
Ashley Yann
Based in Hawaiian Islands
Trip budgets start at $500/night
Ashley Yann
Ask me about
My Story
I’m based in Hawai‘i and specialize in luxury hotels, boutique resorts, and wellness-focused getaways. I love curating seamless travel experiences that blend relaxation, culture, and a touch of indulgence. My travel has taken me across Japan, Mexico, South Africa, and Europe—always in search of the next incredible property to share with my clients.
My Travel Style
Give me a spa day in Kyoto, a mezcal tasting in Oaxaca, or a sunset sail along the Hawaiian coast—I’m in my happy place. I love blending culture, cuisine, and luxury in every trip I plan. It’s all about feeling good, eating well, and exploring the world with style and soul.
My reviews (4)
Josue G.
13 days ago
Ashley was amazing! She helped us plan our honeymoon to Maui and Lanai within a few weeks. Her recommendations for resorts, experiences, and tips were so appreciated. She definitely knows top tier recommendations and couldn’t be more thankful. We’ll be using her again soon! Thank you, Ashley!
Catherine V.
10 months ago
Ashley made planning this trip feel effortless. She took the time to understand my travel preferences and made thoughtful recommendations that perfectly matched the kind of experience I was hoping for. Her communication was always clear, professional, friendly, and very timely, which made the whole process smooth and stress-free, which is always important to me but even more so nearing the end of my pregnancy.
Her recommendations truly enhanced my stay. I especially loved the sound bath she suggested. It was not something I would have chosen on my own, but it became one of the most memorable parts of my trip and I would absolutely book it again. Ashley also encouraged me to plan extra time at the private hale after my spa treatments, and I wish I had taken her advice. Next time I certainly will.
I really appreciated how she balanced listening to my preferences with introducing experiences I might not have considered. The result was a trip that felt personalized, elevated, and deeply enjoyable. I have worked with Ashley several times and will definitely work with her again. I highly recommend her for anyone looking for a trusted travel advisor who makes every detail count. Ashley ensures that whatever the occasion is for your travel (even just because) it’s marked with special touches that make the celebration unforgettable.
Lynda D.
a year ago
Ashley was wonderful to work with! She listened to our hopes and wishes for this trip and made them all come true! She offered suggestions to make the trip even more than we expected!
Jennifer B.
3 years ago
I'm deeply grateful to Ashley for booking this experience for me. She has an incredible gift for seeing/understanding people and what their travel needs are, even when they aren't sure for themselves. At a time in my life when I wasn't sure what I was exactly looking for in a travel experience, she knew exactly how and what to plan and how to support me and my adventure. Her thoughtfulness, intuition, and attention to detail created something truly special.
It was more than just booking a trip, it was about creating and placing me in a nurturing environment and providing an opportunity for growth and renewal that I am so thankful for.
Josue G.
13 days ago
Ashley was amazing! She helped us plan our honeymoon to Maui and Lanai within a few weeks. Her recommendations for resorts, experiences, and tips were so appreciated. She definitely knows top tier recommendations and couldn’t be more thankful. We’ll be using her again soon! Thank you, Ashley!
Catherine V.
10 months ago
Ashley made planning this trip feel effortless. She took the time to understand my travel preferences and made thoughtful recommendations that perfectly matched the kind of experience I was hoping for. Her communication was always clear, professional, friendly, and very timely, which made the whole process smooth and stress-free, which is always important to me but even more so nearing the end of my pregnancy.
Her recommendations truly enhanced my stay. I especially loved the sound bath she suggested. It was not something I would have chosen on my own, but it became one of the most memorable parts of my trip and I would absolutely book it again. Ashley also encouraged me to plan extra time at the private hale after my spa treatments, and I wish I had taken her advice. Next time I certainly will.
I really appreciated how she balanced listening to my preferences with introducing experiences I might not have considered. The result was a trip that felt personalized, elevated, and deeply enjoyable. I have worked with Ashley several times and will definitely work with her again. I highly recommend her for anyone looking for a trusted travel advisor who makes every detail count. Ashley ensures that whatever the occasion is for your travel (even just because) it’s marked with special touches that make the celebration unforgettable.
Lynda D.
a year ago
Ashley was wonderful to work with! She listened to our hopes and wishes for this trip and made them all come true! She offered suggestions to make the trip even more than we expected!
Jennifer B.
3 years ago
I'm deeply grateful to Ashley for booking this experience for me. She has an incredible gift for seeing/understanding people and what their travel needs are, even when they aren't sure for themselves. At a time in my life when I wasn't sure what I was exactly looking for in a travel experience, she knew exactly how and what to plan and how to support me and my adventure. Her thoughtfulness, intuition, and attention to detail created something truly special.
It was more than just booking a trip, it was about creating and placing me in a nurturing environment and providing an opportunity for growth and renewal that I am so thankful for.
My travel ideas (2)

Vintage Heaven in Omotesandō, Tokyo: Designer Finds in One Afternoon
If you want to spend an afternoon diving into Tokyo’s best luxury vintage shopping, Omotesando is your answer. This stylish neighborhood is home to three of Tokyo’s most coveted vintage boutiques, all within walking distance of each other. Start your designer treasure hunt at QOO Vintage and AMORE. If you need to refuel mid-shop, take a little break and grab a bite at Kaiten Sushi Ginza Onodera, conveniently located right between AMORE and QOO. Then grab a matcha pick-me-up at THE MATCHA TOKYO before finishing strong at Casanova Vintage. It’s vintage heaven on a perfectly curated loop, and no criss-crossing of the city is required.

