What’s it really like to sail the Caribbean 1500?

When I asked Dr. Wayne Andersen why he’s sailed his tricked out Moody 54 Habits of Health in the Caribbean 1500 four years in a row his answer made me smile. “I like to have the boat down here in the Winter,” he said in an air conditioned saloon after a speedy passage to the 1500 finish—Nanny Cay marina, Tortola, BVI. “And it’d be easy to have a delivery crew sail the boat from my home port in Annapolis. But, it all comes back to what Steve Black, (the founder of the Caribbean 1500) said before we did our first 1500: ‘Congratulations. You’re about to set off on one of the last great accessible adventures still available.’”

After helping make the adventure of offshore sailing more accessible to countless cruisers since the early 90’s, Steve Black sold the Caribbean 1500 (the annual rallies south from Hampton, Virginia, to the BVI and Bahamas in the fall) and Atlantic Cup (the rally back to the U.S. East Coast via Bermuda in the spring) to the World Cruising Club (organizers of the popular, European-based Atlantic Rally for Cruisers) in 2011. But as I found out as crew aboard Miles and Anne Poor’s Tayana 55 Karina in the 2012 edition, the rally structure that helps the 1500 make offshore sailing a bit more accessible, and the bonds formed by sharing the adventure with other like-minded cruisers are only a few of the many reasons it keeps attracting crews—both offshore newbies and veterans—year after year.

The start before the start

Thanks to Hurricane Sandy, there was no shortage of “adventure” even before the 2012 edition got underway. The 1,000-mile-wide superstorm that devastated New Jersey and New York hit less than a week before the scheduled start in Hampton, and the delays it caused threw a serious wrench into the normal pre-departure week of seminars and safety checks the 1500 is known for. A group of boats were delayed getting to Hampton and some—including Miles and Anne’s Karina—ended up weathering Sandy in Annapolis. The late arrivals in Hampton increased the pre-departure pressure to get everything ready in less time, but thanks to Andy and Mia—World Cruising’s crack organizing and communications team—and the communal spirit of the all the participants, everything was on track for an on-time departure on Sunday. Until some pretty nasty-looking the long range weather forecasts threw 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. We’ve got a nasty storm that’s forecasted to form off Hatteras in a few days and it’s looking like we might be heading out as soon as you get here.”

But that meant we’d be heading out a day early. In the past, the start of the 1500 has been delayed—some years, by almost a week!—to wait for a suitable weather window. It had never left early. And with anywhere from 40-80 boats—paying customers with various anxieties and expectations—entered in any given year, it’s easy to see why. But, Andy and Mia are experienced sailors as well as fantastic organizers and communicators. They worked closely with many of the experienced 1500 crews as well as World Cruising Club management and they did a brilliant job of assessing the weather forecast that basically said leaving a day early would allow the 40-boat-strong fleet to get out in front of the storm (if not, the next window could be another five days, or more). Then they made the call. Crews got the option of a “rolling start” to leave a full day early anytime after the skippers meeting on Saturday. The decision was well received by the fleet and 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 with advice or encouragement when it comes to preparing boats for the rigors of offshore sailing. Meanwhile Anne’s steady voice has been a fixture on the SSB radio chats for years and she also ran the Caribbean 1500 “store” as a volunteer for Steve Black. The Poor’s are 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 you ask? Well, for starters, Miles did all the cooking and he’s an amazing cook. Anne is a savvy navigator as well as a crisp conversationalist. Crewmate Matt Benhoff is Ex-Coast Guard and one of the nicest and most competent sailors I’ve met, and Karina is one of the most seakindly and seaworthy boats I’ve ever been on. Even when we experienced a refreshing spell of 40 knots of breeze against the current on the edge of Gulf Stream, and the seas churned like an unbalanced washing machine, Karina and company were in good shape. And we did in fact beat that nasty storm that was forecasted and lead to our well-called early departure.

Once the queasiness of the one uncomfortable night we had on the edge of the Gulf Stream wore off, we settled into a comfortable routine that was punctuated by several daily events. The first was the morning SSB radio chat. Even when reception was spotty, it was still cool to hear how the crews on the other boats were doing. And if you haven’t done a rally before, apart from all the hard, practical knowledge you’ll receive in pre-departure classes and seminars, being part of a regular radio chat can be a surprisingly fun diversion (and be tremendously useful if you run into problems and need advice from experienced cruisers) offshore. Many rally participants will also report that they only bought and learned how to use a SSB because they were in a rally and they were glad they did.

Another welcome daily event was “shower time”. Yep, you heard right. Each day starting around 1530 we’d each take turns getting cleaned up with a hot, fresh shower. Now it wasn’t like we were taking green waves over the bow and needed to wash the salt of per se, this was more a byproduct of Miles and Anne’s cruising philosophy of “not suffering too much.” I’ve been on more than my fair share of hygiene-challenged passages to really appreciate “shower time” and this is another illustration of the beauty of a cruising rally. The Poor’s desire to not suffer led them to run the engine (and have a 160-gallon capacity fuel bladder secured to the aft deck to significantly increase motoring range) way more than a die-hard racer, and even some cruisers would. But that’s the point. There’s a direct relationship between power offshore and comfort, not to mention hot, watermaker made water! We didn’t “win” anything, but we were one of the first boats to finish and eating bacon and eggs on land when a lot of other boats still had over 100 miles to go isn’t the worse thing in the world.

