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 (26)
Kate D.
20 days ago
Booking with Cindy makes biking travel stress free! For this trip, she was able to get us an amazing upgrade and welcomed us with a bottle of champagne! She is my new favorite part of traveling!
Doug J.
24 days ago
Cindy is an absolute rockstar. We literally had nothing to worry about other than enjoying our trip. Whether it was the accommodations, transfers, dining recommendations or even assisting in getting the most beautiful flower arrangement sent to our room for Valentines day, Cindy took care of it all.
Shadi M.
a month ago
Cindy is great! She helped us find a place last minute when our house fell through. She coordinated the whole thing and the place was ready before we arrived. And we got a lovely welcome gift.
Michelle S.
2 months ago
Cindy went above and beyond to make my stay an enjoyable experience and I really appreciated the thoughtful details and effort she put in to ensure I was happy with my room and the hotel.
Eric W.
2 months ago
Cindy is amazing! Very knowledgeable and easy to speak to. She knew what I was looking for without me having to tell her. I highly recommend her.
Kate D.
20 days ago
Booking with Cindy makes biking travel stress free! For this trip, she was able to get us an amazing upgrade and welcomed us with a bottle of champagne! She is my new favorite part of traveling!
Doug J.
24 days ago
Cindy is an absolute rockstar. We literally had nothing to worry about other than enjoying our trip. Whether it was the accommodations, transfers, dining recommendations or even assisting in getting the most beautiful flower arrangement sent to our room for Valentines day, Cindy took care of it all.
Shadi M.
a month ago
Cindy is great! She helped us find a place last minute when our house fell through. She coordinated the whole thing and the place was ready before we arrived. And we got a lovely welcome gift.
Michelle S.
2 months ago
Cindy went above and beyond to make my stay an enjoyable experience and I really appreciated the thoughtful details and effort she put in to ensure I was happy with my room and the hotel.
Travel photos