Vintage Heaven in Omotesandō, Tokyo: Designer Finds in One Afternoon
If you want to spend an afternoon diving into Tokyo’s best luxury vintage shopping, Omotesando is your answer. This stylish neighborhood is home to three of Tokyo’s most coveted vintage boutiques, all within walking distance of each other. Start your designer treasure hunt at QOO Vintage and AMORE. If you need to refuel mid-shop, take a little break and grab a bite at Kaiten Sushi Ginza Onodera, conveniently located right between AMORE and QOO. Then grab a matcha pick-me-up at THE MATCHA TOKYO before finishing strong at Casanova Vintage. It’s vintage heaven on a perfectly curated loop, and no criss-crossing of the city is required.

A Breezy Guide to Oahu’s Best Beaches and Activities
Oahu holds a special place in my heart because it encapsulates the perfect blend of natural beauty and adventurous spirit. The beaches here are more than just stretches of sand; they are gateways to unforgettable experiences, from the serene sunrises at Lanikai to the exhilarating cliff jumps at Waimea. Each visit offers a new perspective, a fresh adventure and a deeper connection to nature. The island's diverse landscapes and vibrant marine life continually inspire and rejuvenate me, making Oahu not just a destination, but a cherished sanctuary.

A Breezy Guide to Oahu’s Best Beaches and Activities
Oahu holds a special place in my heart because it encapsulates the perfect blend of natural beauty and adventurous spirit. The beaches here are more than just stretches of sand; they are gateways to unforgettable experiences, from the serene sunrises at Lanikai to the exhilarating cliff jumps at Waimea. Each visit offers a new perspective, a fresh adventure and a deeper connection to nature. The island's diverse landscapes and vibrant marine life continually inspire and rejuvenate me, making Oahu not just a destination, but a cherished sanctuary.

Vintage Heaven in Omotesandō, Tokyo: Designer Finds in One Afternoon
If you want to spend an afternoon diving into Tokyo’s best luxury vintage shopping, Omotesando is your answer. This stylish neighborhood is home to three of Tokyo’s most coveted vintage boutiques, all within walking distance of each other. Start your designer treasure hunt at QOO Vintage and AMORE. If you need to refuel mid-shop, take a little break and grab a bite at Kaiten Sushi Ginza Onodera, conveniently located right between AMORE and QOO. Then grab a matcha pick-me-up at THE MATCHA TOKYO before finishing strong at Casanova Vintage. It’s vintage heaven on a perfectly curated loop, and no criss-crossing of the city is required.

Vintage Heaven in Omotesandō, Tokyo: Designer Finds in One Afternoon
If you want to spend an afternoon diving into Tokyo’s best luxury vintage shopping, Omotesando is your answer. This stylish neighborhood is home to three of Tokyo’s most coveted vintage boutiques, all within walking distance of each other. Start your designer treasure hunt at QOO Vintage and AMORE. If you need to refuel mid-shop, take a little break and grab a bite at Kaiten Sushi Ginza Onodera, conveniently located right between AMORE and QOO. Then grab a matcha pick-me-up at THE MATCHA TOKYO before finishing strong at Casanova Vintage. It’s vintage heaven on a perfectly curated loop, and no criss-crossing of the city is required.

A Breezy Guide to Oahu’s Best Beaches and Activities
Oahu holds a special place in my heart because it encapsulates the perfect blend of natural beauty and adventurous spirit. The beaches here are more than just stretches of sand; they are gateways to unforgettable experiences, from the serene sunrises at Lanikai to the exhilarating cliff jumps at Waimea. Each visit offers a new perspective, a fresh adventure and a deeper connection to nature. The island's diverse landscapes and vibrant marine life continually inspire and rejuvenate me, making Oahu not just a destination, but a cherished sanctuary.

A Breezy Guide to Oahu’s Best Beaches and Activities
Oahu holds a special place in my heart because it encapsulates the perfect blend of natural beauty and adventurous spirit. The beaches here are more than just stretches of sand; they are gateways to unforgettable experiences, from the serene sunrises at Lanikai to the exhilarating cliff jumps at Waimea. Each visit offers a new perspective, a fresh adventure and a deeper connection to nature. The island's diverse landscapes and vibrant marine life continually inspire and rejuvenate me, making Oahu not just a destination, but a cherished sanctuary.