Cindy Pearlstein
Based in Miami Beach, FL
English
Cindy Pearlstein
Ask me about
My Story
I spent over a decade as an Executive Assistant in the fashion industry, supporting some of the world’s most discerning travelers. My early career as a flight attendant refined my eye for detail and instilled a deep understanding of elevated service. A childhood lived in many places—yet rooted in Hawai’i—sparked a lifelong passion for travel and inspired a career dedicated to curating exceptional experiences. After 16 years in New York City, I now call Miami Beach home. Beyond travel, I am a mom, wife, and philanthropist who finds joy in Pilates, hot yoga, tennis, and cooking—always seeking balance, connection, and discovery.
Travel Style
With a multicultural background, a childhood between Europe and Hawai’i, and travels to over 35 countries, I bring a refined global perspective to every journey I design. A self-confessed hotel snob and passionate foodie, I seek out the perfect balance of luxury and local flavor—whether that means a Michelin-starred dining room or a family-run spot off the beaten path. I curate bespoke, seamless, and meaningful experiences that go far beyond the ordinary, always with a discerning eye for service and detail.
Reviews (20)
Chelsea M.
24 days ago
Cindy has been an incredible advisor. She’s improved our vacations tremendously just in the short time of using her.
LLoyd S.
a month ago
Cindy is the best, will go 1,000 miles to anticipate client needs and do everything she can to ensure 11/10 experience!
Caroline F.
3 months ago
In a wink of an eye, Cindy had made us a reservation at our hotel, with a lot of perks and a better rate. She goes beyond to help you out with hotels and restaurants. I would recommend Cindy anytime
Ashley G.
3 months ago
Seamless booking experience and Cindy pushed for an amazing upgrade. She also put me in touch with the concierge knowing I loved to workout so that they could book me into local fitness classes. Incredible service - thank you!
Rachael D.
3 months ago
Cindy manages everything and thinks above and beyond about every detail. The process to book with her is always enjoyable because she identifies what’s important to you, gives a range of options and guides you through the decision process. Picking a hotel can be overwhelming but she makes it enjoyable and I’m always confident that wherever I end up staying I’ll be treated to special amenities, most likely an upgrade and that if anything goes awry I have an advocate on my side who is responsive and thorough. I love booking with Cindy!
Chelsea M.
24 days ago
Cindy has been an incredible advisor. She’s improved our vacations tremendously just in the short time of using her.
LLoyd S.
a month ago
Cindy is the best, will go 1,000 miles to anticipate client needs and do everything she can to ensure 11/10 experience!
Caroline F.
3 months ago
In a wink of an eye, Cindy had made us a reservation at our hotel, with a lot of perks and a better rate. She goes beyond to help you out with hotels and restaurants. I would recommend Cindy anytime
Ashley G.
3 months ago
Seamless booking experience and Cindy pushed for an amazing upgrade. She also put me in touch with the concierge knowing I loved to workout so that they could book me into local fitness classes. Incredible service - thank you!
Travel photos
