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Sailing into the New Year ‘Round the Island

Every year on New Year’s Day, San Francisco’s boating community converges on the Alameda Estuary for ‘Round the Island — a semi-organized parade of watercraft that includes sailboats and powerboats of all sizes, as well as the odd rowboat. On New Year’s Day 2021, Nathan and I were still rigging Medusa, our Santa Cruz 27, when the VHF radio crackled alive. “It looks like the Park Street Bridge has opened early,” said the skipper of Pacific Star. “They might just keep the bridge open for us.”

Bridge operator in control tower
Always give the bridge operator a friendly wave. Theirs could be a lonely job, and they’re probably wishing they were sailing!
© 2021 Ros de Vries

During normal years, Alameda’s six yacht clubs throw their doors open to New Year’s Day guests, offering hot breakfasts, chili and hair of the dog. Amidst the 2020/21 pandemic, the clubs are all closed and there was a murmur of reluctance around even being listed as an “organizing” club. Everyone wanted to celebrate the new year, just not publicly. In December, however, Island Yacht Club’s newly elected commodore made a few phone calls. The show would go on. Tradition would prevail, but with a few modifications. IYC would distribute a virtual flyer and share the word with friends, but make it very clear that there would be no club stopovers. Aeolian YC, being the club most experienced with the precarious San Leandro Channel, would communicate with the bridge operators and provide navigational support. Thus, the preferred direction of travel around the Island would be clockwise, with start times coinciding with the 12:35 p.m. high tide. No boat-sharing, and BYO lunch.

'Round the Island
Between bridge openings and changing tides, timing is everything when sailing ‘Round the Island.
© 2021 Ros de Vries

As there was no RSVP system, we really didn’t know who would turn up. But from the moment the radio came alive, we knew that we were in for a special day. A parade of boats was steaming past the end of our dock at Alameda Marina, the vanguard moving at a stately pace, then the laggards maxing their outboard engines to make it through. Later, I found out that boats had turned up from as far afield as Half Moon Bay YC.

Upon exiting the marina, we were immediately escorted by eight or so Islander 36s — a fleet that makes an attempt to ‘Round the Island almost every year. As the skipper of Marilyn told us, “I’ve done this sail for 20 years, but [presumably, because of tides] have only made it around six times.”

'Round the Island fleet
Entering San Francisco Bay is just one of the rewards of this New Year’s Day parade.
© 2021 Ros de Vries

As first-time ‘Round the Islanders asking for advice, we were made very aware of three things. First: There are four bridges. As it turns out, they are operated by friendly bridgetenders who enjoy the annual spectacle as much as we do. Second: The shallow depth of the San Leandro Channel gives people the heebie-jeebies. Yes, people frequently run aground on its sandy sides, even experienced sailors. Third: It’s a very fun way to spend the day. Social distancing didn’t prevent boaters from hollering out, “Happy New Year!” to one another, making inquiries as to who hailed from where, or — when sails went up — playfully teasing us, as our skinny little race boat sashayed through the full-bodied Islander 36 fleet.

Marilyn Munroe spinnaker
Nathan watches Marilyn enjoy a perfect day, flying on the Bay.
© 2021 Ros de Vries

The 15-mile cruise around Alameda is immensely entertaining. Over four to five hours there are bridges to navigate, glamorous homes to envy, the accomplishment of timing the San Leandro Channel just right, and, should you make it through successfully, the expanse of San Francisco Bay. There is also the busy Port of Oakland (where we saw these boaters end their day — during high tide!), drinking holes at Jack London Square to reminisce about, the towering Coast Guard clipper ships, and of course, friends ashore at Alameda Marina. There is resemblance to the grand canals of Europe and the paddleboard-friendly corridors of Southern California’s Newport. Not to mention the approach to Long Beach, where boaters look to the container ships on the horizon, calculating how long they have to transit before one exercises its full-spectrum dominance over the shipping lane.

Ros de Vries
Ros de Vries brought in the New Year in her happy place.
© 2021 Ros de Vries

It is remarkable that we can enjoy all of this in January. While on the East Coast the Atlantic storm season has brought bitter cold, and the Great Lakes have frozen over, in Alameda sunny optimism is all. There are longer days to look forward to, a coronavirus vaccine, and eventually, a return to the heady days of Estuary boat racing, chased by cheap booze and barbecuing at the Marina. That’s our forecast for 2021.

Happy New Year, everyone.

Ros put together this short video of her New Year’s Day sail above. 


  1. David Ross 3 years ago

    Awesome’Round The Island video! Very well done Roz!! Viva IYC!!! 🙂

    • Ros de Vries 3 years ago

      Thank you David! We’re keeping the dream alive, even through the tough times 😀

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