Retire on a Sailboat – What could go wrong? Everything! Do it anyway.

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Recently, when asked once again, “Do you recommend that I sell my house, quit my job, and move onto a boat?” I decided to delve deeper than my typical list of pros and cons for older sailors and interview some friends who moved onto the water in their fifties. Bruce is 70 now, and Connie is 63. Connie holds a degree in gerontology, the study of aging, and has a 100-ton master captain’s license.

retire on a sailboatI really got to know Bruce and Connie when my husband and I sailed from the Virgin Islands to Grenada in 2014. Through a combination of chance meetings and catastrophic failures, we ended up spending Christmas with Bruce and Connie at a marina on Antigua. From there, we buddy sailed with them and two other couples for the remainder of our down island trip.

For this article, I hopped on Zoom with Bruce and Connie and asked, “What would you say to a couple in their fifties who are considering liquidating a large portion of their assets so they can buy a sailboat to live aboard?”

Bruce instantly responded, “Well, the first thing that comes to my mind is the fact that that’s us! As a couple, we were in our early 50s when we started sailing. Why wait? You’re not going to get that much more ahead. Have an adventure while you still have an adventure in you.”

How did you start your sailing career?

Connie told me, we started out of Carrabelle, a lovely little fishing village in the panhandle of Florida. We would sail on Apalachicola Bay. It was a great place to learn, and there we met some people who had sailed the world for 26 years. They were our sailing godparents and took us under their wings. We branched out and moved down to the St. Petersburg area to go on our first overnight sail.

bad sailOf course, the overnight was the most horrible trip in the world. We were stupid and didn’t know what we were doing, so we left in January. It was freaking cold! Just every kind of anything that could go wrong went wrong, but we made it. After that, nothing could stop us. We sailed in Tampa Bay and got out into the actual ocean a little more. Then we headed down to Key West to sail with some friends to the Bahamas.

From the Bahamas, we sailed back to the States and went all the way up to Albany, New York on the Intracoastal. That was magical! We loved seeing the backsides of different towns. It was just really cool. We stopped in Marathon, lived there for a year and a half, and then we met up with a bunch of great cruisers. We left with a buddy boat and went back through the Bahamas, to Turks and Caicos, then spent six months in the Dominican Republic, which we loved.

Sailing to GrenadaAfter that, we went to Puerto Rico, and then we stopped in the Virgin Islands. We decided to stay there for a while because we needed to work. We finally switched from our first boat to our second boat, a 41 Morgan, and took her down island to Grenada. It was beautiful and I loved the variety of the islands on the way, but none of them had anything better than what we have in the Virgin Islands.

I don’t think we ever had plans to sail around the world. People always ask, “Are you circumnavigating?” I don’t feel like it’s a failure if you say no. We met many people that circumnavigated. Of course, Fatty Goodlander; everyone knows Fatty, and even Fatty said St. John is the best sailing in the world.

Fatty and Carolyn GoodlanderYou know, when it comes to utilizing your boat, the Virgins are the best. You’ve got enough wind to sail. You have a million places to stop and different-looking reefs. It’s not like you see the same thing at each location, right? Everything has its own flavor. It’s just the best.

What’s your memory of how we met?

How we met you and Kelly is a great story! We were on St. Kitts, intending to go overnight to Guadeloupe. The weather was not bad, but we had issues with our fuel and our engine. We headed out on Thursday the 12th in the dark, and by the time it was Friday the 13th, there goes the engine! Bruce was working like a crazy man trying to fix it and restart and fix and restart, and on top of that, we tore our headsail. We were whipped.

We decided to put out a security alert letting boats know that we were out there without a headsail or an engine, then we got this response in a lovely English accent on VHF, “This is the Montserrat Police Department. Would you like some assistance? I’ll contact our marine department.”

Immediately, I said to Bruce, I don’t think they have a marine department. The voice came back on the radio, “I’m told we don’t actually have a marine department, but we’ve put a call out for assistance.”

island freighterAfter a lot of back and forth, we got a call that The Midas was coming to help us. I imagined a tugboat, but when The Midas was within range, the captain called us and said, “You need to have your longest lines ready because I’m eight meters off the water.”

I said, “Did you say eight meters?”

He laughed and said, “Yes. 24 feet.”

