Sailing The Canary Islands

Easy Crossings, Tricky Anchorages

One thing we learned pretty quickly in the Canary Islands: anchoring can be hard, but sailing is easy.
At least it’s easy if you’re willing to motor out of the wind shadow first… and then accept that the “fun, fast sail” part might come with gusts up to 40 knots.

I mean, we theoretically knew that. Everyone talks about the acceleration zones between the islands. Trade winds funnel through, the sea state builds, and suddenly your calm crossing turns into a very honest reminder that you’re sailing in the Atlantic now.

Still — we kept getting surprised by just how much wind shows up at certain points. Almost every single time.

La Gomera: Our Favorite Island in the Canaries

In this episode we leave Tenerife and head for La Gomera — and it didn’t take long for La Gomera to become my favorite island in the Canaries.

The crossing gave us exactly what the Canaries are famous for: a fast ride through one of those acceleration zones, and then — as soon as you tuck in behind the island — that magical switch. Wind drops, the water changes, and suddenly it feels like you’ve entered a different world.

We dropped anchor near Playa de Santiago and got our first real glimpse of what makes this island special. Not just the landscape — but the feeling. La Gomera has a calmness to it. A rugged, quiet beauty. Less “tourist machine,” more “real place.”

Playa de Santiago Anchorage and a Hidden Bay

And then we found it: a hidden bay that genuinely took our breath away.

Towering cliffs. Lava-carved caves. A canyon leading inland to views that feel almost unreal. The kind of place where you sit in the cockpit, look around, and automatically speak quieter — as if the bay could hear you.

Somewhere along the way we met a couple living off-grid in an old fishing bay, which was one of those encounters that stick with you. Not because it was dramatic, but because it was a simple reminder: there are many ways to build a meaningful life close to nature… and not all of them require a calendar full of appointments.

We stayed a few days, soaked it in, and when we finally left, I already knew I’d be back.

And I was. Later in the year, I returned on my own and dropped the anchor in Santiago again — this time for a couple of weeks. Because some places don’t just impress you once. They pull you back.