Jazz’s Long Arrival To the Caribbean Sailing Dream

Image: The board I started when I still thought 1 week 1 island vs. the present board.

After years of dreams, planning, sacrificing and saving and annoying the shit out of anyone who would listen to me from the age of 17 on, I got MY SAILBOAT….and then the set up was really hard. The two months I had planned to set up and provision turned into 7 months of 12 hour days, 7 days a week. Where I had wanted to make sure I knew and was a part of every system set up and install, I gave up. After falling months behind, and knowing that every month meant one month less in the Caribbean, Andrew and I split work on who could do it faster. This resulted in me only being halfway up to speed on some of our electronics and engine and other stereotypical male tasks, as many other sailing males were quite happy to assist Andrew. This was far from the only huge block of entry into the sailing world for me from the males in this hobby/lifestyle. I had hoped the main issue for entrance into the community when I was younger and desperate to sail was my lack of funds and therefore of a boat. Not the case. All of my sailing experience was considered invalid for our insurance. Even with the certified ASA courses, racing in high school on the Med, sailing in college, various regattas etc.  Basically I finally got told I was a girl and younger than the typical retiree sailor so buck up and just let some expensive teacher charge us what ended up being a lot, with the basic blackmail that he would not sign us off to sail on our own. I eventually called and pretty much cried to the insurance broker, telling him I would pay that much and more not to have to deal with that sexist asshole who made me hate sailing, myself and my dreams. He went up the chain in the company and got the sign off. This was our first two months on board Villa. Oh, and 2 months cold turkey on cigarettes. But no worries, as soon as we get to Sint Maarten, the easy part, the fun part, the Caribbean sailing dream will begin!

One week in drydock turned to one month, and then the planned one month for replacement windows, provisioning and watermaker install turned into three, and finally we arrived in the Bahamas quite late in the season, April 1st. The later the arrival, the worse the wind direction for comfortable sailing. Having a catamaran makes all sailing in this area, and all the way down to Anguilla, hard as we do not sail toward the wind well. Actually very poorly. So the gentle hobby horse was more of a six foot up and down pounding of the front of the boat while we hung on for dear life, trying to get south before hurricane season while still project-ing and enjoying every moment possible. We had some great days. We had to miss a lot of places. We got to the first well known, safe hiding spot for Hurricane season and had a decision to make. Get all the way to the other side of the hurricane zone, meaning the whole Caribbean and only get one month to enjoy it, or wait another 6 months to get started. It was a hard decision. But there are always new improvements one can make on a boat and I knew we could work hard and make those months valuable…and maybe have some rest (ha!).  And I really didn’t want to have to rush my dream sailing trip.  So we decided to stay in Luperon DR and work hard on our boat.  And no worries: as soon as we get to Sint Maarten, the easy part, the fun part, the Caribbean sailing dream will begin!

With a project schedule that seemed obtainable, an apartment, a car, and a nearby very safe mooring, we began our hurricane work season. Projects like sewing a spinnaker, re-epoxying the water tanks, refurbishing and covering every cushion in the boat. Well, things took time and then working in a developing country in a place with few resources made everything take longer. Getting ill and dealing with apartment and landlord issues took even more time. We took many adventures in the DR, but I didn’t leave very rested and still had a whole cabin full of unfinished projects. But no worries: as soon as we get to Sint Maarten, the easy part, the fun part, the Caribbean sailing dream will begin!

Our first post-DR move was still into the wind, but as Puerto Rico is so big, we got to hug the coastline and stop for many fun trips while traveling with our boat buddies from the DR.  Having already spent time in PR and hoping to extend the amount of time for the Caribbean sailing dream we pushed on through on to the Virgin Islands the British and US.  Hoping to get healthy and slim down a bit before getting to the Caribbean sailing dream, we took this month dry. Unfortunately, the main thing to do in a lot of these ‘virginal’ islands is to visit famous bars. In retrospect it sort of sucks missing so many cool bars, now that COVID has come and there are no more bars. We made the last passage into the wind to arrive at our first Leeward island, Anguilla, and broke the plastic piece holding one of our backstays together on route.  Sucks, but still, Sint Maarten with a great rigger and the beginning of the easy, fun sailing was the next island. And we should arrive there and finish with our Dry January while there! This was the best week of the trip, the excitement of being almost there! Great beaches! Fun drives! Fun dives! Still scary to not be able to sail, and we needed to get rigging checked. But no worries: as soon as we get to Sint Maarten, the easy part, the fun part, the Caribbean sailing dream will begin!

