Spending A Great Day On The Bay And You Can Do It, Too

If I were to tell you that I spent an afternoon on an America’s Cup boat sailing around San Diego Bay, you may think that’s a nice perk of being a blogger.
And while that’s what helped get me on board IL Moro, ITA-16, it’s not anything special about me or my position because you can get on board her, too. And if not on that boat, then Dennis Conner’s famous Stars & Stripes USA-11.
All you have to do is contact Sail USA 11 on Shelter Island. Believe it or not, it gives passenger rides and hosts charters for groups. Even more unbelievable is the price. It’s just $125 for individuals.
And that includes a link to download photos and videos from your trip, as well as free parking at the Kona Kai resort.







So what’s it like? From first-hand experience the word that rushes to my mind the way the adrenaline did through my veins as we pulled away from the dock is this: exhilarating.
First of all, the mainsail is huge. So huge you can’t get it all in a camera frame when craning your neck looking up at it from the deck. (It also takes some time and effort to raise it, as I learned when I was made part of the crew to do this task. Guests just get to sit and relax, by the way, and any other “work” I performed during the sail was a breeze.)
Now you don’t have to be Dennis Conner to know that the bigger the sail, the faster a boat goes and while on IL Moro – the Italian entry in the 1992 San Diego America’s Cup race – we were the class of sailboats on San Diego Bay. It was a powerful feeling to come up and pass other sailboats as if they were standing still. Heck, we were going as fast as some of the powerboats.


And thanks to America’s Cup veteran sailor Mark Strube, who is part of the crew, I can now say that I have skippered an America’s Cup boat. Part of the Sail USA 11 experience is that everyone can get behind one of the large wheels that actually steers the boat.

While doing this, I envisioned myself being Ted Turner, a relative unknown at the time, cruising into the harbor after winning the 1977 America’s Cup. Not realizing that the national media and public was about to get its first real look at this maverick who had taken an obscure Atlanta TV station to cable and bought the Braves baseball team, Turner did a few victory laps, picking up bottles of champagne and bikini-clad girls along the way.
He pulled up to the dock with the girls now topless on the bow – talk about making an entrance! – and himself drunk on champagne. He was so buzzed he fell out of his chair at the press conference!
I quickly snapped back to reality because we were rapidly approaching the seawall of the downtown Embarcadero. Very rapidly. My eyes were staring to get big as I envisioned us crashing into the rocks, making not just all the local news stations but also being all over social media from a viral video, with me at the helm. Oops!
But all smooth and calm, Mark called for a tack and a few seconds later we were headed back toward the safety of the middle of the bay.
By being skipper, a Bucket List item was created and experienced within a few short moments. Earlier, another more long-standing one was fulfilled. That was to crank those sail handles on an America’s Cup boat, like I have seen on TV coverage of the race. Heck, Sail USA 11 even gave me a long-sleeve crew shirt, so I really felt like a part of a well-trained and precise sailing team.
All I did, of course, was follow instructions but apparently I did well enough to get invited back for a sail a few days later.
As far as the sail itself, such as where it goes and what you see, I have detailed it in this review of the Sail USA 11 experience.
Below are links on how to reach Sail USA 11 so you can experience this thrill for yourself.
So pull up your anchor and sail on folks!

Sail USA 11 Contact Information
• Website: https://www.sailusa11.com/
• Phone: (619) 540-1876
• E-mail: [email protected]
• Facebook: www.facebook.com/sailusa11
• Instagram: www.instagram.com/sailusa11
• Twitter: twitter.com/SANDIEGOSAIL
• YouTube: www.youtube.com
Beautiful!
Thank you so much! Glad you enjoyed the article.