The Azores We Almost Missed: Our Flexible São Miguel Adventure

In 2022, Brian and I took one of the most beautiful trips we have ever taken: a trip that finally brought us to the Azores. It did not begin as a simple island-only adventure, and it definitely did not go according to plan. But by the end, all of the detours somehow felt like they had led us exactly where we were supposed to be.

We had originally booked the trip in early 2020, only about a month before the COVID shutdown changed the world. The plan was a six-day Azores adventure with Jeep tours, whale watching, and island exploring. When it was canceled later that year, we were disappointed, but not ready to give up on it. We froze the reservations we could, received credits or refunds for some prepaid pieces, and decided we would get there when we could get there.

When we rebooked for July 2022, we added two days and planned to split the trip between three days in the Azores and three in Lisbon. The package we found through a large escorted-trip company was an amazing value—about $2,000 total for both of us for eight days, including two island Jeep tours, a half-day Lisbon tour, and a full-day mainland Portugal tour. We would eventually spend considerably more than that, but at the time it felt like the start of a wonderful bargain trip.

A Missed Connection and an Unexpected Day in Boston

Our Charlotte-to-Boston departure was delayed by about three and a half hours, which caused us to miss our Boston-to-Lisbon flight. Because our trip had been booked as part of a package, we had to find the next flight to the Azores ourselves. There was not another option until the following day, so we did what we have learned to do when travel goes sideways: stayed flexible, stayed cheerful, and made the best of it.

Close to midnight, we found a hotel at the airport. Brian was up at 4:00 a.m. so he could talk with the airlines as soon as their Portugal office opened at 9:00 a.m. Once he secured new tickets, we had an entire unexpected day in Boston. We took a harbor cruise, revisited part of the Freedom Trail—we had just been there with the kids in April—and had a really good dinner before returning to the hotel, collecting our things, and heading back to the airport very early. After that experience, we were determined not to miss the rebooked flight.

Missing the first day of our Lisbon portion made the decision for us. Instead of trying to squeeze Lisbon into a shortened schedule, we skipped it altogether and spent the extra time in the Azores. After all, that was the trip we had first booked two and a half years earlier.

The changes came with a real cost. Rebooking the flights, adding the Boston hotel, and rebuilding the first three days of the trip added about $2,000 to what we spent. Our travel insurance reimbursed $1,600 of that. It was a strong reminder of why we buy travel insurance for any major trip where a cancellation or disruption could leave us with expenses we cannot recover through a credit. Every policy is different, of course, but on this trip it made a meaningful difference.

Arriving on São Miguel and Finding Our Feet

We landed around 6:30 in the morning. The flight from Boston was only about five hours, so we were tired, but we were also determined to make the most of the day. Our planned hotel for the Azores part of the trip was not available for the first few nights, but we found a nearby room at the Neat Hotel in Ponta Delgada. It turned out to be a happy solution for our first night, with a balcony overlooking the boat harbor and a location that made the center of town easy to explore.

After that first night, we moved to the Grand Hotel Azores Atlântico. It felt wonderfully luxurious, with an oceanfront setting and a location near the best walkable spots in town. It was the kind of hotel that made the unplanned changes feel like part of the vacation rather than a compromise, and we would absolutely stay there again.

We walked almost immediately through central Ponta Delgada and found it beautiful, clean, and extremely pedestrian-friendly. Since our Jeep tours were still a day or two away, we had to discover our own things to do. That was not a hardship. We drank leisurely coffee on the balcony, wandered the harbor, enjoyed wonderful meals, and let ourselves recover at a human pace instead of trying to force a sightseeing schedule.

Pineapples, a Small Tram Tour, and a Last-Minute Whale Watch

One of our easy early discoveries was a local tram tour that combined the town with a pineapple farm. It was only 19 euros and felt like exactly the kind of small, local experience we needed after a long travel day. São Miguel pineapples are grown in glass greenhouses, a distinctive island tradition that began commercially in the nineteenth century. Seeing the plants in their warm, glass-covered rows was much more interesting than simply buying pineapple at a market.

We also managed to find availability on a whale and dolphin tour for 40 euros per person. The boat took us about 14 miles offshore, where we saw multiple whales. I was a little queasy at times, but it was still a genuinely fun experience and one of those travel memories that feels completely different once you are far enough from shore that the island is only a green line on the horizon.

Whale-watching conditions, routes, and sightings are always variable, so I would never promise the exact experience we had. But if you have the flexibility to take a weather-appropriate tour, it is a memorable way to understand that São Miguel is not just a pretty island—it is a small piece of land in the middle of a very big Atlantic Ocean.