WE’VE ARRIVED IN SINT MAARTEN!  Oddly the couple we’d spoken to for several days and dives and had never mentioned once going south (they actually said they were headed north) radioed us on the way, joking about how much faster their great big cat was under sail then our little guy under motor. Strange but maybe we would have friends in Sint Maarten. At check-in, we ran into them and asked where they are anchored so we could meet up. They said “we are at the FKG [the riggers we had been talking about for days] dock, there was only one space and better to ask for forgiveness than permission, right?” The next day FKG said it would be a week as another boat was now ahead of us. We had been talking to them since the day our rigging broke and they’d never mentioned getting re-rigged. This seems like a petty thing to even mention, but it just seemed like one more example in a consistent string of negative interactions with other yachters. Oh well, we only planned to spend a little more than a week in Sint Maarten but we had projects we could do. We started some big projects, got into them and then a week or so later we got re-rigged. It took them 24 hours as expected, and then the next day my little shoulder pain turned demobilizing. Two MRIs and another sexist male doc who would not help until I saw a neurologist, and I’m bedridden, medicated and out of commission virtually completely for weeks and am still in pain and unable to do things like start our dinghy.  

The one-country-one-week plan for the Caribbean Sailing Adventure begins to crumble.  Every week that goes by is a shorter stop for all islands or a choice to skip one.  I tried to stay useful and help by sewing when the pain pills were working and otherwise spent my time traveling to the PTs office, every day and then every other day then 3 times a week, and lying on my back.  Our friends we left behind so we could do our country a week plan caught up with us and life was better with them. When they left we decided to join. I should say mostly Andrew, I could not do anything but lay down with my head and neck immobilized while we sailed to meet them in St. Barts for a couple days and then on to St. Kitts.  

At this point I could walk about a half mile before the pain stopped me from the jolting impacts of my steps. I couldn’t convince Andrew to take a crappy window to get to Antigua when a better one was supposed to open in a few days. Not with my neck in such bad shape, and the 24 hour sail would be bouncy as hell. Still, I felt like I really didn’t have much of a say in anything anymore: it’s not like I can sail the boat. I can’t even really help with anchoring. I just lie there. But before that good sailing window Antigua closed its boarders. The world comes to a halt. Our boat and maybe twenty others that first week are now trapped in St Kitts. There are only three calm anchorages all on the inaccessible side of the island, which won’t matter for weeks. I heal, still in pain but up to almost full functionality. I am still unable to move, now though because of the pandemic. St. Kitts was very strict, and we had full lockdown and 24 hour curfew starting March 31. There were two shopping days allowed a week, one day for each half of the island. This went on until April 27. Then they allowed personal exercise and walks, but with a quarantine from 6am-7pm and essential businesses only. All weekends were full 24 hour lockdown until after we left. By the last weeks of May food for delivery and takeout was allowed and more and more businesses were opened but with a super rolly harbor near the town and super expensive taxis from the good harbour’s marina we mostly just stayed on our boat and went swimming or on solo walks. We finally left St Kitts for Antigua, which opened June first.

I have healed (mostly), the world has not. Our plans, like so many others, have changed. We are lucky to be in such a safe place, in our home that we had provisioned very heavily for the Pacific and we make our own power and water. We use very little fuel and will be fine as long as the hurricanes don’t hit us. 

Anyway, the point of this is mostly, sorry I have been bad about staying in contact. It doesn’t mean I don’t love you, just that at many times I was either crazy busy, in pain or depressed. Welcome to my Caribbean Sailing Dream! I’m excited to get started!

One comment

  1. Jazz, through all the trials and, with this missive, the disappointments, we have followed you with interest and some envy. I feel it is not the achievement of the dream, but the pursuit that brings the greatest joy. It is not the destination, it is the journey that is to be savored. And it is not the unfairness you have encountered, but your powering through that matters. You have so much to be proud of, and every bit of this experience has been wonderful on some level. We wish you and Andrew continued success and hope that your powering though the addition of CV-19 challenges goes well for both of you. We hope to see you both again at some point, either on your journey or on ours. Love, Many hugs, and best wishes. Fair winds and following seas. Jon and Pat.

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