Sailing in the Azores — Small-Group Catamaran Trips | SailZen

Multi-Day Sailing Trips

Explore the Islands at your own rhythm

Our experienced crew will lead you with safety and confidence toward your perfect journey. Whether you are a family seeking memorable moments, friends in search of adventure – we create the trip around your goals. Browse available multi-day sailing trips in the Azores — 2-day getaways to 10-day liveaboard voyages.

Day-Tours in São Miguel

Full-day, half-day, or sunset

Enjoy a sailing tour on the south coast of São Miguel island in comfort. Sail, swim, and go snorkeling in a beautiful anchorage with a close view of the islet of Vila Franca do Campo or sail far away from land. See all São Miguel sailing tours.

SAILING THE AZORES

Crewed yacht charter

Professional captain and cook/mate

Our priority is to guide you safely around the islands and experience this adventure in a familiar environment. As we remain professionals, we do everything we can to provide you with a spectacular experience at sea and on land.

Azores sailing adventure

Feel the freedom of following the wind

When we leave the port, you will see the different shades of blue between the ocean and the sky. The stars, the moon and the sun with the sails above you. Nothing but time to dive into the wilderness and enjoy.

SailZen Sailing Adventure

Responsible ECO-Tourism

Azores Tourism Sustainability

Our trips are filled with positive energy from the environment we sail in. Between the ocean, cetaceans, pelagic species, birds, and the majestic submarine mountains that emerge from the Dolphin Ridge in the North Atlantic, we respect the environment and its culture and share life within this magnificent ecosystem.

Sail the North Atlantic

OCEANIC Long Passages sailing

Our home base is sailing the Azores every summer, but we’re also interested in mile-building trips, non-qualified sail training, and oceanic experience between the Azores and Madeira. Sign up for our newsletter in the footer below, and you could be on one of these adventures one day.

Why would you join us sailing?

SailZen reviews & testimonials

You can read more reviews at Google Business, Facebook or Trip Advisor to get to know what our wonderful passengers have shared about their experiences during our trips.

      EXCELLENT  
   Based on 89 reviews 
    
 
 
 
   
 
 
       Posted on Tripadvisor  
   
   birdddog 
 
 
 
 Verified A six day dream
We sailed for 6 days between Sao Miguel and Santa Maria with André and Chiara on the Explora catamaran. We went swimming in so many amazing places, had beautiful days sailing, a coastal hike on Santa Maria and top notch healthy food on the boat. If I could have I would have gone for much much longer :)
  
 
      Posted on Tripadvisor  
   
   Marie Gonneville 
 
 
 
 Verified Azores Sailing Adventure Trips, Tours & Yacht Charter
What an unforgettable day with André and the SAILZEN crew! ⛵️☀️ From the moment we stepped aboard, they were incredibly welcoming, attentive, and made sure our group of 12 women had everything we needed. Their attention to detail was exceptional — we even had someone in our group who was gluten-free, and they went out of their way to make sure she had gluten-free sandwiches so she could enjoy everything with us. The drinks were flowing, the music was perfect, the atmosphere was fun and relaxed, and we spent the day chasing the sun and enjoying the incredible beauty of the Azores from the water. 🥂🎶 André and the crew truly made us feel taken care of while still letting us relax, laugh, dance, and enjoy every moment. It was one of those days you simply don’t forget. Thank you for such a beautiful experience and incredible memories. We would absolutely recommend SAILZEN to anyone looking for a special day on the water in the Azores! ❤️
  
 
      Posted on Tripadvisor  
   
   Inés P 
 
 
 
 Verified Thank you, André and Kiara, for giving me six days that I will carry with me for a very long time. ❤️🌊
This was so much more than a trip to the Azores. It was discovering a completely different way of travelling — slower, wilder, more connected to nature, and somehow much more alive. These days taught me the magic of sailing: waking up on the boat with the sunrise, watching the stars at night with nothing but the ocean around you, and feeling as if time had simply stopped. I discovered hidden corners of the Azores that I would have never experienced in a conventional trip — secluded beaches and tiny villages, beautifully nestled into the wild landscape, with hardly anyone around. Places so peaceful and beautiful that my friends and I kept saying it felt like we were in heaven. I swam to beaches instead of arriving by road, snorkelled in crystal-clear waters, went on beautiful hikes through the wild landscapes of the islands, and even had the unforgettable experience of eating a fish that had been caught by spearfishing just a few hours earlier. But what made this experience even more special was André, our skipper, and Kiara. From the very beginning, I felt completely safe, cared for and at home with them. They are incredibly professional, but at the same time so warm, close and genuine that, by the end of the trip, it honestly felt like I was travelling with friends. They were incredibly patient, always happy to teach us, share their knowledge and show us little things along the way. They took such good care of us and paid attention to every little detail — from making sure everyone was comfortable to putting so much love and care into preparing our meals. I always felt looked after, while also feeling completely free to enjoy the adventure. I’m so grateful for the way they welcomed us and for how quickly they made the boat feel like home. The Azores are breathtaking — raw, wild and incredibly beautiful. But experiencing them from the sea, waking up in a different place each morning, reaching places that can only be reached by boat, and simply being present in every moment, surrounded by wonderful people, made this experience truly unforgettable. I came back feeling incredibly happy and grateful. Some trips you remember because of the places you visited. This is one I will remember because of how I felt while I was there. Thank you, André and Kiara, for giving me six days that I will carry with me for a very long time.
  
