July 23 – 29, 2025.

Photo album

The three of us assembled on the bleachers in the newly renovated Portland airport, eager to open our identical manila envelopes. Karen set up her phone on a tripod to capture the moment. Several months earlier, myself and two friends hired a travel agent to plan a “mystery trip” for us. We gave her some parameters, a budget, a list of places we’d been and things we like to do. Based on this information, she booked us a flight, a hotel and a rental car. The catch: we wouldn’t know where we were going until we arrived at the airport.

Karen received the mystery envelopes just a couple days before and brought them to the airport. To be fair, our travel agent gave us a packing list and a weather report a week prior to our scheduled flight. So, we had some idea of what we were getting into.

All at once, we tore open the packets: “we’re going to…the Azores?!”

Before we could really process that information, we set out to check our luggage, get through security and find our gate. It had been many years sine I’d taken an international flight, so I felt a little rusty going through all the steps. Since we arrived plenty early and check-in was smooth, we had lots of time to pick up breakfast, drink some coffee and peruse our travel itinerary. A Moon travel guide and basic information packet was included in our travel packet so we could do a little planning. We had a 17 hour travel day ahead, which was plenty of time to read through the materials.

Here, I’ll share some of the highlights of this whirlwind 5-day visit to São Miguel Island in the Azores. It’s hard to believe how much we packed into this quick getaway, too much to tell here!

Ponta Delgada

We arrived at the Ponta Delgada airport after an overnight flight brought us across a zillion time zones. I had no idea where I was or what time it was, but we hit the ground running. As we walked across the open tarmac, it became immediately clear that we weren’t in Oregon anymore. The air was filled with a light mist, it looked like Hawaii and everyone around us spoke a dozen different languages. Talk about disorienting.

Since our hotel was located in Ponta Delgada, the capital city, we spent a lot of time here. Our travel agent booked us a food tour through Hungry Whales. We lucked out and were the only people on the tour, so we had a private walk through of the city, starting with a history lesson in their cozy office space. Then, our guide walked us from place to place, making 6 or so stops to eat food at markets, shops and restaurants. We asked a ton of questions and found our guide engaging, knowledgeable and fun to be around. I can’t wait to do another food tour the next time I travel internationally!

We noticed a ton of people swimming at a public access “beach” right across from the hotel, so we got our swimsuits and towels ready. I put beach in quotation marks because it was essentially a large concrete pad with steps leading into the swimming area in the bay. Lots of people were in the water and sprawled out on their towels on the concrete. This was our first dip in the Atlantic Ocean, and we’d repeat this ritual at a different beach each day!

Ponta Delgada is a great town to walk around and explore. We enjoyed all the public art, cryptic alleyways, little shops and all the food options. We found amazingly cheap and delicious baked goods, great coffee shops, wine and cheese and of course fresh fish everywhere. The red pepper sauce they serve with everything is divine. Be sure to pack some in your suitcase.

Rocha da Relva

We all took turns choosing hikes and activities. This was the first hike we did on the island and Sue chose this trail for us. It took a team effort to negotiate the steep, winding, confusing roads down to a remote-feeling trailhead for Rocha da Relva. We read the sign and began walking down, down, down to an old village at the edge of the ocean. It was a beautiful walk and a great first impression of the island. We saw a few tourists and a friendly stray kitty, plus lots of beautiful plants. The significance of the village and how/why it’s upkept to some degree was not clear to me. But many things would not be clear to me on this trip and that’s really what international travel is all about!

Furnas

Just like Hawaii, the Azores are volcanic islands. We wanted to learn more about the volcano and see some geology in action, so we decided to take a drive to Furnas. Furnas is a small town that is a popular place to visit for both locals and tourists. I planned a hike that would take us around the lake, stopping at the main area for visitors with boiling hot springs and vendors that sold corn on the cob cooked in the volcano.

We parked at the south end and walked counter-clockwise. We decided to follow a user path along the lakeshore since we didn’t want to walk on the road. This petered out into the mud, so we hiked up a steep hill to get back on the road. For a bit, there was a dirt sidewalk to follow. The trail is marked by colored posts, as are all trails on the island. Even though we now followed the colored posts, we had to play chicken with traffic a few times as we were sent down narrow roads with no sidewalks. Already I was not too impressed with the “trail” system!

