Travel Advisor

Advisor - Kyler Canastra

Kyler Canastra

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Expertise

  • Boutique Travel,
  • Cruise,
  • Portugal,
  • Azores,
  • Spain,
  • Europe

Based in

Lisbon, Portugal

Languages spoken

English, Spanish, Portuguese

Profile details


About

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.


Favorite hotels

Kyler's travel photos

Kyler's reviews

Kyler was great to work with. He was always very quick to respond and had great food and tourist recommendations. Kyler worked with the airlines, hotels and car service to set us up for a seamless trip and experience. I look forward to working with Kyler again on my next travel experience.

Get in touch with Kyler

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can expect a response from Kyler within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).

Advisor - Kyler Canastra

Travel Advisor

Kyler Canastra

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