If you’ve been reading our blog since the early days, you’ll remember our chronicle of traversing the Thorny Path to Windward – where sailors fight the headwinds and seas to get from the Bahamas to the top of Eastern Caribbean, around Anguilla or St. Martin. The traditional path is Bahamas-Turks and Caicos-Dominican Republic-Puerto Rico-US Virgin Islands-British Virgin Islands-St. Martin. Taking the Thorny Path requires a good boat, lots of stamina, and time/patience to wait for the right weather conditions.
So after our trip home (and my wisdom-teeth-removal-surgery, which becomes relevant below) we returned to Gratitude and started plotting our course through the southern Bahamas: Emerald Bay to Rum Cay, Rum Cay to Atwood Harbour, Atwood to Mayaguana, then Mayaguana to Providenciales in the Turks and Caicos.
We’d made this journey before. What could go wrong? (Famous last words, haha.)
Challenge #1
Our first challenge arose somewhere between Rum Cay and Atwood Harbour. We had decent weather and speed, but about halfway there I began to look ahead on our chart plotter (the GPS system for our boat) so that I could create a waypoint for entering Atwood. That’s when I noticed that ALL the detail around the southern cays had DISAPPEARED. We had big vague shapes for land masses… but no depths, no reefs, no rocks, and no underwater hazards. The critical data we needed was just unavailable.
What the heck?!?!?


This was a situation we’d discussed, with each other and with other sailors. Old-school navigators preach PAPER CHARTS. We’ve never been convinced that we need paper for every destination, but we definitely agreed that you always need a backup plan. Our main chart plotter has been very reliable, but as we all know, “surprises happen” at sea. If it can break, at some point it will. And without charts, your vessel is at extreme risk.
Project-manager-and-risk-mitigator Andy had procured a mobile app with a set of electronic charts on his iPad a while back, so now was the time to call them up. (For our fellow sailors, the app is iNavX, and it worked beautifully as a backup solution.) Once we spotted the entrance to Atwood Harbor, when we’d need the chart detail for narrower and shallower waters, I held the iPad while Andy helmed Gratitude. That way I could study the chart and he could watch the water. It got us safely through the reef surrounding the harbor and to an appropriate spot to anchor.
Once we anchored, Andy began troubleshooting the issue with our chartplotter. The short answer was that last summer we’d had to send our plotter off for repairs. Part of that process included installation of a new map chip, and unbeknownst to us it did not cover the Caribbean like our old chip did, so at some point in journey we were too far south to have the detail we needed. We ordered a new map chip and arranged for it to be delivered to us, but we wouldn’t have it until we reached Puerto Rico. In the meantime, our backup charting system would have to suffice.
Challenge #2
We’d both been looking forward to doing some diving in T&C. The water there is incredible, and the reefs are healthy, teeming with sea life. However, my dental surgical recovery really began to cramp our style. I continued to have pain in my jaw, and then somewhere in the southern Bahamas I realized two things: one, there was some kind of hole or connection between my upper tooth cavity and my sinuses; and two, that area was infected. (I learned that this is called a ”sinus communication.” I’ll spare you the gory details.)
So, when we finally arrived in T&C, there was no diving. Instead, we sought out a rental car and a local dentist. He was able to prescribe me some antibiotics, and I got in touch with my oral surgeon back home, who gave me a protocol to follow.
Being in chronic pain takes a mental toll. Thankfully this situation is rare for both of us, but it does give me great sympathy for those who struggle with it regularly. The pain was manageable with the right medicines, but it was just enough that I couldn’t work out or do anything like hike or take long walks. Because my issue was dental, I couldn’t enjoy my meals – I ate just enough for sustenance, but took no pleasure in dining. And of course swimming, snorkeling, and diving were out of the question, with a sinus infection. Suffice it to say that all these factors took a LOT of the fun out of the cruising life.

