The foundation of Tripsy Travel was set in 1993, when founder Cyndi Williams began her career in the travel industry. After decades of extensive global travel, elite industry connections, and the design of highly complex itineraries for discerning travelers, Cyndi launched her own agency; built on the principles of precision, discretion, and uncompromising excellence.
Today, Tripsy Travel stands as a nationally recognized, award-winning luxury travel agency, known for delivering hyper-curated, fully bespoke travel experiences. Our work has been featured in leading media outlets, celebrated for exceptional client service and mastery in designing itineraries that exceed expectations at every level.
Bespoke Itineraries – Every journey is uniquely designed to reflect your individual tastes, travel style, and priorities.
Exclusive Access – Privileged entry to experiences, properties, and services unavailable to the public, through our extensive network of global luxury partners.
Comprehensive Management – Every detail—flights, accommodations, transfers, dining, and private experiences—is handled with precision, ensuring a seamless travel experience from departure to return.
Expert Navigation – Our decades of specialist training and destination expertise eliminate uncertainty and save valuable time, while maximizing the return on your travel investment.
Exceptional Value – Through strategic industry relationships, we provide enhanced benefits, preferred rates, and exclusive amenities that elevate every aspect of your journey.
We are trusted by clients nationwide who require white-glove service, absolute discretion, and consistently exceptional results. At Tripsy Travel, we don’t just plan travel. We design experiences that redefine luxury and create memories to last a lifetime.
Certified Travel Agency® Owner
Cyndi Williams, is a respected authority in luxury travel with over three decades of experience curating exceptional journeys. As the founder of Tripsy Travel, she is widely recognized as an industry leader, advocate, and innovator, featured in national media, honored with prestigious awards, and trusted by clients who expect only the very best.
Long before luxury travel was a trend, Cyndi was circling the globe, collecting passport stamps, exploring hidden gems, and experiencing the world’s most extraordinary destinations. Her lifelong passion for travel, coupled with a visionary approach to client service, shaped the foundation of Tripsy Travel: a boutique agency dedicated to crafting seamless, extraordinary experiences for discerning travelers.
Under her leadership, Tripsy has earned a reputation as one of the premier luxury boutique agencies in the industry. Her client-centric philosophy goes beyond planning trips; it is about understanding the lifestyles, preferences, and expectations of each client, and transforming them into once-in-a-lifetime journeys with impeccable attention to detail.
Cyndi is also a proud member of ASTA, Travel Leaders, CLIA, and IATAN, and she continues to serve as a voice for the travel industry through her ongoing advocacy work.
“For me, true luxury travel isn’t about checking boxes on a list, it’s about creating moments that feel effortless, rare, and unforgettable.”
– Cyndi Williams, Founder
Learn about Cyndi’s Certification here: https://wanderlustceo.com/certified-travel-agency/
Certified Travel Professional®
Stephani brings a global perspective and deep hospitality expertise to her role as Vice President of Operations at Tripsy Travel. With a degree in Hospitality and Tourism and over 15 years of immersive international living, she has experienced the world in a way few travel professionals can, swimming with manta rays in Hawaii, cycling the seawall in Vancouver, savoring the best of Texas barbecue in Austin, and exploring the cultural and natural treasures of Canada from coast to coast.
Her career began in luxury hotels and resorts, where she gained firsthand knowledge of the high standards and refined operations that discerning travelers expect. That foundation, paired with her extensive global experience, including studying abroad in Namibia while adventuring through diverse ecosystems and conservation projects, shaped her passion for curating exceptional journeys that combine exploration, comfort, and exclusivity.
As VP of Operations, Stephani oversees the seamless execution of Tripsy Travel’s bespoke services while continuing to specialize in Hawaii, select Canadian destinations, and luxury cruising. Her visionary approach ensures that every detail is flawlessly managed, allowing clients to experience the world in ways that are both deeply personal and effortlessly exceptional.
“Luxury travel is about discovering the world in ways that feel deeply personal, yet effortlessly exceptional.” – Stephani Voge
Learn about Stephani’s Certification here: https://wanderlustceo.com/certified-travel-professional/
Certified Travel Professional®
Samantha brings a lifetime of global experience and a professional foundation in hospitality to her role as a Luxury Travel Planner at Tripsy Travel. Born and raised in Chicago as the daughter of two airline professionals, she was traveling internationally before she could walk, visiting Egypt, China, France, and the UK all before the age of ten.
Her passion for travel led her to earn a Bachelor’s Degree in Travel Industry Management, after which she spent a decade in leadership roles at luxury hotels across Hawaii. Her career later brought her to Austin and Los Angeles, where she continues to combine her hospitality expertise with her love of curating extraordinary journeys for discerning clients.
With 43 countries visited and more than 20 cruises experienced firsthand, Samantha specializes in designing bespoke international itineraries that reflect both cultural authenticity and elevated comfort. From the beaches of the Maldives (her personal favorite escape) to the safaris of Kenya, the coastlines of Croatia, or the vineyards of France, she crafts journeys that balance adventure with indulgence, ensuring every trip is seamless, personalized, and unforgettable.
“The greatest luxury in travel is experiencing the world in a way that feels uniquely your own.”–Samantha Jayakumar
Learn about Samantha’s Certification here: https://wanderlustceo.com/certified-travel-professional/
Certified Travel Professional®
With decades of experience in the travel industry, Tana brings both seasoned expertise and a personal passion for exploration to her role as a Luxury Travel Planner at Tripsy Travel. She began her career with Clipper Cruise Lines, where she sailed along the U.S. East Coast and down through the Virgin Islands aboard one of the world’s most distinctive small ships. That early experience immersed her in the elegance of yacht-style cruising and gave her a rare opportunity to explore iconic waterways, vibrant cities, and cultural landmarks while connecting with travelers from around the globe.
Since then, Tana has continued to travel extensively, refining her knowledge of destinations and deepening her appreciation for the transformative power of travel. Today, she specializes in creating seamless, elevated itineraries for clients who want to experience the Caribbean, Hawaii, luxury cruises, yacht charters, all-inclusive escapes, and curated U.S. getaways.
Tana is known for her warm approach and her ability to translate her lifelong love of travel into extraordinary journeys for her clients. Her guiding philosophy is simple yet powerful:
“Whether I’m traveling myself or planning through you, creating unforgettable moments is what makes me feel alive.” – Tana Boyne
Learn about Tana’s Certification here: https://wanderlustceo.com/certified-travel-professional/
Viel Dela Torre brings years of hospitality and administrative expertise to her role on the Tripsy Travel operations team. With a degree in Hospitality Management and an international internship at a luxury resort in Japan, Viel’s career reflects both a global perspective and a commitment to excellence in service.
Her background spans quality assurance, contract processing, and front-of-house roles in some of Orlando’s most recognized resorts. This breadth of experience has honed her precision in managing complex documentation, her discretion in handling client information, and her dedication to delivering the seamless support required in luxury travel operations.
At Tripsy Travel, Viel ensures that the intricate details behind every journey are flawlessly executed, allowing our travel professionals to focus entirely on crafting exceptional client experiences. Her strengths in organization, cross-departmental coordination, and hospitality service standards make her an invaluable part of the team that powers our exclusive, concierge-level service.
“The magic of luxury travel happens when the details are seamless, my role is to make sure every detail supports the extraordinary.” – Viel Dela Torre
Learn about Viel’s designation here: https://wanderlustceo.com/associate-travel-professional/
