When I asked Dr. Wayne Andersen why he has sailed his tricked-out Moody 54 Habits of Health in the Caribbean 1500 rally four years in a row, his answer made me smile. “I like to have the boat down here in the winter,” he told me after a speedy passage to Nanny Cay in Tortola, BVI. “It would be easy to have a delivery crew sail the boat down. But it all comes back to what Steve Black told us before we did our first 1500: ‘Congratulations. You’re about to set off on one of the last great accessible adventures.’”

After helping make the adventure of offshore sailing more accessible to countless cruisers since the early 1990s, Steve Black, founder of the rally, sold out to the World Cruising Club (organizers of the popular Atlantic Rally for Cruisers, among others) in 2011. But as I found out crewing aboard Miles and Anne Poor’s Tayana 55 Karina in the 2012 edition, the accessibility of the rally and the strong bonds formed by its participants aren’t the only reasons it keeps attracting bluewater sailors—both newbies and veterans—year after year.

The start before the start

Thanks to Hurricane Sandy, there was no shortage of “adventure” this time around, even before the rally got underway. The nearly 1,000-mile-wide superstorm hit less than a week before the scheduled start in Hampton, Virginia, and threw a serious wrench into the 1500’s normal pre-departure round of seminars and safety checks. Several boats were delayed getting to Hampton and some—including Karina—ended up weathering the storm in Annapolis. The late arrivals increased the pre-departure pressure in Hampton, but thanks to Andy Schell and Mia Karlsson—World Cruising Club’s crack organizing and communications team—and the communal spirit of all the participants, everything was on track for the scheduled departure on Sunday, November 4. At least until some nasty-looking long-range weather forecasts threw yet another wrench into the works.

My phone rang: “Hey Bill,” said Miles less than two days before I was to fly out of Boston. “What time are you scheduled to arrive on Saturday?”

“About noon,” I replied.

“Okay, good. There’s a storm due to form off Hatteras in a few days, and it looks like we might be heading out as soon as you get here.”

The start of the 1500 has often been delayed—in some years by almost a week—due to weather, but it had never left early. With anywhere from 40 to 80 boats—paying customers no less—entered on any given year, it’s easy to see why. Andy and Mia worked closely with many of the experienced 1500 crews and WCC management and did a brilliant job assessing the forecast. Leaving a day early would allow the 40-boat fleet to get out in front of the storm. Otherwise it would be another five days or more until the next weather window. Their solution called for a “rolling start,” allowing crews to leave a full day early anytime after the skipper’s meeting on Saturday. The decision was not only well received, but it proved to be the right one.

Onboard Karina

Miles and Anne have participated in every 1500 since 2004. Miles has been the volunteer fleet surgeon, he’s conducted numerous pre-departure safety checks, and he’s always willing to help other skippers with advice and encouragement. Similarly, Anne has been a fixture on the rally’s SSB radio net for years and also ran the Caribbean 1500 “store” as a volunteer for Steve Black. They are only two of the many personalities that make up the rich fabric of the 1500, and I was lucky to catch a ride with them.

How lucky? Well, for starters, Miles did all the cooking and he’s an amazing cook. Anne is also a savvy navigator and a crisp conversationalist; my fellow crew, Matt Benhoff, is one of the nicest, most competent sailors I’ve met; and Karina is one of the most seakindly boats I’ve ever been on. Even in 40 knots of wind on the edge of Gulf Stream, with the seas churning like an unbalanced washing machine, Karina and company remained in good shape. 

Once the queasiness of that one uncomfortable night in the Stream wore off, we settled into a comfortable daily routine. First came the morning SSB radio chat. Even when reception was spotty, it was nice hearing how the crews on other boats were doing. If you’ve never done a rally, apart from all the practical knowledge you’ll pick up beforehand, being part of a regular radio net can be a surprisingly fun diversion. It is also tremendously useful if you run into problems and need any advice during your passage. Many rally-goers told me they only bought and learned how to use a radio because they were in a rally, and that they were glad they did.

