Sailing and all things nautical has always been an enormous piece of my life. I became obsessed with the idea in early 1994, and like a dog with a bone I stayed focused on the project. I eventually gave a circumnavigation a go. I didn’t make it, however, I did cruise for over three years aboard my Westsail32 Christa. You can see my trackline below that I created in google maps. You can even click on an anchor icon and see where I anchored!

Spreader Perch Dominica Eastern Caribbean

Spreader Perch Dominica Eastern Caribbean

I wrote quite a lengthly paper on the lead up. What events would occur in someone’s life that would propel somebody forward to such a goal. Please click here to read the as yet unfinished memoir.

I penned a couple of articles for Latitude38 magazine which gives some more sailing context to my life. Read below!


Back in ’99, Latitude 38 did a little story on me when I was an active duty Coast Guardsman on Yerba Buena Island. In the article, I indicated that I was just treading water for my last seven years of service so I could take my pension, retire, and go sailing. Well, it’s happening this month — although I did have a bit of a bump in the road when, in July of ’05, the Coast Guard decided to ship me back to Woods Hole on Cape Cod. If only the service had the patience to let me sail Christa, my 1975 Westsail 32 and home for the past nine  years, to the East Coast via the Panama Canal. Of course, I probably would have failed to report for duty, as I would have already been out sailing, and that’s all I really give a crap about.

It was also in July of ’05 that, with a heavy heart and waves of jealousy, I watched my true amigo and fellow Coast Guardsman Tom Larson retire after 20 years. He and his lovely wife, First Mate Amy, bugged out on the ’05 Baja Ha-Ha aboard their Yorktown 35 Sandpiper, and now are in Indonesia. I’ve had the mental struggle of checking in on their blog for the past couple of years. I was very excited for them, but it made my daily rising and heading to work that much more challenging. I’m not sure which was more traumatizing: knowing I was two years behind Tom and Amy, or watching my much-loved Westsail leave KKMI shipyard on the bed of a tractor trailer. Like a nervous Nelly I called the driver daily for position and GPS reports. The thought of my boat transiting Donner Pass was almost too much.

On the hook Boqueron Puerto Rico

On the hook Boqueron Puerto Rico

Christa safely ‘sailed’ across our beautiful country, and landed safely at Silver Springs Marina in Wakefield, Rhode Island. Since then, I’ve sailed her up to Woods Hole, lived aboard her, and worked on her while biding my time until retirement. I endured two  New England winters aboard at Woods Hole, but who am I to complain? And this summer I had the privilege of living aboard at the Navy Base in Newport, Rhode Island, making last minute preparations for my upcoming circumnavigation.

This summer I took some leave and sailed Christa from Newport to the Rappahannock River in the Chesapeake Bay, via New York City, Delaware Bay, and the Chesapeake and Delaware Canal. Now I’m back in New England for my last 10 days in the Coast Guard. My retirement ceremony will have been on October 10, and October 11 will find me on Christa making tracks south toward the tropical latitudes. Man, am I jacked! I’m 40 years old, healthy as can be, my boat is paid off, I have money in the bank, and a life-long pension to boot. Now all I need is a first mate in a flowery sundress. But I couldn’t be more grateful to the American public — and especially our troops in combat, past and present — for giving me this freedom. I certainly got the better end of this deal.

On the horizon, I see myself sailing (motoring actually) the ICW until Charleston, where I’ll make the jump to Florida. Hopefully, I’ll be celebrating Christmas in the Bahamas. I intend to spend the winter of ’07/’08 in the Caribbean, and lay up in Cartagena for the ’08 Atlantic hurricane season. Then it’s onward to the western Caribbean for another season of bliss before transiting the Canal into the South Pacific. Sounds nice, doesn’t it?

My connections to San Francisco Bay remain strong. I was stationed in the Bay at the Command Center on YBI, aboard the Cutters Morgenthau and Point Brower, both of which are homeported in the Bay. I even endured a tour at Lake Tahoe, where I purchased my first sailboat. Let’s not forget that I lived aboard Christa in Horseshoe Cove and at the Sausalito Yacht Harbor for several years. I used to sail to work, anchor up in Clipper Cove, and take the dink the rest of the way in. What a life I have led thus far, and I’m just getting started. To solidify my Northern California connections, I even own a home in Sonoma that I intend to return to someday.

Christian Allaire

Christa, Westsail 32

Formerly of Sausalito / Heading to the Caribbean

 Christa — Westsail 32

Christian Allaire

The Thorny Path

(San Francisco)

I just had another one of those fantastic days here in the tropics aboard my 34-year-old Westsail 32. It started like all the others have since I arrived here in the Virgin Islands two months ago. I awoke naturally to the rising of the sun as a rooster crowed in the morning light. I then heated some water for my customary injection of caffeine, and took a quick peek out the hatch. As usual, I felt a sense of slight relaxation when I noted that Christa hadn’t moved during the night.

