On a cold November 3rd day we departed York River to start the Caribbean 1500 Rally with our trusty crew Tracy and Darryl, fellow AYC sailors. Our lines were cast off by our good friend Harry and we made the start gun in the nick of time. We eased out of the Chesapeake in light winds and proceeded to our insertion point to enter the Gulf Stream. The stream as opposed to the majority of the trip was teaming with pods of dolphins. One dolphin came back to the cockpit at night and kept surfacing to get a good look at us. Some of the rally boats caught fish all the way down to the Caribbean. The age old route is go East to 65 degrees longitude and then head south to the islands. This route guarantees minimal upwind points of sail. It turns out this year that logic was turned upside down as a huge front swept through the US and followed the fleet into the Atlantic. Boats staying on the rhumb line had an opportunity to take the system all the way down to Tortola. We were unsure of the front intensity and continued the traditional easting. It turns out like all of our trips we had to sail hard on the wind around 95% of the entire passage. The good news is the far east side escaped much of the heavy squalls and higher seas so we had a smooth ride for the most part. On the morning of the 11th Jim noticed a small tear on the upper mainsail luff so it was taken down for the remainder of the trip and Genoa and engine were used in lightening air to keep the upwind angle. We ate great cooked meals the whole way down. On the 13th Amy spotted Virgin Gorda, we cruised past Anegada, crossed the finish line off Beef Island, and went down the Francis Drake Channel to enter Nanny Cay Marina at nightfall. Entering the unknown channel at night was a little stressful as Darryl lit up unlit markers and a rock jetty with the spotlight. We were welcome at the dock by rally control and finished crews with a round of painkillers. The trip was a challenge yet rewarding since no goals in life should be too easy, right? We are now officially on “island time”.