75,000 Miles Sailed… Then They Chose Alaró

“Our voyage of discovering the island is just starting.”

Trevor and Judy Hill left their life in Phoenix, Arizona to chase something bigger: freedom. What began as daydreams during the 2008 financial crisis became an extraordinary reality—more than six years living aboard their Oyster yacht, Intrepid, sailing across oceans, joining the Oyster World Rally, and visiting 40–50 countries along the way.

In this episode, Helen sits down with Trevor and Judy to explore what life is really like at sea, how travel reshaped their relationship and priorities, and why—after seeing so much of the world—they chose Mallorca as the place to build their next chapter.

They share the honest thinking behind choosing village life in Alaró, and what it takes to buy property in Spain as foreigners—patience, persistence, and learning that “the first thing is no”.

If you’ve ever dreamed of moving to Mallorca (or reinventing your life entirely), Trevor and Judy’s story will leave you inspired—and better prepared.

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Transcript

Introduction: Trevor & Judy Hill from Arizona

Hello, I’m Helen Cumins and this is Mallorca Living, a space dedicated to those who are dreaming of making Mallorca their home. Today I’m here with Trevor and Judy Hill from the US. We’re going to talk about their journey to Mallorca, which started on a boat arriving here this time last year, and finally choosing to live in Alaro.

Trevor and Judy, you’re very welcome. I’ve been looking forward to this podcast for a long time because I really feel you have a unique story to share with our listeners. That story started some years ago when you decided to leave your normal life and spend more than six years living on a boat, traveling the world. So tell us, where did that decision come from?

How sailing dreams began during the 2008 crisis

It probably started 20 years ago, really, during the financial crisis in 2008. I was working in corporate America and not having a lot of fun at that particular moment. I used to take pictures out of the Oyster calendar and put them up on my wall and daydream about getting through the financial crisis. I thought if I ever made it out, we would go sailing.

I was self-employed at that point. We owned utility companies, water and wastewater utilities, and it was a difficult time to survive through the financial crisis. It was a real moment where we didn’t know if we were going to come out the other side of it.

We’d always had a passion for sailing. We used to take our kids on family vacations. I grew up in Vancouver, so we would sail as kids in the Gulf Islands, charter boats and sail through all those fantastic areas. When we moved to Phoenix, we sailed relatively seldom, but I would have called myself competent from a sailing dinghies perspective, though a long way from being competent sailors of the boat we eventually evolved to.

For me, I was 100% in. It was exciting. I was the girl with the glass rosé, not handling the ropes, so it was a great opportunity to learn a whole new world and new challenges. The most difficult thing to give up was probably friendships, because we had great friends, but our kids were launched in university, so we felt it was a good time. In the end, a lot of friends came to find us in different parts of the world.

Leaving corporate life to live on a boat

In 2018, ten years after the crisis, we had dug ourselves out and I had the chance to leave corporate America. We decided to buy a boat, driven by our interest in sailing around the world. To do that, you need a particular kind of bluewater sailing boat, which narrows down the choices. It just so happened that the kind we bought, an Oyster, was advertising for what they called the Oyster World Rally.

Joining the Oyster World Rally

The rally brings together 25 or 30 similar boats and similar people to sail around the world together. It’s an amazing concept, joining a whole lifestyle and community. You feel more supported and guided than trying to do it solo. There was a lot we didn’t know, and it turned out to be a great way to do it, better than we expected. People came from everywhere, all over the world, and we made great friends from all these different countries, all sharing this common experience.

The rally sets a date on the calendar, for us it was the 9th of January 2022, but getting to that date takes a few years of preparation. You have to buy your boat, and then we hired people to train us, a full-time instructor to take us from our rudimentary sailing experience to superyacht bluewater sailing, which is quite different.

Training for bluewater sailing

We dedicated almost nine months to that training, to get our tickets and train ourselves up. For many people, this would be a whole new career, but we wanted to be competent and insurable as the people driving the boat. We wanted to participate actively, to have that experience of actually doing it, so it created more of a team feeling on our boat.

We started with five people on board, but after the rally, we no longer needed the crew and have sailed on our own since. Sometimes a cousin joins us, but most of the time it’s just us two, which is challenging and rewarding.

