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 (12)
Naomi S.
16 days ago
I found Ashleigh through a referral in a community Facebook group when I was looking for a travel agent, and I’m so glad I did. From our very first phone call, she was warm, engaging, and genuinely took the time to understand what I was looking for. I immediately felt heard, and her positive, upbeat approach made me feel confident I was in good hands. She initially sent a few options, and when I explained why they weren’t the right fit for this trip, she was incredibly open and receptive. I never felt judged and she was happy to go back and find better matches. Throughout the process, she has been very responsive by text, email, and phone, and thoughtful in finding options that work within my budget. What really stands out is how quickly she “got” me. I feel completely comfortable being honest about what I like and don’t like, and she always meets that with professionalism and enthusiasm. Even when she’s not familiar with a property, she takes the initiative to gather the information needed so I can make confident decisions. Now that my trip is booked, I can confidently say I’ve found the right travel agent..dedicated, attentive, and makes you feel like a priority. I truly value this working relationship and will absolutely be using her again. I highly recommend her to anyone looking for a knowledgeable, responsive, and genuinely caring travel agent.
Thomas M.
about 2 months ago
Ashleigh was fantastic to work with when booking our cruise. She handled everything efficiently and made the planning process simple and enjoyable. Her communication was excellent, and she was always quick to respond to our questions.
We did experience a hiccup with our flight to the cruise, which was outside her control, but Ashleigh remained calm, supportive, and did her best to assist us during the situation. That level of care and professionalism meant a lot to us.
We are very grateful for her service and would highly recommend Ashleigh to anyone looking for a reliable and dedicated travel agent.
Elena K.
about 2 months ago
Ashleigh is the person to call when you’re looking to plan a luxurious vacation that still fits within your budget and priorities. From our very first call, she made the entire process feel easy and personal—it felt less like a transaction and more like catching up with a friend about our family’s travel plans.
She helped us plan an all-inclusive resort trip to Jamaica and was incredible at narrowing down options that were truly family-friendly. She took the time to understand exactly what we needed and ensured our accommodations with the hotel were perfectly suited for our family.
Ashleigh’s passion for getting every detail right really stands out. She’s thoughtful, creative, and highly detail-oriented, and she tailors her approach to each client rather than offering a one-size-fits-all experience.
She made the entire process seamless and stress-free. I’ll absolutely be booking with her again and would highly recommend her to anyone looking to plan a well-curated, memorable vacation.
Chris O.
3 months ago
Ashleigh was fantastic from beginning to end. Our trip dates changed and she was very accommodating during our rescheduled dates. She was also proactive to provide transportation accommodations to and from the airport, along with ensuring we received the best possible hotel experience.
I highly recommend her for any travel needs!
Hawa J.
4 months ago
Oh Ashleigh…what can I say? She has helped me every step of the way. From last minute flights to rebooking. She has gone above and beyond for me! She has done more than what she has ever had to do. I would use Ashleigh as my travel agent for every trip I have going forward. Please do not hesitate to have Ashleigh book a trip for you, you won’t regret it. She will always give you her best!!! Thanks so much Ashleigh!!!
Naomi S.
16 days ago
I found Ashleigh through a referral in a community Facebook group when I was looking for a travel agent, and I’m so glad I did. From our very first phone call, she was warm, engaging, and genuinely took the time to understand what I was looking for. I immediately felt heard, and her positive, upbeat approach made me feel confident I was in good hands. She initially sent a few options, and when I explained why they weren’t the right fit for this trip, she was incredibly open and receptive. I never felt judged and she was happy to go back and find better matches. Throughout the process, she has been very responsive by text, email, and phone, and thoughtful in finding options that work within my budget. What really stands out is how quickly she “got” me. I feel completely comfortable being honest about what I like and don’t like, and she always meets that with professionalism and enthusiasm. Even when she’s not familiar with a property, she takes the initiative to gather the information needed so I can make confident decisions. Now that my trip is booked, I can confidently say I’ve found the right travel agent..dedicated, attentive, and makes you feel like a priority. I truly value this working relationship and will absolutely be using her again. I highly recommend her to anyone looking for a knowledgeable, responsive, and genuinely caring travel agent.
Thomas M.
about 2 months ago
Ashleigh was fantastic to work with when booking our cruise. She handled everything efficiently and made the planning process simple and enjoyable. Her communication was excellent, and she was always quick to respond to our questions.
We did experience a hiccup with our flight to the cruise, which was outside her control, but Ashleigh remained calm, supportive, and did her best to assist us during the situation. That level of care and professionalism meant a lot to us.
We are very grateful for her service and would highly recommend Ashleigh to anyone looking for a reliable and dedicated travel agent.
Elena K.
about 2 months ago
Ashleigh is the person to call when you’re looking to plan a luxurious vacation that still fits within your budget and priorities. From our very first call, she made the entire process feel easy and personal—it felt less like a transaction and more like catching up with a friend about our family’s travel plans.
She helped us plan an all-inclusive resort trip to Jamaica and was incredible at narrowing down options that were truly family-friendly. She took the time to understand exactly what we needed and ensured our accommodations with the hotel were perfectly suited for our family.
Ashleigh’s passion for getting every detail right really stands out. She’s thoughtful, creative, and highly detail-oriented, and she tailors her approach to each client rather than offering a one-size-fits-all experience.
She made the entire process seamless and stress-free. I’ll absolutely be booking with her again and would highly recommend her to anyone looking to plan a well-curated, memorable vacation.
Chris O.
3 months ago
Ashleigh was fantastic from beginning to end. Our trip dates changed and she was very accommodating during our rescheduled dates. She was also proactive to provide transportation accommodations to and from the airport, along with ensuring we received the best possible hotel experience.
I highly recommend her for any travel needs!