At a particularly sketchy intersection, we ran across the street to follow a secondary road that led into a deep, lush forest with a few scattered houses and a school. It was one of my favorite parts of the hike. But as we approached a church and more city buildings, I realized we’d taken a wrong turn. Once we got re-oriented on the map, we turned back to rejoin the main route and get back to the lake. By the time we reached the main parking area and throngs of tourists, we had worked up an appetite. We got our corn on the cob (not worth it) and a pineapple shake served in a hollowed out pineapple (delicious).

As luck would have it, we walked through the thermal pools area just as the locals were removing steaming pots full of Cozido das Furnas from the hot ground. We walked along the short boardwalks to get a closer look at the natural and human activity occurring at the pools. It was a lot smaller area than, say, Yellowstone, but it was a worthwhile experience.

The last segment of the trail took us through bamboo forests, past giant ferns and through lush landscapes with flowers from all over the world. Since the Azores have been a meeting place for sailors from nearly every continent, the flora represent an eclectic mix of tropical bloomers from near and far. Nearly none of the plants are native to the islands. While the hydrangea has become an iconic symbol of the Azores (they grow like weeds in the rich, volcanic soil), they were only recently imported from Japan in the 19th century.

Our feet were tired by the time we arrived at the interpretive center near the end of the loop. We ducked inside to get out of the warm, humid air and to learn more about the volcano. The center has a small entry fee and a handful of exhibits and videos. It was strangely dark inside, with not much information to learn, but the staff was very friendly and they offered us each a cup of cold tea.

Sete Cidades

We were all smitten by the gorgeous photos of the blue and green lagoons at Sete Cidades that we saw in all the tourist brochures, so we planned a full day at this iconic hotspot. On the way there, Karen wanted to make a quick detour to some hotel ruins that she’d heard about online. The secret’s out about this spot because it was absolutely crawling with tourists, even early in the morning. Once a luxury hotel, the business was only open for 18 months before the owners went bankrupt. Sounds like a lot of rich people bullshit, scandal and likely scamming the government for tax breaks and investment money. I hate this stuff, but Karen was really into it so we joined the crowd.

The building was mostly concrete and trash, but enough of the carpeting was left behind in the humid Azorean weather to harbor ungodly amounts of mold and other awful stuff that I tried to hold my nose as we raced through the hallways and climbed the stairs. I couldn’t wait to get out.

We followed some tourists through a window frame and onto the roof. There, I was able to breathe again. We got beautiful views of the lakes, but was really captivated me were the mini gardens that had formed around the roof vents. While everyone else was livestreaming views of the island, I was nosing around the greenery looking for bugs and flowers. I was surprised at the diversity of life in those little vegetation islands! I found bumblebees, drone flies and damselflies oblivious to the crumbling human hubris all around them. Considering that I’d hardly noticed a single insect anywhere else on the island, this made me really happy.

By the time we got to the lake shore, the wind had begun to whip up. We had planned to rent paddleboards and cruise around the lake, but all the rental shops were closed for the day because of the wind. So, we read books, had a picnic and bailed out of there. Our consolation prize was a quick hike near Joao Bom called Atalho dos Vermelhos. Like other hikes on the island, it followed colored posts and traversed a mixture of walking paths, country roads and paved roads.

Maia

We took our last dip in the ocean in the small town of Maia. The Piscinas naturais das Calhetas da Maia are a series of semi-protected pools on the north side of the island. In the 1980’s, locals built a concrete pathway connecting the mainland to some rocky outcrops just offshore. This created the appearance of natural swimming pools (piscinas naturais) with much calmer water than the ocean surrounding it. We packed up for an afternoon at the beach and walked down the rainbow-colored steps to the bridge across the ocean. A thin film of water sloshed across our feet as we carefully made our way to the volcanic rock on the other side (definitely not universally accessible!)

Many people were already there, enjoying the beautiful day. We scrambled over the rocks to find a flattish spot to set our towels and backpacks, then walked down to the aluminum ladder leading into the water. We swam in the calm, cool water. Children and teenagers jumped in the water from the rocks, climbed out using the ladder and repeated, over and over again. People of all ages lounged on the rocks. A few people snorkeled nearby. It was such a wonderful place for everyone to enjoy the water, the rocks, the sun.

