Featured Instructor: Captain Bob Diamond

By: Instructors, Schools

Spinnaker Sailing/ Redwood City Captain Bob Diamond is This Month’s Featured Instructor

Spinnaker Sailing in Redwood City is one of the original ASA schools. It is not only a school with plenty of years under its belt, but it is also a school with experienced instructors who are among the best in the sailing business. Bob Diamond is the head instructor at Spinnaker Sailing, as well as a co-author of ASA’s Sailing Made Easy textbook. For the past 25 years, Bob Diamond is the guy who has the life you have always wanted as he has led sailing trips all around the world.

Captain Bob Diamond is this month’s ASA Featured Instructor.

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ASA: What got you into sailing?

Captain Bob Diamond:

It was in the early 1970’s that I was student teaching to earn an elementary teacher credential. One day the principal, Ernie Rideout approached me while I was on playground duty to ask if I would go sailing with him. Why not? I thought. The next Saturday I met him at the Santa Cruz Yacht Harbor. His boat was a 23’ 1940’s vintage wooden Bear class sloop. The boat looked to be in great shape with the exception of a rusty outboard stored on the cabin sole that looked like it hadn’t been used in years.

We sailed out of the slip and then on to Capitola and back. Ernie taught me how to handle the jib sheets for the beat back. Prior to that, I had only sailed a few times with relatives who didn’t let me handle anything. Helping sail the boat made it a lot more fun.

I had been working as a camp counselor and a bus driver every summer while going to college and it was the very next day that we had a staff meeting in preparation for the upcoming summer camp session. As fate would have it I mentioned to the camp director that I went sailing the previous day. She asked if I liked it and after saying I did, she said, “That’s great!” It became apparent why she was so excited when she told me that the sailing instructor for the camp had just quit and she had no other replacement.

There was time enough for me to take a Coast Guard Auxiliary classroom course on sailing before camp started and after finishing the course all I could say about my sailing ability was that I knew more about sailing than the kids at the camp did. By the end of the 6 week camp session I was enjoying sailing so much I bought a Banshee, a 13’ dinghy right there at the sailing lake where I took the kids sailing. After racing with San Jose Sailing Club for a few years moved up to a Hunter-27 which made possible to cruise the San Francisco Bay and nearby coastal waters with my wife. Through associations with members of SJSC I participated in racing in the San Francisco area and longer races from California to Cabo San Lucas and from San Francisco to Kauai. By this time sailing was no longer a hobby for me; it was an obsession. I hired on at Spinnaker Sailing in 1984 and continued teaching sailing as a career ever since.

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ASA: What was your most memorable student or class?
Captain Bob Diamond:

Around 1990 there was a class that consisted of 4 doctors from Stanford Hospital. I was amazed at how quickly they were able to master the names and functions of all of the parts of the standing and running rigging in the first lesson. I always point out to new students that it takes time and repetition to learn all the new words in sailing. It was when I asked how the doctors managed to pick everything up so quickly they told me they were all anesthesiologists and it was their business to know their lines. What a gas!

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ASA: Your favorite place to sail?
Captain Bob Diamond:

As a sailing instructor who has taken students and guests on bareboat charter trips some 90 or more times, to destinations in the Caribbean, the Mediterranean, the South Pacific, and the Sea of Cortez it’s impossible to pick one favorite. There are so many great places to sail and each of them offers something different. I do have different favorites for different reasons.

The British Virgin Islands are my favorite for taking large groups with multiple boats. With English as the language and the U.S. Dollar the official currency, the cruising is easier. With good trade winds without high seas and vast infrastructure for bareboat cruisers BVI is a great place to take people, especially those without much cruising experience.

The Leeward Islands of Tahiti excel in exotic beauty and warm hospitality. There isn’t as much cruising traffic as in the Caribbean so it really feels special to be there and yet, everything needed is readily accessible. Each island is surrounded by a barrier reef so anchorages and mooring areas are all in protected lagoons with flat water while it’s deep ocean water between the islands giving sailors the feel of deep ocean sailing during the short stretches between islands.

Of all the great places to sail in the Mediterranean my favorite is the Dalmatian Coast and islands of Croatia. It’s as busy with charter cruisers as it is in the Virgin Islands but there are many harbors to hold all the boats with great infrastructure. Expenses including fantastic dining are reasonable and English is widely understood. As elsewhere in the Mediterranean boats are almost always Med Tied (what else?) but in Croatia the harbors are equipped with lazy lines which make it so much easier that the first time I encountered lazy line Med docking it was almost like valet parking.

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ASA: Why do you sail?
Captain Bob Diamond:

Sailing never gets old. There are always new things to experience and new people to meet and to share experiences with. Spending time with people enjoying new experiences is the best part.

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ASA: What do people not know about sailing that they should?

Captain Bob Diamond:

What non-sailors need to know about sailing is that they can do it. With sailing schools and clubs around the country it doesn’t have to take a lot of financial recourses to get started. It doesn’t take a lot of mental or physical prowess, either. It’s hugely rewarding to see skill, knowledge and even wisdom developing with experience and fun to be had all the way along the journey.

“Everybody has to do something. Why not sail?” -Captain Bob Diamond

Bob Diamond is the sailing vacations director involved in organizing and running all of Spinnaker overseas charter vacations. Bob has been leading trips to all parts of the world for over 25 years.