First impressions of Mallorca & Palma

We had come to Mallorca a few times, even before buying this boat. We were here in 2016 and 2017 looking at boats, and we were amazed by the island, the city, and the fact that it’s the mecca for sailing in the Med. It really is the biggest hub, historically for hundreds of years. There’s a lot of culture around sailing and proximity to spectacular sailing. If you’re going to sail in the Med, this is the place to do it from.

We actually bought our boat here in 2018 through the Oyster agency on the island. I was tracking all the Oysters I thought would be suitable for our adventure, and found one that seemed good. I visited it on business in Australia, then we chartered it in Croatia and again in the Caribbean. I stalked the owner for many years and finally made a deal in 2018.

For us, it was about finding a boat we could still manage ourselves, but was big enough to be comfortable. The boat is called Intrepid, and it’s been good to us.

Life at sea: roles, challenges & rewards

Living on a boat for such a long period has been good for our relationship because we’ve become a team. We each have different roles and responsibilities on the boat and depend on each other for those things. You can’t sail it by yourself, so we need each other to do different tasks. The boat is big enough that if we need space, we can have it, so it’s been really nice.

Our children have joined us along the way. We’ve had Christmas in different locations for six years, and they’ve joined us here and there on the rally and in different places where we’re sailing.

Exploring 50 Countries and unforgettable sailing destinations

We’ve probably visited 40 or 50 countries during that time. Since 2019, we’ve sailed about 75,000 miles, crossed the Atlantic five times and the Pacific once. We’ve covered so much, though we haven’t been to the far north or far south yet, and those are becoming intriguing as the next places to explore.

For standout places, we have a few stock answers. City-wise, we loved Cartagena, it’s beautiful and colorful. Cape Town was a great experience, we sailed in and loved it there. Island-wise, Fiji was just beautiful, with amazing diving. One great experience was anchoring near the island where the movie Castaway with Tom Hanks was filmed. We had friends who had never seen the movie, and we can put a movie screen on the back of our deck. So we played Castaway at the Castaway Island in Fiji, which was a really fun, special moment.

Why Sailing is a metaphor for freedom

Sailing is a metaphor for freedom. That’s why it’s on the cover of every retirement brochure, a picture of a sailboat and a couple, for good reason. When you get into this life, get your boat and learn everything, you’re in a position where you can do whatever you can think of. This summer we sailed right into downtown Venice, to St. Mark’s Square. We wondered if you could sail right to the square, and we did. You could get off the boat and walk straight in. We’d been to Venice many times, but never like that. That’s the point, there are all these places if you can think of them. Someone in Oyster sent around a message asking if we wanted to sail to Svalbard, the most northerly city in the world at 78 degrees north, only 12 degrees from the pole. We thought that sounds pretty interesting, so that’s in 2027, our next step.

While we’ve been doing this, we’ve continued to run businesses in the US. After I retired, I thought I knew something after 40 years, and got tempted to make investments. Sometimes the roles expanded more than we bargained for, but we’ve learned to integrate it well. Starlink has been a game-changer for communications. We have our fingers in a few pies in the US still, and probably will for some time. We have life there too, lots of friends, so we’re not fully disconnected.

Why they chose Mallorca after 50+ countries

Mallorca offers so many things we’re interested in. Sailing, for one, and cycling, which we love to do and will get back to soon, and hiking. It’s just a great city, the people are lovely, and every village is different. The island offers so many things you just don’t find anywhere else. We kept coming back to it when thinking about where we’d like to live.

After this big experience of the last five or six years, we felt we couldn’t go back to our old life. We almost did, we were looking at real estate in the US, but then felt it was going a bit backwards. It wasn’t that we don’t love our friends, but we needed to keep challenging ourselves and doing something new. So we thought, no, let’s go back to the plan of Mallorca. It appealed to us after sailing all this time. It’s really hard to go back to before.

The journey to find the perfect property in Mallorca with Helen’s team

Initially, we thought we wanted land, a finca in the country. We had looked at hundreds of homes online and sent about 30 to you. You guys narrowed it down to 15 because you had so much knowledge about the property and areas that we didn’t even consider. You would say things like “this area is not good in the summer,” so that was incredibly helpful.

