Deb Fay

Luxury Travel Advisor · Winnipeg, Manitoba

Thoughtfully crafted journeys. Meaningful experiences.

Deb Fay reviewing a travel itinerary at an elegant café

The Story Behind the Journey

A Passion for Travel That Goes Deeper Than the Destination

I believe the best journeys are designed around the traveller, not the destination. Every trip begins with understanding your interests, travel style and what you hope to experience. That's how truly memorable travel begins.


I plan more than vacations, I create thoughtful travel experiences that reflect who you are. Whether you're celebrating a milestone, travelling solo, or planning an unforgettable golf getaway, every itinerary is tailored with care and attention to detail. My goal is to make every journey seamless, personal and meaningful.

When you work with me, you'll get one point of contact who listens first, then builds a trip around your pace, your interests and your budget, never a cookie-cutter package. You'll know what to expect at every stage, from the first idea to the moment you land back home, with support along the way if plans need to shift.

Travel is about more than where you go, it's about how you feel while you're there and the memories you bring home. From our first conversation until you return, I'm here to guide you every step of the way. So you can travel with confidence and simply enjoy the journey.


Golf Travel Expertise

More Than the Course — A Complete Golf Journey

I design golf journeys around you, combining exceptional courses with the character of each destination and the experiences that make a trip truly memorable.

Key destinations include Portugal, the United Kingdom, and beyond. Each is carefully chosen for the quality of its golf, the beauty of its surroundings, and the opportunity to experience the culture, cuisine, and character of the destination.

Your golf journey may include:

  • Carefully selected golf courses that match your playing style and preferences
  • Exceptional accommodations chosen for comfort, location and experience
  • Dining and wine experiences tied to each destination
  • Cultural experiences and off-course adventures that bring the destination to life
  • Seamless itinerary planning and personalized support from start to finish

Solo Travel Philosophy

Travel Confidently. Travel on Your Own Terms.

I design solo journeys around you, taking the time to understand how you want to travel, what interests you, and what you want to experience along the way. Your journey is thoughtfully planned to give you the freedom of travelling on your own while knowing the important details have been taken care of.

Travelling solo does not mean travelling alone. Your journey can include opportunities to meet people, connect with local culture, enjoy memorable meals, explore at your own pace, or simply have time to yourself.


Your journey may include:

  • Carefully selected accommodations where you can feel comfortable and secure
  • Guided and small group experiences that create opportunities to connect with others
  • Destination knowledge and local insight to help you feel confident wherever you go
  • A thoughtfully structured itinerary that gives you both freedom and support
  • Particular care when travel follows a significant life change or new chapter

From choosing the right destination and accommodations to arranging experiences and the details in between, I create a journey that feels personal, comfortable, and uniquely yours.

A woman enjoying a solo travel moment at an outdoor café in Europe

Meet our experienced team

Our Experts

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Your Journey Starts with a Conversation

If Deb's approach resonates with you — if you're dreaming of a golf journey, a solo adventure, or a trip to mark something meaningful — reach out and let's talk about what your ideal experience looks like.