Today we’d like to introduce you to Shawn Owen.
Shawn, we appreciate you taking the time to share your story with us today. Where does your story begin?
I grew up in Snowshoe, West Virginia, and my path has taken me from snowboarding and music to sailing. My first real introduction to sailing was a family trip through the Florida Keys when I was about 12, and that experience stayed with me.
I moved to Annapolis in 2007 and built a career performing music, both solo and with the Shawn Owen Band. Music actually helped bring me back to sailing. I met the owners of a local catamaran charter company while playing a gig, and they later invited my wife and me on a boat delivery in the Caribbean. That trip got me hooked all over again.
From there, I took every opportunity to get on the water, crew on deliveries, and learn. I eventually earned my captain’s license, became a sailing instructor, and started Chronic Sailing to share that experience with others.
Today, we offer charters, sailing lessons, and captain services in Annapolis. Music is still part of the story, especially through Tunesday, our free floating concert series on Back Creek. It’s been a winding path, but it’s brought together the things I enjoy most: music, life on the water, and bringing people together.
We all face challenges, but looking back would you describe it as a relatively smooth road?
It’s definitely been a learning process. Coming from a music background, building a career in sailing meant putting in the time on the water, learning from experienced captains, and working toward my license and teaching certifications. There wasn’t a shortcut—it happened gradually, through taking opportunities and continuing to learn.
Building Chronic Sailing brought another set of challenges. Balancing the work of running a business with being out on the water and giving each guest or student a great experience. Add music and family life, and there’s a lot to juggle.
I’m definitely still learning how to balance it all. What’s helped is being willing to ask questions, learn from the people around me, keep showing up and fail upward. Each step, forward and backward, has helped me build the experience and relationships that make the next one possible.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I’m a captain, sailing instructor, musician, and the founder of Chronic Sailing in Annapolis. We offer sailing lessons, private charters, boat deliveries, and support for boat owners, with a particular focus on catamarans. Whether someone is stepping aboard for the first time or preparing to captain their own boat, I help them build confidence and get more out of their time on the water.
My background in music has shaped how I approach that work. You learn to connect with different people, read the room, and create an experience that feels personal. I bring that same approach aboard, tailoring a lesson or charter to the people joining us.
One thing I’m especially proud of is Tunesday, our free floating concert series on Back Creek. It brings local musicians and the community together on the water and connects two parts of my life that have meant so much to me.
What sets Chronic Sailing apart is that personal connection. I want people to leave with great memories, new skills, and the feeling that sailing is something they can make part of their own lives.
How do you think about luck?
Some of the biggest turns in my life started with being in the right place at the right time. I met the owners of a catamaran charter company while playing a music gig, and that connection eventually led to an invitation to help deliver a boat in the Caribbean. I couldn’t have planned that, but it reignited my love of sailing and helped set me on the path toward Chronic Sailing.
The lucky part was meeting them. Everything that followed required showing up, being willing to learn, and putting in the time. That experience taught me to stay open to opportunities, especially when they don’t look like what I expected.
I’ve been fortunate to meet people who shared their knowledge and gave me a chance. As an instructor and business owner, I try to offer that same encouragement to others. You never know what one invitation or a day on the water might lead to for someone.
Pricing:
- Beginner sailing certification (ASA 101): $700 per student for a two-day course.
- Cruising catamaran certification (ASA 114): $1,250 per student for a two-day course.
- Eight-day sailing and catamaran certification package (ASA 101–104 + 114): $3,000 per student.
- Private sailing lessons and yacht charters: Contact us for a personalized quote.
- Tunesday floating concert series: Free, family-friendly, and open to the community.
Contact Info:
- Website: https://chronicsailing.com
- Instagram: https://www.instagram.com/chronicsailing/
- Facebook: https://www.facebook.com/chronicsailing
- LinkedIn: https://www.linkedin.com/company/chronic-sailing
- Youtube: https://www.youtube.com/@chronicsailing
- Other: https://www.bbb.org/us/md/annapolis/profile/boat-rentals/chronic-sailing-llc-0011-90376110
