Meet THE Team
Our award-winning team here at Tripsy Travel is delighted to help craft a vacation beyond your wildest expectations. We understand that a vacation is an investment of your time and resources and we pride ourselves on collaborating with you to deliver a fantastic adventure, packed with unique surprises and all the experiences you are hoping for.
We treat every client like family, crafting each vacation like it is our own, down to the smallest detail. Our years of experience in the industry enable us to design truly unique and custom experiences, save you time and stress, and deliver exceptional vacations year after year.
Cyndi Williams
Founder and CEO
Cyndi Williams is a travel industry veteran with over 20 years of experience. Regarded as an industry leader, influencer, and advocate; Cyndi has been featured in the media, won national awards, and works regularly on behalf of travel industry advocacy.
Before wanderlust was a buzz word, Cyndi was traveling the world, racking up frequent flyer miles at lightning speed, and taking bucket list journeys like other people go to the coffee shop. She’s had a lifetime of amazing travel experiences, which she accredits to evolving her perspective and love for our amazing planet. Today Cyndi is focused on her industry advocacy work, and supporting our team here at Tripsy.
Cyndi’s visionary client-centric approach has resulted in multiple agency awards, and revolutionizing the way we collaborate with our clients to create the vacations of their dreams. Under Cyndi’s leadership Tripsy has quickly grown a reputation as one of the best luxury boutique agencies in the industry.
Cyndi and her husband of fourteen years were married in Walt Disney World and now reside in Austin, with their two beautiful children, and two dogs Lucy and Mavis.
Cyndi is also a proud member of ASTA, Travel Leaders, CLIA, and IATAN.
“Traveling makes the world a little smaller, and the love a little bigger.”
– Cyndi Williams, Founder
Stephani Voge
Luxury Travel Planner
Stephani is a Denver native who has spent that last 12 years living in Hawaii swimming with manta rays, Vancouver, BC biking though Stanley Park and Austin Texas trying all the BBQ Texas has to offer. Most recently she moved to Ottawa, Ontario where she can be found ice skating in the winter and exploring all that eastern Canada has to offer in the summer. She has had the luxury of being able to immerse herself into these very different cultures and truly experience what each one has to offer.
She has a degree in Hospitality and Tourism with an emphasis in Hotel Management. While studying abroad in Namibia, Africa she spent three weeks of adventure, traveling and camping across diverse ecosystems; visiting conservation sites, historic sites and wildlife conservation projects. Prior to travel planning, she previously worked in various hotels in both a resort and city settings and is familiar with their operations. Having a passion for travel and a love for ensuring a vacation of a lifetime, Stephani is truly a dedicated luxury travel advisor.
Stephani specializes in Hawaii travel. Between hiking to hidden waterfalls and scuba diving the crystal clear waters, she is a wealth of knowledge due to her time living on the islands. She has also attended the Disney College of Knowledge and loves to create a lifetime of memories, specifically with Adventures by Disney where your family becomes part of the story as you are immersed in the people, places and cultures of wherever your adventures take you throughout the world.
Currently, Stephani lives in Ottawa with her wonderful husband, two beautiful daughters, and their energetic dogs, Koa the Maltese and Murphy the Greater Swiss Mountain Dog. They spend most of their weekends hiking, on the river walk or experiencing new restaurants and parks throughout the city.
Stephani’s Specialties include: Hawaii, select Canada locations and Cruises.
Samantha Jayakumar
Luxury Travel Planner
Samantha was born and raised in Chicago, Illinois and is a self-proclaimed “airline brat”. With both her parents employed by a major airline she has been traveling since she was only a few days old. Her love of travel started young with trips to Egypt, China, France, and the UK before she was ten.
Her family’s travel background led her to obtain her Bachelor’s Degree in Travel Industry Management at the University of Hawaii. After University Samantha spent 10 years in Hawaii in various management roles at luxury hotels. Samantha’s hospitality career later brought her to Austin, Texas then Los Angeles, California where she currently resides.
Samantha and her husband had a destination wedding in Cancun, Mexico ten years ago and have been racking up the frequent flyer miles ever since.
Samantha’s expertise is in International Travel. She has visited 43 countries and been on over 20 cruises. Whether you want to go to Sri Lanka , Croatia, Kenya or France Samantha can help you plan the perfect trip! Ask her about the Maldives, it is her favorite destination to get away and unwind.
Samantha’s Specialties Include: International Luxury Travel
Tana Williams
Luxury Travel Planner
Tana started working in the travel industry 30 years ago as part of the Clipper Cruise Lines team, which was the largest yacht and smallest cruise ship sailing the US East Coast down to the Virgin Islands. During that time Tana was afforded the most incredible experience as a young person to see so many cities, inter-coastal water ways, famous land marks and meet some wonderful people. Tana has continued to travel throughout the years, and now she helps others plan and get the most enjoyment out of their vacation adventures. Tana says “Traveling myself or through you makes me feel alive!”
Tana’s specialties: Caribbean, Hawaii, Cruises, domestic U.S., and All-Inclusive vacations.