Our Story & Sailing Crew
We're TripAdvisor's #1 overall experience in San Diego. Here's why.
Sail San Diego is a boutique, family-run sailing company and one of San Diego’s tenured operations. Over nearly four decades, Sail San Diego has grown to become the city’s premier sailing provider, offering corporate outings, private events, whale watching tours, and our daily signature sails.
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Built on Hard Work, Good People, and a Love of Sailing.
I got my start scrubbing barnacles off boats at 15. That’s how I met Tim and Michelle Hanley, the previous owners of Sail San Diego. They taught me everything—boat maintenance, business management, and how to sail. By the time I was 18, I was running tours myself.
I wasn’t planning on college—I wanted my captain’s license—but Tim gave me an ultimatum: take the football scholarship or find a new job. So I went, studied business, and spent every summer back on the water. By 28, I was helping run the company. In 2021, I bought it.
A year later, I married January, the love of my life. She runs the retail side, and together we’ve grown the fleet to seven premium sailboats—including our biggest yet, with room for 22 guests.
A lot’s changed over the years, but one thing never will: there’s no better way to experience San Diego than out on the water with us.
Cal & January Muir
The Sail San Diego Team
Sure, our captains and crew are incredibly skilled sailors. They've got the highest USCG captain's licenses in the business, are certified in CPR and first aid, and are totally compliant with our strict drug and alcohol testing.
But what makes them special is that they’re also dedicated ocean advocates and environmental stewards. They have extensive experience navigating the open seas and a profound knowledge of marine ecosystems. Our team is devoted to advancing sustainable sailing practices and safeguarding the ocean for tomorrow’s generations.
Captains
Captain
David Hobbs
Team Member Since 2023
Years of Experience: 29
Favorite Sea Animal: Dolphin
Captain
Kenley Prober
Team Member Since 2023
Years of Experience: 8
Favorite Sea Animal: Dolphin
Captain
Greg Tupaj
Team Member Since 2013
Years of Experience: 34 (licensed since 1991)
Favorite Sea Animal: Gray Whale
Captain
Frank Murphy
Team Member Since 2017
Years of Experience: 40+ (licensed for 12)
Favorite Sea Animal: Velella
Captain
Stu Jackson
Team Member Since 2017
Years of Experience: 15
Favorite Sea Animal: Velella
Captain
Kris Green
Team Member Since 2021
Years of Experience: 20
Favorite Sea Animal: Sea Lion
Captain
Zack Dirks
Team Member Since 2022
Years of Experience: 10
Favorite Sea Animal: Sea Otter
Captain
Breanna Artnz
Captain
Richard Coning
Crew
Marketing Manager
Anna Ferguson
Team Member Since 2021
Favorite Sea Animal: Seahorse
Office Support
Kate Locke
Team Member since 2024
Favorite Sea Animal: Bottlenose Dolphin
Office Support
Chloe Sharp
Team Member since 2025
Favorite Sea Animal: Sea Turtle
Dock Crew
Chris Wilson
Team Member Since 2024
Favorite Sea Animal: Whale Shark
Our Fleet
After decades of cruising and racing aboard hundreds of types of boats, we have sought out specific boats that all have the same thing in common, extremely stable and maneuverable, safe, comfortable, modern and a blast to sail. We take great pride in the quality of our fleet and spend thousand of hours every year making sure they are mechanically safe and sound.
We shouldn’t need any of this equipment on your sail, but if we do, the following equipment is on board. Life Jackets, fire extinguishers, throwable device, Vhf radio.
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