The great part of your business is that you can come to Palma as a tourist or on a sailboat and get a tiny snapshot of the island. You see the airport, the sailing community in the city, drive to Deia and do the tourist things, but you don’t really know anything. We quickly felt that. We didn’t know what we didn’t know. In sailing, you learn quickly there’s no pretense, and we took the same approach with you. What we don’t know could bite us.

When we came across your business, we thought this is what we need, someone who really understands what it is to live here, as opposed to being a tourist. Everyone knows Mallorca from a tourist perspective, but far fewer people know all the nuances. I remember one of our first conversations, you said things like “That home is lovely, but in the winter you’ll never see the sun,” or “This place is nice but it’s an hour and a half from the city, you’ll never go there,” or “The restaurants are closed in the winter.” You talked to us about the demographics, and it became very clear that we really didn’t know what we didn’t know.

Because we live on the ocean, we didn’t need an oceanfront property, so we were drawn to the center of the island or the mountains. You helped us understand with a lot of patience that certain properties, while pretty, wouldn’t work for us for various reasons. That journey was really useful and demonstrative for how to better make the decision.

It was so much fun exploring together. Because you’re into cycling, I could tell you about the routes, and you were very curious to learn as much as possible. In each place, we really went through the advantages and disadvantages of each location in a very honest way. When you’re going through the process of transitioning to a new place, you need a sounding board, somebody who has your back, who’s not trying to pull you in one direction or another. We never felt that with you, you were just very generous and neutral.

One of the things we didn’t know, which was very interesting, was about the zoning. In America, you see these beautiful homes, and like many people we fell in love with the finca idea, a farmhouse with land. You think off the boat, we’ll have all this space, a stone house but modern inside. But then you figure out with help how the rural zoning requires a gigantic piece of land with only 1% coverage. If you want a 500 meter home, you need 500,000 square feet of land, which is a farm. Then you think, are we going to become farmers? Or are we going to be sailors? When you explained that, we realized this was a real consideration.

We also realized we didn’t want to be a slave to the house. We’ve done that before. One property on the edge of Alaro had spectacular views, but needed work inside, and managing that without knowing anything about how to do it was overwhelming. Another home was beautiful with amazing views, but the accessibility wasn’t easy, you had to be a mountain goat to get up there, and we thought about getting back on our bikes.

The community aspect became very important. We’re sociable people who like to be surrounded by like-minded, fun people. That wasn’t initially the primary factor, but as we processed all the properties and thoughts, it helped narrow down what we really wanted. The final decision was this beautiful house in the middle of Alaro.

Discovering Alaró’s community and quality of life

Yes, in the village. So talk us through that. How did Alaró become your choice?

Well, along the process you describe, we started to say to you that it would be really nice to have a finca, but we’d like to be able to walk into town. And you were like, “Well, those two things may or may not coexist.” The further we went in, the more we looked at homes that were closer and closer to different towns. Then you showed us this fantastic Can Falco home by François over at the Cortes and Clark group. That was actually the first time we saw the fit and finish of a home that, frankly, we were more used to. In the boating world, the woodwork and workmanship is spectacularly good. Some of the homes we’d seen, although they were great, didn’t always have that fit and finish, yet they had a very high price tag.

We were also very enthusiastic about this property developer because through seeing many homes on the island, we figured out that what they’re offering is a whole other level. They build homes as if they’re for themselves rather than to sell. They’re very creative with unique touches that make it nice, not just cookie cutter. Even though it’s new, they’ve added beautiful special things and fully finished it. They furnish these homes with a style that fits the island and location.

That first home we saw had so many things we loved, and we also really loved François and his wife Jess. They were very warm, inviting, and helpful. In the end, being somebody who’s very detail oriented is great because you know what you want, having owned many homes. He seemed very accommodating with everything.

When we went back to him and said we love Can Falco, with its proximity to town and beautiful views, but 600 square meters is a lot for just the two of us, he mentioned they had another place just down the street that wasn’t on the market yet and not even started being built. We were still able to make some decisions, which was great. You had raved about François and the team multiple times, and we’d hit it off with them. He said we could come walk through the construction site, and when we did, we knew this was it.

That was during the Alaró market on Saturday, which is also a highlight. It wasn’t only the house that captivated you, it was the whole feeling of Alaró and the community there. So many fantastic community members, the little restaurants, like the two Dutch sisters who run Sis Cafe, and Trasterrro which is an Argentinian family. There’s all this culture from around the world coming to this spot to set up shop and be part of the community. It’s so interesting, and everyone is very accommodating with our limited Spanish skills, which is our new challenge.