Another welcome daily event was “shower time.” Yep, you read that right. Each day starting around 1530 we took turns showering. This was a by-product of Miles and Anne’s cruising philosophy of “not suffering too much,” and I’ve been on enough hygiene-challenged passages to really appreciate it. The Poors carried a 160-gallon fuel bladder on Karina’s aft deck and were very willing to burn diesel to run their watermaker. Believe me, offshore there’s a direct relationship between power and comfort.

The 1900 radio chat marked the end of our day, and it was then that the power of the net became apparent, as Miles and the other veterans talked the newbies through various problems. One time, for example, Miles advised another skipper on how to safely deal with a line that had wrapped itself around his propeller. However, the evening chat wasn’t all business. There was plenty of “you should have seen the fish we caught” chatter, too. 

Why join the 1500?

I was looking forward to meeting rally participants in Hampton, but alas, I was only in Hampton for about an hour before we all motored away from the dock. I did, though, get a chance to catch up with the other crews after we arrived in Tortola, and in the process learned a lot about what the 1500 is, and what it isn’t.

My first victim was the intoxicatingly energetic Dr. Andersen, from Annapolis, whom I quoted earlier. Dr. A is a best-selling author who writes about, you guessed it, healthy living. He told me that in addition to the pure “adventure” of offshore sailing, he loves participating in the 1500 because it’s a great way to gain experience. He was also impressed with the professionalism of the 1500 organization and appreciates the social aspect. “This year was the most fun,” he reported, “because I was able to introduce a group of good friends to the adventure of offshore sailing.”

Paul Fridman, from San Francisco, had a different experience aboard his Outremer 49 catamaran Baloo. While we were offshore, Paul and Miles had discussed a situation with sick crew on the SSB, and Miles suggested some possible causes and treatments. Paul’s crew turned out to be fine, but Paul told me having access to a doctor via radio was comforting. He also admitted he’d sailed in the Baja HaHa rally on the west coast and hoped to find a similar social program in the 1500. He was disappointed that Sandy had curtailed the social program in Hampton and said that he would probably look for a rally with fewer safety requirements in the future.

For Neil and Shawn Sullivan of Fredericksburg, Virginia, the 2012 rally marked the beginning of their first season cruising and living aboard their Antares 44i Escapade. Neil loved what the 1500 provided and was looking forward to exploring the islands. It was during my conversation with Neil that I ran into his neighbor, Dietmar Weselin, who I’d sailed with on a 1500 years earlier. Although Dietmar had sailed his own boat in the last seven 1500s, he’d crewed for Neil this year because he wanted “to help pass the torch to the next generation.” I could see by the smile on Neil’s face in Nanny Cay he had done just that. 

Under new management

During my time in Tortola, I also had a chance to talk to Andy and Mia, who said that while they and the World Cruising Club team are working very hard to preserve the old vibe of the 1500, they are also working to make improvements. Throughout our conversation Andy stressed that the Caribbean 1500 is not a hand-holding exercise, but designed to provide participants with “with the best possible skills and information” so they can make decisions for themselves. The call to leave a day early is a perfect example. Although organizers made a well-reasoned suggestion, the ultimate decision of when to leave was left to each skipper. 

Looking ahead Andy said he hopes future rallies will become a bit more like long-distance road races. “You can run 26 miles by yourself,” he says, “but for most folks, it’s way more fun to be part of an organized event—a spectacle.” He also looks to the success of the ARC as a model for future 1500s. “A competitive element can be fun for some. Of course, it won’t be for everybody, but the ARC has full ‘race’ teams that are fast and fun to follow.” 

Speaking for myself, I’ve been on passages where everything was a little off—from days on end of stupidly strong headwinds, broken toilets and one passage where the skipper forgot the coffee! But on this trip the miles ticked away as easy as you please, and after showers, steak dinners, stimulating conversation, pleasant sailing, naps and dolphins frolicking in our bow wave, the hills of Tortola came into view just in time. Turns out we had run out of ice cream.

Want to enter the 2013 Caribbean 1500? Visit worldcruising.com

Photos by Bill Springer, Maria Karlsson, & Andy Schell