Kaitlan Leonard
She/Her
Based in Dallas, Texas (and often elsewhere)
Trips starting at $500/night
Bespoke Escapes
Ask us about
Our Story
My journey began in Ireland, on the trip where my husband proposed. Something shifted for me there. I realized travel isn’t about the destination or the itinerary—it’s about the moments that stay with you long after you’ve come home.
Since then, and over the past decade, I’ve explored over 50 countries across all seven continents—from the vast plains of Kenya to the raw silence of Patagonia, from the coastlines of Greece to the remote lodges of Indonesia. Each experience has deepened my understanding of what separates a good journey from an extraordinary one: intention, access, and an unwavering attention to detail.
Before founding Bespoke Escapes, I built a career in corporate marketing, technology, and project management—and that foundation shapes every aspect of how I run my business. The precision, the structure, the ability to anticipate complexity before it becomes a problem—these are as essential as the travel expertise itself.
What drives it all, though, is a genuine love for the people I work with. Getting to know my clients—how they travel, what they love, what they’re hoping to experience—makes the planning process something I look forward to as much as the journey itself. The best trips I’ve designed have always started with a great conversation.
Travel Style
My career in luxury travel has been shaped by a deep belief exceptional travel requires more than destination knowledge—it requires a genuine understanding of what makes a journey truly unforgettable. Throughout my career, I’ve built the relationships, the expertise, and the exacting standards that translate into journeys my clients remember for a lifetime.
As a Virtuoso-affiliated advisor and Condé Nast Top Travel Specialist, I bring both the access and the artistry that exceptional travel deserves.
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Reviews (12)
Brandyn D.
travel to Mykonos
3 months ago
Kaitlan is incredible! Communication was always timely, clear, detailed, and always helpful - not much back and forth, more so just: “here is everything you could need!”. Kaitlan did an excellent job taking our preferences into account and providing fitting recommendations for us despite this being our first trip together. It was a truly seamless experience and we especially appreciate Kaitlan pulling together an amazing trip under very short notice for us. Thank you, thank you, thank you.
Nikki F.
travel to Mallorca
3 months ago
Kaitan was super helpful, responsive, and great overall.
Lillie H.
travel to Hawai'i
3 months ago
Kaitlan was communicative, timely, and answered all the questions I had. We just used her hotel booking link but the free breakfast and $100 resort credit were a great bonus - anything to save some money in Hawaii!
Katherine S.
travel to Hawai'i
over 1 year ago
I love booking with Kaitlan! It's been life changing! Booking Sensei through Kaitlan ensures you get the best price, a room credit, and included breakfast which is an incredible deal on a gorgeous property. The first time I booked at Sensei with Kaitlan, she was able to negotiate a rate that was no longer published which saved me money on the room, which I happily spent on property
Mo B.
travel to Aruba
over 1 year ago
Kaitlan is the best, so helpful and accommodating. She ensures everything about your stay is taken care of. She is helpful and organized, - I love working with her.
Brandyn D.
travel to Mykonos
3 months ago
Kaitlan is incredible! Communication was always timely, clear, detailed, and always helpful - not much back and forth, more so just: “here is everything you could need!”. Kaitlan did an excellent job taking our preferences into account and providing fitting recommendations for us despite this being our first trip together. It was a truly seamless experience and we especially appreciate Kaitlan pulling together an amazing trip under very short notice for us. Thank you, thank you, thank you.
Nikki F.
travel to Mallorca
3 months ago
Kaitan was super helpful, responsive, and great overall.
Lillie H.
travel to Hawai'i
3 months ago
Kaitlan was communicative, timely, and answered all the questions I had. We just used her hotel booking link but the free breakfast and $100 resort credit were a great bonus - anything to save some money in Hawaii!
