Sailing the Caribbean Islands

INTRODUCTION

What’s it REALLY like to sail the Caribbean islands? We are frequently asked this question. For two seasons, we’ve sailed the island chain and this book relates our daily adventures. Whether you’re an armchair sailor, a lover of adventure in general or you are contemplating sailing down island yourself, we think you will enjoy sharing our many adventures and humorous incidents. And you'll enjoy meeting the characters along the way that can only be found in the Caribbean.

We wished we had a book like this prior to sailing the Caribbean. It is such a leap of faith to go sailing into the unknown. We assembled the various cruising guides and they had much useful information. However, none answered the question, What’s it really like to sail the Caribbean? It is our hope that this book will answer that question and, for those so inclined, give you the assurances that, yes, you really can do it yourself.

I was in my early 60’s and my wife, Gale, was in her late 50’s when we woke up one morning and said, Let’s do it! We had been coastal cruisers and racers aboard our Frers 41. But sailing the Caribbean was a life long dream. We decided that, if we were going to do it, we’d better get on with it or the opportunity would pass us by.

We purchased a sturdy and comfy boat in early spring 2003, a Hylas 54 that was designed for island hopping. After sailing her up from Ft. Lauderdale to Jamestown, RI, we continued on to Maine for a shakedown cruise. Late summer was spent outfitting the boat and getting ready to deliver the boat to the Caribbean during the fall of 2003.

On our trip down to the Caribbean, we first sailed to Bermuda and then down to St. Thomas. We left on a cold windy day but then had a good passage through the Gulf Stream and on into Bermuda. Our boat handled the offshore waves well and there was much camaraderie among the people on board.

During our first season, we experienced unusually squally, rainy and windy conditions…not at all like the brochures! However, our second season was picture perfect with sunny skies and gentle breezes.

While ten years have passed since we completed our adventure, not much changes in the Caribbean. All of the characters mentioned in this book are still there. There’s a much larger, full-service marina on St. Lucia, but that’s about it.

We hope you enjoy sharing our adventures and hope that you, too, will take the plunge and sail the islands. Your only regrets will be if you don’t.

Gale and Gerry Bay

THE BOAT

Hylas boats are the ideal cruising boat as far as we’re concerned. They’re similar in design to the popular British Oyster yachts but have American systems. Our Hylas was a 54-footer with a center cockpit. This gave us a very large owner’s stateroom, which you really need for extended cruising comforts. It’s cutter rigged but we found that we seldom used the staysail and eventually removed the sail and its permanent stay. We made a removable stay and kept the sail as a storm jib, which, thankfully, we never used. She weights 54,000 pounds and is very sturdy.

FT. LAUDERDALE TO JAMESTOWN, RI

After purchasing the boat in Ft. Lauderdale, we went on our first real offshore sail to deliver the boat to Rhode Island. As you will see from the log that follows, our adventures and surprises began immediately. We sailed up with a Captain that works for Hylas, Sam Lewis, a mate of his, Jack, my daughter, Heather, and a friend, Mike Camera. We had a satellite link on the boat and used this to send daily reports on our adventures to family and friends. What follows is that daily log so you can go sailing with us and share our adventures!

Sunday, June 15, 2003

Our flights down to Fort Lauderdale went smoothly and we got to the boat about 8:30. Our delivery captain, Sam, met us with some bad news. The boat is all ready to go but the refrigeration broke down. Can’t be fixed until Monday AM. This actually worked ok for us since we could use the day to go through procedures, set sails, etc. for our trip. It would have been a scramble to leave this AM. Also there is a stalled front off of Hatteras with 25 knot northeasterlies and I was thinking we might have to put in for a day or two anyway once we got up there.

This morning is very rainy here so we’re waiting for things to clear. Mike is up hanging out and Heather is sleeping. We all went out for dinner last night and I got back to the boat about 11:30. They stayed out and hit a few bars.

I’ll try to send a daily report but it will all depend on how rocky it is and whether we can maintain our satellite link.

