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Meet Justin Renfro of Chill Charters in Harbor Island

Today we’d like to introduce you to Justin Renfro.

Justin, please share your story with us. How did you get to where you are today?
A couple years ago, I was bored and looking for a new hobby. I was living up in San Francisco working for a tech non-profit and things were going well — I was just looking to expand beyond the meeting up with friends at a bar routine. On Craigslist I found a listing for a sailboat partnership and I decided that would be cool. From my first trip out on the Bay I was hooked. I couldn’t get enough of being out on the water. I was always looking for an excuse to go hang on the boat.

I sailed for a few years and then eventually decided to expand by getting my own motor boat. I actually liked the motor boat more because it was easy to get going, I could be out on the Bay in less than 5 minutes, I didn’t need other people to do it, and it was better for exploring. I was going out every day for about a year before I made the decision to make a run at making it a business.

I knew I didn’t want to start the business in San Francisco — it’s really cold and it was getting more and more expensive to live there. San Diego seemed like the perfect location — a huge Bay, great weather, and good vibes. In January I packed up my life and made the jump. I purchased my boat in February and I’ve been working full time to make this dream a reality. My first open weekend in business was the 4th of July and over the past three months I’ve been doing multiple charters every week — it’s all coming together!

Has it been a smooth road?
Anything but smooth. It’s about as rocky a road as I’ve ever been on — it’s definitely the hardest job I’ve ever had. To have to manage everything — the tax stuff and rules, the book keeping, offline and online marketing, maintenance, social media — it’s a never ending laundry list of stuff that needs to get done.

Maintenance has been the hardest part for me. The learning curve is steep and when things break I feel I’m starting at square one every time. It’s painful.

The loneliness is also a hard reality. In San Francisco I was leading a team of 50+ people — which allowed me to delegate a lot of stuff I didn’t like and have a constant stream of social interaction. I had people to count on and people that counted on me, I had structure, and a community that I loved. Being a solopreneur has been a huge shift from that and been a huge adjustment.

I don’t see the struggles as a negative though — I’ve learned more in the past 8 months than in any other period in my life. This steep learning curve is good for me….despite the pain. Easy to say in reflection, harder in the day to day — but I know that I’ll look at this period in my life and be thankful for all the personal and professional learnings.

So, as you know, we’re impressed with Chill Charters – tell our readers more, for example what you’re most proud of as a company and what sets you apart from others.
Chill Charters delivers amazing experiences out on the San Diego Bay.

We offer private customized tours for up to 6 people. There’s a ton of different options when you’re out on a boat in San Diego Bay — and my focus is to curate an experience that caters to your interests. Whether you’re looking to party, relax, or explore — I’m focused on providing a safe, clean, and fun experience every time. ​

I showcase the different experiences I’m able to provide at my website. Here are the ones I like the most:

– anchor n chill party cruises — a one hour loop around the Bay followed by a party in La Playa (which is a little cove nestled in between Point Loma and Shelter Island). I have a big 6 ft. x 6 ft. tube that I blow up, two stand up paddle boards, and fishing poles — everything you need for a fun couple hours of boat fun.

– Night cruises — as soon as the sun sets, the Bay becomes super calm. To be out on the Bay by with your best friends – with the epic San Diego skyline as your backdrop – nothing beats it (except for an epic sunset — see below)

– Sunsets — nothing beats an epic sunset from the open ocean. When it’s clear off the Point, I’ll take people out to watch the sunset from the open ocean. When you get that color — oh me, oh my!

– Concerts — Humphrey’s concerts are always a blast and I also love the Bayside Summer Concert Series. It’s always a good time and you can hear the music super well.

I think the personalization of each charter is what separates me from everyone else. I’m able to cater to your specific interests and you really don’t get that with anyone else. I have a lot of range with my boat — there’s a lot of options for stuff to do and I have the knowledge and experience to make every trip an awesome one.

Let’s touch on your thoughts about our city – what do you like the most and least?
The weather is the single best thing about San Diego. I love wearing sweat-shorts and sandals and I can crush that game here. Other honorable mentions about the awesomeness of San Diego include breweries, outdoor patios and our vicinity to Mexico.

I have a strong personal belief that all beaches should be dog and alcohol friendly. That’s the first thing I would change if I were mayor.


  • I charge $125/hour for up to 6 people
  • If you mention this article, I’ll give you a homies $50 credit on your next charter

Contact Info:

Image Credit:
Mikka Jiminez
Mike and Jenn Edwards

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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