 Not all days have been so delightful since I started my lazy circumnavigation in September of ’07. For I quickly discovered that  I was woefully naive regarding the ‘Thorny Path’ to the Caribbean, and what a mental strain it would be to bash into the teeth of the trades day after day. Had I known what I know now, I would have sailed to the Virgins via Bermuda. But I’m getting ahead of myself.

 Christain ’98 while on active duty with the U.S. Coast Guard on San Francisco Bay. I’d come across the lore of the Westsail 32 in a most curious way. While stationed at Point Judith, Rhode Island, in ’91, I was a Motor Life Boat (MLB) coxswain who did a first-hand battle with the Halloween Storm of October ’91 — which eventually gained fame in the book The Perfect Storm. While not directly involved in any of the rescues chronicled in Sebastian Junger’s excellent book, in real time I’d keenly followed the many problems the Coast Guard had on its hands. But I especially remember reading the situation reports regarding the Westsail 32 Satori and the plight of her crew.

 Andrea Gail, and with the Queen Elizabeth 2 being struck by a 100-foot wave in the North Atlantic, the Coast Guard Cutter Tamaroastruggled mightily in a seaway to try to reach Satori. As it would turn out, Satori, having been abandoned, washed up on a beach a few days later — with no significant damage! That, I thought to myself, must be one seaworthy vessel! Fast forward a few years, with my dream of sailing around the world solidified in my mind, when I was thumbing through the Classy Classifieds in the back of Latitude and — bam! — I noted that there was a Westsail 32 — same as Satori — for sale in Vallejo. Not long after that, I became the proud owner.

 I spent the next nine years living aboard Christa in Alameda and Sausalito on the West Coast, at Woods Hole on Cape Cod and Newport, Rhode Island on the East Coast. During that time I learned how to sail Christa, upgraded her, and generally soaked up life aboard. I made several offshore voyages up and down the California coast, and on the East Coast gunkholed around the Cape and the jewels of Nantucket, Martha’s Vineyard and the Elizabeth Islands. Coupled with all the water under my keel while in the Coast Guard, including time in the Southern Ocean aboard a Polar Class icebreaker, the breaking bar of the Columbia River, and several trips to the Bering Sea, I thought I had a clue. But the ocean is no place for hubris. While I do have all kinds of valuable seamanship experience, nothing had really prepared me for the difficulty of singlehanding a 32-foot sailboat. I don’t want to overplay the difficulty, and as the younger generation would say, want to keep it real. But my experience is that cruising is nothing like the way they portray it in glossy sailing magazines. I don’t think they could really capture the essence of the experience anyway, and if they could, it probably wouldn’t be good for their ad sales. The intensity of something like cruising singlehanded can’t be explained, it has to be experienced.

 The following is a recap of my experiences to date: I departed Rhode Island, where I had spent the summer of ’07 at the Newport Navy Base Marina, taking care of last minute preparations and fulfilling my remaining obligations to the Coast Guard. With a continuous eye toward the tropics, ever mindful of the hurricane season, I made my way down Long Island Sound in September. My good buddy John, whom I had been stationed with in the Coast Guard many years before, joined me for a nostalgic stop in Point Judith, where we’d been stationed together. Continuing on, with stops for terrible weather, we negotiated Hell’s Gate and sailed down the East River with Manhattan to starboard. It was a truly beautiful experience made more poignant by the fact it was September 11th, and that my brother and his family lived just a stone’s throw away in the East Village. The Atlantic later greeted us with a fair current and a fresh NNW breeze, and we put the Monitor windvane in charge for rounding Sandy Hook toward Atlantic City.  As the wind waned, we changed to the green monster, my new cruising spinnaker. As the sun set with the spinnaker pulling us along, I was nearly moved to tears by the moment.

 With the days having gotten shorter and colder, I meandered down the IntraCoastal Waterway, making 50 miles or so a day. During a two-week stop at Fort Pierce, Florida to visit family for Thanksgiving, I decided to replace the wooden bowsprit with a stainless one from Bud Taplin, the patron saint of Westsail parts. I had no real reason to think the wooden bowsprit had been weakened by rot, but there was no foolproof way to ease my worry. One call to Bud shored things up. Knowing I was heading out for a trip that would last years, he said, “Well, stainless doesn’t rot.” With that, I had a ‘Visa moment’. After a week of continuous labor, I had replaced the old bowsprit. I don’t have an engineering background, and replacing the bowsprit was one of those projects where I felt my limited skills would be put to the test. But as with most projects on Christa, I discovered that I had underestimated my skills, and simply suffered from a lack of confidence. While replacing the bowsprit wasn’t easy, it was logical. Having now done countless boat projects, I’ve found this to have always been the case. So if you’re a new boat owner and wonder how the fellow down the dock became so good at boat maintenance and projects, the answer is simple: trial and error — and copious amounts of boat bucks.

