Join the Mailing List Sign Up!


Kruger Escapes: Then & Now


In 2009, Karl and Jessica Kruger took a sailing trip with their 2-year old daughter from Orcas Island to Alaska along the Inside Passage. It was on this trip that the dream of marrying skiing/surfing and sailing was cemented in Karl’s mind and heart. Karl, an outdoor enthusiast of board sports, water and mountains, had a long running dream of owning an outdoor adventure business.  With wife Jessica, together they dreamed up Kruger Escapes, offering long sailboat-based adventure trips from the San Juan Islands in Washington.  Unfortunately, their dream was hatched during the economic crash of 2009.

They called 60 different banks but every time, they heard rejection.  “If we said ‘boat’, they said ‘I’m sorry’” shared Jessica.  So, they found a private investor to get them started on the business buying a sailboat that could accommodate their dream.  However, the period of that loan quickly came about, and they needed to seek out a bank to refinance with.  Finally they met a champion at Peoples Bank who worked hard with them to try and fund their refinance, but in the end, couldn’t.  Peoples Bank referred the couple to Community Capital Development, now Business Impact NW.

So how did Business Impact NW fund what banks could not?  Roland Chaiton, Senior Loan Officer, “could see the window to make it all happen.”  “Roland is our hero!” says Jessica.  Roland helped the couple receive three separate loans for Kruger Escapes; two for sailing vessels, and one for business expenses.  The business slowly started growing through social media, TripAdvisor, the San Juan Island Visitor’s Bureau and word of mouth.


Karl and Jessica are hoping to expand their business to offer more than just day trips, adventure sailing with skiing, and trips up the Inside Passage.  They hope to offer excursions to Hawaii, the Aleutian Islands, and possibly even retool their business plan to focus on stand up paddleboarding (SUP) sailing trips.

Karl recently became the first person ever to finish the Race to Alaska on a Stand Up Paddleboard.  Yes, he completed the entire Inside Passage on a stand up paddleboard, coming in 17th place against sailboats on a 750 mile trek in 50 degree water. He’s since received a lot of attention that he hopes to funnel into down-wind and flat water SUP adventures offered by Kruger Escapes.

So has the adventure of owning a business lived up to the couple’s adventurous dreams?  “We are both decidedly introverted – we’ve both grown into people who are more capable, willing and able to make connections with people” says Karl.  “We’ve had to prove to everybody that we’re serious” about making this business successful, he added.  They are proud to employ a local chef part-time for trip catering, had a student intern, and hired a teenager over the summer from a local sailing team.  “It’s a positive experience for us – hiring locally” says Jessica.  They’ve also started organizing beach cleanups bringing together family, friends and the community.

They wanted to offer advice to other entrepreneurs like them who dream of owning their own business doing what they love. On the administration side, Jessica shares: “From day one, identify and hire an accountant, bookkeeper and lawyer and have those people with you from the very beginning…then they grow with you.”  “It’s a slow build to get there” adds Karl.  Most of their business is new, earning “street cred” and positive reviews, but they are also enjoying time with guests who return year after year. With 84 5-star reviews on TripAdvisor as of this writing, they are certainly focusing on customer service, post-sale follow-up, and offering the best possible sailing experience they can.  Their success is all thanks to their love of the outdoors and their drive to make their lifestyle into a business.

You can find Kruger Escapes online at https://krugerescapes.com/ and on Facebook, as well as through TripAdvisor and various media and tourism websites.

About the author

Scroll to top