Haily Celestin

Haily has always believed that life plays back like a highlight reel. Years from now, we won’t remember the emails we answered or the endless items on our to-do list. We’ll remember the moments that stopped us in our tracks. Watching elephants cross a river at sunset in Botswana. Sharing a bottle of wine in a tiny Italian village where nobody is in a hurry. Sailing through a remote fjord in Greenland and watching children experience a new culture for the very first time. Those are the moments that stay with us.

Originally from Louisiana, Haily spent the first part of her career as an operating room nurse, a profession that demanded precision, adaptability, and the ability to remain calm when plans change. Looking back, many of those same skills have shaped the way she approaches travel planning today.

Her path to travel advising wasn’t exactly traditional. During the pandemic, she and her husband embarked on a five-month sailing expedition from the Caribbean to Greenland aboard their own sailboat – crossing oceans and exploring Azores, Scotland, Iceland, and the Faroe Islands along the way. Traveling by sailboat teaches you things no itinerary can: you can’t rush the weather, you can’t force the conditions, and the journey itself becomes the destination. That experience reinforced something she had always believed. The best travel isn’t about how many places you see. It’s about how deeply you experience them.

Today, Haily calls the Caribbean home and designs highly personalized journeys for busy professionals, couples, and families through her company, Beyond the Fifth. Her clients have demanding careers and very little free time. Their time away is valuable, and she doesn’t take that lightly. When she’s not planning her next client’s adventure, you’ll usually find her on the water, preferably with a crisp glass of Chablis in hand.