To hear firsthand accounts from the participants of the rally, check out their stories on the right under “Tales from the Rally.”

Twenty years ago, an enthusiastic cruiser introduced a group of boats to the concept of an offshore sailing rally, where they could travel as a community from the states to the Caribbean to while away the winter. That cruising enthusiast was Steve Black and this month, 20 years later, he and the Cruising Rally Association completed the 20th annual Caribbean 1500, a rally from Bluewater Yachting Center in Hampton, Virginia to Nanny Cay Resort and Marina in Tortola, BVI.

This year’s 54-boat fleet was exceptionally international, with boats from 23 states, Canada, England, Japan, Germany and New Zealand. They ranged in size from a Cal 30 to two Sundeer 60s. Veteran ralliers owned over 40 percent of the boats and many of them recorded their personal bests this year, thanks to the prevalent northeastern winds that didn’t seem to tire of blowing hard.

Overall Handicap Honors went to the crew of Bojangles IV, a Gulfstar 50 Ketch owned by the Kilgour family from Toronto, Canada. The first to finish was Crazy Horse, a Sundeer 60 owned by Bill and Rosemary Thomas of Middletown, MD. They completed the passage in 6 days 9 hours and 15 minutes.

During the rally, the CRA sent out Evening Roll Calls from Nanny Cay to over 15,000 online spectators. For the most part, these updates celebrated better-than-usual winds out of the northeast, reporting “our gang continues to barrel-roll toward the BVI, with most reporting East to North-East winds in the low to mid twenties. If anyone ran the engine today, it was strictly to recharge the batteries.”

The roll calls included updates on boat positions and shared the scuttlebutt of the fleet, with reports such as, “Ohana, Peleken, Archangel and Stolen Hour all reported fresh fish on their plates this evening.”

By November 12, all 54 boats had tied up in Nanny Cay, safe and sound and ready for the festivities to begin.

“In the past several years, rally participants racked up motoring hours in light air and calm seas. This year, the winds stayed up for the entire passage. Many of the boats finished with less than a dozen motoring hours and maintained hull speed for most of the trip,” said Steve Black.