Monday, June 16

After morning showers yesterday, the weather was hot but nice. We worked on the boat and ran errands until 4:30. I don’t know how we would have left yesterday anyway. This morning is hot with little wind. The forecast is for pleasant weather for at least two days but with light winds. We still have our eye on the stalled front over Cape Hatteras. Current forecast for up there about the time we arrive is 20-30 knots and 9-foot seas. Hmmmmm....

We hoisted the spinnaker in its sock yesterday...it’s big! We’re hoping to set it today when we leave. They are working on the refrigeration now and we are hopeful that we can get it fixed and leave this AM.

I’m a little concerned about our provisions. Sam only had six gallons of drinking water on board for 5 people in the heat for 6 or so days and we have one loaf of bread and one bunch of bananas. We did a lot of shopping yesterday.

Sam wants to do a rotating watch system where we never stand the same watch. I prefer a constant setup because everyone can get into a routine and adjust their sleep clocks. Oh well...I’m paying him so we’ll go with his program...maybe I’ll learn something. Can’t wait to get going!

Monday, June 16--6:10 PM

We’re off! We repaired the refrigeration by noon and loaded the boat with food. We thought it was a little light so Heather ran to the store.

We left at 1 PM and went down the river. We fueled up and left Ft. Lauderdale at 2:30. As we sailed out to the Gulf Stream, we saw a flying fish and a great big turtle...biggest one I’ve ever seen. We sailed for two hours but the wind came around to the nose so we dropped the jib and are motor sailing. I think in about an hour we’ll be in the stream.

Winds 10-15 ESE and 1-3 foot chop. Boat speed around 5-6 knots but speed over the ground is 8.5 knots...we’re on our way. I took the first watch...3-6 and will be on 12-3 tonight. Mike will be with Sam at 9-12. Heather will stand only the 12-3 watch in the afternoon in exchange for cooking duties.

Wednesday, June 18

Position: 31 56.5 & 78 14.6 motor sailing at 7 knots. Speed over the ground is 8.2 knots. Big easterly swell developed overnight...max swell looks like 6-8 feet. Winds 12.5 knots. Not very pleasant with a big swell and light winds.

The big event around dinnertime was that Mike saw a Dolphin. No one else did so we’re giving him a hard time.

Last night Mike and I had an out-of-body experience. On the aft deck, there are two jumper seats. WindSong was steering itself along very nicely so we both decided to sit back there. We watched the stars and the meteors for hours while the boat just trucked along...beautiful.

My watch was 9-12 but a few hours after I went to bed, this big swell developed and it was very hard to sleep.

Heather’s doing fine although it is increasingly tough to cook with the big swells.

More mechanical problems...the refrigerator is out so all of our food will be spoiling in the heat...and we’ll have to drink warm beer!

We await the weather briefing to lay out our plans from here. Looks like we’ll put into Beaufort for repairs, fuel, etc.

Wednesday, June 18--5:33 PM

Evening report: Position 33 05 N 77 12 W. Approximately offshore of Cape Fear and 199 miles from Beaufort, NC. Wind continues light 5-10 knots. Boat speed 6.4 knots. VERY BIG SWELLS...10 feet plus! Still sunny and hot but we can see gray clouds on the horizon...I’m about to go on watch 6-9 PM and then 3-6 AM.

We anticipate arriving in Beaufort sometime in the morning and we’ll be in cell phone range coming in. Weather reports indicate deteriorating conditions tomorrow with 30 knots SW. That will be real ugly on top of this big swell so we’ll be happy to get in. Preliminary reports for the next couple of days indicate a strong northerly Friday and Saturday so that will really chop up the ocean. We may be here for a few days.

Heather is cooking chicken a la king, which is really tough in our current conditions.

I asked Mike if there was anything eventful today and he said, Yes, we saw a ship. So that’s how it is out here. We took the mainsail in and out a couple of times but it’s too rolly to keep it full. We’re all felling great and having fun swapping stories, napping and standing watches.

Thursday, June 19--11:01 AM

Position: Tied up at the Town Creek Marina, Beaufort, NC. Speed-0. Weather cloudy with intermittent showers--Winds: Light.

