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Meet Jessica Holbert of Sail Liberty in Harbor Island

Today we’d like to introduce you to Jessica Holbert.

Philip Schutt has been sailing his whole life and had wanted to start his own sailing tour company since he arrived in San Diego in 2006. Acquiring his ideal boat was no easy task- he found Liberty on Lake Michigan in 2014 and had her hauled over the Rockies directly to a boat yard. She needed a lot of time and attention. Which Philip, his brother John and a talented painter named David gave her over the better part of a year. They brought her back to her former glory and she has been the darling of  Dock D at Sunroad Resort Marina ever since. Together with his wife Jessica (JJ to her friends) who manages the business, they have created a unique, consistently 5-star reviewed sailing tour company.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
Not having yet won the lottery or inherited money from a long-lost rich aunt, they have had not a shortage of sacrifices. Philip had to give up his job as a maintenance supervisor/captain for a local sailing club to restore Liberty. Jessica was teaching ESL part-time and both put in long hours on the business, learning about such things as marketing, online booking platforms and the hotel concierge circuit.

The business, as most do, started slow and there was much self-doubt as their efforts took their time to turn into income. Philip eventually took a full-time position as manager of the aquatic center for San Diego State. He works there still, meaning if he has a sunset sail during the week, he puts in now less than a 14-hr day. Over the weekend, the most popular time for sailing he continues to sail, meaning he rarely gets a full day off. Jessica has given up teaching to take over managing the business full-time. All this while raising their son, Hobie.

All that said, the business, while still considered new by any standard is heading in the right direction, meaning they took a lot more people out last year than this year. Still a ways off from smooth sailing, they are definitely on their way.

So let’s switch gears a bit and go into the Sail Liberty story. Tell us more about the business.
We are family-owned and operated and this is a business born from love of sailing. We are known for our unique, classic boat, personable captain (Philip) and outstanding customer service (Jessica). Our tours are for small groups (up to 6 people only), which leads to an intimate experience chatting with other passengers and the captain. The company has consistent 5-star reviews on Yelp and Trip Advisor. It is our love of sailing and desire to create a memorable experience for each passenger that comes aboard to tour San Diego harbor with us. This drives us and keeps Liberty in tiptop shape, all with our own two hands (each;)

We offer a team building program, where staff members, under the captain’s command, sail the boat together as a crew. It’s so cool!

Has luck played a meaningful role in your life and business?
Good luck: great contacts in the business that could be said to be our competitors, but who have only supported us. Great camaraderie in the industry all around.

Bad luck: more like bad decisions, especially when it comes to spending money on marketing. Being so small yet wanting to be seen by all is our greatest challenge. How to get people to find the little guys?


  • Sunset sails: $95 per person, private charter $510
  • Couples Private Tour: 2 people special: $285
  • Afternoon sails: $95 per person, private charter $510
  • Weekday Sunset Special: $85 per person

Contact Info:

  • Address: 955 Harbor Island Dr, San Diego, CA 92101
  • Website:
  • Phone: 619-889-5988
  • Email:

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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