After swimming, I climbed back to my towel and pulled out my painting kit. I wanted to capture the idyllic scene. I completed a sketch and then dived into the painting…then the rain came. It was a light mist at first, but it quickly converted to drizzle, then rain. Everyone began to pack up their things and hurry to shore. Our peaceful afternoon hangout was cut short. But, after we dried off and changed clothes, the rain stopped. We did a quick Google restaurant search and landed on “Fim de Século” based on its positive reviews. We were NOT disappointed. Between the three of us, we split a fish platter for two and a couple appetizers. The fish plate incorporated the catch of the day with seasonal vegetables. Everything was simply prepared but fresh, delicious and perfectly cooked. We enjoyed the grilled tuna and mackerel so much. It was our best meal on the island!

When we asked for the bill, we were informed that their credit card machine wasn’t working. We didn’t have enough cash for the meal, so we sent Karen on a wild goose chase to find an ATM. What is international travel without a few inconveniences? It took her over an hour to accomplish this mission, during which time Sue and I chatted and ordered some espressos. By the time we got back to the hotel, we were exhausted. But, since it was our last night of the trip, we went to the bar for dessert and cocktails. It’s vacation, so we wanted to enjoy every second.

Things I loved about this trip

Everyone loves a top five list! Here we go…

1. Swimming in the ocean every day. Not only were there great beaches everywhere, they were all free. Most of them had ample parking plus restrooms, changing rooms and outdoor showers. Current conditions are posted at beach access points and red, yellow or green flags let you know how safe it is to swim that day.
2. Eating fresh seafood. We ate so much fish on this trip and it was all fresh and delicious. We also tried the local specialty, limpets, which was not for me.
3. Taking a food tour. This was the first time I’d ever done such a thing and we all had a blast. We also could hardly eat for the rest of the day!
4. Azorean pineapple. These pineapples are grown in greenhouses and are literally the best in the world. They’re seedless, small, plump and delicious. You can eat the core, too. Farmers use smoke to prompt the plants to set fruit, which is unlike pineapple production in other parts of the world. It is more costly and time-intensive, so the fruit is more expensive. But it’s worth it, and you can buy these Azorean pineapples at local markets: just be sure to look for the “local” tag!
5. The colors. Everything about São Miguel Island was beautiful. The architecture, the trees, the flowers, the streets and sidewalks. Our food tour guide taught us a bit about the history of how they used limestone and basalt to build the highly decorative, patterned sidewalks and roads. Since the Azores are volcanic, there are quite a bit of structures constructed from black basalt rock. That helps to center the diversity of colorful tropical flowers that grow like mad all over the island.

What I’d do next time

Would I do a mystery trip again? YES Would I visit the Azores again? SIM! (also yes). I loved that I didn’t spend months agonizing over every detail. The three of us were able to plan a really fun and memorable trip in the time it took to fly there. And, since we only visited one of the islands, I’ve got to go back to visit the other eight! Each one has a different story to tell, so I’ve just scratched the surface.

There are still a few continents I haven’t visited yet, so there are plenty of possible mystery destinations in my future. While I’ve centered domestic travel since hitting the road in 2023, I am still very interested in traveling abroad. There is much to learn about the rest of the world and immersion in a different place culture is a much more authentic way to learn than reading text on a screen (this is also true for domestic travel: please leave your house!)

Would I do a mystery trip with my friends again, YES! I really enjoyed spending so much quality time with them. Although we don’t get to see each other often, when we do it is always really nourishing. I’m so grateful to have deep friendships that have lasted the test of time. And no scary, narrow road in a foreign country with signs we don’t understand will tear that friendship apart.

Resources

A brief history of the Azores (part 1): It all starts in the 15th century…

Azores trails: The Azores official tourism website, featuring hiking maps and trail descriptions.

Basic Portuguese phrases for beginners and travellers: note that European Portuguese, Brazilian Portuguese and Azorean Portuguese all sound pretty different. But since most people (especially in the hospitality industry) speak English well, you won’t need too much Portuguese to get by.

Driving in Portugual: traffic rules and road signs: trust me when I say I was frantically looking these up from the back seat of the car, and that it took all three of us working together to figure out how to navigate the road system here.

Magical Mystery Tours: I highly recommend using the travel agent that we chose for this trip.

10 fun facts (that you probably didn’t know) about São Miguel, the Azores: look, another list!