The Siren Song of the Azores Islands

It’s been two years since we spent time in the Azores and the call to return is getting stronger by the day. This cluster of nine islands smack dab in the middle of the Atlantic Ocean captured my heart and soul — and I’m always quick to recommend it to clients who even hint that beautiful landscapes will factor into their next destination choice.

The Azores have remained relatively unknown to mainstream global tourists, which is, for me, part of the appeal. It’s almost as if the Portuguese have been gatekeeping these magical islands since the 15th century, when navigators first stumbled onto these volcanic outposts and decided, wisely, to stay. And in some ways they have. The Azores government, having watched overtourism hollow out places like Iceland and Venice, implemented strict barriers to prevent the same fate on the islands. The territory maintains a regional cap on the total number of hotel beds allowed to exist across all nine islands — which explains why we often found ourselves alone on trails that felt like paradise.

São Miguel — Where it All Begins

We flew into São Miguel, the largest and most populous of the nine islands, and knew within the first hours that we were in for something extraordinary. Ponta Delgada, the capital, is a genuinely lovely seaside city — all dark volcanic stone, whitewashed churches, and instant gratification for the overnight flight.

Despite being somewhat jet-lagged, we arrived in the morning, had a quick bite, and headed straight to our first waterfall hike. The effort required was minimal. The payoff was staggering — the most beautiful waterfall I’d ever seen. We had it entirely to ourselves until someone arrived just in time to take our picture.

That evening we checked into the Terra Nostra Garden Hotel — worth planning an entire trip around. The hotel sits within magnificent botanical gardens that bustle with visitors during the day, but close to the public by late afternoon, becoming the exclusive domain of hotel guests until mid-morning.

Which is how we found ourselves at 3:00 in the morning — jet-lag, bless it — pulling on our swimsuits and slipping into natural hot springs in the middle of a sleeping garden, completely alone. We strolled the paths afterward in the dark, steam rising around us, not another soul in sight.

The hiking on São Miguel is, simply put, some of the best I’ve ever experienced — and if you know me, you know I hike a lot. From the rim of ancient calderas (photograph required, words insufficient) to seaside trails that wind in and out of the most charming small towns, every step rewards you. We passed what I am convinced were the happiest cows on earth — smiling, if cows can smile, at their extraordinary good fortune to have the most beautiful ocean views and greenest pastures imaginable.

Pico — Vines, Ladders, and Things That Cackle in the Night

Pico is dominated by its volcano — the highest peak in Portugal — and by the extraordinary UNESCO-designated vineyards that cover the island’s coastline in a mosaic of black lava rock walls. We hiked through those vineyards all the way down to the sea, where the trail ended at a ladder bolted into the rock face. We climbed down into the Atlantic. It was exactly as wonderful as it sounds.

But the most unforgettable moment on Pico happened long after dark.

We were staying at a wellness retreat on the ocean when we heard a sound unlike anything either of us had ever heard. We opened the window to thousands of flying somethings streaming past in the darkness, making a noise that can only be described as a kind of frantic, otherworldly cackling. This went on for half an hour before gradually fading.

The next morning we asked the hotel staff what on earth we had witnessed. She told us matter-of-factly: cagarro. Cory’s shearwaters. These remarkable seabirds spend their entire days foraging far out at sea and return to their rocky cliff nests after sunset — but they’re not particularly good at locating their nests, or their mates, in the dark. The cackling, she explained, is them reconnecting. With their homes. With each other.

I haven’t stopped thinking about it since.

Flores — Where the Waterfalls Have Waterfalls

Widely considered one of the most beautiful islands in the archipelago — and the furthest from São Miguel — Flores requires a little more intention to get to. It is absolutely worth the flight. If São Miguel’s waterfall took my breath away, Flores stopped it entirely. This island doesn’t have waterfalls — it has walls of them. Cascading from cliffs in every direction, green beyond anything I can adequately describe. One of the most beautiful places I have ever been. 

This island doesn’t have waterfalls — it has walls of them. Cascading from cliffs in every direction, green beyond anything I can adequately describe, Flores feels like a place that shouldn’t exist outside of a dream. It is, without question, one of the most beautiful places I have ever been.

Faial — The Blue Island

Faial earns its nickname — Ilha Azul, the Blue Island — from the vast hydrangea fields that blanket the island every summer in impossible shades of blue and purple. The marina at Horta is legendary among transatlantic sailors, its walls covered in decades of painted tributes from crews who made port here on their way across the ocean. There’s something deeply moving about standing among all those names and dates and flags.

The Islands We Haven’t Visited Yet

The Azores archipelago includes five islands we haven’t yet explored — Terceira, Graciosa, São Jorge, Santa Maria, and Corvo — each with its own distinct personality. Terceira is known for its UNESCO-listed capital, Angra do Heroísmo, and its rich history as a stopping point for ships crossing the Atlantic. São Jorge is dramatic and narrow, known for its fajãs — flat coastal shelves formed by ancient lava flows — and its distinctive cured cheese. Graciosa is the flattest and most pastoral of the islands, gentle and quiet. Santa Maria is the sunniest, with sandy beaches unusual for the Azores. And Corvo, the smallest island in the archipelago, is home to fewer than 400 people and one of the most pristine calderas in the world.

I’ll get to all of them. The siren song won’t let me do otherwise.

A Few Things Worth Knowing Before You Go

The Islands are closer than you might think — Because the Azores are a Portuguese archipelago, many travelers assume Lisbon is the natural jumping-off point — and it absolutely can be. But the islands are also just a five-hour direct flight from Boston, making them well worth considering as a standalone destination rather than an add-on.

Island hopping — I’m all about slow travel so don’t recommend over-zealous island-hopping. That said, inter-island flights in the Azores are short and inexpensive. If you’ve got a couple of weeks, you can easily visit three islands (we did four and I was left wanting more time on each island).

Plan Ahead — As previously mentioned, there’s a cap on the number of hotel beds, so availability can be an issue if you wait to reserve your hotels (shameless reminder, I can help you with that at no cost to you). The same goes for rental cars (which I highly recommend).

Weather — Azorean weather is famously unpredictable and that’s not an exaggeration. We set out every day prepared for rain, wind, and sunshine — sometimes all three before noon. Pack layers, embrace the drama, and don’t let a forecast talk you out of anything. It never once hampered our experience. If anything, it added to it.

Go for the hiking — The hiking deserves its own billing. Trails for every fitness level, scenery that will stop you in your tracks, and enough of them to fill a trip twice over. Bring good boots — they’ll earn their place in your bag.

Two years out and I’m still finding words for what the Azores did to me. A place that protects itself as fiercely as it rewards the people lucky enough to find it. A place where the birds cackle in the dark and the hot springs bubble up in the middle of sleeping gardens and the waterfalls have waterfalls.

The siren song is real. I’d advise you not to resist it.

Christina Bowen is the founder of Wild World Travels, a sustainable travel advisory based in Denver, Colorado. She specializes in off-the-beaten-path, culturally respectful travel experiences.