You’ve told me before that Alaró became popular with the international community because it became a hub for the families of captains from yachts. They didn’t choose to live in Palma, they actually based their family in Alaró, and it just grew from there. That’s why you have this lovely integration of international and local community. The local community seemed very open and welcoming.

I don’t know how the Spanish people who lived there for 50 years feel about all the people who moved in. For some, their businesses are probably thriving. For others, they might feel there are a lot of foreign people in their town, but we’ve never felt that. Everyone is very kind. There’s a lot going on in that little town. When you look from the outside, you don’t necessarily see it, but there’s a terrific bike shop, five or six great cafes, and probably ten good restaurants, some world class. You have hiking and cycling right there. We walk out our door and go for a hike right up to the restaurant.

It’s close to the airport and close to Palma, and we’re close to our boat. Also the north of the island is just as close as Palma, so it’s a great central location. It’s one of the few towns that’s at the end of the road. In some other beautiful towns like Santa Maria or Bunyola, the main road tends to go through them, which isn’t bad, but in Alaró you drive into town and it ends. You get out of your car and walk into the square, which is a bit unique on the island. The square and how it’s developed around there with the restaurants, shops, and markets are all designed around that theme. The Saturday market is mandatory attendance, you get your chicken, coffee, flowers, fresh vegetables, and it has a real sense of community. You can’t go down there without running into people. Then you go up to Sis Cafe for brunch afterwards. We’re finding the program to be very easy to understand. It’s been a great choice.

The value of a property buyers agency

I’d like to ask you for our listeners about the service. You decided to opt for a property buyers agency service, and many people still don’t really understand what that is, although in North America it’s the standard model. What did you find most useful or beneficial about the service during your process?

I like your model a lot. If you go to LA and want to buy a house, the person there will show you houses, but here we actually needed quite a bit more than that because we weren’t even really sure. We thought we were going to buy a place here, but we could have moved to Italy, Sardinia, Portugal, the UK, or anywhere. We had zero location constraint at this stage.

Once we decided not to be in Palma, which was a decision we could have easily made to stay in the city, but because we had the boat close by we thought we should branch out, that’s where your service was so helpful. You know all the different areas. Every house we sent you was in a different place.

On one viewing day, we reviewed about six properties, but they were with six different real estate agents. This was a seamless experience for us, but if we had tried to coordinate all that ourselves, it would have been quite a challenge. We didn’t know, as Judy says, one vision was to get a place right in Palma, one of those fantastic redone five-story homes, and live right in the city with all the restaurants and shops. But then you realize there are downsides to that. You can’t get your car in there really, it’s impossible, and it can be quite noisy and crowded in the summer, which is fantastic but you might not want to choose that. With you, we looked at six or seven condos in the city and they were spectacular, but you have to go in with your eyes open. There was no parking, which is complex especially if you’re lugging sailing stuff around.

For us, your service, and I like the business model in that it’s risk-free for the buyer. You didn’t know if we were going to buy a home, if we were able to find one, or even commit to Mallorca. There was some risk there for you, you have to be a good judge of character. But for us, it allowed us to tap into your experience and your company and extract all this 25 years of value.

You’ve also made a real science of categorizing all these things, like where to eat. Go to Helen’s page because there’s 500 fantastic restaurants. Or if you want a great beach, here’s the best ones. You haven’t just hung out here for 25 years, you’ve put it into categories. Any questions we had, you were able to answer, and that helped us shape our view of how to think about how our life would be. Even your interest in cycling was very interesting to us because we think we’ll spend a lot of time doing that. Suddenly it was like, okay, here’s the places, here’s the cafes where cyclists go, here’s the roads that we all use. For us, it was much more than what a typical real estate relationship would have been. Very high value for us.

When we started, you were sitting on our boat and we knew nothing, and a month later we were writing a contract on a townhouse in a village in the middle of the island, which was nowhere close to the initial vision.

