Lindsay Fein

After a successful decade long career in non-profit development and fundraising, I took a leap in my mid-thirties to pursue a passion that had always been at the center of my life: travel. What started as helping friends and family plan vacations quickly grew into a thriving business built around one simple goal, helping clients create unforgettable memories with the people they love most.

Today, I work with families, couples, and groups to design seamless vacations that balance relaxation, adventure, and meaningful experiences. Whether it’s a luxury all-inclusive escape in Mexico, a multi-generational trip to the Caribbean, a magical Disney vacation, or an action-packed Universal theme park getaway, I help clients navigate the countless options and details so they can focus on enjoying the journey.

As a frequent traveler and resort visitor, I regularly tour hotels and destinations throughout Mexico and the Caribbean, allowing me to provide firsthand recommendations tailored to each client’s travel style and priorities. From family-friendly resorts with incredible kids’ programs to adults-only luxury retreats and celebration travel for birthdays, anniversaries, and milestone moments, I believe every vacation should feel uniquely designed for the people taking it.

As a Disney Destinations specialist with advanced destination training and extensive firsthand experience, I help families maximize their time, understand ever-changing planning strategies, and create stress-free vacations filled with magical moments. I also specialize in Universal Orlando and Hollywood vacations, helping clients navigate resort options, Express Pass strategies, and everything needed to make the most of their time in the parks.

I have helped hundreds of travelers plan vacations ranging from weekend getaways to bucket-list adventures, earning recognition as a top-producing advisor within Small World BIG FUN. My approach is equal parts expert guidance and personal service because I know that the best vacations aren’t just about where you go. They’re about the memories you bring home.

When I’m not planning travel, you’ll usually find me exploring new destinations with my husband and three daughters. You can also find me working on the PTA Board my local elementary school, playing mahjong with friends, or catching up on my favorite Bravo shows.

I believe great stories start with a boarding pass, and I’d love to help you start writing your next one.