Maybe it’s because it’s a special year in 2014. Maybe it’s because folks are excited about the large fleet. Maybe it’s the beautiful weather on the Chesapeake. For whatever reason, a larger-than-usual number of boats have already made their way to Portsmouth and are tied up in Ocean Marine Yacht Center, ready for the week’s festivities.

Click here for a PDF of this week's Carib1500 Portsmouth Program of Events.

25 years ago this week, the inaugural Caribbean 1500 fleet assembled on the southern Bay and prepared to head offshore on one of ‘the last great adventures’ available to ordinary people who decided to become extraordinary if only for a short period of time as they crossed a large stretch of ocean. Back then, late rally founder Steve Black wouldn’t have had to worry about writing news stories for the web. Or about satellite tracking or sending emails to the fleet at sea. 1986 was a simpler time perhaps, at least technologically, for the rally organizers, but no less of an adventure.

But it’s 2014 now, and as we look back on the last 25 years of ocean passages that the 1500 fleet has made, we also look ahead to this year’s event and how it’s shaping up. 

15 boats are now berthed in Ocean Marine for the week’s activities, which kicked off last night with the first happy hour at the Bier Garden in Olde Town Portsmouth, sponsored by Hanse Yachts. High Street was hopping. Each year they close down the main drag in town to vehicle traffic and put on a ‘safe’ trick-or-treating event for the local kids. Vampires, mummies, zombies and a Dracula or two roamed the streets looking for candy that the local businesses were passing out along the sidewalk while the rally crews swilled Kolsch and ‘Schwarzbier’ at the Bier Garden.

‘Mom’ and ‘Dad’, as their known to their loyal local patrons, proprietors of the Bier Garden, hosted the crews in the outside garden area. It was a lovely evening for a few beers, with temperatures falling into the 60s and stars poking out in the clear sky above the tress that shrouded the garden area in ambiance. Crews shared stories of their plans for the coming winter cruising season, and exchanged ideas for the passage south.

“We brought our boat all the way up from Florida just to the 1500!” exclaimed Frank and Patti from the catamaran Sunsplash. They’re not alone. Corsair, a gorgeous dark-blue Bristol 57 (and thus far, the leader in the clubhouse for my ‘Most Beautiful Yacht’ vote), made a similar trip north from Florida just to join the rally. 

“This has been a 5 or 6 year dream of ours,” said Frank of Sunsplash. “We’ve followed the rally very closely over those years and just had to be a part of it, even if it meant bringing the boat a few hundred miles up the coast just to make the start.”

Frank and Patti are new to the offshore game. Speaking with them last night brought up an interesting point about the 1500. Naysayers put down the event as a ‘rally for newbies,’ implying that somehow the folks new to ocean sailing don’t know what they’re doing. It begs the age-old ‘chicken or the egg’ questions – i.e., how does one get experience without ever having an experience? But Frank and Patti are proving that while they might be new to the game, their crew certainly is not. They’re here to learn from the real Salty Dogs, the tight band of crewmembers who have at least 10,000 miles sailing in the 1500. And that makes the 1500 very cool indeed.

“We’ve got Loren Thompson and Dave Hornbach onboard as our crew,” Frank told me. Loren and Dave have both done the 1500 over a dozen times combined, and have many thousands of miles on the route between the Chesapeake and the islands, in both directions. “Patti and I brought the boat up the coast by ourselves, but we realized that a few hundred miles was enough for us to handle as a couple. We did it, and we’re proud of it, but we realize we’ll need the help once we go ‘off the deep end.’ I’m still going to be the captain and ultimately responsible for the boat, but I’ll be leaning heavily on Loren and Dave for their advice on how to handle specific situations. I’m hoping to learn from the best.”

Frank is a pilot in real life, and understands that sometimes the guy in the left seat – the captain of the plane – actually has less experience than the guy in the right seat (the copilot). “In those instances, you’ve got to understand that the guy next to you might know more than you do,” Frank explained. “You’ve got to balance the notion that as the left-seat guy, you’re ultimately responsible. But with that responsibility comes the responsibility to actually take the guys advice that’s sitting to your right. It’s a team effort.”

Frank and Patti are by no means alone as newcomers to the offshore game, a fact that makes the 1500 unique. This year about 1/3 of the fleet are veteran sailors who’ve done the route before, and you can be sure that knowledge and expertise will be spreading around the docks at Ocean Marine this week like wildfire, the goal being that after a week of intense preparations, the knowledge base of the entire fleet has stepped up a level.

Peter Burch and Lyall Burgess are adding to that knowledge base, roaming the docks conducting the safety equipment checklists, which are taking on an even higher level of importance in 2014 given the Salty Dawg Rally incident from last year that saw 6 boats issue Mayday calls to the coast guard. Pete has many thousands of ocean miles on various boats over the years, and has done so many inspections that he’s sure he’s seen it all. 

“One time, a catamaran argued against the need for a liferaft,” Pete told us yesterday. “He claimed ‘with two hulls and a foam core, how could I possible sink?’ I asked him what he’d do about a fire. ‘Oh, I hadn’t thought of that!’ he said. Amazing!” 

Lyall, though younger than Pete, holds and RYA Yachtmaster certification, and has crossed the Atlantic and Pacific several times, and adds his own level of experience as the ARC Europe event manager. The two make up a formidable team when it comes to the safety checks, and thanks to their experience, their advice is taken seriously.

The program in Portsmouth continues today as we welcome more new arrivals – as I write, 1500 veteran Moonshadow just pulled into their slip on A dock. Miles & Anne Poor arrived last evening on their veteran Tayana 55 Karina, and handful more boats are due in over the course of today. 

We’re back at the Bier Garden tonight for some more ‘steins of lager’, sponsored again, appropriately, by German boat builder Hanse Yachts, before the first day of the seminar program begins at Roger Brown’s tomorrow.

Follow the hourly updates of what’s going on at Ocean Marine on the Carib1500 Facebook page, and check thegallery daily for new photos.

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