Azores & Madeira: The Perfect 50th Birthday Adventure
When my husband started talking about how he wanted to celebrate his 50th birthday, we knew we wanted to do something a little different.
We wanted adventure. We wanted beautiful hotels. We wanted great food, incredible scenery, and a destination that felt like a true escape. And, most importantly, we wanted somewhere neither of us had been before.
Enter: the Azores and Madeira.
These two Portuguese islands had been on my radar for a while, and after traveling there, I can confidently say they are two of the most underrated destinations I’ve experienced. And while they are both lush, dramatic and incredibly beautiful, they couldn’t feel more different.
The Azores: Think Hawaii Without the Crowds
Our first stop was São Miguel in the Azores, and my first thought was: Why isn’t everyone talking about this place?
The landscape is absolutely spectacular — volcanic craters, dramatic coastlines, thermal springs, waterfalls, rolling green hills and hydrangeas everywhere you look.
We happened to visit during hydrangea season, which made the island even more magical. The roads were lined with enormous blue and purple hydrangeas, and the combination of the flowers and the intensely green landscape felt almost surreal.
We stayed at White Suites, an adults-only property that was a wonderful fit for this trip. It felt intimate, stylish and peaceful — exactly what we wanted for a birthday getaway without kids.
We also spent time at Santa Barbara Eco-Beach Resort, which was another standout. The setting is incredible, right along the coast, and the whole property has a relaxed, understated feel. It was one of those places where you immediately want to slow down and stay awhile.
A Taste of the Azores
One of our favorite experiences was a wine and food tour.
Food is such an important part of experiencing a destination, and this was a great way to get a better feel for the local culture and flavors of the Azores. We were able to taste local specialties, learn more about the island and, of course, enjoy some fantastic food and wine along the way.
It was the kind of experience that felt authentic rather than overly touristy — exactly what I look for when I travel.
Exploring Sete Cidades by E-Bike
Another highlight was our Sete Cidades e-bike tour.
Sete Cidades is one of those places that is almost impossible to describe until you see it in person. The massive volcanic crater, the lakes and the surrounding green landscape are spectacular.
Exploring by e-bike was such a fun way to experience it. We could cover more ground while still being outside and immersed in the scenery.
And because it was an e-bike tour, we could enjoy the adventure without feeling like we had signed up for an Olympic cycling event!
For active travelers, this was definitely one of the highlights of our time in the Azores.
Next Stop: Madeira
From the Azores, we headed to Madeira. There are several island to island flights a day, and these islands are very different!
If the Azores felt wild, peaceful and off-the-beaten-path, Madeira felt a little more polished, energetic and sophisticated.
We stayed at Reid’s Palace, and it was exactly the kind of hotel I wanted for a milestone birthday trip.
It is luxurious, historic and absolutely beautiful, but it also has a sense of energy to it. There was a real buzz around the hotel, and it felt like a place where people actually come to celebrate and enjoy themselves.
The setting overlooking the Atlantic is spectacular, and after several adventurous days, coming back to Reid’s Palace felt like the perfect combination of luxury and relaxation.
Hiking in Madeira
One of the things I loved most about Madeira was how easy it was to combine adventure with luxury.
We spent time hiking some of Madeira’s incredible trails, and the scenery is unlike anything I had experienced before.
Madeira is known for its levadas, the historic irrigation channels that wind through the mountains, and hiking along them gives you a completely different perspective of the island.
You move from lush forests to dramatic mountain peaks to waterfalls and coastal views — sometimes all within the same day.
And then you can go back to a beautiful hotel, take a shower, have a cocktail and enjoy a great dinner.
That is my kind of adventure.
And Then There Was the Mountain Biking…
My husband is an avid mountain biker, so naturally, a trip like this had to include some serious biking.
And Madeira delivered.
He told me that some of the riding there was among the best mountain biking he has ever done.
The combination of steep mountains, technical trails, incredible views and varied terrain made it an unforgettable experience for him.
While he was off tackling the mountains, I was perfectly happy exploring, hiking and enjoying the island in my own way.
Honestly, that is one of my favorite things about a destination like Madeira — there is something for everyone.
Azores or Madeira?
If you are trying to decide between the two, I wouldn’t necessarily choose.
Go to both.
They complement each other beautifully.
The Azores felt more remote, wild and incredibly connected to nature. Madeira felt more polished, lively and luxurious, with a fantastic mix of outdoor adventure and sophisticated hotels and restaurants.
And together, they made for an incredible milestone birthday trip.
Would I Recommend It?
Absolutely.
This is a destination I would especially recommend for couples, milestone celebrations, active travelers and anyone looking for something beyond the typical European vacation.
It isn’t necessarily the easiest destination to plan on your own — which is exactly where having a travel advisor can make a difference. Knowing which island to visit, how long to stay, where to base yourself, which hotels are worth it and which experiences are truly special can completely change the trip.
And that is one of my favorite parts of my job: going somewhere myself, figuring it out, and then being able to share that firsthand experience with my clients.
Our 50th birthday adventure gave us a little bit of everything — beautiful hotels, incredible scenery, adventure, hiking, biking, great food and plenty of time together.
Not a bad way to celebrate 50.
