The Sail San Diego Crew

The Sail San Diego crew has a combined 50 plus years in the chartering business as well as the yacht sales industry. We know great boats and we know how to provide the kind of service the rich and famous are accustomed to. Now we're bringing this same service to you!

Our Captains are all U.S. Coast Guard certified. We have the cream of the crop here in San Diego. We're sought by quality captains that have moved here from all over the US who've worked on sailboats all over the world.

Capt. Mike Roll

As a second generation native San Diegan, I developed my love of the ocean at an early age. When I was 12 my mother put me in sailing lessons. In 1986 my dad bought a Catalina 30 sloop. We started club racing and that lead to a passion for long distance ocean racing on faster sail boats. Racing has taken me from LA to Honolulu 5 times and over 40 times to Mexico including Cabo, Puerto Vallarta and Ensenada.

A few years ago after a long career in manufacturing I obtained my captains license and now enjoy the best "job" in the world sharing my love of San Diego and sailing with guests of Sail San Diego.

Capt. Art Harrison

I started sailing at Long Beach State College in 1970.  I was the lessons chairman and later the Commodore of what was a very active organization at that time. I've been an active sailor and boat owner ever since.

My interest in the sea lead me to become a whale watch docent in the 80's at one of the early programs at Cabrillo marine museum. I later became a licensed captain and ASA sailing instructor.

I've had many adventures on the ocean, including meeting my wife at Catalina Island.

Capt. Shon Kitchen

Also known as "The Anchorman", Capt. Shon spent 24 years in the U.S. Navy, serving as an operations specialist, engineer, navigator, instructor, search and rescue swimmer and boat captain. During the last 16 years of service, he served in Naval Special Warfare. In 2008, while intricately involved with the world's premier Boat Unit, SWCC (pronounced SWICK), he took his first sailing lesson. Capt. Shon honorably retired in August 2016 and found a new career as a sailing yacht captain in San Diego, his hometown.

Capt. Shon promotes safe worthwhile boat handling, on all waters, year round. His passion is to share the love and respect of the ocean and San Diego harbor with tourists and locals.

Capt. Greg Tupaj

Capt. Greg Tupaj has been in the Marine industry for over 25 years, and holds a 100-ton Coast Guard license. He has worked on both coasts, Hawaii, and the Caribbean on many different vessels, including fishing, sailing, and powerboats. Sailing is Greg's passion. He absolutely loves sharing his passion with guests who want to experience this amazing sport, helping them enjoy their day on the water to the fullest.

Capt. Anthony Austin

A San Diego native, Anthony “the Happy Captain” Austin has over 35 years of sailing experience. Capt. Anthony currently holds a USCG 100-ton captain's license with sailing and towing endorsements. He has traveled over 5,000 miles on the water in the past 2 years. Formerly captain of the 83' tall ship "Amazing Grace", Anthony brings years of experience teaching, sailing, managing, transporting and operating chartered yachts.
I’m Captain Anthony Austin, and I’m not embarrassed to tell you: I’m the happiest Captain in America! I love the sea, and I love boats! I get joy out of what I do every day, and I want to share that joy with you, my guests. I love making my customers happy too!

Capt. Frank Murphy

Sailing small boats over endless carefree summer days on Long Island Sound as a kid was a perfect introduction to what generations have discovered: “There is nothing - absolutely nothing - half so much worth doing as simply messing around in boats!” (Kenneth Grahame). Many years, many boats, and many more nautical miles later, Frank’s enthusiasm and zeal for being on the water under sail has only grown. Originally a rewarding pastime, sailing later launched epic adventures (cruising Baja and western coastal Mexico extensively), incredible experiences, and many, many wonderful friendships along the way. Frank looks forward to providing - and sharing - an amazing sailing experience with you aboard the Sail San Diego fleet!

Capt. Tim Hanley, Operations Mgr

Capt. TimI first sailed many summers starting at the age of 12 on the Chesapeake Bay.  I purchased my first sailboat in Atlantic City, NJ  in 1989. I first began captaining boats for a living in the Caribbean in 1996 thru 2003 and worked in the Mediterranean for several summers after that.

I've sailed across the Atlantic Ocean, all over the Caribbean,  from LA to Hawaii, up and down both coasts of the U.S. I could live anywhere in the country, I choose San Diego and have been here the last 9 years!

