Our first destination this year would be the Virgin Islands and we plan to continue south, cruising the Leeward and Windward Islands, returning to the Chesapeake Bay in June. The passage to the Virgin Islands direct from the Virginia Capes is approximately 1300 nm and normally takes approximately 7-10 days. We arranged to have two friends as extra crew – one is Bob E. from Sarnia, Ontario, who is the Dad of the family we cruised with last winter on our same model boat named Our White Magic. The other crew member is Wally P. from Virginia Beach – one of Dave's longtime sailing friends. Both Bob and Wally are highly skilled sailors. This would be Wally’s first visit to the Caribbean. Leaving around the same time from the Chesapeake Bay are several other boat friends and around 80 boats in the Caribbean 1500 Sailing Rally – all heading to the Virgin Islands. So, in a sense, we’ll be around many boats for this passage.

Finally, after months of preparation we were almost ready for departure to the Virgin Islands. Our basic passage plan, subject to near term weather predictions, would be to depart the Chesapeake Bay at Cape Henry and parallel the VA/NC coast south towards Cape Hatteras; turn further east to cross the Gulf Stream somewhere in the vicinity of Cape Hatteras; then either go directly to the Virgin Islands in a straight line or favor early easting towards an imaginary point south of Bermuda, then turning south hoping to pick up the trade winds from the east for a beam reach to the Virgins. This "early easting" would prepare us for the winds to gradually shift to being more from the east the further south we go.

As departure time approached the weather gods intervened and a tropical disturbance was being forecast to develop in the SE Caribbean Sea. As early as October 25, our weather router Chris Parker advised us that a November 1 departure did not look advisable. Sure enough, Hurricane Tomas eventually developed – taking his time about it – and screwed up passage planning for all the boats and crews collecting in the Chesapeake and along the east coast wanting to leave for the Caribbean. Finally Tomas was getting out of the way and a departure between Nov. 5 and 7 looked possible. This delay was not all bad as it allowed us to ease the preparation frenzy a bit.

Friends John and Joan (with pup Sailor) on Alize were also busily preparing for the same passage, as we had planned for months to make the passage together. They had entered the Caribbean 1500 Rally. The Rally-coordinated departure time was similarly delayed.

The weather window began to firm up Nov. 5 for a departure on either the 7th or 8th and we began frequent phone contact with Bob who was working on his boat in Reedville, VA, to coordinate his arrival in Norfolk. On the 6th Chris Parker advised us to try to make a Gulf Stream crossing SE of Cape Hatteras during the daylight morning on the 8th, otherwise we’d have to either wait a few days longer or stay close to the coast until much further south before crossing the stream. The wind was forecast to be NW at the crossing point the morning of the 8th, but veer to the NE later Monday for several days. Crossing the NE flowing Gulf Stream with wind opposing from the NE typically creates unpleasant to unsafe sea conditions. This meant leaving Norfolk late in the day on the 7th to get to the advised crossing point at the advised time. Bob and Wally agreed with this plan and we finally left Norfolk at 1700 AST Sunday, Nov 7. (We did not "fall back" when daylight savings time changed to standard time, thus keeping our time the same as Atlantic Standard Time which we’d be in soon enough.) Local weather conditions were cool but not too cold and the wind was behind us at 15-25 knots leaving the Bay. We were sailing on just the genoa, keeping the mainsail down in the strong downwind conditions. This resulted in our departure about 18 hours ahead of the Caribbean 1500 Rally as our departure time was more nimble – as a single boat we could react quicker to the changing weather without trying to coordinate with 80 other boats.