Our  Story

Like any good story, Joe’s interest in sailing started with a few drinks and a good friend. Dave Ciesla and Joe attended a boat show in Denver in 1991, and signed up for sailing lessons. After completing the beginning ASA classes, Dave bought a sailboat and the two of them started spending their nights and weekends racing on the various mountain reservoirs around Colorado.

 

In 1993 in need of a vacation and some beach time, Joe booked his first trip through SunSail/Moorings in the British Virgin Islands. During that trip Joe fell in love with the beautiful islands and for the next 27 years he sailed as often as possible and amassed a knowledge of the Virgin Islands not available with most local charter captains.  

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Joe was born in Minneapolis, MN but Colorado will always be home. His family moved to Aurora, Colorado in 1970. Joe graduated from CU Boulder in 1989 with a degree in economics, but had no real career plans. He spent the next few years taking odd jobs in Vail, Maui, Martha’s Vineyard and Chicago. Eventually, he came back to Denver and settled down. In 1991 he started his career in commercial real estate and spent 29 years specializing in leasing office buildings.

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Joe’s first love is Colorado, and you can always find him outside. From hiking, camping, fishing, concerts, etc. Colorado was a great place to raise a family and a special place to call home. When he’s not sailing you will most likely find Joe on two-wheels; mountain biking, road biking, dirt biking or cruising around on his Harley. Joe loves his toys and is always looking for a new way to explore the outdoors.

 

We met in 2003 when Holly started working at the same commercial real estate company as Joe. We didn’t like each other much in the beginning but eventually a friendship developed, and we started dating in 2010 and marred in 2014.

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Holly was born in Las Vegas, Nevada and spent her childhood in Pahrump, Nevada a very small town on the California/Nevada border. Her formative years went by in southern Utah before her parents moved to Denver, Colorado in 1999. Holly has called Denver home ever since; her family has since moved back to Pahrump, and she visits them as often as possible.

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Holly loves to hike, she has always lived near the mountains and enjoys the quiet time in nature a long trail can provide. Holly’s background is in marketing and administration in commercial real estate; like Joe she is a licensed agent but prefers to spend her time coming up with marketing strategies and designs for investment listings and organizing transactions. This crazy dream to buy a sailboat and move to the Caribbean was always Joe’s idea but Holly would follow Joe anywhere and if she’s honest… it beats working a desk job.

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Holly took her first sailing trip in the summer of 2013. She had no idea what to expect; it was her first time on a catamaran, first time in the Virgin Islands, first time spending ten days trapped on a boat with her boyfriend and his two kids and some friends…. it didn't go well. Holly admits she completely overpacked, got sunburned, was seasick and a bit uncomfortable… she might of even slammed a few doors in frustration. In a strange way this makes her uniquely qualified to ensure your sailing vacation goes smoother than her first experience. During that first trip Holly learned the importance of eating and sleeping well, finding a quiet corner when needed and packing for comfort. It was an amazing vacation that we all look back on fondly; it was the first time Holly saw Joe truly relax and check-out from work.

 

In 2020 we were at a bit of a crossroads. Joe’s oldest daughter Ally had just graduated from college and secured a job in the Biomedical Engineering industry, his son Tom was starting his sophomore year of college studying Aerospace Engineering in Arizona. We decided to sell our house in central Denver, it was basically empty, and we were tired of the noise and growth in Denver. Our house sold quickly, and we moved into a rental in south Denver while we planned our next move. The original plan was to buy some acreage, settle down and a create a home for the kids to come back to. But there was a nagging in the back of Joe’s mind, he had always wanted to get his captains license and run sailing charters in the Virgin Islands. It seemed like we were at a now or never moment in our life, we had the perfect window of opportunity to walk away, take a sabbatical and pursue Joe’s dream. But we were scared.

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Joe’s world in commercial real estate came to an abrupt halt in 2020, no one was going to the office anymore and work opportunities became limited. We tried to buy a couple houses but struck out and it seemed like everything was pointing us toward leaving. In the fall of 2020 Holly’s dad died unexpectedly, there is something about a 61-year-old dying in a freak accident that makes you realize just how short life really is. That sealed the deal for us, and we made the move down to St Thomas in December of 2020. We know Holly’s dad is getting a kick out of watching our crazy adventure and he’s keeping us safe when we sail across oceans in the middle of the night.

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Although this was originally “Joe’s Dream” it’s an amazing opportunity that Holly has fully embraced. Spend any amount of time with us and you see us fall into a natural, comfortable rhythm, with a fair amount of laughter. We know each other strengths and we naturally work really well together. Holly is a caretaker and compulsively organized; she takes care of the interior of the boat making sure everyone is fed, comfortable and happy. Joe’s love for sailing and the ocean is contagious; when Joe takes the helm he ensures safety, entertainment and a well-timed schedule. But both of us will pitch hit for the other when needed.

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We look forward to welcoming you into our home and sharing the Virgin Islands with you.

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Joe & Holly Sigdestad