Relationships: The Heartbeat of Luxury Travel Experiences

What is the difference between a $400 hotel room and a $400 tour? Psychologists will tell you it comes down to one word: experience. Which is why the room may never be mentioned again, but the tour will pepper conversations, decisions, and even future trip planning. Humans crave connection, seek narratives, and thrive when learning. Keeping this at the forefront of any travel venture is key to success. Through travel experiences, people engage with experts, each other, and their environment. 

“What’s really different about [Sailing Collective] versus others is that there isn’t a divide between service and guests. I’m not in a polo and khakis–my worst nightmare,” is how Flannery Klette-Kolton, Culinary Director and Chef at Sailing Collective, opened a recent conversation. Klette-Kolton doesn’t simply cook, which sets Sailing Collective apart. And, importantly, it’s what others looking to provide an authentic luxury experience must consider if they want to succeed.

It’s More Than a Boat Trip

Sailing Collective offers sailing tours and private charters around the world. Guests board a luxury vessel and meet a team of culinary and other professionals who focus on providing the most exceptional experience for them. The staff is on a mission to get to know their guests, and they focus on this from first contact. 

Gone are the days of passing off a canned itinerary as either a luxury or an experience. 

Guests Must Feel Seen

What positions Klette-Kolton and Sailing Collective in the market is their person-centric approach to travel planning and execution. Of course, they have routes, stops, and relationships with vendors who offer a variety of tours, classes, and more. But it’s anything but canned. Instead, the crew has deep knowledge and understanding of various options. They use guests’ input to ensure everyone’s personalized experience matches their wants.

Guests receive a significant list of options. Klette-Kolton and the rest of the team want to know which guests in a group want to be active, hiking and snorkeling, and also which ones prefer to relax on the boat, napping and reading. They also know the things that delight all guests and make sure to build in time for guests to opt to snorkel in a coral river while in French Polynesia or visit the San Benedetto market in Sardinia.

“We want people to know they’re seen. To feel taken care of and looked out for,” Klette-Kolton explained. And this comes across in every part of the experience. Including her enthusiasm for the way Sailing Collective manages to provide meals. Rather than a multi-chef staff, guests have the same chef throughout the trip for all meals. “One of my favorite parts of this experience is getting to cook for people for an extended period of time. I like observing people, studying them and how they eat and tailoring my approach to fit them better as the week goes on. By cooking for them for a week instead of one meal, I can have a greater impact.”

Of course, Klette-Kolton has things she loves to cook. Still, for her, it’s more about developing an idea of what will delight guests and then hitting those notes at each meal, providing a curated culinary experience that keeps improving. 

Heart at the Heart

Anyone talking to Klette-Kolton will discover that her excitement is not about cooking on a boat. It’s about her absolute love for what she describes as the “reciprocity of cooking for someone.” For her, it’s not just about cooking. It’s about “feeding them and experiencing them eating.”

It’s easy to understand how this eating experience would keep a luxury travel venture afloat. In contrast, a canned experience cannot fetch the same clientele, and because business is business, we have to talk about its price. Klette-Kolton and the other professionals working at Sailing Collective are providing far more than meals. Provisioning is done in ports, allowing for the freshest possible ingredients with literally no travel time. 

The culinary staff knows exactly where to find the ingredients they need, no matter what they decide to cook. “I really love provisioning in Athens. There’s this huge covered market that has several concentric rings of food. The center is fish, and then the perimeter is all the butcher shops.” Here, she also focuses on relationships. “I have vendors I see a few times a year, and it always feels special.”

Specialty shops make the experience even better. “One street outside of the market, there’s two streets that are just fresh produce. Not much farther, there’s a little shop that’s nuts and dried fruit, and then at the end of that is cheese, charcuterie, and spices.”

As a professional, she’s also learned what you can get at the grocery store versus the things that absolutely have to come from the market. Carta Musica, for example, is traditional paper-thin crackers Klotte-Kolton says you must get at the fresh market because they are handmade.

The Sailing Collective Difference

Building an experience based on people’s preferences for food and activities, when done right, has lasting effects. Klette-Kolton describes the culinary aspect of sailing with her as akin to being a houseguest. “We’re hanging out all week, talking all of the time. People in the kitchen ask questions while I’m cooking, and I’m talking to them while they’re eating. But I’m also turning off the lights and making coffee before they wake.”

This type of connection stretches beyond the trip. In fact, the trip is just the beginning of the relationship, and she encourages guests to stay in touch by texting her cooking and food questions. She answers and loves seeing how the reciprocity of cooking and eating changes them. “I love seeing how the experience has inspired them to cook for themselves, to maybe try a new cuisine. I get a lot of photos with notes saying, “You inspired me, so I made this!”

Lessons to be Learned

All hospitality professionals can learn a lot from the Sailing Collective model. Even if their business isn’t chartered sails worldwide, it’s about relationships. Relationships between staff and guests, staff and vendors, and guests and their environment. Taking time to learn what guests like and dislike is the difference between making a suggestion that falls flat or one that delights. Paying attention to likes and dislikes, and using this to make people feel seen, is how to build hospitality like a pro.