Never, ever, agree to take a 1,000 mile trek on a boat that you've have not seen, while seated in a bar several hundred miles away. Yet, this is exactly what I did about six years ago when I was a little younger, a little thicker in the skull, and perhaps still na√�ve to the strength of mother ocean.

My friend Jack Bulger and I had arrived in Ft. Lauderdale to help Mark Mitchell, a captain friend deliver a few boats. Our plan was to take a new Grand Banks 42 from Lauderdale to Antigua in the Windward Islands. However, our ride wasn't quite ready, and Jack and I did not have the flexibility to hang out in Lauderdale.

"Well then how do you guys feel about going to the Bahamas to take another boat down to St. Thomas?" asked Mark while slurping down his conch chowder.

"When would we leave?" I asked enthusiastically.

"Today," shot back Mark. "I think there's a flight in a few hours."

Demonstrating a pattern of behavior that was an underlying theme throughout our ten-day adventure, Jack and I grabbed our sea bags without hesitation and headed for the airport. 

Agreeing to make such an endeavor–where we would find ourselves hundreds of miles from land–before we got any details was mistake number one in a long string of missteps we took on the path to the Virgin Islands. This stumbling, combined with some dumb luck, placed the boat and us in a few uncomfortable situations.

We caught up with the Grand Banks 42, Spindrift, in Marsh Harbour, Bahamas anchored off of the Conch Inn. Shame on us for thinking we could arrive in the morning, provision, check the systems and then depart by the late afternoon. After having weathered Hurricane Dennis, which thrashed this area of the Bahamas, Spindrift was not in the turnkey shape that Mark described. In his defense, we never asked Mark one question about the boat's maintenance schedule or condition. We were only thinking about palm trees, crystal clear water, and a relaxing cruise through paradise just like Jimmy Buffet describes.

The reality was a little different. It took us several days to make repairs and get the boat ready for sea. I brushed over a few other areas, but one lesson I learned long before this trip, was that the mechanical systems need to be in tip-shape, serviced, and ready to go.

I wish I had put as much effort into obtaining a better picture about the weather. The winds sustained 25 knots with higher gusts for several days. There was a high to the north and a low to the south, and we were caught in the middle in a sloppy and disturbed system. The forecast called for 10-foot seas in the ocean for the next several days. Jack and I weighed our options, looking at our schedules (he had to get home and plan for his own wedding) before deciding to head to George Town, in the Exumas.

The harbor into old San Juan in Puerto Rico is always a welcome sight.

I quickly learned the lesson about the size of waves and what a 10-footer really feels like and looks like. Going through the cut at North Man O'War, the seas were on our nose and judging by their relationship to our mast, we occasionally hit what I'm confident were 12-15 footers.

On that first night, the setting sun brought higher winds, gusting to more than 35 knots, blowing the tops off the waves, filling the air with white water and my heart with dread. What the hell were we thinking, deliberatley heading into such foul conditions? That tiki bar in Marsh Harbour looked pretty good at this point.

At dusk, nasty boat gremlins began to work their way through Spindrift.We lost both the radar and GPS, and only then did I realize I forgot to pack my handheld GPS in my sea bag during the rush! The seas were building slamming our after quarter, the sun was fading, and we were heading into an unkind, hazardous sea, blind.

I decided to gain some sea room and head 25 miles off of Eleuthera to a pre-determined waypoint and then turn southwest for Eleuthera Point. If my dead reckoning skills came through, we would be about six miles off of Eleuthera at sunrise. Eleuthera Point is easy to spot and we could then eyeball our way to George Town.

During my watch, I stewed about our predicament. I was mad that the boat was not in great shape. I was mad that my leisurely cruise had turned into "Survival: The Home Game," and I was mad at myself for foolishly placing Spindrift, and my friend in harm's way. Everything we were experiencing was more or less self-inflicted. Around 4am, we noticed a cruise ship off our starboard bow heading southwest. A radio call to the bridge confirmed our position and they notified us they were going to Little San Salvador. We followed this city of light into the Exuma Sound, and into safety.

I exhaled the mother of all sighs when we made the transition to calmer seas. The rising sun warmed the spirit, and my little episode of self-doubt faded. I did vow, however, to never place myself in that position again.

That evening while docked in George Town, we met up with my friend Tommy McCoy, president of Trawlers In Paradise, and Jim Cress, president of Nordic Tug. They were delivering a new Nordic Tug 42 to Tommy's charter fleet in St. Thomas. Like brothers in arms, we traded sea stories around the dinner table long into the night.We were dogged by issues and nasty weather the entire way to St. Thomas. Although Tommy relived the stress of navigating without electronics by allowing us to play follow the leader.

Can you teach an old dog new tricks? Yes, I think so. As much as I love blue water cruising, I passed on a delivery from St. Croix to New York a few years back. Why? When I arrived, I found a boat in horrible shape and a narrow weather window. I decided to pass, and spent the next several days lying on the beach. Maybe I'm becoming soft, but I'll take safer any day of the week.