Here’s How One Top Travel Advisor Crafts the Perfect Itinerary for Any Destination

The most rewarding trips are those that gently push your boundaries and leave you with a new perspective. But creating a journey that ventures off the well-trodden path while still delivering comfort can be challenging. I’ve been designing itineraries for discerning, adventurous travelers for more than two decades. Here’s what I’ve learned about crafting a trip that’s both low-stress and deeply fulfilling—and how you can implement the tips into your trip planning, too.

Build Contrast into Your Itinerary

Consecutive destinations can start to blur if they feel too similar. Back-to-back safaris, jungle lodges, or chateaus—no matter how impressive they are individually—might start to lose their appeal. That’s why it’s important to prioritize contrast on a trip. Each destination in an itinerary should justify itself by being palpably different from the last. Move from a buzzing city to a remote desert. Follow a rainforest stay with time on a wild coastline. Even within one region, make each stop serve a different mood or activity.

Stay at a Variety of Accommodations

Contrast also applies to your lodging. Of course, you should absolutely treat yourself to a stay at an iconic hotel or a showstopper suite. But then blend that style of stay with a characterful boutique, design-led eco-lodge, or off-the-grid camp. Staying at properties that have their own feel makes each stop feel more meaningful and gives you a rich sense of place.

Focus on the Flow of the Trip

The best travel days feel seamless, but that doesn’t happen by chance. If you’re going to multiple places in a row, try to plan that as a circuit, rather than traveling in and out of the same location multiple times. It’s also wise to think about what each form of transport can offer. Flights are efficient, road trips open up more opportunities for discovery, and an epic train journey becomes a scenic highlight in and of itself. 

Begin Slowly

Start your trip at a slower pace, rather than jumping right into a bustling city. Taking a couple of days to decompress, whether that’s in nature or a smaller town, allows you to ease your way through jetlag (if applicable), tune into your surroundings, and settle into the travel mindset so you’re ready for busier destinations later in the vacation. 

For Longer Travel, Stay Relaxed

Longer trips demand space to breathe. This might mean scheduling “down days” with no plans, ensuring the accommodation has enough rooms for every family member to take time to themselves, or, if you know you’ll need to work a little bit along the way, setting up a room with dedicated desk space and a strong Wi-Fi connection.

Stay a Little Longer

One common mistake I see travelers make is trying to cram too much into one trip. A meaningful getaway isn’t a sprint through the highlights. It involves taking the time to go beyond the Instagram spots, explore, and ask questions. Yes, you’ll want to visit the must-sees of a destination, like the Eiffel Tower in Paris, but allow yourself the freedom to veer off course and develop your own relationship with the environment around you.

Learn from Expert Storytellers

The best part of traveling to a new destination is forging connections with the people who live there. A great way to do this is to schedule tours operated by local guides, visit boutique shops instead of chains, and speak directly with local residents. As a seasoned travel advisor, connecting you with guides who are passionate about the area they live in is something I always prioritize.

Steve Wilson is a member of Travel + Leisure’s A-List and specializes in sabbatical trips. You can create a tailor-made itinerary with Wilson at [email protected].