Why the Jeep Tours Were the Highlight

The Jeep tours were the highlight of the entire trip. We took one tour focused on the south and east sides of the island, then another the next day in the north and west. We had the same guide both days, which made the second day feel even more relaxed. The Jeep was roomy: on the first day it was just us and one other couple; on the second, there were two additional couples, but the three-row setup never felt cramped.

A Jeep tour worked especially well for us because São Miguel is full of places that reward a slow, scenic route: little roads, high overlooks, forests, waterfalls, tiny villages, and places where you simply want to pull over and take a picture. Driving yourselves can be wonderful too, but I loved being able to watch the views instead of concentrating on unfamiliar, winding roads.

The East and North: Tea Fields, Furnas, Nordeste, and Big Views

On our first Jeep day, we explored the south and east sides of the island, stopping repeatedly for coastal photographs and views around Nordeste, Pico da Vara, Lagoa das Furnas, and Ponta do Cintrão. The landscape seemed to change every few minutes—from open ocean and cliffs to deep green slopes, hydrangeas, and misty forest roads.

One of my favorite stops was Chá Gorreana, where we saw the tea plantation and factory. Gorreana has operated since 1883 and is recognized as Europe’s oldest tea plantation. The tea is made from Camellia sinensis, the same plant used for black and green tea, and the fields rolling down toward the coast were as beautiful as the visit was interesting. We watched the story of the tea from field to processing and came away appreciating that this was a real working place, not simply a pretty photo stop.

The smaller stops mattered just as much: a waterfall tucked into lush greenery, a mossy old aqueduct, and coastal viewpoints that made us keep saying, ‘Just one more picture.’ The northeast of São Miguel felt wonderfully uncrowded and almost unreal in its shades of green.

The West: Sete Cidades and a Concert Inside a Volcano

The next day, we headed to the western side of São Miguel and stopped again and again around the rim of the former Sete Cidades volcano. The crater landscape is huge, green, and almost impossible to take in from just one viewpoint. Below us were the famous lakes, surrounded by the steep sides of the caldera.

We happened to be there while a concert venue was being set up near the lakes inside the crater. It turned out to be the 2022 Atlantis Concert for Earth, a two-day conservation-focused event in Sete Cidades. Black Eyed Peas performed there, while Sting was part of the program virtually. Seeing a stage come together in such an extraordinary natural setting was one of those strange little travel surprises you could never schedule.

Sete Cidades is the image many people associate with São Miguel, and I understand why. The views were spectacular, but what I remember most is the scale: clouds moving over the rim, hydrangeas in the foreground, and the feeling of looking down into a landscape created by volcanic forces long before anyone could have imagined holding a concert there.

Lunch in Varzea, Volcanic Rock at Mosteiros, and Warm Ocean Water

We stopped for an authentic and very satisfying lunch in the tiny town of Varzea, a meal that felt especially good after a morning of viewpoints and winding roads. This is another reason I loved the Jeep tour: our guide could bring us to places we might not have found—or felt comfortable choosing—on our own.

Later, we visited the black volcanic shoreline at Mosteiros. The dark rocks against the bright Atlantic were dramatic and entirely different from the lush farmland and flower-lined overlooks we had seen earlier in the day. São Miguel has volcanic character everywhere, but Mosteiros made it feel close enough to touch.

We also stopped at Ponta da Ferraria, on the island’s western coast near Ginetes. This is the spot where natural thermal springs warm the ocean water among the volcanic rocks. At lower tide, the natural pool can be warmer than 86°F (30°C), but conditions and temperature vary with the tide and the sea. We saw plenty of people swimming and enjoying that surprising blend of Atlantic waves and geothermal heat. It was one of the clearest reminders that São Miguel is an island built by volcanic energy.

The Trip We Want to Repeat

We have talked about returning to the Azores ever since this trip. São Miguel gave us so much in a few days—coastlines, crater lakes, tea, pineapples, whales, food, flowers, waterfalls, and people who made a delayed and reworked itinerary feel surprisingly easy to enjoy. Next time, we would love to explore some of the other islands too.

People often compare the Azores to the ‘Hawaii of Europe,’ and I understand the shorthand: there are volcanic landscapes, lush green mountains, dramatic ocean views, and a powerful sense of being far from ordinary routines. But São Miguel has its own personality. For us, it was not just beautiful; it was the place that rewarded every bit of flexibility the journey asked of us.

Our original trip was canceled. Our replacement trip began with a missed connection. We lost Lisbon, spent an unexpected day in Boston, and had to improvise a hotel. Yet the universe, as it sometimes does, seemed to right itself. We ended up with the longer Azores experience we had wanted in the first place—and one of our favorite trips we have ever taken.