People Before Places

How I Design Meaningful Itineraries

A great itinerary is more than just a list of places. It’s built around the people taking the trip. Here is why personalization matters and why that approach changes everything.

Every successful itinerary is a reflection of the client. Their room preferences, tastes, interests, and how they like to travel all shape every detail included in the trip. So here’s how I go about it.

First, It’s Important to Know Your Client

Before beginning to plan, I always set up a time to meet or call with my clients. The more you interact with someone, the more you understand what they are looking for. Aside from gathering information on their budget, timeline, and destination in mind, it is also an important opportunity to pick up on their wants and needs for the trip. Are they looking for something calm and peaceful? Are they after something more social and extravagant? Are they travelling with little kids? Is it a solo trip? Do they prefer flexibility or structure? Do they have a particular routine? These are all quick, but important, questions that can be answered through conversation.

You would be surprised how much you can learn about someone simply by talking to them.

Here’s a Checklist of Questions I Always Like to Ask

Here’s what makes The Circle so special:

1. What does “luxury” mean to you? Private villa and total seclusion or exclusive access and curated experiences.

2. What do you want to feel on this trip? Adventure, restoration, romance, or wonder.

3. What has been your best travel experience, and what made it that way?

4. What are your non-negotiables and dealbreakers?

Second, You Need to Plan Out the Details

After meeting with the client, I like to have a brainstorming session where I curate different options for them to run by. Hotels, restaurants, activities, locations – you name it, I’m thinking of it. This is where I take everything I learned from our first conversation and start turning it into something tangible. Not every option will make the final cut, and that’s the point. I would rather have too much to work with than not enough, so I cast a wide net before I start narrowing things down.

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Third, Make Sure You’re On the Same Page

Once I have a direction in mind, I always check in with the client to make sure they agree with what is being proposed. This is where we start to add details to the itinerary. Hotels, dates, and flight preferences– we get into the knitty-gritty. Are there specific things they want to do in this particular destination? A special celebration to account for? All of these details start to reveal themselves in this step. I find that clients often have new ideas they want to mention in the second conversation, and this check-in gives them the space to bring those up before anything is confirmed.

Fourth, Find the Right Partners

In this industry, we all know how important it is to work with the right people. Choosing the right partners is truly a make-or-break for the client’s experience. At Exclusolo, I have a clear standard I want to meet, and I always work with partners I trust. Drivers, guides, and any third-party services have all been vetted to ensure they meet that standard. A trip can be perfectly planned on paper, but if the execution falls short, that is what the client remembers. Getting this step right is non-negotiable.

Fifth, And Final Step, Refine the Itinerary

Once everything is in place, I go back through the itinerary with fresh eyes. This is where the small details get ironed out – the timing, the transitions, the moments in between. Does the pace feel right? Is there enough breathing room? Are the right experiences in the right order? A well-refined itinerary is one where the client doesn’t have to think about logistics. Everything just flows.

I also like to add personalized touches throughout the trip. Whether it’s greeting a client in person at their welcome dinner or having a bottle of wine waiting at their hotel, the small details go a long way. And regardless of the trip, I am always available throughout their entire stay to check in and make sure everything is running smoothly. I view my clients as more than just bookings.

I genuinely care how their trip goes, and I want them to fall in love with the destination they’ve chosen.

At the end of the day, no two trips look the same, and that is intentional. Every client brings something different to the table, and my job is to listen carefully enough to reflect that in the itinerary properly. It is not always a quick process, but it is always worth it. When a client comes back and tells you it was the best trip they have ever taken, that is how you know you’ve done the right job. That the personalized approach is working.