We straightened our long lines, and suddenly, the winds and the seas completely stopped. A gigantic wall came up next to us. It was an island freighter 1500 feet long. The captain pulled us gently. I figured we would come flying out of the water, but he kept us at a six-foot draw. He just slungshot into Montserrat and shone his huge light on us until we got anchored, then went on.

retire on a sailboatThat was days before Christmas. After that, we sailed to Antigua with you and splurged on slips at the marina. I loved our setup on that boat; we could fit eight around the table. After that, it was buddy sailing down to Granada with you, Kelly, Buck, John, Suzy, Randy, and Janet.

Do you recommend buddy sailing?

I do! Besides the fact that it’s fun, you’re on the radio with each other, and there’s just that wonderful feeling of camaraderie. When we left for Montserrat to go to Antigua, John towed us the last 10 miles. We were so thankful. If something happens, you know you’ll have someone who will help you. That’s one of the marvelous things; in the event of something going awry, you have that sense that someone is there for you. Even if they can’t help you, at least they’ll hang out to make sure you don’t just float to Cartagena.

Retire on a sailboatAlso, you’re not duplicating systems; each boat brings something — an attitude, an understanding, sailing experience; then you’re one pie instead of six pieces of pie. Together, you have a much more extensive skill set. So yeah, I would look for like-minded sailors with different levels of experience.

Sailing is the great equalizer. It doesn’t matter if you’re on a 100-foot powerboat or a 27-foot sailboat. You all experience the wind and the waves and weather conditions and the reefs, and that’s what makes you the same. You’re no more or less because you got millions of dollars.

How much does it cost to retire on a sailboat?

You’ve got dockage, you’ve got insurance, you’ve got the maintenance, you’ve got a lot of expenses. What I’m saying is you can’t really retire; you need income. You know, people always ask, “How much does it cost to live in a boat?”

My answer is, “Every nickel you’ve got! Whatever you’ve saved, you’ll spend it.”

sailboat haul outThe paradox is that we knew people with a monthly income of $500 and others who had $5000 coming in from retirement funds or pensions or whatnot, but no matter how much money came in, it all went out again. You would think if it only cost $500 to live on a sailboat, then the ones who have $5000 can save $4500. It doesn’t work that way, though. In with the tide, out with the tide.

But regardless of the cost, I say, take the hard right turn. Make that big change in your life; it’s just going to open up this incredibly wonderful world.

What is your fondest sailing memory?

My fondest memories are of making music. We have done that from the beginning. We met up with the buddy boat that we traveled with for several years and would sit around and play guitar on his boat or our boat. In the Dominican Republic, they had an open mic night that was just so magical. Young kids would get up and do standup comedy. Nobody was afraid to do anything. You had people who were not really great, but they would get up and try their best and it was fine. One guy had a repertoire of four songs, so every week, for six months, we heard those same four songs. And that’s okay. Everybody loved it.

Sailing to GrenadaMusic and friends were the best parts for us. You don’t have a lot of time, so you don’t do this whole formal thing? When you’re sailing, you just throw it all to the wind and jump in and become fast, instant friends, for however long it lasts. It doesn’t last forever, and that’s okay. We have some really good friends that we haven’t seen since 2009, and we probably will never see them again. Another couple moved to Australia, and you know, we’re probably never going to see them again either. But the time we had was fabulous!

It’s just such a neighboring thing. You don’t find that on land, but you definitely find it in the cruising community, which is precious, invaluable, tangible, real, and memorable. I recollect all these things because they meant something to me. I hold them in my heart. You know, they weren’t just passing things. They were special. Sometimes you’re lucky enough to know when you’re in it, that it’s special right then. Yeah. And you’re like, “Wow, this is special.” Sometimes you don’t know unless you just look back and go, “Man, that was a special time.” You know, but it’s great.

Bruce concluded our interview with, “I don’t have the same energy I had when I was 55. Fifteen years ago, I had lots of energy and my knees worked! I could get into cramped spaces. I could do eight or ten-hour days on the water, so it was the right time for me. Do it before you’re too old.

Retire on a sailboatWhen I turned 65, sailing became a different experience. I started using my body differently. We weren’t spring chickens when we started either, but man, now it’s like my mind makes commitments my body can’t fulfill.

I say, while you’ve got that energy, heck, get out there and do it. Even if you’ve got a brand-new boat, you’re still going to want to personalize it. And so there’s always going to be things to do. Now is the time!”

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