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.

Holly is the caretaker and organizer of the operation, ensuring that every guest is well-fed, comfortable, and enjoying their vacation. Joe’s passion for sailing and the ocean is contagious; at the helm, he focuses on safety, adventure, and creating the perfect itinerary. Together, they provide a personalized charter experience that combines hospitality, local knowledge, and a genuine love for life on the water.

Captain Joe
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.

Chef Holly
Holly was born in Las Vegas, Nevada, and raised in Pahrump, a small town near the California-Nevada border. Her passion for food began early. Her grandmother was a professional chef, and her mother loved baking, so Holly spent much of her childhood in the kitchen learning treasured family recipes infused with Southwestern flavors.

Her family home was always the gathering place for friends and relatives, and Sunday dinners often became lively celebrations centered around great food and good company. Those experiences shaped Holly’s love of hospitality and entertaining.

As both chef and crew member aboard Knot 5280, Holly plays an essential role in creating memorable charter experiences. To prepare for life aboard, she expanded her culinary skills through private instruction and online training, elevating her cooking to a level that delights charter guests. She understands how valuable vacation time is and takes great pride in creating exceptional meals and a relaxing, worry-free experience for every family that sails with them.

After an 18-year career as a marketing manager in commercial real estate, Holly made the leap from corporate life to Caribbean living, joining Joe in turning their shared dream into reality.

Joe Sigdestad

Captain

USA

Languages: English

Holly Sigdestad

Chef/First Mate

Joe & Holly