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It Takes Team Work

At Winni, we are big on team work.  
Our entire team has more than 100 years of travel industry experience combined, and we are dedicated to bringing you the best travel deals and partners for our Winni Wanderer™ newsletter, and exciting giveaway opportunities.

Sandy Cleary

Founder & CEO

Sandy (aka The High-Heeled Investor®) is our fearless leader and the inspiration behind Winni. As an award-winning travel industry entrepreneur, angel investor, philanthropist (and actual rocket scientist), Sandy, throughout her career has stressed the importance of businesses giving back and partnering with others for a good cause. Sandy received the prestigious Lifetime Achievement Award from CLIA as well as many other cruise line specific awards for her dedication to the cruise travel industry. After selling her own cruise travel business in 2017 that she built from the ground up, she decided to dedicate her time and money to investing in others that share her mission of making a positive impact in the world. After witnessing the heartbreaking and devastating impact that the pandemic had on her much loved travel industry, she decided she wanted to “jump back in” and be a part of the industry rebuild. She worked with her Winni Marketing team to develop a multifaceted process that benefits consumers, travel suppliers and agents alike. The value of this process was that it was not only affordable but also increased potential leads, converted more sales, introduced first-timers to the joy of travel, as well as keeping the interest of veteran travelers piqued.

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Her mission… To partner with travel industry businesses that have her similar passion, drive, and ethics while bringing her in-depth knowledge and experience of the travel industry to the table to find unique travel opportunities for Winni Wanderer ™ consumers.

Sandy tells Winni… “Wanderlust is real and travel is the only way to soothe a wandering soul. Traveling brings an inner peace and unique knowledge of the world around us. The more we travel, the smaller we realize both the world itself, and our differences, actually are.”  


Favorite places Sandy Has traveled… Las Vegas, Napa, Hawaii, Alaska, Australia, Galapagos, and


Sandy’s bucket list destinations/experiences… African Safari, Antarctica, Machu Picchu... and a Blue Origin or Space-X flight into space (After all, she is a rocket scientist 😉)

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Darlene Carenza

Director of Marketing & Strategy

Darlene has more than 18 years of experience in marketing and copywriting for brands such as Travelzoo, Sony Pictures, Cotton Incorporated and CBS Sports. She has worked closely with some of the biggest cruise, air, hotel and resort brands in the travel industry to deliver a well-rounded approach to the creation of lead generation campaigns, travel content and travel deals for consumers.

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Her mission… To inform and inspire our readers, and to help them reignite their passion for travel and create meaningful experiences that leave a lasting impact.


Darlene tells Winni… “Some of my favorite childhood memories were when my mother would wake me up on a Saturday morning and tell me to “pack up” because we were getting in the car and driving somewhere. We didn’t have a lot of money to spend (or a plan), but it didn’t matter. We lived in upstate New York at the time, so we’d drive to a New England seaside village, a small town in Vermont, across the border to Montreal to see a baseball game, or just camp out at the nearest campground and explore. We even drove cross-country when I graduated college. This sparked my love of travel, and I’ve been lucky enough to build a career in the travel industry, and expand my travels beyond the U.S., but it is memories like these that I want to help others create. It is my hope that Winni Wanderer will be a source of inspiration to others to just “pack up” and explore.


Favorite places Darlene has traveled… Maine; Hawaii (all of the islands); Positano & Venice/Italy; Laguna Beach, California; Park City, Utah; Disney World and Disneyland.


Darlene’s bucket list destinations/experiences… Australia, Lake Louise (Canada), Paris, and a cross country road trip with my family (like I did with my parents when I graduated college 😊).

We’d love to hear from you!

Our content creators, deal hunters and website designers are behind the scenes putting their heart and soul into bringing you, the traveler, all of the deals, tips and giveaways that keep the wanderlust spark alive. Our passion lies not only in travel but partnering with travel suppliers and sharing the best kept insider tips to make traveling easy and more enjoyable. We love to hear from all of you about your adventures and invite you to drop us a line with some of your best travel tips.  We live to wander, and hope you will too!
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