I hit a (relatively) low point in our sailing journey not long ago, and it made me thoughtful about what we share here on this blog, and how we share it. As a glass-half-full kind of gal, I can definitely err on the side of just presenting the fun and exciting aspects of our sailing life. The “curated view” of cruising, only highlights, Insta-style.


But we won’t be living this way forever, and I want our account of this season to be balanced, truly helpful to anyone who comes after us or is even *thinking* of doing this. So while this post is going to be full of beautiful photos and good memories from our return to Antigua and cruising in Guadeloupe, I’m going to include some of our challenges.
When we arrived back in Antigua from our trip home, Andy was eager to get off the dock and out to an anchorage. I was eager to get some provisioning done and check out the weather for our journey south. Truthfully, my heart was still at home, and I was just not quite ready to be back on the boat. So we compromised and stayed at the dock on Sunday, doing our provisioning and planning. We decided we’d check out of the marina and the country on Monday morning, then move a couple of hours south to anchor in English Harbour and stage our departure for Guadeloupe early on Tuesday morning.
However, Antigua’s Customs and Immigrations Office threw a wrench into our plans. After a last-minute grocery run on Monday, we created an online Departures document and brought our boat papers to Customs. We were prepared for the bureaucracy – the British islands love their paperwork and their labyrinthine processes. We were NOT prepared, however, for the Negative Nancy (no, I will not call her a Karen, for obvious reasons!!) we encountered there.
A cruiser’s life is dependent on maintaining a positive relationship with government officials. These are the people with the power to approve or deny your entry into their island. Their rules may seem petty at times, but we do recognize that they are representing their citizens and government, and they deserve our respect.
Negative Nancy, however, was a fine example of petty bureaucracy on a bad day. Things began badly when I tried to log in to the customs computer terminal and kept getting denied. Turns out I had registered our departure on the wrong website. (Note to fellow cruisers: eseaclear.com is NOT THE SAME as sailclear.com!) I knew that – but I got it wrong anyway.
That paled, however, in comparison to my next major infraction. That’s right – I CORRECTED A CUSTOMS OFFICER. Gosh, I cannot tell you how bad a look that is. It was just a momentary lapse in remembering who has all the power here, but still. Here’s a small sample of the interaction:
Negative Nancy: “When are you leaving?”
Karen: “At 5 a.m. tomorrow.”
NN: “You’re here too early. Come back at 2:00.”
Karen: “No, we read that we have 24 hours to leave after we clear out.”
NN: “Are you ASKING ME OR TELLING ME?”
Things went downhill from there. Andy was nearby listening to all of this, and one thing he cannot abide is someone dressing down his wife. (He has my back.) Let’s just say that his comments threw gasoline on the situation, and Negative Nancy launched into an epic lecture accusing us of lying about our departure, or trying to cheat the system, and putting ourselves at risk of having the Antigua Coast Guard hunt us down and “escort” us out of the country.
I don’t know about you, but being called a liar and a scofflaw (when we were there at the Customs Office with papers and fees in hand) just did not sit very well with us. Andy managed to bow out of the conversation, and I managed to hold my tongue and convince Ms. Negativity to go ahead and stamp our papers and allow us to leave her country legally and without a Coast Guard escort. As a consequence, however, we must leave within the hour and would NOT be allowed to overnight in English Harbour as we’d hoped.
Which is why we departed Jolly Harbour at noon on a Monday and immediately commenced sailing to Guadeloupe, where we would arrive to anchor after dark. It was not ideal, but after being yelled at, vilified, and generally maligned by Negative Nancy, I was willing to take my chances with an after-hours arrival.
The funny thing that happened on that trip, however, was like a little reminder that God sees me, knows my heart, and loves me. I definitely stewed and cried about my negative encounter with Nancy, but I know, in such situations, that counting my blessings (practicing gratitude) is usually my quickest path back to equilibrium. I was doing that when Andy called to me from the helm: “Hey, I think I see some dolphins. Come look!”
A dolphin sighting is always special, but this was something new – something we’ve never seen out in the wild. What Andy had spotted was two WHALES. Whales! Maybe sperm whales?
The video I took isn’t great. But it will still give you the idea:
We arrived in Deshaies, the northernmost port in Guadeloupe, around 9 p.m. It is a nice harbor, but a little crowded sometimes, so we dropped our anchor pretty far out from town. There were several boats around us and we were still in the harbor, but not in the nice shallow part. That was a consequence of running afoul of Nancy, and one we almost paid dearly for a few days later!
But before I get to that, I’ll share a couple of photos of our visit to the Botanical Gardens. You have to walk almost a mile uphill to get there, and it is well worth the effort!




Diving, and Drama!
We arrived in Deshaies on a Monday, and we scheduled a dive for Saturday. It was pretty nice. We didn’t see anything new underwater, but that afternoon we were in for a huge shock. We passed by Gratitude on our way back to shore, and all looked well. We retrieved our gear, loaded the dinghy, and then walked down the street for some lunch. We were just finishing our meal when one of our dive guides approached our table to tell us that our anchor had dragged and our sailboat was heading out TO SEA!
Obviously, this is the kind of news that jolts you into action. We sprang up, paid our bill, and hastened back to the dinghy. Once we got back out into the harbor, we could see Gratitude afloat offshore. Noooo! Fortunately for us, some fellow boaters realized what was happening and dinghied out to our boat to try and help. When we arrived, they had gotten the anchor mostly in and were working on starting the engines to halt our western drift. We finished what they had started, then we motored back into the harbor and got our new friends to help us tie up to a mooring ball.
{Andy here – we tend to obsess over lessons learned, and it seems that we never stop learning. In this case, we did everything right up to a point. We paid out the proper anchor rode, we set and tested the anchor thoroughly, and we monitored it carefully for days, but… there were three factors that worked against us here. First of all, we were anchored on a shelf that dropped off very steeply away from shore. Second, we were away from the ship. Third, while we were away, we had 35 knot winds blow in the direction of that drop. The silver lining was that we were blown away from any obstacles or imminent dangers. Still, after nearly five years of living aboard, this was a first, and it was highly unsettling. Three boats dragged anchor that day. If we had been aboard, it would have been no big deal, but it was almost a very big deal.}
Obviously we didn’t stop to take any photos of this (somewhat) traumatic event… but I do have a few photos from our dive to share.






The anchor drama caused us to put the brakes on our subsequent plans for Deshaies – after that experience, neither of us felt comfortable leaving the boat all day for the hiking and sightseeing we had intended to do. So we hung out a couple more days and then continued south.
Pigeon Island and Iles des Saintes
I gotta admit, the adrenaline rush of our close anchoring call definitely diminished my enjoyment of our cruising week. However, the Jacques Cousteau Marine Park off of Pigeon Island seemed tailor-made to restore our sense of adventure. It is easy to dinghy out to a mooring in the park and go diving on your own. And what excellent diving it is…





From Pigeon Island it was a day sail down to Iles des Saintes, one of our very favorite spots in all the Caribbean. It’s a little bit of European pleasures in a tropical setting – French food, wine, ice cream, and shopping, as well as more diving!



Our next stop on this journey was Dominica, which we’ll write about in our next post. Meanwhile, here’s one more taste of sailing reality: Generator maintenance!


Andy took the time in Guadeloupe to replace the impeller on our generator. This little part of the cooling system wears out every so often, so keeping it intact and functional is critical.