Home Leeward Islands More Upwind Sailing in the Caribbean

More Upwind Sailing in the Caribbean

written by Terysa March 6, 2016

This Is Getting Tedious!

We really thought that sailing in the Caribbean would be easy. But we’ve had more upwind sailing over the past few months than we ever had in Europe! And, quite frankly, we’re a little sick of it.

We probably would have been quite happy whiling away another week or more in Les Saintes, it was so perfect, but all good things must come to an end and we had Guadeloupe to explore.

We made our way to Deshaies which is apparently where Death in Paradise is filmed. We spent many cold winter evenings watching this slightly lame detective show, mainly so we could fantasise about one day being in the Caribbean ourselves. However, when we arrived in Deshaies, it certainly didn’t resemble the island paradise depicted on the screen.

The view from the boat was very pretty- when it finally stopped raining!

The view from the boat was very pretty- when it finally stopped raining!


Deshaies is a little bit dilapidated and run down, but it’s got it’s positives: lots of bars and restaurants hanging over the water and it’s another french island which is a big plus already. However, we just weren’t feeling it. There weren’t many people around and there wasn’t a vibrant atmosphere despite the anchorage being full and cruise ships in the harbour.

Unfortunately the weather wasn’t brilliant- it was often cloudy and grey and we spent one long, boring day stuck on the boat because it was bucketing down all day long. At least we ended the day with a lovely clean boat again!

At least we got a lovely rainbow out of it!



What A Lovely Tree

We did make an effort to go and explore. We spent a pleasant morning in the botanic gardens up a nearby hill, which was steeper than it looked. We walked there and were absolutely drenched in sweat by the time we arrived. We also baulked at the €15 entry, but there was no way we were leaving after going to all the effort of getting here, so we paid up and spent a couple of hours wandering around and admiring the gardens. I’m not much of a garden person- I can’t even keep our basil plant alive- but it was very peaceful and beautiful being amongst so many colourful flowers and plants. We finished off the morning with an iced tea and some kind of local snack which was like fried pita bread (except way yummier) stuffed with sausages, ham and salad and enjoyed the view back to the harbour. We could just make out our little boat, which is always a reassuring sight. It hadn’t floated away yet!

Not a bad view! Our boat's down there somewhere...

Not a bad view! Our boat’s down there somewhere…

Botanic Garden

Botanic Garden

Ooh, pretty tree! Too bad that little kid photobombed my pic!

Ooh, pretty tree! Too bad that little kid photobombed my pic!

There was a beach just to the north of Deshaies that we wanted to check out, but there was no point in trekking down there when it was raining, so we gave it a miss- and, quite frankly, we’ve seen plenty of gorgeous beaches while we’ve been sailing the Caribbean this year. In an effort to find something positive about the anchorage, we jumped into the water for a snorkel by the rocks, but the visibility was really poor so abandoned that almost immediately.

Get Me Outta Here

It was time to go, it seemed. The forecast wasn’t particularly amazing, but we’d already lingered a day longer than planned due to strong north-easterly winds and rain, so we were keen to head off. Always a bad reason to leave a port! You’d think we would have learned by now, but apparently not. We woke up to wind howling through the anchorage, but our guide book said that Deshaies acts like a wind scoop and you often get very windy conditions in the anchorage which are far worse than what is actually going on outside. So we brought up the anchor and got the heck out of there.

It wasn’t the best decision we ever made, and we got a 6 hour kicking for it. There’s a saying, which is so true: you either get a comfortable sail or a fast sail. Well, we got a very fast sail and it was one of our least comfortable this season. The seas were lumpy and we had 20 knots in front of the beam for the whole journey. So much for the beam reach we’d been hoping for. I went downstairs for a lie down, but my stomach rebelled so back up to the cockpit I went. A couple of heavy downpours temporarily washed the salt off the boat, and Nick huddled under the sprayhood while I once again braved going downstairs while the rain lasted, coming back up as soon as it stopped. This is not what I imagined sailing in the Caribbean to be like!

I hardly ever feel sick when sailing, but today we were both looking a little green. I just stared at the miles ticking down, waiting for it all to be over. We hadn’t made anything to eat (another mistake- one day we’ll learn!) so made do with a stale baguette and a jar of peanut butter. No ham and salad sandwiches today!


We could see Antigua from about 20 miles out and on closer approach the difference between Guadeloupe and the islands south of it, and the landscape and topography in front of us became clear. Antigua is much lower and drier than any island we’ve visited so far, covered in low scrub rather than the lush greenery of most of the islands to the south. Les Saintes were similar, but Guadeloupe was mountainous and forested. It made for a pleasant change.

We motored into Falmouth Harbour, relieved to be out of the wind at last. We couldn’t believe how much room there was to anchor and felt very indecisive about exactly where to drop our hook- usually it’s just a matter of squeezing ourselves into whatever small space is available! So we went around in circles a couple of times before settling on a spot right in the middle of the harbour. The anchor held immediately- oh, happy days- and we could finally sit back and turn our attention to admiring the superyachts looming nearby. We were finally in Antigua, where we will remain until the end of the month.

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