Buying property in Spain: bureaucracy, banks & visas

Finding the property is one thing, but there’s a big process behind it. Actually, finding the property is almost the easy part, right? Fixing your heart on that and saying okay, but then the fun starts with the option contract and the NIE number and all the different requirements. Can you tell us about that a little bit from an American perspective? Spain is very famous for its bureaucracy.

I would recommend patience. Patience is a word that comes up time and time again on this podcast. It is very different than buying in the US. In the US, it’s very simple really. You can make a deal and close in a few weeks. All the title aspects and mortgages are quite well understood. Here, it all seems like it’s been done for the first time a little bit.

Our house was a new build, which is a different situation than a house that’s not new build, so it was a little more complex. And you found it during the renovation process, it wasn’t completed. So you had to be very patient. I always remember about the visa situation, which unfortunately was just ending right at the moment. But Trevor wasn’t going to give up. You’re told a lot of times here, “No.” First thing, isn’t it? And Trevor was like, “I don’t buy that.”

It was sort of humorous in a way. We knew we wanted to do this thing, and because of our situation we’re still residents and taxpayers of the US. We did want to get our golden visa. We do have a visa associated with our boat life, but we wanted to tap into a Spanish mortgage because the cost of capital is very low and very compelling. We didn’t have to probably do all those things, but we wanted to maximize the benefit. The administrative part was complex, even with the seller of the property. We made the decision not to so much fight on the price, but we gave him a gigantic list of things we wanted included because we just didn’t want to deal with the brain damage of figuring all that out after the fact. We said, “Okay, we’ll meet your price, but here’s a hundred things that need to be in the house when it’s finished.” Small things, but because you knew what you wanted.

He was great. They said they even learned a lot that now in the future they would add those things. Some of them are standards now, which is great. They were fantastic about that. You could have ground them down on price or whatever, but instead we did it that way, and that helped us a lot because the place was really finished in a good way.

With your team, we marched through all these different things, with your recommendations on lawyers, accountants, and banks. We ultimately built a relatively complex structure. But you got a really great deal. We had time. The house was the house.

Your persistence though. I would have given up. He was not going to give up. The last day we were like, “Done.” We did get our golden visas, and we did. Congratulations. And Beatriz, the consultant, helped a lot. She was terrific, and we pushed her to her limit like everyone else. I think the bank is finally tired of hearing from me every single day with my shiny good morning note.

What’s great about you, Trevor, is you’re always nice and always patient. You never get upset, you never seem to get angry, but you’re just persistent. We’ve learned that the first thing, like you said, they’ll say, “No.” So then you’ll say, “Okay,” and then you’ll listen, and then they always come to, “Well, maybe we can work something.” You have to just learn. It’s sort of a Spanish way. We’ve learned that it’s a cultural thing, it’s like a test. They kind of just say no. And then if you say, “Oh, yeah, but I have this,” at some point they suddenly flip over and then they’ll do anything in their power to help you. It’s just something to get used to.

Do you feel you’re much more knowledgeable now having done this transaction? Well, yeah. I think I could probably coach people through this now and save them some brain damage. Maybe we can set up the Trevor consultancy service as an add-on to Helen’s property buyers agency.

It’s totally worth it to have suffered through it because now we’re in a fantastic situation. We have a great house with a great relationship with our contractor, and you, and the lawyers, and accountants, and the banks, and the visa stuff. It’s all very good now. It took arguably a year to get through it, but now we’re in a terrific, enviable position. The deal that you negotiated from the whole lending perspective was phenomenal. The point is, if you really want it, it’s possible, but you’ll be told no many times. You’ll find a way if you keep persisting. Don’t give up, it will happen.

These banking people are incredible here. The amount of attention we ended up getting, not that we’re craving attention, but we have met with the senior people in these banks on a dozen occasions probably. They bring you in and we have coffee and we set up all these various structures. In the end, they’re lovely, beautiful people really willing to help. It doesn’t seem like the path for them is very clear either. We’re kind of working through it together, and in the end we got to a place that was good for everybody.

What you negotiated and put together was phenomenal. It just wouldn’t make any sense that you would use your own capital to buy a property when you can have a structure like what you’ve done. The point for listeners is that everything is actually possible. You just need to negotiate and be persistent. Find the way, and if people say no, then you say, “Well, how about we do it this way?” or “Let’s look at this option.”