Well, just as I sent last night’s email about having a boring day, we had one of the most fascinating times of our trip. Just as I hit the send button and began a phone call to Gale, Jack yelled, Dolphins! Sure enough, about a half dozen dolphins appeared, jumping through the water and cavorting under the bow. They stayed for quite a while just playing with us. We all stood on the bow watching them...they swam effortlessly. Then they all disappeared in the blink of an eye. But not to worry...over the course of the next hour or two, they reappeared frequently. We could see them coming several hundred yards away, leaping through the air and then swimming and jumping around the boat.

We enjoyed the dolphin show during dinner. Heather cooked Charley’s chicken a la king, which was absolutely delicious. And then, all of a sudden we saw a whale! The dolphins were swimming and jumping around. The whale blew a couple of times and then, probably annoyed with the dolphins, it sounded.

Darkness fell and I went off watch at 9 PM. Just as I was bedding down, I heard the one thing you don’t want to hear when you’re 100 miles offshore and a gale is on the way...the engine died. It seemed that we had overestimated the capacity of one of our four tanks and ran it dry. This is a problem offshore with the boat rocking and rolling.

Sam swung into action over the next half hour and got the engine bled and going again. Heather sprung into action and got the mainsail out. But then one of the scariest things happened. The dolphins were still around the boat and were breathing. Their sounds were eerie in the darkness. So here we were out in the middle of the ocean with the boat in who knows what shape and with strange animals circling us. We think they may have heard the engine die and came back to make sure we were ok.

This morning, I did the 3 AM to 6 AM watch. It was rainy with a few lightning strikes. Then about 7 AM we entered the entrance to Beaufort. We smelled land for the first time in a few days and it smelled sweet. This is a quaint little harbor.

I can’t believe we motored all the way up here from Ft. Lauderdale with only 2 hours of sailing. I’ve dreamed of doing the Gulf Stream and my image is always bombing along under sail on a beautiful reach in 20 knots of breeze...the difference between dreams and reality!

We hope they can fix the boat this afternoon or tomorrow. The weather forecast is weird. Offshore is a gale but coastal, they are predicting benign conditions...doesn’t make any sense. We will wait until this clarifies.

All food is spoiled...we’ll have to restock. Showers are fantastic!

Thursday, June 19--6:03 PM

Boat speed--0. Weather: Hot but not as bad as FL. Winds: 15-20 knots...so now it blows once we are in port!

Boat parts are ordered and, hopefully, they will arrive tomorrow. Our delay is not too serious because the weather north of us is not good and it won’t clear in Jamestown until Monday.

I had one of the best showers I’ve ever had...got rid of several layers of sweat, salt, etc.

While Sam worked on the boat, the rest of us went into the quaint, pretty little seaside town of Beaufort, NC. The two things of significant interest are:

They have an absolutely first rate maritime museum.

Big Daddy Wesley’s Grocery, Bait and Tackle Shop, which, among other oddities provides bail and bond service, should you need it.

I should mention that Heather did an unbelievable job of cooking last night in the big swells and as soon as she was finished, the swells began to subside!

We are told that Beaufort has three bars. I think we will go check out that rumor.

Friday, June 20--8:59 AM

I should know better than to send a summary of the day until it is all over.

We were sitting in the bar watching the weather. It seems as though the jet stream is way up north, which should mean great weather from here to New England. But, they say a low-pressure system broke off from the jet stream and came down here to sit on us. We watched the TV as it showed a big squall line coming. Sure enough it hit us big! Lightning was hitting all around us. On two different occasions, it hit the power poles holding up the high voltage lines across the channel with many sparks flying all over. Just like the Fourth of July...quite a show. We were happy we weren’t on WindSong with its 73-foot mast.

Had a fun time last night with a crew dinner. A bachelorette party was at the table next to us. They were on a scavenger hunt and one of the things they needed was a man’s chest hair. Somehow, I got nominated and I’m told the rest of the story was hilarious...