Katherine S.
travel to Hawai'i
over 1 year ago
I love booking with Kaitlan! It's been life changing! Booking Sensei through Kaitlan ensures you get the best price, a room credit, and included breakfast which is an incredible deal on a gorgeous property. The first time I booked at Sensei with Kaitlan, she was able to negotiate a rate that was no longer published which saved me money on the room, which I happily spent on property
Travel ideas (7)
Wine, Dine & Adventure in South Africa
South Africa is one of my favorite places to visit - it truly has it all. You can explore the city for a few days, hike, head to the beach, explore wine country, and then end your trip on a relaxing, yet epic, safari. It's a beautiful and friendly country that makes for an ideal honeymoon or couples trip for any foodie or adventurer.
Wine, Dine & Adventure in South Africa
South Africa is one of my favorite places to visit - it truly has it all. You can explore the city for a few days, hike, head to the beach, explore wine country, and then end your trip on a relaxing, yet epic, safari. It's a beautiful and friendly country that makes for an ideal honeymoon or couples trip for any foodie or adventurer.
Insider’s Guide to St. Barths
St. Barths is a Caribbean gem like no other. Renowned for its upscale boutiques, stunning beaches, world-class dining, and vibrant beach clubs and nightlife, it offers an unparalleled blend of luxury and charm. But to truly experience all that St. Barths has to offer, thoughtful planning is essential — from booking the most sought-after accommodations and managing complex transfers to securing those hard-to-get restaurant reservations.
Insider’s Guide to St. Barths
St. Barths is a Caribbean gem like no other. Renowned for its upscale boutiques, stunning beaches, world-class dining, and vibrant beach clubs and nightlife, it offers an unparalleled blend of luxury and charm. But to truly experience all that St. Barths has to offer, thoughtful planning is essential — from booking the most sought-after accommodations and managing complex transfers to securing those hard-to-get restaurant reservations.
A Luxurious Journey Through the Greek Islands
Greece is an exceptional destination for milestone celebrations — whether it’s a birthday, anniversary, honeymoon or a multigenerational getaway. It offers the perfect blend of adventure, history, natural beauty and relaxation. While Santorini is a perennial favorite, Greece’s magic extends far beyond its most well-known islands, revealing hidden gems waiting to be explored.
A Luxurious Journey Through the Greek Islands
Greece is an exceptional destination for milestone celebrations — whether it’s a birthday, anniversary, honeymoon or a multigenerational getaway. It offers the perfect blend of adventure, history, natural beauty and relaxation. While Santorini is a perennial favorite, Greece’s magic extends far beyond its most well-known islands, revealing hidden gems waiting to be explored.
Voyage to Antarctica with Lindblad National Geographic Endurance
In December 2024, I embarked on an unforgettable expedition cruise with Lindblad aboard the National Geographic Endurance. This state-of-the-art icebreaker ship boasts six decks and an impressive range of amenities, including a spa, two exquisite dining venues, a cocktail lounge, a library, a gym, hot tubs, fire pits, and even cozy igloos! While the onboard luxuries are remarkable, the true highlight of the journey was the adventure itself. With two daily excursions led by incredibly knowledgeable naturalists, the experience was nothing short of extraordinary. I would return in a heartbeat and wholeheartedly recommend this once-in-a-lifetime voyage to anyone dreaming of exploring the 7th continent!
Voyage to Antarctica with Lindblad National Geographic Endurance
In December 2024, I embarked on an unforgettable expedition cruise with Lindblad aboard the National Geographic Endurance. This state-of-the-art icebreaker ship boasts six decks and an impressive range of amenities, including a spa, two exquisite dining venues, a cocktail lounge, a library, a gym, hot tubs, fire pits, and even cozy igloos! While the onboard luxuries are remarkable, the true highlight of the journey was the adventure itself. With two daily excursions led by incredibly knowledgeable naturalists, the experience was nothing short of extraordinary. I would return in a heartbeat and wholeheartedly recommend this once-in-a-lifetime voyage to anyone dreaming of exploring the 7th continent!
Miami Beach EDITION Site Inspection
I had the pleasure of experiencing the Miami Beach EDITION this Monday for a site inspection. The hotel had a very modern and minimalist feel to it! Very family-friendly as all pools accommodates children.
Miami Beach EDITION Site Inspection
I had the pleasure of experiencing the Miami Beach EDITION this Monday for a site inspection. The hotel had a very modern and minimalist feel to it! Very family-friendly as all pools accommodates children.
