Joe Sigdestad
After a 31-year career as a commercial real estate broker in Denver, Colorado, Joe decided to pursue a lifelong dream: owning a sailing catamaran and running charter vacations in the British Virgin Islands. In 2020, Joe and Holly purchased Knot 5280, and since then they have sailed more than 15,000 nautical miles and hosted over 90 charters.
Joe and Holly first met in 2003 when Holly joined the same commercial real estate company where Joe worked. What began as a friendship eventually grew into a relationship, and they married in 2014. While sailing the Caribbean may have started as “Joe’s dream,” it quickly became a shared adventure that Holly has embraced.
Guests quickly notice the natural rhythm Joe and Holly share, along with plenty of laughter along the way. They understand each other’s strengths and work seamless as a team to create an unforgettable charter experience. Knot 5280 is a comfortable, family-friendly boat designed to make guests feel at home from the moment they step aboard.
Joe’s passion for sailing and the ocean is contagious; at the helm, he focuses on safety, adventure, and creating the perfect itinerary.
Joe learned to sail racing monohulls on Colorado’s mountain reservoirs. Although he remains a competitive sailor, he is an easygoing captain who enjoys sharing his knowledge with guests interested in learning the fundamentals of sailing while aboard Knot 5280.
In 1993, seeking sunshine and a break from Colorado, Joe booked his first sailing vacation through Sunsail/Moorings in the British Virgin Islands. He immediately fell in love with the islands, their people, and the waters. Over the next 27 years, he returned whenever possible, developing an intimate knowledge of the Virgin Islands that few charter captains can match.
Colorado will always hold a special place in Joe’s heart. He loves spending time outdoors and enjoys hiking, camping, fishing, live music and virtually any outdoor adventure. When he’s not sailing, you will likely find him on two wheels – mountain biking, road biking, dirt biking, or cruising on his Harley. Joe is always looking for new ways to explore and enjoy the outdoors.














