Before visiting the Azores, I expected beautiful scenery. I expected volcanic lakes, green hills, dramatic coastlines, and great food.
What I didn’t expect was how much the islands would make me think about home. Just 5.5 hours by direct flight from Montreal and under 6 hours direct from Toronto, Boston and NY, the Azores feels surprisingly close. Yet somehow, they feel a world away from the pace many of us have become accustomed to back home.
After spending time on São Miguel, I left with a deeper appreciation not only for the islands, but for the people who call them home.
The Magic of the Fog
One thing I quickly learned is that many travel photos do the Azores a disservice. They often show blue skies and perfect conditions. The reality is far more beautiful. The fog arrives without warning. Clouds roll across crater lakes and hillsides. Sunlight breaks through for a few moments before disappearing again. Entire landscapes appear and vanish within minutes. At first, I found myself hoping the clouds would clear. By the end of the trip, I was hoping they wouldn’t. The changing weather is not something to tolerate in the Azores. It’s what makes the islands feel magical. Standing above Sete Cidades, watching clouds drift across the crater while sunlight illuminated different parts of the landscape, felt almost cinematic. No photograph can fully capture it because it is constantly changing.
The Azores are not simply meant to be viewed. They are meant to be experienced. And perhaps that’s why these islands stay with you long after you’ve returned home.
The Morning Ritual
Most mornings began the same way. A walk to the water and a swim in the Atlantic. The water was cold. Cold enough that every instinct tells you not to go in. Yet every morning, local residents were already there doing exactly the same thing. Young, old, men, women, rain or shine. They greeted one another with the friendly “bom dia” and enjoyed their swim, exchanged a few words, and went on with their day. There was something beautiful about the simplicity of it. No rush, no performance, just a quiet daily ritual shared by an island community. As the days passed, I found myself looking forward to those swims almost as much as the excursions.
The People Are the Story
The scenery may be spectacular, but the people are what stay with you. One of our guides, Leandro, shared something that resonated deeply with me. He told us how much he loves to travel. He spoke about visiting incredible destinations around the world, including Japan, which he described as one of the most beautiful places he had ever seen. Yet every trip seems to remind him how much he loves returning home to the Azores. I immediately understood what he meant. I often feel the same way about Montreal. Travel has a funny way of doing that. We leave home searching for something new, only to gain a greater appreciation for what was already there. Listening to Leandro speak about the islands, it was impossible not to feel his pride. Not the pride of someone selling a destination. The pride of someone sharing his home. By the end of the trip, I found myself wanting to return, not simply to see more of the Azores, but to better understand and appreciate the place he loves so much.
The Stories Behind the Views
Another guide, Eduardo, had a remarkable ability to bring places to life. He was quieter than some guides I’ve met, more reserved and thoughtful, yet his passion for the Azores came through in everything he did. Whether we were visiting viewpoints, exploring local history, or touring the tea plantation, he transformed what could have been simple sightseeing into meaningful experiences. What impressed me most was his restraint. Many guides feel the need to fill every moment with facts and stories. Eduardo understood something more important. He knew when to speak, but he also knew when to let the landscape do the talking.
He seemed comfortable with silence, allowing people to absorb what they were seeing rather than immediately moving on to the next explanation. That takes confidence. I’m not sure he fully realizes it, but he has that confidence in abundance. Throughout the trip, he shared stories, history, and local perspectives that helped us better understand the islands and the people who call them home. Yet somehow it never felt like a lecture. It felt like spending time with someone who genuinely cared about sharing his corner of the world.
By the end of the trip, I realized that the best guides don’t simply show you a destination. They help you connect with it. Eduardo did exactly that.
The food exceeded every expectation.
Fresh seafood, local cheeses, perfectly grilled fish, excellent beef, and some surprisingly memorable wines all became part of the experience. I particularly enjoyed discovering wines from Pico Island and sampling local gin while watching the harbour settle into the evening. Like much of the Azores, nothing felt overly complicated or pretentious. Just fresh ingredients, prepared well, and enjoyed at a slower pace. Meals lasted longer in the Azores. People lingered. Nobody seemed eager to rush off to the next thing or glance at their watch. There was a pace to life that felt refreshingly different from what many of us experience at home. The islands seem to encourage you to slow down, look around, and enjoy where you are. That’s something many of us could probably use more of.
One afternoon, I decided to do very little. No excursion, no itinerary, no checklist. I wandered through Ponta Delgada, stopped for a drink, sat by the water, watched people come and go, and simply enjoyed being there. Oddly enough, it became one of my favourite memories of the trip. It’s also where I came to fully appreciate the balance of Wingbuddy’s semi-organized approach. The major excursions, transportation, tickets, transfers, and guides had all been taken care of, allowing me to enjoy the destination rather than manage it. That mattered more than I expected. The Azores have become increasingly popular, and several locals shared stories of visitors missing key sites, struggling to find parking, or spending valuable vacation time navigating logistics. In some of the most popular areas, parking is limited, roads are narrow, and access can be more challenging than it first appears.
Having the important pieces organized created something many travellers are looking for but don’t always find: freedom without stress. The guided experiences ensured we didn’t miss the highlights, while the built-in free time allowed us to explore, relax, and enjoy the islands at our own pace. For me, it turned out to be the perfect balance.
As I reflect on the trip, I realize the reasons I would return have less to do with the scenery, the food, or even the attractions, impressive as they all are.
I would return because of the people.
Because of conversations with Leandro about travel, home, and what makes a place special. Because of Eduardo’s thoughtful way of helping us understand the islands. Because of the locals gathering for their morning swim regardless of the weather. Because of the fog drifting across crater lakes before suddenly revealing a completely different landscape a few minutes later.
The Azores reminded me that the best travel experiences aren’t always about seeing more. Sometimes they’re about slowing down enough to truly appreciate where you are. Perhaps most importantly, the Azores reminded me of something Leandro had shared earlier in the trip. Travel has a way of helping us appreciate home even more. Sometimes we need to leave it for a little while to remember why we love it so much.
This Wingbuddy Azores Escape is a hassle-free, semi-organized tour that combines breathtaking volcanic landscapes, crystal-clear crater lakes, and lush greenery with rich Portuguese culture and cuisine. With direct flights from Montreal and Toronto, seamless logistics, and a balanced mix of guided activities and free time, it offers an authentic yet effortless way to explore the islands at a relaxed pace. The tour is perfect for travellers who want adventure without the stress of planning.