 Having run out of room, I’m saving my story of the dangers of the herding instinct of cruisers for the next issue.

— christian 04/25/09

 Christa — Westsail 32

Christian Allaire

Going With The Herd(Sausalito)

 [In a continuation of his Changes in the June issue, Christian considers the dangers of the ‘herding instinct’ common among cruisers.]

 With the end of hurricane season last fall, I left Miami on a westerly bound for Gun Cay in the Bahamas. With my penchant for  underestimation fully established, I hit the Gulf Stream with the wind just north of west. It quickly became apparent that Gun Cay, Bimini — or maybe even the entire Bahamian island chain — was either moving with the tectonic plates or I had underestimated the northerly set of the Gulf Stream. I had to work hard all day to mitigate the set, and even so was only able to enter the Bahamian bank several miles north of Bimini.

 I had read about and seen the photographs of the intensity of the blue of the water in the Bahamas, and I was not disappointed. The transition from the deep blue to the shallow hues has been a highlight of my trip thus far. With good fortune and a west wind still at my back, I decided to skip Bimini and soldier on throughout the night and check in at Chub Cay.

 I did not particularly enjoy my experience in the Bahamas, largely because the wind blew relentlessly while I was there. From what I gather, the winter of ’07-08 was a banner year for the trades. They blew and blew and blew.

I largely based my decision to head to the Caribbean via the ‘thorny path’ on Bruce Van Sant’s A Gentleman’s Guide to Passages South. While I don’t want to bash the guide because it really is chock full of great information, I did find it a bit optimistic. Van Sant clearly states that if you do X, you will receive a serious pounding, so make sure you do the ten steps that make up alternative step Y. But when it came to the Bahamas, I thought I’d just wait for a cold front to sweep through from the north, then broad reach my way south. Simple. Well, once again my naiveté reared its head. Maybe you can do that some years, but not my year — as I was to discover as I tried to claw my way south. I would love to lay blame on the Westsail’s legendary lack of windward ability, but the fact is that my Westsail is not that bad to windward. In any event, every boat struggles to windward.

In terms of the Bahamas, you certainly can wait for a front and its associated clocking of the wind. However, I found few anchorages that offered all-around protection, and this meant at some point during the front’s passage my boat was going to be exposed. It usually meant riding a bucking bronco, and, depending on the front’s length and characteristics, meant a transit through a reef at the other end in less than favorable conditions. This is exactly how I entered Nassau. It’s true that it has a large and well-marked entrance, but the combination of 25 knots of wind, a large following sea, and busy shipping made it a challenge.

South from Nassau, I continued to try to play the fronts sweeping down from the East Coast of the U.S. But there was another complicating factor that I hadn’t counted on — meeting other cruisers. I really became attached to these folks and didn’t want to leave. The herding instinct of cruisers is real, and it’s probably even stronger for those of us who singlehand. The result is that folks sit in cockpits and talk weather windows obsessively — and I’m usually leading the charge. Any conversation that tries to be taken elsewhere was swiftly brought back to what counts — my lack of progress to windward.

All cruisers have different comfort levels, and obviously some boats do some things better than others. As a result, what is a weather window for longer and more weatherly boats is not necessarily a weather window for me. But when the herd was leaving, I surely didn’t want to be left behind. I certainly was not stupid enough to knowingly launch out into a full gale just to keep up — it was more of how much of a pounding I was willing to accept. And the level of pounding has a direct correlation to the number of repairs that you’ll have to make at the next port.

And so it was for my departure from Long Island, just east of the Exumas, for Playa Cay well to the southeast. I left with four other boats on a marginal forecast. The other boats had significant waterline advantage, so they quickly pulled ahead. I listened on the radio as they started to labor in increasing winds that were heading them and would head me. By nightfall I decided to break off and make for Rum Cay — and an unwanted nighttime arrival. I pretty much did what you’re not supposed to do — enter a poorly charted, coral head-strewn anchorage in 25 knots of wind at night while nearing exhaustion.

I was able to speak with a Canadian boat that was already in the anchorage at Rum Cay and discuss the odds of my coming to grief upon entering. I decided to try it — and made it in without incident. When I awoke the next morning, I saw there was a coral head just below the surface only 50 feet ahead of me. I was quickly gaining spirituality.

While upset that my random detour severed my ties with the herd, I quickly found another ‘herd’ in the form of one boat — the Jansen family’s Mason 48 Adamo. I had briefly chatted with them at Long Island, but now we were together in Rum Cay, and they’d followed my death-defying entrance on channel 68 the night before. In fact, they’d turned on their spreader lights, which became like a beacon to a very tired sailor, giving me a critical point of reference. I couldn’t have been more appreciative.

