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Meet Jason Thomsen of Lucky Sol Sailing

Today we’d like to introduce you to Jason Thomsen.

Jason, please share your story with us. How did you get to where you are today?
My wife and I moved to San Diego in 2008. I was an active duty Marine at the time and received orders to MCAS Miramar where I served as an Aviation Supply Officer. When my active duty tour ended we decided to take some time off and live on a sailboat in the Sea of Cortez.

We bought a boat, got her ready, and in April of 2012 we set sail from San Diego on an 800-mile journey South to Cabo San Lucas. After a few weeks meandering down the coast, we rounded the tip of the Baja peninsula and into the Sea of Cortez. We spent 3 more months exploring this natural wonder that Jaques Cousteau called “The Aquarium of the world”. It definitely lived up to Mr. Cousteau’s moniker.

Our adventure was a once in a lifetime experience that we will never forget. Upon returning to San Diego I had to get back to work. I considered taking a job which utilized my Marine Corps experience but my time in the Sea of Cortez was pulling me in a different direction. I knew that I wanted to share a piece of our experience there with others, so in 2015 Lucky Sol Sailing started welcoming people aboard. After almost three years of giving tourists and locals sailing tours of our beautiful bay I couldn’t be happier with my decision to take a chance and start this company.

Has it been a smooth road?
Like most small business owners, when I started I was focused almost entirely on my product or service. Offering an incredible sailing experience to my guests. It didn’t take long for me to realize that was the easy part of running a business. I knew how to sail a boat and show guests a good time on the water but websites, social media, online advertising, and all the other non-sailing stuff were new to me. Luckily I was able to figure it out with the help of a marketing mentor who was willing to trade his service for time on the water. I’m by no means an expert yet but getting better and still learning.

We’d love to hear more about your business.
Lucky Sol Sailing is a tour company offering San Diego’s finest sailing tours. Our company is small, just two boats and a handful of Captains. This allows us to be very selective in our recruitment of Captains and give our guests a highly personalized experience. Our Captains are friendly and knowledgeable about our sailing grounds and very safe and competent sailors. Our size also allows our guests to customize their experience. We can shift tour times, pickup or drop off at other docks, have your favorite food or beverages onboard, or reschedule for free, just to name a few.

Basically, if you request it and we can make it happen we’ll do it. We’ve helped our guests celebrate marriage proposals, birthdays, anniversaries, bachelor and bachelorette parties, graduation parties, as well as the spreading of loves one’s ashes as the sea. Our commitment to providing guests the best possible experience is reflected in our online reviews. We have the highest percentage of 5-star reviews in our market and zero negative reviews. We take great pride in this. We also offer sailing lessons and certification that is recognized worldwide through NauticEd. Although, we’ve only given a handful of lessons we’ve had great feedback and are excited to do more in the future.

Lastly, we offer fractional sailing membership to experienced sailors on our Catalina 27 sloop. Fractional membership is kind of like a yacht time-share and is the future of yacht usage for the masses and offers the most affordability compared to rental or ownership.

Is our city a good place to do what you do?
San Diego is probably the best place on the west coast to go sailing. We have year-round perfect weather, a large well-protected bay, and beautiful sights to take in while on the water. We also have tens of millions of tourists visiting San Diego every year. So, as far as quality of experience and customer availability our city is an ideal location to start a sailing business.

Finding a location to start your business could be a real challenge for a newcomer. Many marinas in town don’t allow charter businesses and the ones that do only allow it in a limited number of slips. In the marinas that do allow it, there is a fair amount of protectionism from the larger companies who encourage marinas to disallow new businesses that would compete with them.

It kinda makes sense from the marina’s perspective. They’d rather have one large successful charter business than ten struggling small businesses. But knowing that doesn’t make it any less frustrating when you’re trying to get your company off the ground.


  • $79 – Individual Ticket on a 3hr Public Group Sail (Daytime or Sunset, 6 guests max)
  • $349 – Weekday 3hr Private Charter (Mon-Thu, up to 6 guests)
  • $399 – Weekend 3hr Private Charter (Fri-Sun, up to 6 guests)
  • Sailing Lessons Starting at $149/person
  • Fractional Yacht Membership Starting at $159/mo

Contact Info:

Getting in touch: SDVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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