it was too cold. It was. Ice on the boat, it isn’t really fun. So we went down to visit friends [00:17:00] in Florida and thought Florida was a pretty good spot to be. So we did sell the boat two years, three years ago, and now we have a small RV. So that’s where we do our exploring now.

Dennis: [00:17:11] They call it trading keels for wheels. So it’s a common thing people do.

Sue: [00:17:17] So how do you find now living on land compared to living at sea and having the water around you?

Deb: [00:17:23] It’s different.

Dennis: [00:17:24] Fresh fish is a problem.

Deb: [00:17:25] Yeah. Getting fresh fish is difficult. What I think, and I don’t have an explanation for this phenomenon, but we did notice whenever we were on the boat that whatever space Dennis occupied, for whatever reason, equally important, I needed to be in that space, you know?

So it was like, okay, how are we going to share this small little space. So I was surprised when we got into a house, at least for the first year, the same, same thing was occurring. We needed to be in that same little space and we finally have spread out a little bit. I like having a garden. It was difficult on the boat to have a garden [00:18:00] and,im into water colour painting now, which is a skill I enjoy because I never thought I could be an artist.

I never thought I had the talent.  I had no interests. I didn’t have much art education when I was growing up, so I just kind of dismissed myself. I couldn’t do something like that. We were down in Bocas Del Toro and Panama. Then a woman announced that she had some extra supplies. She was a watercolor artist, and if anybody wanted to try their hand to come down to local bodega and for whatever reason that time I decided I’m going to give it a try. And what are the nicest things is when you can rediscover yourself like in your mid fifties late fifties so I’ve continued with that. So we’ve kind of gotten other interests that make up for it. We keep in touch with a lot of cruising friends. A lot of them now are back on land

Dennis: [00:18:53] And I just want to add, while Debbie was doing art and the cruising community was there, was at that marina, there was a [00:19:00] guy who was a professional juggler. He performed on the streets in San Francisco and in Florida. So he was willing to teach me and a couple of other people how to juggle. So while, Debbie was learning art. I discovered juggling. Not that I’m highly skilled, but I can  keep three things in the air

Sue: [00:19:20] what talent you’re developing,

Dennis: [00:19:22] You never know what you’re going to come out with.

Deb: [00:19:24] Yeah.

Sue: [00:19:25] I’m wondering in terms of listeners who may be thinking themselves about taking a step into the unknown, perhaps doing something new, going on an adventure, what lessons or reflections have you gained from your experience that you would think would be useful for them to consider?

Deb: [00:19:42] I truly believe that if you really want to try something new something that you have never done before – you can truly do it. You have to have the confidence to believe in yourself. And along with that belief, of course, you [00:20:00] do all the necessary preparations. You know, if you need to study some skill. That will get you there are you’re going to do that if you need to, read books or learn topics that you never knew before, you’ll take that course of action

Dennis: [00:20:15] I’ll  just make an analogy. My analogy would be like a stepping off the high board in a swimming pool. You know, you read the books, you find out that actually you can go off the high board and not die and keep your mouth shut. Hold your nose But at some point you’re going to walk out to the end of that swim platform, and you’re going to take that leap. And that’s the hardest part is to take that first step. And if you have enough confidence to do the preparation ahead of time and read the books and you can make that step, you’ll be fine because everything else just falls into place.

Sue: [00:20:48] So that self belief, the confidence to take that step, that’s an important thing for somebody. So if you were reflecting back on all of your experience, your decision to go sailing, to be away for that significant [00:21:00] period of time together, traveling to these new countries, what do each of you think you’ve learned about life and yourself through that experience that you had?

Deb: [00:21:09] You learn very quickly that having a sense of humor is important. Don’t take it too serious.

Dennis: [00:21:15] I was not prepared for the experiences that we had. Because I really hadn’t  thought it out that well in detail. I didn’t intend to, but I found that it was so rewarding to visit foreign lands. and actually live with other cultures and it just broadens your mind and that is just beyond my comprehension that it would be that kind of experience. So that for me that was the biggest thing.

Sue: [00:21:44] It sounds like you’re looking at the world through different set of eyes now than what you were before you did it.

Deb: [00:21:49] I think that’s a fair judgment.

Sue: [00:21:51] We wish you well or whatever adventures you have next, but it’s been fantastic to talk to you today. Thank you so much for your time.

Dennis: [00:21:58] Thank you for having us. [00:22:00]