Meet Gillian Earle | Luxury Travel Agency Owner

We had the good fortune of connecting with Gillian Earle and we’ve shared our conversation below.

Hi Gillian, we’d love to hear more about how you thought about starting your own business?
Honestly, it started with rum. When my youngest left for college, I packed up, left New York City, and moved to St. Thomas. I spent a year sitting on the beach drinking dark rum and pretending I was retired. It took about twelve months to realize I am far too young, curious, and restless to ever retire.

So I did what any rational person would do: I booked a trip around the world. Somewhere between Istanbul and Gili Air, people started asking if I could plan their trips because they wanted to travel the way I do: off the radar, meaningful, and designed with intention. That is when it clicked. I could either go back to agencies that did not understand this level of travel or I could create my own and do it properly.

I had experienced too many agencies that promised ease and delivered chaos, including the one that turned my own destination wedding into a logistical disaster. I swore I would never let another traveler go through that. Gillian’s Jaunts was born from that promise to craft experiences so personal and rare that clients stop feeling like tourists and start feeling like insiders.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
Gillian’s Jaunts was born from the idea that true travel should feel personal, not prescribed. I built the company for people who have outgrown ordinary itineraries and want something thoughtful, rare, and quietly extraordinary. We find the places that have not yet been overrun, the ones that do not need a hashtag to be worth visiting, and we connect travelers to them with care and respect.

Every journey we design supports the people and communities who make it possible. Whether it is a private yacht expedition or one of our Unwellness Retreats, the goal is the same. Each trip should feel like discovery again, meaningful, imperfect, and alive with a sense of place.

It was not easy creating something that sits outside the industry’s comfort zone, but that challenge became our identity. What sets Gillian’s Jaunts apart is the way we listen, curate, and deliver. My clients trust me because I never sell them a trip. I build one with them.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
When a friend comes to visit, I start the week with coffee at Imperial Moto Café in Little River. The espresso is excellent and the energy is easy. From there, the Rubell Museum is an ideal first stop, always full of something unexpected.

A day on the water is essential. I arrange a private boat outing through Biscayne Bay that passes quiet islands and hidden coves, the kind of perspective that reminds you why people fall in love with this city. Dinner afterward at House of Food Porn turns into its own experience, creative and entirely unlike anywhere else.

One afternoon is reserved for calm at the Russian and Turkish Baths in Miami Beach. It is a ritual I never skip. Evenings shift between cocktails at the Red Phone Booth and dinners at Boia De or Mandolin Aegean Bistro. The week ends slowly, a late breakfast and a final moment by the water, which always feels like the right way to leave Miami.

Who else deserves some credit and recognition?
My shoutout goes to my children, who are still my biggest cheerleaders. When my youngest left for college, I thought that chapter of my life was ending, but it turned out to be the start of something entirely new. Watching them grow into confident, curious adults reminded me that reinvention is never reserved for one season of life. Their independence gave me permission to rediscover my own, and now my daughter takes off on her own adventures the same way I once did. There’s something incredibly satisfying about seeing the next generation chase the world with the same curiosity that built mine.

Website: https://www.gilliansjaunts.com/

Instagram: gilliansjaunts/

Linkedin: in/gilliansjaunts/

Facebook: https://www.facebook.com/gilliansjaunts