Advisor - Cindy Pearlstein

Cindy Pearlstein

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  • Based in icon

    Based in Miami Beach, FL

  • Based in icon

    English

Ask me about

Food & Wine
Luxury Travel
NYC
Miami
Tokyo
Europe

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)

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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.

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!

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

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!

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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!

Travel photos

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