There’s complexity here with wealth taxes and other taxes. What we ended up structuring was a mortgage but also a relationship with the private wealth group out of Luxembourg, which is an affiliate bank to Caixa Bank. They set that bank up for a very specific reason, to deal with people like us. We have two very powerful banking relationships that emerged out of Caixa Bank, with the offshore aspects we were looking for and the onshore mortgage structure that leverages their capital. It couldn’t be better really in the context of structure for our needs.

I love to share this with listeners because when you’re a foreigner coming into a new country, you don’t speak the language, you can be very apprehensive and maybe fall at the first fence when somebody says, “Oh, no, that’s not possible here.” But your story is actually inspiring because everything is possible. You just need to find the route. Even with your golden visa, you got it. Everybody told you you wouldn’t get it, and you did. If you want, you can actually get everything here.

For us, we had the ability to be patient because we live on our boat. We were not in any rush, so we had time to work through all this. But many people are similar. Usually when somebody’s buying a home in Mallorca, it will be their primary residence, so they generally have time. We’ve actually moved an American family at the beginning of this year from LA because their house burned down in the fires. They were without NIE numbers or anything. They bought a house here and were living in it within two weeks. That was phenomenal. They got everything organized and made it happen in two weeks. That’s also possible where people would tell you, “Oh no, you need six months, whatever.” It is possible when you know the right approach and the right people. It’s great for listeners to hear that there is this flexibility, these possibilities. You just need to find the road through.

Enjoying Alaró life, local wines, and final thoughts

In the end, you kind of forget about the bit of complexity along the way. Already it’s blurring because you’re enjoying your home. Trevor put in this beautiful wine cellar in our house, and now you’re in the process of filling it with beautiful Spanish wine. Only local wine actually. Within five kilometers of our house, there’s ten world-class wineries. Another thing we didn’t really know was that families have come from all over, Swedes and Germans and others, to build these great wineries in our little triangle of towns. These wines don’t get out into the world, they’re too small production, but they’re right there. We can walk to them. So we’ve discovered these fantastic places, and eventually we’ll meet the people who run them and own them.

You’ve decided to fill your wine cellar with local wine. Yes, we have this fantastic wine cellar that François and his team made for us as one of the items on our list, and it’s beautiful. What I love about your home is that you can have a quality of life living there that’s exceptional, without becoming a slave to your house. It just seems so easy. You have many little corners for different possibilities. It’s truly checked every box.

Quickfire questions

Before we finish, I want to ask you some of our quickfire questions.

Beach or mountain or both?
Oh, well beach on the boat and mountain in the house. You get the best of both worlds.

Sunrise or sunset?
Our place is uniquely good for sunset. The sun sets over the local mountain on our beautiful pool deck.

Summer heat or winter calm?
Summer heat on the boat, winter calm in the house.

Siesta or fiesta?
Oh, I think you’re more fiesta.

Pamboli or ensaïmada?
Probably savory, so pamboli.

North coast or south coast?
We rented a house in Alcúdia and it turned out to be fantastic up there. Great beaches and beautiful, and it was good in the winter. Both are great. You can’t go wrong.

Our voyage of discovering the island and all the beaches and all the bicycle routes is just starting. So much to discover.

I hope I’ll have the honor to be able to take you out on some of these cycling routes. You’re nearly there now. Next week, our first outing. I’ll show you the real Mallorca. We look forward to that.

Many years of joy and happiness in Mallorca. Thank you for choosing the island. I think the island is all the better for attracting people like yourselves, and I’m sure we’re going to have many good times to look forward to.

Thank you for holding our hand through the whole process. You made it happen.

It’s a pleasure because honestly, when people are so grateful and such a joy to work with and always very nice, that’s the joy actually for us. Thank you. And Lucy was an amazing support. Great.

If you’re dreaming of making Mallorca your home, let me invite you to use our property buyers agency service. With our service and our help, we can guide you to the right location that fits with your lifestyle. We’ll also help you find the perfect home that fits with your dream. Contact us today for an online consultation or book an appointment and come and see us in Palma. We would love to help you make your transition to Mallorca a reality.

Helen Cummins Property Buyers Agency
Helen Cummins Property Buyers Agency

Address details

75,000 miles sailed… then they chose alaró

hc/ Living & Business

C/ del Jardi Botanic 2 07012 Palma de Mallorca