• September 15th, 2020

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The story of today brings us to the Virgin Islands, in the Caribbean. Mandy, a Captain and co-founder of Sailing Kuma Too, shares with us the journey that brought her and her husband to escape the comfortable and secure life they were living in Florida, to live a more peaceful life that lets them travel 4 months a year.

  • Mandy


My name is Mandy Rosello. Although I was born in Pittsburgh, in Pennsylvania, I moved to Clearwater, in Florida, out of high-school to work at an airport with private and corporate aircraft. When I was interviewed for my job, I met my husband, Joe. With an adventurous soul, from rock climbing to sky diving, I’ve always had dreams of traveling the world. As a teenager, I started scuba diving with my dad and began taking diving trips around the Caribbean. I fell in love with the aquamarine waters and green hillsides of the islands. Joe and I had a mutual love of the ocean, and within a few months, we took a trip to Puerto Rico that started a life path that we began chasing wholeheartedly. Fifteen years later, we now live in the Caribbean, on our 47-foot catamaran.


Que cherchiez-vous dans la vie?

Since I was teenage, my goal was to live internationally. After years of traveling around the US, Europe, South America, the South Pacific, and most frequently, the Caribbean, Joe and I made a goal to move to the Caribbean. We longed for a slower pace of life, turquoise water, and to be part of a community that didn’t revolve around the corporate grind. There was little enjoyment at ‘home’ between vacations. It’s not that we didn’t love each other, or our family and friends, or our home (which I bought for myself on my 21st birthday), but it didn’t feel like I was where I was supposed to be in life.

Qu'est-ce qui vous a empêché d'y parvenir?

I thought money was stopping us from achieving our dreams. We lived a comfortable life with the ability to travel and take vacations multiple times per year. By accepting a job in the Caribbean, we’d give up our steady income and have to give up the freedom to travel. In hindsight, stability and comfort were also a barrier, although I didn’t realize it at the time. You get comfortable with your life. In our case, we were comfortable with our steady income, health insurance, the home we owned, and having our family and friends close-by.

Quel a été le déclencheur du changement?

We were on vacation in the British Virgin Islands and fell in love with them, the water, the ambiance, the weather, and most of all, the people. Lounging on the beach at Cane Garden Bay, Tortola, we struck up a conversation with a sailor. He told us that he lived on his boat and offered sailing charters.
We had been crew in sailboat races for a few years then in Florida, so we already knew how to sail. How was there a whole world that revolved around sailing that we had no idea even existed?
When we returned to Florida, we knew it was time for a change. After years of talking and research, it was time for action.

Comment était votre voyage? Qu'avez-vous mis en action?

We returned home from Tortola in June 2015 and Googled “sailing the Caribbean.” This brought up dozens of YouTube videos of people sailing around the world. Within a few weeks, we had both spent hundreds of hours researching sailboats, sailing charters, and the financial aspect. We realized this was actually a viable option for us, and a plan began to evolve.
We cancelled all of our upcoming vacations and changed our ‘vacation’ fund to a ‘down payment’ fund for a sailboat. We picked up part time jobs and saved literally every penny.
In January 2016 while watching the Travel Channel, I stood up and said, “if we’re going to do this, let’s do it!” That day, I began packing up the house and preparing for an estate sale. In August 2016, we purchased our boat, Kuma Too.

Comment pensez-vous que votre vie serait maintenant si vous aviez continué dans la même direction?

I don’t think we’d be truly happy. A few months after I quit my job, the company went out of business abruptly, so I would have been suddenly unemployed scrambling for a new job. We would still be living in the same house and probably still be traveling a few times years. After each trip, we’d return home and say ‘we could totally live there!’ and start researching what it would take to move, then eventually just start planning the next vacation. Our bank account would have a lot more in it! I think we would be living a very comfortable ‘typical American Dream’ lifestyle, yet that never appealed to us.

Comment est ta vie aujourd'hui?

We live aboard our 47-foot sailing catamaran in the Caribbean exploring palm tree lined beaches, sipping local rum, and indulging in the bounty the sea has to offer. We offer sailing charters around the US and British Virgin Islands November to June then we explore the Caribbean on our own in the summer. While on charter, we work long days on-call to our guests 24/7, but we have 4 months to do what we love, travel! Although running a charter boat is hard work, we focus on the little things daily: we watch the sunset each night, listen to the birds and goats each morning, and love a fresh rain shower.

Que diriez-vous à quelqu'un qui lit votre histoire?

You can absolutely achieve your goals. By creating a detailed plan and setting smaller goals, you will see your dream isn’t impossible. It becomes a realistic goal when you can see the steps it takes to get to the top!
I found money to be the most deterring factor of my dream. We made a comfortable living by blue-collar standards but were by no means wealthy. It was our ability to save and recognize needs versus wants that enabled us to save enough money to purchase our boat.
In talking with others, we found that people use excuses to justify not following their dreams. The fine print in the phase “follow your dreams” is that following your dreams is very hard and takes sacrifice, but is doable if you are dedicated to accomplishing it. One thing for sure is that when our journey starts to come to an end, we won’t be saying “I wish we would have…”


Quels sont vos 3 livres les plus inspirants?

Quels sont vos 3 films, séries ou documentaires les plus inspirants?

Distant Shores. It is a TV Series that we used to watch as the dream of living on a sailboat began to form. This Canadian couple shares their experiences on land and sea, and include the behind the scene, not just the romance, of living on a boat. This helped us create a realistic vision of what our life on board would be like.

Sailing SV Delos. This is one of the most popular YouTube series. We stumbled upon Delos with our first Google search and were hooked immediately. Like Distant Shores, the owner travels around the world on his sailboat, Delos. We felt personally connected with him, and the other sailors he brings on board Delos because of his age, background, and lifestyle. Much of our preparation for life on board came from Sailing SV Delos.

The Polar Sea. This is a documentary about sailing the Northwest Passage. The narrator started the journey on a sailboat and through a series of events ends up 'hitch hiking' (for lack of a better word) across the Northwest Passage on different means of transportation. Life on a sailboat is all about going with the flow. Watching the documentary showed that no matter how much planning goes into a passage, things will always change.

Quelles sont vos 3 chansons préférées?

Babel, by Mumford & Sons. This song transports me to the time we were preparing to sell our home, so we had many late nights packing with it playing in the background.

The Downeaster 'Alexa', by Billy Joel. This is one of the first songs our friends played on board, so it's a special memory for the beginning of our sailing life.


Time to Smile, by Xavier Rudd and Izintaba. It is probably my most favorite song because of the feeling I get listening to it. The song starts with a journey; it's happy and upbeat.

Quelle est votre citation la plus inspirante?

If you're not living on the edge, you're taking up too much space, by Stephen Hunt. I read that on the door of the first airplane I jumped out of at 16 years old. I love the phrase because to me it means that if you're not constantly pushing yourself to the edge of your comfort zone, you will never fulfil what you were meant to achieve in life. If something is intimidating or scary, then it's worth pursuing.

Parlez-nous de votre photo préférée!


This photo inspires me because it's our life goal in one snapshot. Using only the power of the wind, Kuma Too sails amoung the green hills and deep blue water of the Virgin Islands. It shows our home and our business that will take us around the world.

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