From City Life to Wine Tasting, Argentina Has It All
Argentina is a beautiful country with welcoming locals, as well as a plethora of places to explore. Take advantage of both city and country life by splitting your time between Buenos Aires and Mendoza, and make sure to leave enough time to visit an Estancia along the way! Year round warm & mild weather makes it an opportune location to visit year round.
From City Life to Wine Tasting, Argentina Has It All
Argentina is a beautiful country with welcoming locals, as well as a plethora of places to explore. Take advantage of both city and country life by splitting your time between Buenos Aires and Mendoza, and make sure to leave enough time to visit an Estancia along the way! Year round warm & mild weather makes it an opportune location to visit year round.
A Mix of Luxury & Adventure in Kenya & Zanzibar
Kenya is a wonderful destination for a safari - you'll feel like you're in the Lion King with the open fields, trees, landscape, and abundance of animals. It's hard to miss the big five in the Masai Mara, and the number of lions alone was incredible. Make your time in Kenya more worthwhile by starting or ending your time here in Nairobi and explore all the city has to offer. On your way home, be sure to stop in Zanzibar, for some relaxation with pristine beaches and accommodations, and even mix in some adventure by diving or snorkeling.
A Mix of Luxury & Adventure in Kenya & Zanzibar
Kenya is a wonderful destination for a safari - you'll feel like you're in the Lion King with the open fields, trees, landscape, and abundance of animals. It's hard to miss the big five in the Masai Mara, and the number of lions alone was incredible. Make your time in Kenya more worthwhile by starting or ending your time here in Nairobi and explore all the city has to offer. On your way home, be sure to stop in Zanzibar, for some relaxation with pristine beaches and accommodations, and even mix in some adventure by diving or snorkeling.
Wine, Dine & Adventure in South Africa
South Africa is one of my favorite places to visit - it truly has it all. You can explore the city for a few days, hike, head to the beach, explore wine country, and then end your trip on a relaxing, yet epic, safari. It's a beautiful and friendly country that makes for an ideal honeymoon or couples trip for any foodie or adventurer.
Wine, Dine & Adventure in South Africa
South Africa is one of my favorite places to visit - it truly has it all. You can explore the city for a few days, hike, head to the beach, explore wine country, and then end your trip on a relaxing, yet epic, safari. It's a beautiful and friendly country that makes for an ideal honeymoon or couples trip for any foodie or adventurer.
Insider’s Guide to St. Barths
St. Barths is a Caribbean gem like no other. Renowned for its upscale boutiques, stunning beaches, world-class dining, and vibrant beach clubs and nightlife, it offers an unparalleled blend of luxury and charm. But to truly experience all that St. Barths has to offer, thoughtful planning is essential — from booking the most sought-after accommodations and managing complex transfers to securing those hard-to-get restaurant reservations.
Insider’s Guide to St. Barths
St. Barths is a Caribbean gem like no other. Renowned for its upscale boutiques, stunning beaches, world-class dining, and vibrant beach clubs and nightlife, it offers an unparalleled blend of luxury and charm. But to truly experience all that St. Barths has to offer, thoughtful planning is essential — from booking the most sought-after accommodations and managing complex transfers to securing those hard-to-get restaurant reservations.
A Luxurious Journey Through the Greek Islands
Greece is an exceptional destination for milestone celebrations — whether it’s a birthday, anniversary, honeymoon or a multigenerational getaway. It offers the perfect blend of adventure, history, natural beauty and relaxation. While Santorini is a perennial favorite, Greece’s magic extends far beyond its most well-known islands, revealing hidden gems waiting to be explored.
A Luxurious Journey Through the Greek Islands
Greece is an exceptional destination for milestone celebrations — whether it’s a birthday, anniversary, honeymoon or a multigenerational getaway. It offers the perfect blend of adventure, history, natural beauty and relaxation. While Santorini is a perennial favorite, Greece’s magic extends far beyond its most well-known islands, revealing hidden gems waiting to be explored.