The Making of a Dream Trip

Go behind the scenes of the process that shapes every Fig Travel Co. itinerary

By Tiffany Figueiredo

Every dream trip begins with a feeling. Sometimes it’s the desire to see a place you’ve imagined for years, or the wish to celebrate something meaningful, or simply the hope of stepping out of the familiar and breathing a little deeper. My work is to understand that feeling and translate it into a journey that feels effortless, thoughtful, and beautifully made.

It starts with a discovery call.

This is where I listen closely. Clients often describe the trip they think they want, but the real story sits beneath that first description. A couple may ask for Santorini when what they truly crave is quiet and privacy, which leads us instead to Paros or the Peloponnese. A family may request the Serengeti, even though their interests align more naturally with Botswana’s waterways or South Africa’s private reserves. Part of my job is distinguishing what is said from what is meant, because the best trips happen when the itinerary matches the feeling you’re actually chasing.

An engagement fee confirms your place on my calendar and allows the real work to begin.

This is when hours of research, refinement, and relationship-building happen behind the scenes. I’m thinking about pacing, connection times, the order of destinations, and the rhythm of each day. I know which properties are overplayed, which deliver genuine magic, and which are the right fit for how you want to travel. I know where to splurge, where to save, and how to create balance so the entire experience feels seamless.

Here’s what many people don’t realize: trying to piece this together yourself through Google or ChatGPT searches, or by replicating what a friend did, rarely yields the same result. You don’t have access to the same inventory, the insider knowledge of which lodges are worth the premium, or the relationships that secure tables at fully booked restaurants. More importantly, you don’t have someone who knows you, your preferences, and your travel style and can shape every detail around that understanding.

Then comes the design work.

Although I work with a talented team and collaborate with top destination partners around the world, I personally touch and control every itinerary. The vision always begins with me and my understanding of you. This isn’t delegated. Your trip is shaped by years of experience, countless site visits, and relationships built over time with the best properties, guides, and fixers in every destination.

Once the itinerary begins to take form, we add the layers that turn a trip into a dream. Flights, transfers, restaurant reservations, spa appointments, private touring, and all the details that make a journey feel elevated. Food is a passion of mine, and I bring that lens to every itinerary, especially when arranging culinary experiences and the kind of reservations that can shape a trip in the most beautiful way.

How I’m compensated and why it works in your favor.

While I do charge a nominal engagement fee, I don’t charge you a markup on hotels, experiences, or services. Instead, I’m compensated by the suppliers I work with. My value to them is you: the right traveler, at the right property, at the right time. They pay me because I deliver discerning clients who appreciate what they offer.

You always pay the same rate as the general public, but here’s where the value becomes clear: as a preferred partner with every major hotel brand in the industry, my clients receive complimentary breakfast, hotel credits, room upgrades when available, early check-in, late checkout, and other perks that travelers booking directly don’t get. The rate is the same, but the experience is elevated. My clients often realize meaningful savings over their peers who book on their own, not to mention the intangible value of being treated like a VIP and having an advocate working on their behalf from booking to homecoming.

Your finished itinerary arrives in the Fig Travel Co. app.

Inside, you’ll find everything you need from daily plans to maps, packing notes, visa guidance, and tipping suggestions. It becomes your companion throughout the journey, keeping every detail organized and accessible even when you’re offline.

While you travel, my team and I are here for you at every moment.

If weather shifts your plans or if a flight is delayed, we handle it quietly in the background. If you want a last-minute dinner in a fully booked restaurant or a spontaneous day trip, we make it happen. You are never left to navigate surprises alone.

At the heart of a Fig Travel Co. journey is a simple promise: I will take the time to understand what you dream of, what you value, and how you want to feel. I will remember your preferences, your travel rhythms, and the things that matter most to you. I will design a trip that reflects who you are, not a template of where the masses are going. And I will bring together the right places, the right moments, and the right people to create a journey that feels both beautifully imagined and unmistakably yours.

Let’s make your dream trip come true now.