 
      Posted on Tripadvisor  
   
   Javier Borén 
 
 
 
 Verified Magic (once again) at Açores Islands
My experience with SailZen was simply amazing. It was my second time sailing with them and I can only say great things about this company. Professional, passionate, and deeply human. Thank you for everything, André and Chiara. Talking about money well spent! 10/10
  
 
      Posted on Tripadvisor  
   
   Wanderer19154752772 
 
 
 
 Verified UNIQUE AND UNFORGETTABLE
It is difficult to put into words what these five days have meant to me. Five days sailing around the Azores, sharing a boat with seven wonderful people — five friends and two staff members who, by the end of the trip, no longer felt like staff at all, but simply like friends. And yet, what I am taking home with me feels like so much more than a trip. I am taking memories, sensations, laughter and moments that I know will stay with me for a very long time. And if there is one person who made all of this possible, it is André. André adapted every day to the sea conditions, the weather, our sailing plans and even to how we were feeling physically, always looking for ways to make the experience as special as possible. He knows the islands in a way that only someone who was born there can. He knows where to go, when to go, when to sail, when to stop — and when simply to let the sea decide. But above all, André has something that is difficult to explain: a way of experiencing the sea that is contagious. His love for sailing, nature and the environment is present in everything he does. Whenever conditions allowed, we sailed under wind power, letting the wind and the sea determine our course. And somehow, his connection with the ocean became our connection too. There are so many moments I will remember: Spearfishing and then eating what we had caught ourselves that same evening. Anchoring beside completely deserted, almost impossibly beautiful beaches. Hiking through places where it felt as though the whole island belonged to us. Swimming at night beneath a moonless sky, surrounded by bioluminescent plankton. Every movement made tiny lights appear in the water around us. It felt as though we were swimming among the stars. Snorkelling in waters full of life, surrounded by fish and even manta rays. Sailing at night, barely able to see anything, guided only by our senses. Incredible sunrises and sunsets, morning swims before breakfast, amazing food, music, dancing and laughter. But above all, I will remember the connection that grew between all of us. Because I think that is what made this experience truly special. None of these moments happened simply because we were in the Azores. They happened because of the way André understands what a journey should be. His way of captaining goes far beyond taking a boat from one place to another. It is knowing when to sail, when to stop, when to change the plans and when to simply go with the flow. It is creating the kind of atmosphere where a group of friends can become something even closer — sharing meals, songs, laughter, adventures and moments that already feel like memories from a much longer time ago. And somehow, for those five days, the boat became its own little world, where we were completely disconnected from everything else and simply enjoyed being together. I find it difficult to imagine a better way to discover the Azores than from the sea, and even harder to imagine experiencing them with someone who knows them, loves them and lives them in the way André does. If I ever embark on an experience like this again, I know one thing for certain: wherever André may be, I will want to sail with him again. Thank you, André, for five days that were technically only five days, but somehow feel like so much more. The boat is back in the harbour, the trip is over, and we have all gone our separate ways. But a part of me still feels like it is out there somewhere — somewhere between the islands, the wind, the stars and the ocean. And I think that is the greatest gift a journey can leave behind. Thank you for five unforgettable days. I will carry them with me forever.
  
 
      Posted on Tripadvisor  
   
   Lucía Borén 
 
 
 
 Verified Counting the days to come back!
This is my third trip with SailZen an, once again, it was nothing short of spectacular. The professionalism, kindness and knowledge on the team in all areas—both guest treatment and sailing skills—made this week both safe and wild, and to all levels and forgettable. I have sailed in other places in the world, but Azores has my heart. Will be back as soon as possible!
  
 
      Posted on Tripadvisor  
   
   Cjmb67 
 
 
 
 Verified Perfect Vila Franca Islet Visit
We chartered the catamaran for half a day, and had an amazing trip. Captain Andre runs a family business and he makes you feel like family. After going around the islet, we found a cove for swimming and paddle boarding. We had a delicious snack of local cheeses and the drink selection was good, complete with mocktails and cocktails. The captain grew up in the area and has many stories that complements his telling of historical facts. We found the trip worth every penny and would love to sail again with this company for longer trips in this spacious catamaran.
  
 
      Posted on Tripadvisor  
   
   unavailinle 
 
 
 
 Verified Wonderful Experience with SailZen
Our sailing trip with SailZen was the highlight of our 7 day trip to São Miguel. We spent a full day with André and Claudine and they were a delight to be with. The excursion was the perfect balance between adventure and relaxation.
  
 
      Posted on Tripadvisor  
   
   Lori L 
 
 
 
 Verified Amazing day with Sailzen
My family of 5 had an amazing time on our sailing trip! In addition to relaxing both in the cabin and on deck, we chose to snorkel and paddle board! We were well taken care of and enjoyed delicious snacks. My boys even had the opportunity to play chess in the cabin! The catamaran is beautiful and well stocked! We will be recommending Sailzen to anyone with an upcoming trip to Sao Miguel! Book this! You will not regret it!
  
 
      Posted on Tripadvisor  
   
   shagshag 
 
 
 
 Verified Exceptional day
Extraordinary experience to do without hesitation. Both adults and children were delighted by what the Sailzen crew offered. An outing suitable for everyone, supervised by super friendly professionals. We were dazzled, our taste buds were delighted, and we made wonderful memories. Thank you so much!
  
 
  
  
 
 
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