Good night from WindSong

Friday, June 20--10:10 PM

The boat is fixed. We shipped in a pump for the refrigeration only to find out that a couple of wires were loose and the pump is ok.

The head and water system turned out to be the big challenge. The head broke coming into Beaufort and spilled a lot of stuff into the bilge. Fortunately, a dedicated service guy finally got it working and the boat cleaned up.

Heather and Mike are terrific...they went out this afternoon and provisioned the boat. Jack and I worked on navigation while Sam checked weather and fixed stuff.

I wasn’t able to shave offshore so I got a little bit of whiskers growing. I asked Heather whether I looked like one of those cool movie star types and she said, No, you look like a homeless person! Hmmmmmmm....

Lots of good stories swapped tonight and lots of kidding around.

Weather forecast is looking pretty good so we are off at 5 AM tomorrow morning...heading for home...570 miles away...

Saturday, June 21--6:39 PM

The wind shifted to our nose and dropped to 3-5 knots. Boat speed 1-2 knots so I decided to try the engine and see if we could at least do something.

As we have traveled up the coast, we noticed a shudder when the engine was cranked up so we’ve been reluctant to use it. But when we cranked it up now and kept increasing the revs to see if the shudder reappeared, it didn’t. We are totally mystified but happy as we are now making 6 knots boats speed and 8.4 knots over the ground. (We later learned that the shudder was due to the propeller cavitating while motor sailing due to the sailing energy overpowering the motor energy.)

We’re heading for home. Diamond Shoal Light at Cape Hatteras is visible. Yea!

When the wind died, I threw a quarter over the side to get a quarter’s worth of wind. We don’t want a dollar’s worth! Heather and Mike are dancing to Zydeco music on the aft deck while shrimp and sausage jambalaya are cooking down below. Sun’s out and it’s warm...

Sunday, June 22--9:28 AM

Position: 36 29.95 N; 74 23.76 W. This is roughly on the North Carolina/Virginia border on a straight line between Cape Hatteras and Block Island...we’re heading offshore again. Winds: 12-18 knots...Waves: 3-6 feet.

Partly cloudy and chilly...we’re chasing the backside of the low pressure up the east coast, which is giving us nice winds. I’m wearing jeans, fleece and wind breaker and was quite chilly on my 6-9 AM watch. I’ll put foul weather gear on for the next one. Boat speed: 7.5-8.5 knots. Mike says he saw 9 knots.

Last night was a glorious sunset off of Diamond Shoal Light at Cape Hatteras. About 7 PM we saw two small whales go by the stern of the boat...very exciting. We also saw about a half dozen this morning off the starboard bow...150 yards away.

It was a glorious brisk morning and the boat was charging along on a close reach. However, the mechanical systems report was not good. Both alternators and the generator were out so, even though we had triple redundancy, nothing was working and we were dangerously low on our batteries. Considering that we have electric heads and all our navigation systems need 12 volts, this was rather serious. Sam changed the fuel filter on the engine. The engine was dying periodically and I think that will fix it.

Other problems include the loss of the refrigeration system again...all of our food will probably spoil...and the fresh water system is not working. Good grief! (Sam just got the water going. We have a second pump and we switched that on...now if we can only figure out the refrigeration).

In spite of all of these problems, we are having a wonderful time. The stars are brilliant, the camaraderie is great and the sailing (finally) is spectacular. And I sure can tell you one thing...there’s a lot of water out here and very little else!

Oh, I should tell you about my 9-12 watch last night. We had a great big ship coming right at us and he was supposed to give way but didn’t. I turned Winds

Song 45 degrees and he passed behind us less than a mile away. Too close for comfort on the wide-open ocean. Also we occasionally run across very small fishing boats with hardly any lights...nuts!

Well, I only got about 2-1/2 hours sleep last night so I’m off for a nap.

Having made the turn at Hatteras, we can sense that home and family are not too far away...Tuesday?

