Planning the Perfect Getaway: Inside Go With Gray with Gray Ellender
How Gray Ellender Built a Luxury Travel Business from Her Love of Planning
Hi Founders,
This week on The Founders Society Podcast, we sat down with Gray Ellender, founder of Go With Gray, a boutique travel agency specializing in dream honeymoons and luxury vacations. What started as a passion for planning her own honeymoon turned into a thriving business that helps clients craft unforgettable travel experiences around the globe.
Gray’s story is one of taking a personal love for organization, creativity, and adventure and turning it into a business that now connects her to top-tier hotels, destination partners, and exclusive perks for her clients. If you’ve ever wondered what goes into luxury travel planning—or just need some inspiration for your next big trip—this episode is for you.
From Occupational Therapy to Luxury Travel
Some journeys begin with a single step; Gray’s started with a story—many stories, actually. Working in healthcare as an occupational therapist, she enjoyed listening as her patients reminisced about their lives & travels. At the same time, she was planning her own wedding, dreaming up a honeymoon that would become more than just a getaway—it would spark a calling.
After a whirlwind escape to St. Barths, Gray realized she wasn’t just passionate about travel; she loved the art of curating it. The details, the logistics, the alchemy of turning ideas into unforgettable experiences—it all clicked. By September 2022, Go With Gray was born, and by 2023, she had embraced it full-time, crafting honeymoons, babymoons, and once-in-a-lifetime adventures for others. Because sometimes, the best journeys begin in the most unexpected places.
What Go With Gray Offers
Not every traveler needs the same kind of adventure, and that’s exactly why Gray designed Go With Gray with flexibility in mind. Whether you're dreaming of a seamless, all-out itinerary or just need a well-connected hand to elevate your stay, she offers three tailored ways to travel:
✨ Hotel-Only Bookings – Perfect for those who simply need accommodations but want VIP perks.
✨ Full-Service Planning – A completely customized itinerary with multi-stop planning and exclusive experiences.
✨ Know & Go – A hybrid option for travelers who know where they’re headed but want expert guidance to refine the details.
No matter the path, Gray ensures each journey is more than just a trip—it’s an experience worth savoring.
The Secret to Planning the Best Trips? Relationships.
What sets Gray apart isn’t just her expertise—it’s her relationships. She doesn’t just work with destination experts; she builds genuine connections with them, turning professional partnerships into friendships. These bonds stretch across the globe, from luxury hoteliers who greet her clients like VIPs to local guides who welcome them like old friends.
By attending top industry trade shows, Gray fosters these connections in person, ensuring that when her travelers arrive, they’re not just guests—they’re part of a network built on trust and warmth. She collaborates with destination management teams who provide on-the-ground support, not just as service providers, but as hosts who truly care.
The result? Her clients don’t just travel; they experience destinations through the eyes of those who call them home. With Gray, every journey feels personal—because behind every itinerary is a world of friendships waiting to be shared.
Lessons from Gray’s Journey
Building a business in travel isn’t just about curating dream itineraries—it’s about navigating the unexpected. Her biggest takeaways?
✨ Your passion can become your business – You don’t have to start in the industry to succeed in it. Gray took her warm, reassuring bedside manner from healthcare and carried it into travel, offering clients the same sense of trust and care.
✨ Relationships are everything – The right connections open the right doors, whether in business or travel. Gray has built a network that doesn’t just support her—it enhances every journey she plans.
✨ Evolve with your experiences – Every business high and low is a chance to refine, improve, and create a brand that clients are genuinely excited to book with.
Around the World with Gray
Need a little travel inspiration? Here are some of Gray’s top picks for your next escape:
Sun-Soaked Honeymoon: Cap Juluca Resort, Anguilla – A dreamy, white-sand retreat that Gray fell in love with on a mother-daughter trip last July.
Blissful Babymoon: Rosewood Mayakoba, Mexico – A serene, picturesque oasis just an hour from Cancun, perfect for soaking up those last quiet moments before baby arrives.
Foreign Family Affair: Italy – Gray is currently planning a trip for a family with an Italian travel partner who specializes in kid-friendly experiences like pasta-making classes and scavenger hunts through historic sites.
Elevated Adventure: Safari in South Africa – Start in Cape Town, sip wine in the nearby winelands, embark on an unforgettable safari, and (for those craving extra relaxation) end with a beach stay in Mozambique.
Exclusive Relaxation: If you’re craving a private, adults-only escape, try an overwater villa in the Maldives or even a private island in the British Virgin Islands—pure paradise.
Off the Beaten Path: Nayara Tented Camp, Costa Rica – A luxury jungle retreat where adventure meets tranquility.
And Gray’s personal favorite? ✨ Hotel Manapany, St. Barths – Rent a car, explore the island, and don’t miss dinner at Le Tamarin. Trust her, it’s magic.
Tidbits for the Week!
We wrapped up our conversation with Gray the best way we know how—by swapping our latest favorites:
Hayley is finding creative inspiration while working her way through The Artist’s Way.
Meg is surviving seasonal sickness with bone broth hot chocolate (yes, really—check out her favorite TikTok recipe!).
Gray just unlocked the ultimate self-care hack: using her ClassPass credits for massages, facials, nails, and even haircuts around Charleston. Stack ‘em up and treat yourself.
Consider this your weekly nudge to indulge in something good—whether it’s a book, a cup of cocoa, or an unforgettable trip with our friend, Gray. See you next week on the Founders Society Podcast!
Find us online:
The Founders Society on Instagram: @founderssociety
Go With Gray’s website
Go With Gray on Instagram: @gowithgraytravel
Thanks for being part of The Founders Society! We hope this episode inspires you to dream bigger when it comes to travel, business, and the experiences you create.
Xoxo,
Meg & Hayley