Kyler Canastra
Based in Lisbon, Portugal
English, Spanish, Portuguese
Kyler Canastra
Ask me about
My Story
A Portuguese-American with two passports full of stories, I’ve spent the past 11 years living between Spain and Portugal—two countries I know like the back of my hand. My passion for travel is rooted in curiosity: discovering new cultures, savoring local flavors, and finding beauty in both the iconic and the unexpected. Whether it’s a hidden village in Andalusia or a coastal gem outside of Lisbon, I specialize in helping travelers experience Europe—and the world—like locals.
Travel Style
For me, travel is about depth and connection. I’m drawn to places where I can truly understand the culture—through language, food, history, and social context. I seek out the stories behind the landmarks, the flavors passed down through generations, and the conversations that bring a place to life. Whether I’m chatting with a street vendor in Santiago de Chile or digging into regional dishes in the Azores, I always travel with curiosity and intention. That’s the lens I bring to trip planning, too—helping clients experience destinations in ways that feel personal, grounded, and unforgettable. And while I love getting lost in local streets, I also believe cruises can be an incredible way to explore—pairing convenience with opportunities to experience multiple cultures in one journey.
Reviews (13)
Caroline M.
travel to Seville
about 1 month ago
Kyler is a dream to work with, he made our trip to Seville so easy. He's extremely knowledgeable, adaptable and caring. Highly recommend booking a trip with Kyler!
Ana Bess M.
travel to Madrid
about 2 months ago
Kyler was so accommodating and flexible. We didn't have much time to plan and both felt so overwhelmed with our work schedules so I can imagine we weren't the easiest to work with! Overall Kyler's flexibility, insight, and support made the experience really special. Thank you.
Ben M.
travel to Lisbon
2 months ago
Our advisor, Kyler was incredible. He not only was super detail oriented in preparation for our trip, but offered the right amount of options for what we wanted to do, helped us with both the admin side of planning a trip while also offering his own expertise, and had such fun surprises for us along the way! We ended up loving so many of his recommendations, and his thoughtful and kind support and suggestions were wonderful. I would trust Kyler with any recommendations in any city! He even kindly shared his Google map lists which were just an added bonus. It really felt like he did all the work and we were able to just sit back and enjoy our honeymoon without a care. Highly recommend working with Kyler!
Madeleine D.
travel to Barcelona
3 months ago
Kyler was amazing! He made this booking experience seamless. He has very clear and kind communication. I would love to book with him again in the future.
Mary Anne L.
travel by cruise
4 months ago
Kyler went above and beyond helping me book this cruise as well as helping me with accommodations, excursions, transfers, etc. I really appreciated his help very much. This made my trip much easier and I was able to enjoy my vacation! I will definitely book with Kyler again!
Caroline M.
travel to Seville
about 1 month ago
Kyler is a dream to work with, he made our trip to Seville so easy. He's extremely knowledgeable, adaptable and caring. Highly recommend booking a trip with Kyler!
Ana Bess M.
travel to Madrid
about 2 months ago
Kyler was so accommodating and flexible. We didn't have much time to plan and both felt so overwhelmed with our work schedules so I can imagine we weren't the easiest to work with! Overall Kyler's flexibility, insight, and support made the experience really special. Thank you.
Ben M.
travel to Lisbon
2 months ago
Our advisor, Kyler was incredible. He not only was super detail oriented in preparation for our trip, but offered the right amount of options for what we wanted to do, helped us with both the admin side of planning a trip while also offering his own expertise, and had such fun surprises for us along the way! We ended up loving so many of his recommendations, and his thoughtful and kind support and suggestions were wonderful. I would trust Kyler with any recommendations in any city! He even kindly shared his Google map lists which were just an added bonus. It really felt like he did all the work and we were able to just sit back and enjoy our honeymoon without a care. Highly recommend working with Kyler!
Madeleine D.
travel to Barcelona
3 months ago
Kyler was amazing! He made this booking experience seamless. He has very clear and kind communication. I would love to book with him again in the future.
Travel photos