As usual, the wind just cranked for the next two weeks. But the time I spent in Rum Cay with the Jansens was truly special. I think they fed me every single night aboard their boat. Adamo and I then had a delightful transit under power from Rum Cay to the Turks and Caicos Islands. They even loaned me one of their sons, 16-year-old Doug, for the transit. But they are a real baby factory, so they could spare him.

My time in the T&Cs was spent replenishing fuel and food. After being in the Bahamas, where I couldn’t find decent shopping, it was nice to get back to the endless aisles of food that we Americans are used to.

The gaggle of boats in the anchorage at Provo were all waiting for a decent weather window to stage ourselves to Big Sand Cay in the eastern portion of the islands. This required motoring across the T&C Bank, which is only seven feet deep and sprinkled with many coral heads. Adamo and I left at sunrise. It was a long day, and I spent the majority of it standing on the spreaders. When I sighted coral heads, I rapidly made my way down to the deck, disengaged the Tillerpilot, and steered clear. Toward late afternoon, Adamo and I had made it safely across the bank, with things going smoothly. We both downloaded the latest GRIB files and checked the latest offshore forecast. It was then I made one of my worst decisions ever.

The forecast wasn’t that bad, with easterly wind of 15 to 22 knots, due to ease halfway between the T&Cs and the Dominican Republic. I should have known to include more margin for error in my plan by heading for Big Sand Cay — as I’d originally intended — instead of continuing on. But once again the herd instinct strongly influenced my decision. True, it was one of those situations in which some boats took off for the D.R., while some decided to stage at Big Sand Cay — as recommended in Van Sant’s guide. It’s at times such as this that having a strong vessel like a Westsail can be a disadvantage. I knew that my boat was up for the conditions. The bigger question was whether or not I was.

To make a long story short, instead of easing, the wind strengthened to 35 by midnight. Christa sailed beautifully with just a staysail and a double-reefed main. But as the seas got to 10 feet, she started to pound. Unable to lay my goal of Luperon, I decided to take Van Sant’s advice of cracking the sheets and head for Manzanillo, farther to the west in the D.R. What I hadn’t realized is that it would require me to first sail dead downwind approaching dangerous Monte Christi Shoals, then sail to windward(!) — having already sailed for 45 hours with little food or sleep — for 17 miles against 35-knot winds and short, breaking seas. When I realized what I was in for, it nearly broke me.

My only other options were to head for the Ragged Islands in the Bahamas — which would effectively end my Caribbean cruise — or continue on to Fort Libre, Haiti. I was able to raise the skipper of a Southern Cross 35 who had just dropped his anchor in Manzanillo  after the dreaded 17-mile beat. If he’d done it, I decided that I could  do it, too! And so it was we beat into 35-knot winds and more, with  breaking waves and water completely filling the cockpit several times. But once I realized that my boat would handle the extreme strain on the rig, I became exhilarated. I also thanked my lucky stars and Bud Taplin for having replaced the bowsprit with the stainless steel model. Confidence in the boat and its equipment become everything when the chips are down.

Needless to say I made it into Manzanillo. And I made it on down to the Eastern Caribbean, where I spent the hurricane season at Salinas, Puerto Rico, with many more lessons learned and adventures along the way.

 I shall leave you with a quote from Peter Muilenburg’s book Adrift on a Sea of Blue Light. “So it goes, on land and sea, that all of life’s wrecks force us to drag deep on the cup of knowledge and swallow its bitter but potent dregs. If the ocean held no reefs or squalls, if no ships sank and no one ever drowned, who would ever bother to go to sea?”

— christian 03/10/09

Christian — A couple of comments, if we might, on your very interesting Changes. Boats are very different, so what makes sense for one skipper in a given situation doesn’t necessarily apply to the skipper of a different boat. For example, there are a lot of upwind bashes we would have attempted with our old boat, the heavy Ocean 71 ketch Big O, that we’d never try with our Surfin’ 63 cat Profligate. Different boats do well in different sailing situations.

But the other half of the equation is how well a boat is sailed. An experienced skipper who knows how to sail his/her boat well can sail the pants off an average skipper. Nowhere does this become more obvious than when sailing to weather in rough conditions, when the difference in VMG can easily be 200% or more. As such, we’re going to dispute your statement that “all boats struggle to weather”. It’s all relative, of course, but some boat/skipper combinations absolutely thrive on going to weather, while others really struggle badly. It’s not the end of the world for a skipper/boat combo that struggles to weather; skippers just have to take it into account when planning passages and such.

By the way, having made the often wicked hip-hop passage from Florida to the Eastern Caribbean, we predict the rest of your circumnavigation will likely be a comparative walk in the park.



Leave a Reply

Your email address will not be published. Required fields are marked *