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Travel More. Stress Less.
Stay Trippin® was created for those ready to escape the grind, reconnect with what matters, and experience the world without waiting for the “perfect time.”
In a world full of work, stress, and burnout, travel becomes more than a getaway — it’s therapy, transformation, and a way of life.
Specializing in group travel, luxury cruises, corporate retreats, and bucket-list adventures, Stay Trippin® is for the bold spirit who craves more adventure, deeper memories, and a lifestyle built on freedom, fun, and fulfillment.
From expertly hosted group getaways to seamless corporate escapes, from breathtaking cruise itineraries to once-in-a-lifetime journeys, this is the passport to unforgettable experiences — whether traveling like it’s retirement already or simply making the most of every moment.
Because life isn’t just about working and waiting.
It’s about living now, exploring often, and doing it unapologetically.
Tiffany Herring is the heart behind Stay Trippin®—a travel brand created to inspire bold, freedom-filled lifestyles through unforgettable experiences around the world.
After years of navigating a demanding 9-5 and feeling the weight of burnout, Tiffany turned to travel as a way to reconnect—with herself, with purpose, and with the world. That journey sparked a mission to help others do the same.
Through Stay Trippin®, Tiffany curates trips and experiences for people who are ready to stop waiting for “someday” and start living now. Whether you’re dreaming of a bucket-list adventure, craving connection through group travel, or just need a reset, Tiffany brings clarity, care, and curated vibes to every journey.
She believes travel isn’t just about going places—it’s about reclaiming joy, peace, and possibility in your life.
If you’re ready to travel more, stress less, and live like you’re retired (even if you’re not), Tiffany’s got your next escape covered.
Trips Booked
Years Of Experience
Clients Satisfaction
Where adventure meets ambition—travel lovers explore curated trips and connect with like-minded adventurers, while travel entrepreneurs gain the mentorship and strategies to build sustainable success.
By signing up, you’re taking the first step toward living unapologetically. This isn’t just another email list—it’s your gateway to exclusive travel experiences, transformative insights, and the tools to create a life on your own terms. Join a community where freedom is celebrated, boldness thrives, and YOU come first.