Michele Pasquale, CEO

Michele is the right person to be at our helm. Growing up in Seattle as the daughter of a Marine Biologist, she has been around water and boats all of her life. She makes Sail San Diego stand out from her years working for the company known as Nordstrom This is where she excelled as a manager and learned to provide the quality and highest rated customer service possible. Later, Michele was given the opportunity to work for the exclusive custom yachts sales companies in Seattle, developing an expertise for style and design. She gained extensive experience from the best brokerage houses in the world and learned about building some of the best Yachts available. Fraser Yachts, Horizon, Holland Choey Lee to name a few. Using her customer service experience, and her eye for presentation, Michele contributed greatly to the success of Sail San Diego. Since taking ownership of Sail San Diego 10 years ago, it has grown from 1 old 36ft Cal to now 3 - 40ft Catalina Yachts and a brand new beautiful Bavaria Yacht. Because of her commitment to excellence in customer service as well as providing guests with the highest quality experience, Sail San Diego is now the leading charter company and must do attraction for anyone to get out on the beautiful waters of San Diego.

Chaluim Muir, Sales and Marketing Director

Chaluim (Cal) has a tremendous amount of passion for fishing, sailing and the open water. Cal was Sail San Diego's first deckhand back in 2005 before he left on a football scholarship to attend Graceland University, where he would receive a degree in Business Administration and Marketing. Before joining the team at Sail San Diego, Cal started a yacht lodging business (like a bed and breakfast) called Dockside Yacht Lodging.

What our guests say about Sail San Diego

Thanks- We loved it! The trip was wonderful.  The Captain was charming, A perfect afternoon.


We went whale watching new year's day and had Captain Art Harrison. he was entertaining and informative. it was very foggy so we came back in but Art took us back out even though our tour time was almost over and the fog lifted. We ended up seeing a mother and a calf Grey Whale, as well as a pod of dolphins.

Art was sensational. It was obvious our safety was his first concern but he also really wanted us to have good experience and see whales.
They boat had warm clothing and blankets as well as complimentary drinks and snacks. Wonderful experience.


Dad & I Out for a Sail

My 74 yr old dad and I took an afternoon cruise with Captain Tim a few weeks ago, and I can’t tell you how wonderful it was, and what a lovely time we all had. My dad used to sail (and race) on the Great Lakes back in the 70′s, so he has has had some experience – and *raved* about Capt. Tim’s expert skippering skills and how fabulous the boat is. In my dad’s words “It’s such a pleasure to to be on board a sailboat when the Captain knows what he’s doing!” As for me, I want to come aboard again to whale watch!


This was a great sailing tour. Captain Art Harrison was very entertaining and knowledgeable, and managed to find a pod of 3-4 young whales, even though it was early in the season. This is a strongly recommended tour!


Before you die go sailing with Sail San Diego. Saw some whales, dolphins and were overwhelmed by the beauty of the Pacific Ocean. Had a great time with our Captain. It’s worth the extra money……great clean 40 foot sailboat. Wonderful experience!!!


What an amazing time our party of eight had sailing last Tuesday.  The forty foot Catalina, the steady breeze, a great captain and constant laughter . . . the joy of being one with the water, sun and wind was transcendental.

Our friends have emailed from Eureka, CA and said the whole experience was beyond description, “You would have to experience San Diego Sail to understand the embrace of its sacred joy with friends and the earth.”  Sounds mystical but true for all of us Thanks Again.


Our second trip out on the bay with Captain Mike. This time we brought our friend Kim for her birthday. We enjoyed the company of another couple from Arkansas in town for a conference. Captain Mike gave us history and highlights of the bay area. Steered us safely beyond the point and back. A great afternoon of sunshine and relaxation. They supplied the snacks, sodas, beer and had glasses for our birthday champagne. Captain Mike told us about the whale watching so we’re sailing again in February!


We travel to San Diego every year, around Christmas, and this is the highlight of our trip. The sailing is terrific and the staff is amazing. Everyone is so friendly and knowledgeable.

The various Captains we have sailed with, are so much fun and offer all kinds of information. My son is amazed every time he steps on the boat. This is an awesome company to book with. The Best!


This was by far the best experience we have had. We've never sailed before and this far exceeded expectations. You definitely get more than what you pay for. The accommodations on the boat were exceptional and the captain was an amazing guide!

We can't wait to come back and do it again. There are a lot of sailing companies, but I doubt you get treatment like this one. The extras were so great. We did have a hard time finding the location and were running late, and they were still so wonderful. Leave early to make sure you find it-it's definitely worth it!! Can't wait to go back to do it again.


We had a first class time on the sail. There was some confusion on the day we were suppose to sail and we offered to sail the next day but they took us the day we thought. We had a great time with the Captain.

The boats are first class and the little extras-free drinks, snacks, extra jackets are a real plus. Everyone at SSD gets an A+ for customer service. We would do it again. We have sailed several times in various locations and this was by far the best.


2646 Shelter Island Drive, San Diego, CA 92106 | Call +1 619-297-7426 | Email:

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