The 1900 SSB radio chat served as the final sign-off before we settled into the sleep schedule of our night watches (we enjoyed totally civilized 2-hour night watches on Karina) and it was usually during the evening chat when the power of the radio net showed it’s problem-solving power. Miles and others talked to crews and helped with issues like what to do with a sticky folding propeller, and Miles even advised one rally captain on how to safely deal with having a line wrapped around their propeller at night. And since Miles is an experienced doctor, he was also able to provide useful advice on medial situations too. But the evening chat wasn’t all business. There was some “You should have seen the fish we caught”–type chatter too.

Weather you are a member of a rally or not, the reality of offshore cruising is that you’re really all alone out there. But being in a rally does have a built-in social element that dulls the edge of the “out there” just a bit—if you want that.

Why 1500?

I was looking forward to getting to know as many rally participants as possible and learning why they chose to participate in the 1500 when we were in Hampton, but alas, I was only in Hampton for about an hour before we all were pulling away from the dock. But I did get a chance to catch up with a few crews when we arrived in Tortola and their answers provide some insight into what the 1500 is, and what it isn’t.

My first victim was the intoxicatingly energetic Dr. Wayne Andersen from Annapolis, Maryland, who owns that Moody 54, Habits of Health, that 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” offshore sailing provides, he loves participating in the 1500 because it’s a great way to build competence by gaining valuable experience. He also was impressed with the professionalism of the 1500 organization and he appreciated the social aspect as well. But more than anything, “This year was the most fun,” he reports, “because I was able to introduce a group of good friends to the adventure of offshore sailing.”
Meanwhile Paul Fridman of San Francisco, California, had a different experience aboard his Outremer 49 catamaran Baloo. While we were offshore, Paul and Miles had discussed a situation he had with sick crewman on the SSB and Miles suggested some possible causes and treatments. I learned that his crew turned out to be fine, and Paul told me that the access to a doctor on the SSB that being part of the 1500 made possible was comforting, but he also admitted that he’d participated in Baja HaHa on the west coast in the past, and he was hoping for a similar social program. He did admit that Sandy played a part in curtailing the social program in Hampton, but he also told me he’d probably look for a rally with fewer safety requirements in the future as well.

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 the social aspect and safety net that the 1500 provided and he was looking forward to exploring the islands. And it was during my conversation with Neil that I ran into Neil’s neighbor Dietmar Weselin. I remembered Ditemar from a 1500 I’d sailed years ago. He’s sailed his own boat in the last seven 1500’s, but he crewed for Neil this year because “I’m selling the boat,” he reported with a little sadness. “But I want to help pass the torch to the next generation.” And by the smile I saw on Neil’s face in Nanny Cay, it’s obvious he did just that.

Under new management

For Miles and Anne as well as many of the other experienced Caribbean 1500 entrants I talked to, participating the 1500 is special. They’ve come to love many of the people they’ve met over the years, and the cruising network they’ve formed has proved to be quite useful as well. And like Dietmar, I’ve witnessed Miles and Anne helping fellow sailors gain confidence and experience offshore as part of the 1500. These are all traits that Steve Black valued when he was running things and obviously, the folks at World Cruising Club value these things as well.

I had a chance to talk to Andy and Mia in Tortola and while they and the World Cruising Club team are working very hard to preserve the vibe of the 1500 they are also working to make some improvements as well. As a new Dad, I’ll be the first to say how awesome it was for my wonderfully accepting wife and a 4 month old baby to be able track my progress, (and see how soon I’d be home) on www.carib1500.com in real time at home. Sailtracker is hardly new technology but it’s just one of the elements that makes the 1500 more fun an accessible for everyone. However, Andy also stresses that the Caribbean 1500 is NOT and hand-holding exercise. “We prepare you with the best possible skills and information so you’ll have the tools to make decisions for yourself.” The call to leave a day early was a perfect example. They made a well-reasoned suggestion but ultimately the decision was each individual captain’s. Three boats chose not to leave on Saturday. They got out the following Friday and caught up with the rest of the fleet a little over a week later.

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

There are detractors to any perceived change that the World Cruising Club wants to bring to the 1500, and some have even gone so far as to organize their own rally that “starts” in Hampton on the same day as the 1500, and finishes in Tortola. I didn’t see or hear from  any of the members of the “Salty Dawg Rally,” but I did learn that it’s free to participate and that it’s specifically designed for experienced cruisers.


I’ve been on some trips where everything—days on end of stupidly strong headwinds, broken heads, um, I mean toilets, and on one passage, the captain forgot the coffee!!!—was just a little off. But on this trip, the miles ticked down just as easy as you please, and after numerous showers, and steak dinners, and stimulating conversation, and pleasant sailing, and naps, and dolphins frolicking in our bow wave, the lights of St Thomas and the hills of Tortola came into view on the horizon. It was just in time. We’d run out of ice cream.

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