Ashleigh Finn
Based in Toronto
English
Ashleigh Finn
Ask me about
My Story
I’m a Toronto-based travel advisor with over 20 years in luxury hospitality, most notably with Four Seasons Hotels & Resorts. That foundation means I approach travel planning with the same care, precision, and personalized service clients expect from the world’s leading luxury brands.
Having worked on the hotel side, I understand how properties operate behind the scenes—allowing me to advocate effectively for my clients when it comes to room placement, special requests, and elevated on-property experiences.
I specialize in group and corporate travel, including retreats, incentive programs, conferences, and team offsites, while also designing seamless leisure travel for families, couples, and solo travelers. No matter the trip, my goal is always the same: a thoughtful, stress-free experience where every detail is handled with care.
Travel Style
I believe that luxury isn’t defined by a price tag—it’s defined by how a trip feels. No matter the budget, my goal is to create a travel experience that feels thoughtful, seamless, and elevated from start to finish.
With a background in luxury hospitality, I approach every itinerary with a service-first mindset and meticulous attention to detail. That means prioritizing comfort, smart planning, and meaningful touches that enhance the overall experience—whether it’s selecting the right property for your needs, timing travel days to reduce stress, or adding small but impactful details that make a trip feel special.
I work with each client to maximize value, ensuring your investment is spent where it matters most. From well-paced itineraries and trusted partners to personalized recommendations and proactive support, every journey is designed to feel intentional, polished, and effortless.
My style is refined yet approachable, practical yet indulgent. Whether you’re planning a family vacation, a milestone celebration, or a corporate retreat, you can expect a level of care, professionalism, and personalization inspired by the world’s leading luxury brands—regardless of budget.
Reviews (6)
Daniel T.
a month ago
Ashleigh is wonderful to work with. She went above and beyond planning a trip for my son and his friend. The initial presentation was well done ticking all the preference boxes, the booking process was smooth and efficient, and Ashleigh was super responsive when there were questions. The trip was a great success, and we will definitely work with her again.
Latoya S.
5 months ago
I can’t recommend Ashleigh enough as a travel agent. She truly went above and beyond to make our trip to Barcelona seamless and stress-free. Her attention to detail, responsiveness, and genuine care stood out every step of the way, and it’s clear she’s passionate about helping people have the best possible travel experiences. I would absolutely trust Ashleigh with future trips and happily recommend her to anyone planning a getaway.
Paul S.
6 months ago
Ashleigh was amazing to work with! She made the entire planning process so easy and stress-free, handled all the details, and was always available when we had questions. We felt very well taken care of and would absolutely book with her again.
Matthew U.
8 months ago
Ashleigh is the best travel agent we ever had!! My husband and I travel a lot and we are so happy to have FINALLY found someone who is just on top of everything. She makes herself available all the time: day, night and weekends. She is always looking for ways to make a good trip even better. She is organized, attentive, and patient. She offers lots of different ideas and options. She diarizes important dates and follows up with us. She went as far as preparing a detailed itinerary for us. Even after the trip was over, she followed up and cared to know how our trip went. Can’t wait to plan our next trip with Ashleigh again!
Jan L.
10 months ago
Ashleigh is amazing! I would definitely work with Ashleigh to book my next vacation. I have recommended Ashleigh to my friends for her outstanding service.
Daniel T.
a month ago
Ashleigh is wonderful to work with. She went above and beyond planning a trip for my son and his friend. The initial presentation was well done ticking all the preference boxes, the booking process was smooth and efficient, and Ashleigh was super responsive when there were questions. The trip was a great success, and we will definitely work with her again.
Latoya S.
5 months ago
I can’t recommend Ashleigh enough as a travel agent. She truly went above and beyond to make our trip to Barcelona seamless and stress-free. Her attention to detail, responsiveness, and genuine care stood out every step of the way, and it’s clear she’s passionate about helping people have the best possible travel experiences. I would absolutely trust Ashleigh with future trips and happily recommend her to anyone planning a getaway.
Paul S.
6 months ago
Ashleigh was amazing to work with! She made the entire planning process so easy and stress-free, handled all the details, and was always available when we had questions. We felt very well taken care of and would absolutely book with her again.
Matthew U.
8 months ago
Ashleigh is the best travel agent we ever had!! My husband and I travel a lot and we are so happy to have FINALLY found someone who is just on top of everything. She makes herself available all the time: day, night and weekends. She is always looking for ways to make a good trip even better. She is organized, attentive, and patient. She offers lots of different ideas and options. She diarizes important dates and follows up with us. She went as far as preparing a detailed itinerary for us. Even after the trip was over, she followed up and cared to know how our trip went. Can’t wait to plan our next trip with Ashleigh again!