The 2006 Caribbean Rally officially got underway November 8th, days later than scheduled due to inclement weather with a low-pressure system passing through the area. Weatherman Ken Campbell made the recommendation to the race officials to postpone the start of the seventy-five entries and the committee heeded his advice. Two yachts did venture out though taking an early start, " Between the Sheets and Faraway Eyes", reporting 25 to 30 knot winds on the nose and heavy seas through the night. "Faraway Eyes" electing to hove to for the night radioed in to the committee that they were having a rough go of it but they were safe.

On the start line of the 8th, the fleet found light Northerly winds and foggy weather to be the order of the day. The following day did bring on some better conditions with a good twenty knot wind speed as the fleet ventured into the Gulf Stream, with the winds predicted to taper off into the evening.

November 10th the fishing lures were trailing out behind many of the racers with "Artic Tern" reporting the first fish landed onboard. The yacht "Thalia" had radioed in a medical emergency to the Coast Guard and one of the yachts crew was air lifted to the shore. The fleet was to be plagued by very light air for days to follow, but the fishing did indeed improve with  "Thumbs Up" landing a rather large Yellow Fin Tuna to the crews delight. At one point, there was rumor going around the fleet over the radio that the race should be renamed the "Caribbean Trawler Trek 1500" as the entire fleet was now under power in no wind conditions.

November 14th unveiled the same conditions of no wind with many of the fleet now running low on fuel making their way to Tortola. "Between the Sheets" was reporting their position just six miles from the finish line, but the committee also pointed out that they did have that two day jump on the fleet at the start!

November 16th is the day that the trade winds finally kicked in albeit that a large percentage of the fleet were very close to the finish line and the SSB transmissions were having their issues with the fleet reporting in to the race committee. The good news of the day was the expected finishers and the trailing boats were now closing in on the leaders. Many of the stragglers were sailing hard to make the awards dinner at Village Cay, Saturday the 18th, with six of the yachts still out at sea with three holding over in Bermuda.

The rally class has been determined and the Overall Winner was Hi Yo Silver, Ray Diones Pacific Seacraft 40. First to finish was Gil Smith's Joy for All. Clean Wake Award recipients were Hunter and Devi Sharp. Tempest Trophy winners were Rick and Terri on Sophisticated Lady. The Hal Sutphen Seamanship Award was presented to Dr. Miles and Anne Poor on Karina.

The fleet is now enjoying the savors of their efforts to reach Tortola, cruising all through the islands!