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WE TRAVEL NOT TO ESCAPE LIFE, BUT FOR LIFE NOT TO ESCAPE US.

Discover the world with Stay Trippin®

Experience Travel Like Never Before

Explore New Horizons

Stay Trippin® is your invitation to break routine, explore boldly, and experience the world with a tribe that gets it. Our curated group trips are designed to give you the best of every destination — no stress, no guesswork, just unforgettable vibes and like-minded travelers ready to live fully.

Upcoming Trips

Brilliant Lady MerMaiden Voyage (17-25 October 2025)

 Embark on an unforgettable 8-night voyage from Miami aboard Brilliant Lady’s MerMaiden sailing. Explore the stunning Caribbean with stops in St. Maarten, where vibrant culture meets crystal-clear waters, and Tortola, home to lush landscapes and legendary rum distilleries. After soaking up the sun at sea, indulge in the exclusive Beach Club at Bimini before returning to Miami—because this isn’t just a cruise, it’s an experience.

cruise details

Birthday Soiree Deux Cruise (28 March - April 4 2026)

Set sail on an unforgettable Caribbean journey through some of the region’s most captivating islands. From the vibrant culture and lush landscapes of Martinique and Guadeloupe, to the breathtaking beaches and mountain views of St. Lucia and Barbados, each stop offers its own unique flavor and adventure. Enjoy a relaxing sea day to soak in the ocean breeze before exploring the tropical beauty of St. Vincent and the spice-scented markets of Grenada. Return to Martinique refreshed and inspired, having experienced the perfect blend of culture, nature, and island charm. This cruise promises vibrant days, warm nights, and memories that last a lifetime.

cruise details

Cruise La Vie: Christmas Edition (18-25 December 2026)

Embark on a captivating Mediterranean voyage from the vibrant streets of Barcelona to the timeless charm of Valletta. Explore Marseille’s rich history and bustling markets, savor the elegance of Genoa’s seaside beauty, and discover the ancient wonders of Civitavecchia, Rome’s gateway. Wander through Messina’s Sicilian splendor before returning to Barcelona, where your journey began—filled with unforgettable moments and Mediterranean magic at every turn.

cruise details

Book Your Own Travel

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Welcome to Stay Trippin®

At Stay Trippin®, we empower bold movers to travel like they’re already retired—with freedom, intention, and purpose guiding every journey.


Whether you’re joining one of our curated group trips or working with me one-on-one to plan your perfect getaway, I’m here to help you explore the world on your terms—stress-free and unapologetically you.


This isn’t just travel — it’s designing a lifestyle of adventure, connection, and freedom you can live every day. Ready to travel boldly and live like you’re retired right now? Let’s make it happen.

Why Stay Trippin®?

Because travel is never just about the destination—it’s about the freedom to live life on your terms, fully and intentionally. Why wait to embrace that freedom? Live like you’re retired today, unapologetically and without compromise.


Stay Trippin® is designed for bold individuals who refuse to settle for anything less than extraordinary—those who seek authentic experiences that elevate, empower, and transform.


Our carefully curated journeys go beyond sightseeing—they create space for connection, growth, and a deeper sense of purpose. With Stay Trippin®, you don’t just see the world—you step confidently into the freedom and fulfillment you deserve.

Our Signature Experiences

  • Group Trips (Hosted & Unhosted): Whether you want the full curated experience with a host to guide every moment or prefer traveling with a group independently, we offer seamless, unforgettable journeys designed to connect you with like-minded explorers while giving you the freedom to travel your way.


  • Cruises (Ocean, River & Expedition): From luxurious ocean liners to intimate river cruises and daring expeditions, we curate journeys that combine comfort, adventure, and discovery. Explore the world’s most breathtaking waterways while enjoying impeccable service and exclusive experiences.


  • Corporate Travel: Elevate your company’s travel with customized solutions that balance productivity and pleasure. From incentive trips to team retreats in inspiring destinations, we craft seamless travel experiences that motivate, reward, and build lasting connections.


  • Bucket List Adventures: Check off your dreams with access to the world’s most iconic destinations — from pristine beaches to vibrant cities and beyond. These are once-in-a-lifetime journeys tailored for those who demand excellence and seek to live fully, unapologetically.

Why wait? Live like you’re retired today. Stay Trippin®.

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Freedom, Boldness, YOU!

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.

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