Sunday, June 22--5:37 PM

Position: 37 13.78 N; 73 55.05 W...a zillion miles off the Chesapeake or the Delmarva peninsula or somewhere. Heading for Block Island. Motor sailing in 6 knots of wind doing 6.3 knots. Flat sea...looks like Long Island Sound. No clouds anywhere. Our best day of sailing so far. Almost all day we have been doing 7.5 to 8.5 knots sailing on a close reach. Just beautiful and WindSong is a very fast boat off the wind. Unfortunately, the wind went light late in the day and so it’s back on the engine.

As the wind was dying, we decided to set the chute to see what it could do. It’s been burning a hole in my pocket and I was dying to see it. We set it and it was very pretty...just like Gale and I thought it would be with its red, while and blue colors. We sailed for a while but the wind was light so we had to bag it. We plan to come roaring into Jamestown on Tuesday on the Chute as the wind swings into the SW. Weather forecast is excellent, although the winds may go light on us from here on in. The pressure water is back on and I took a shower...terrific...all’s right with the world.

Today’s dolphin show was the best ever. Literally dozens of dolphins appeared. They were jumping 6 feet into the air and just playing. They were so thick under the bow I couldn’t imagine how they avoided each other. They are so quick it is just amazing.

Mike and I spent a great afternoon reading Modern Bride cover to cover...a magazine that Heather brought aboard. You can see that we were getting a little bored! We didn’t like many dresses but the models were terrific. Sam is very happy tonight because nothing has broken for three hours!

We’re having cocktail time in the cockpit on this lovely night. Heather just came up with mini quiches for hors d'oeuvres. Since the refrigeration is out, Heather is ruminating on what she can make without killing us. I’m sure she will be successful...

Monday, June 23--8:26 AM

Position: 38 39.3 N; 73 03.8 W or roughly 100 miles offshore from Philadelphia coming up the NJ coast and 170 miles to Jamestown, RI. My 3-6 AM watch ended with 20 knots of breeze and I saw 8.9 knots of boat speed...now it’s 5 knots wind and we’re motor sailing at 5 knots. Sunny skies but chilly...need to wear foul weather gear to stay warm.

This morning was one of the most beautiful I have ever experienced. As dawn approached, the undersides of some clouds were lit up a bright orange color and then the sun began to rise and the orange intensified all over the sky. As I was leaning my chin on my elbow against the cockpit staring dreamily (Sleepily?) at the sunrise, a dolphin jumped clean out of the water right in front of me. The morning dolphin show began with about 6-10 of them roaring around, jumping, etc. And to top it all off, there was a spritzer of a shower behind the boat that created an unbelievable double rainbow that touched the water on both ends.

I wish I could put into words how wonderful it is to be sailing offshore and experiencing things that you can’t get on land. Last night, we saw a pod of small whales just before sunset. That was neat because Heather had missed the previous two sightings.

Dinner was a Pasta primavera with added chicken that Heather managed to invent from the dribs and drabs that we have left. Refrigeration is still out. Sam fixed the alternators by replacing a belt. Heather and I took showers last night that were terrific! Then the pressure went out again.

Our preliminary look at our ETA in Jamestown is tomorrow mid-day depending on the weather gods. It will be great to be back on shore to see our loved ones...it has been a while and we miss you. The sea has offered us much adventure and much joy. For some of us, we will return to our shore lives with an experience never to be forgotten. For Sam and me, we will return to the sea...Sam to do another delivery and me to bring family on board for a trip to Maine and more adventures.

Monday, June 23--evening report, 5 PM

Position: 39 28.0 N; 72 34.1 W or off the New Jersey coast. 111 miles from Block Island and 131 miles from home. Considering we’ve sailed probably a thousand miles this seems like it’s just around the corner.

We’re on the engine on flat glassy seas...no wind...doing 6.5 knots. At this rate, we’ll be at Block Island at about 10 AM. Big decision is to take a few hours off and participate in Block Island Race Week or continue on :). With our pretty spinnaker, we could at least look good.

Weather is very nice...blue skies, no clouds. The problem with sailing is that when the weather is nice, there is no wind and when there is wind, it is stormy! Only golfers are crazier than sailors.