Making New Cruising Buddies
The next part of our trip required a 72-hour passage to the eastern coast of Puerto Rico. We had decided to skip the stops in the Dominican Republic, so that we could avoid the weeks of waiting for good weather. Instead, we opted for the longer PR passage, which also required favorable weather, but we’d only have to wait for one window instead of four to six of them.
Our decision was validated once we crossed over from Providenciales, in the northern Turks, to Cockburn Harbour, in South Caicos. I was still dealing with dental pain, but we had a nice weather window shaping up for a favorable passage soon. Should I fly home and delay our passage? Or should we press on, get the boat to PR, and possibly fly home from there, if still necessary?
In the midst of the debate, we heard a dinghy engine getting closer and closer to our aft cockpit. We went outside to meet new friends, Chris and Laura from Zephyr, a Lagoon 45 catamaran. They, too, were planning a passage to Puerto Rico, and were linked up with two other sailboats with similar plans. Did we want to join them and make the passage together?
Buddy-boating has a lot of advantages. You have other boats in radio range if anything goes wrong; you can compare notes on wind and wave conditions; you can use the VHF radio to alert each other to unexpected hazards along your path, like fish traps or cargo vessels. On a passage like this one, Andy and I trade off duties at the helm every 3 hours, sleeping and eating in our off hours. With buddy boats, we’d have an extra layer of security and companionship not available otherwise.
So that’s how we set off for Puerto Rico, in the company of Zephyr as well as Passat II, with Steve and Vicki and their two children. They also had the ability to receive updated weather reports via their Garmin Inreach devices, so we were especially grateful to have current weather access through them.
Our weather window was indeed favorable for most of our trip. It was a little bouncy on Saturday morning’s departure, but by late afternoon the waves settled down and we were quite comfortable. Sunday was uneventful. On Monday we finally got close enough to Puerto Rico to be in cell range, and that was a big win! We were back in the land of unlimited cell phone and WiFi usage (without roaming charges).
Challenge #3
HOWEVER! On Monday night our luck started deteriorating. In the southern Bahamas passages we’d lost a jib sheet (one of the lines that secures and adjusts our forward sail). Then one of the mainsail’s reefing lines, which we use to reduce the area of the sail in high winds, got hopelessly jammed and thus out-of-commission. Which meant that we could raise it only part of the way to the top. Then in the Turks and Caicos a block broke on our boom. The boom is the horizontal beam that we adjust to move our mainsail back and forth, depending on the wind directions. The broken block caused the boom to start swinging wildly, making it impossible to pull the sail to the port side. We rigged it back together with some spare line so that we could keep the mainsail up, but we knew we’d need a repair in PR.
If all that wasn’t enough, on Monday night, several MORE things went wrong all at once, and of course it happened in the dark and when the seas had begun to get much rougher. I was on watch just before midnight, talking on the phone to our daughter Anne, when I heard a loud banging sound. I hung up quickly and left the helm to take a look. It was dark, but my best guess was that a batten had worked its way out of our mainsail and was hanging loose against the mast. (Battens are long fiberglass rods that act as ”ribs” to give the sail stability.) Dang! I ran below to wake Andy, because I knew better than to climb up on a wet deck on passage when no one else is awake and on watch. And when I returned to the helm, the banging had stopped.
Once Andy had joined me above deck, we determined that the batten had come out and been swept overboard. Then we realized that our halyard line had gotten jammed, which meant we had to figure out how to unjam it so that we could lower the mainsail. All of this in the dark, after 48+ hours of sleep-deprivation, rough seas, and dental pain.
What can I say? We’re human beings. These conditions did not bring out the best in us. There might have been some yelling at each other. I might have stomped off to bed and left Andy to figure out the halyard solution on his helm watch. We’re not proud of moments like these, but honestly, they do happen occasionally. If you’re going to go off and have adventures, you’re going to get pushed past your limits every once in a while.
When I awoke again at 3 a.m., Andy had indeed figured out a solution for the jammed halyard, and we worked together to implement it and get the mainsail safely down. And about 4 hours later we finally turned Gratitude out of the headwinds and southward, along the eastern coast of Puerto Rico, following our backup iPad charts. We anchored outside of Fajardo and I collapsed into my first of several “recovery naps.”

Time with Friends – The Silver Lining
The payoff from all these challenges was supposed to be a week of hiking, snorkeling, swimming, and exploring Puerto Rico with our friends Bill and Beth Yates. Alas, my dental pain continued, and all the sail repairs we needed meant we could not sail to Culebra with them as we had hoped. So we practiced flexibility and made new plans. It was still wonderful to have friends aboard, and they were very understanding of my limitations.










and took a short hike along a beach path.
After Bill and Beth returned home, we had one more important trip to make: COSTCO! Provisioning at Costco is a must when you brave the Thorny Path. USDA beef, well-priced wine, and of course the lunch counter are not to be missed.


One last shout-out to Puerto Rico goes to the Yacht Club marina at Palmas del Mar. It was almost IMPOSSIBLE to find a slip for our poor battered Gratitude, but Glenda at PdM came through for us. Not only did she find us a dock with power and water, she also put us in touch with a rigger named Quino who was able to repair our broken blocks and get us new lines and sheets. He also delivered the sad news that we would need a new mainsail, but that’s a story for a future entry.
Great read!!! Miss yall and the adventures!! Hope to see you soon.
Glad to hear of the adventures! Tell Andy I said howdy!
We have some great memories of the week, despite the “challenges”. Thanks again for welcoming us when you were feeling so poorly.
Oh, Beth, I hope we get a do-over maybe next year. I’d like to have y’all visit again when I can do all the fun things! ❤️