Azores Self-Drive Itinerary: Top Sights for a Road Trip

It was printed in bold on the car rental paperwork: “Don’t Forget Your Driving License.” In the days before we left I repeated the same warning to myself, over and over, and even placed my license in a special spot so I wouldn’t misplace it.

And yet I forgot it.

That omission was more than a minor irritation. My wife, Hayley, and I had booked a week-long self-drive tour of São Miguel, the largest of the nine main Azorean islands. During planning we learned the island stretches about 40 miles long and nine miles wide, and public transport is limited and unreliable. The whole point of the trip was to explore by car — and in our partnership I am usually the one behind the wheel.

The flight carried us across the Atlantic: São Miguel sits roughly 4.5 hours from Boston by direct flight. On arrival we bypassed the rental counters and went straight to the taxi rank, both to get to our hotel and to test whether we could cover our itinerary by taxi alone. One short fare later and that idea evaporated.

We decided to change roles: Hayley would drive and I would be the navigator.

That shift paid off quickly. With our own vehicle we drove west, switchbacking up the slopes of the Sete Cidades Massif, one of the island’s volcanic formations. Mist rolled down from the summit and wrapped the road in gauzy layers. Hayley switched on the wipers and headlights while we climbed slowly through the gray.

Then, at the summit, the fog opened as if by magic. We pulled into a lookout and stared down into a vast caldera where two lakes lay side by side — one strikingly blue, the other a deep green. The landscape, shaped by violent volcanic forces long past, now exuded a calm, almost gentle beauty.

Our descent toward the coast followed narrow roads lined with flowering azaleas and blue throatwort, creating the sense that we were driving through exquisitely tended gardens. Every coastal viewpoint offered dramatic drops to the ocean and waves crashing against cliffs, with blooms flaring in pinks and blues along the roadside.

The highlight of our stay was a night at the Terra Nostra Garden Hotel in Furnas, a spa town known for its thermal activity. Set amid a lush botanical garden and appointed with Art Deco elegance, the hotel gave us a moment to relax and acknowledge that, despite my forgotten license, the trip had come together beautifully.

On the flight home we got an aerial farewell: the network of scenic roads we’d driven, patchwork pastures dotted with cattle, neat tea plantations, and small, picture-book villages woven into the landscape. It felt surprising to see such an intact, rural slice of Europe so near the eastern seaboard. São Miguel remains a well-kept secret — and the fate of my driving license remains, much like the island’s hidden corners, a small mystery.