We’ve had a great day...we’ve seen much sea life--a big shark, two turtles, BIG fish or whales jumping...not sure which, dolphins, etc. We saw a sunfish, which is really cool. These things are 3 feet in diameter and just lay on the surface. Sort of like a big, surface flounder. Haven’t seen a ship since 10 AM.

We had a fantastic sail today. About 1 PM a 10-knot southwesterly sprung up so we set the chute. We sailed all afternoon doing 6-7 knots. Then the wind died so it’s back on the iron mainsail.

Last night at cocktail time, we were a little bored so I went into my computer and read about a dozen of my favorite jokes from our email joke ring. Somehow, they were even funnier offshore than they were when I first received them.

As we’ve been sailing, we notice a tremendous haze/smog off to port while it has been very clear off to starboard--we knew we were off the Jersey coast.

Mike has worked his way into a permanent job as Mate aboard WindSong. Heather has recently promoted him from Cabin Boy to Swabbie. Heather is the most creative person I’ve ever met making fantastic meals with the refrigerator out while trimming the chute and keeping our spirits up with her banter. And Jack is a great sailor and electronics guy...a lot of fun to be with.

We know we are getting close to civilization because we have seen four separate groups of balloons out here floating on the water. Lots of birthdays going on onshore.

Heather is making lasagna...going to cook it extra long to make sure we don’t get poisoned...Mike’s steering, Sam’s telling stories, Jack’s ready to go on watch and I’m waiting for dinner so that I can get a catnap before I go on watch at midnight...

Heather says we need to be met with cold beer...lots of it...

So here I sit on our last beautiful night offshore, sitting in the cockpit of WindSong, enjoying a libation with great comrades, awaiting the evening dolphin show and aching to give Gale a hug...

Tuesday, June 24--7:31 AM

Mike stood the 12-3 AM watch with me. We saw the boat was making a strange wake when we realized that the dolphins were back. We wondered how many nights they were with us and we didn’t know it.

We’re getting more ship traffic and seeing the flotsam and jetsam of shore life.

Current position is 20 miles from the SW corner of Block Island and 45 miles from the docks at Conanicut Marine where we will re-water and refuel. That would put us at the dock at about 2:30 this afternoon or a little earlier if we get any wind or a current boost. Can’t wait...

Position is 40 50.2; 71 45.7

No wind

Motoring

Slight morning fog

Clear skies and sunny

Glassy calm

We are desperate for a cold beer and Mike has solved the problem. We found a bag with some holes in it. When towed behind the boat, our beer bag was a success. But a real cold one from a fridge on shore would really make our day!

OUR WELCOME HOME

...as written by my 96-year-old mother upon our arrival...

"We couldn’t wait either...to WELCOME WINDSONG and her fearless crew to her home port in Jamestown. We gathered up all our flags, leis, balloons, various noisemakers and, most important of all...COLD BEER as requested by Heather. Quickly making a bunch of sandwiches to sustain us in our vigil, we dashed out to the Beavertail Lighthouse to scan the horizon for the first sight of WindSong. From a tiny spot she quickly bloomed into the boat of our dreams with her beautiful spinnaker full of wind and the crew waving and hollering as we were!

Soon, everyone on shore was screaming and jumping up and down! We had made friends with a delightful couple in a Winnebago and they volunteered the use of their PA system giving us a bigger range for our tumultuous welcome!!! Jumping in our cars, we dashed for Channel Bells (our old, shingle-style home has a name as many of the area’s summer cottages have) to repeat our spontaneous welcome.

The kids scrambled for the best view, which, obviously, was the roof of Channel Bells while Gale made a beeline for a close up view on the shore to take pictures. With her spinnaker still billowing, WindSong majestically sailed by on course to touch land at the Conanicut Marina to refuel prior to docking at the Jamestown Boat Yard where our welcome committee was ready with Champagne and hugs and kisses for our intrepid heroes. Then the partying began in earnest accompanied by stories of the sea and the trials and tribulations of those of us who had only made the trip vicariously. We drank our celebratory wine and sprinkled a few drops on the