Why You Should Consider Traveling Without An Itinerary

There might be studies that suggest planning a trip can be more rewarding than the trip itself — but opting to plan a trip without an itinerary might be the key to having a truly relaxing and deeply fulfilling time abroad.

Going without an itinerary and simply figuring things out day-by-day allows for more flexibility, deeper connections, and the freedom to dive deeper into the little things that have piqued your curiosity.

Here are some of the surprising benefits that travelers have found when they chose to forego a traditional itinerary:

It allows for deeper relaxation

“From our experience working with high-end travelers, we’ve found that flexibility is one of the biggest luxuries,” said Mane Teovanovic, CEO of The Ace VIP, a luxury villa rental and concierge service company in Mykonos, Greece. “Many of our guests tell us that waking up without a rigid schedule allows them to fully immerse themselves in the beauty of Mykonos at their own pace. Strict itineraries can add unnecessary pressure, especially for groups, where not everyone wants to do the same activities at the same time.”

It fosters deeper connections

According to Tamaya Walker McClendon, founder of Sisters and Suitcases, traveling without an itinerary helps to foster deeper connections. “One particular experience that stands out is a time I traveled to Italy’s Amalfi Coast. I gave myself permission to be me, I was traveling solo and wasn’t on anyone's schedule. I let my guard down, I slowed down. I was curious,” she explained. “I asked questions and encouraged locals to ask questions of me. I sat and engaged in meaningful conversation with strangers and women whom I had just met for the first time which later turned into friendships.”

“I remember meeting Ruth and Teakie for lunch at a seaside restaurant right outside of the town Sorrento. Lunch turned into dinner, dinner turned into a couple sending limoncello shots to our table and me sampling some of tastiest green olives I’ve ever had from two friends' plates that were seated next to me to the owner bringing us complimentary desserts and us being in a restaurant for eight hours, laughing from the pits of our stomach, crying happy tears and sharing stories and reflecting on how us striking up a conversation with one another at hotel changed the course of journey.”

You notice the little details

“A few years ago, I flew into Tokyo with only my hotel booked. No set plans. I figured I’d just walk around and see where the day took me,” said Jackie Steele, hospitality professional, Disney expert, and content manager at Magic Guides. “I ended up stumbling into a small neighborhood festival with food stalls, local performances, and zero tourists. It wasn’t in any guide. I wouldn’t have found it if I’d stuck to a plan. It made the whole trip feel more personal, more real.”

According to Steele, the benefit is that you stop rushing and you stop ticking off boxes. You notice little details—like how quiet the side streets get in the morning, or the way a random coffee shop can become your favorite memory.

You can deep-dive into things that capture you

“One of the biggest benefits is the freedom to explore at your own pace,” said traveler and medical professional, Natalia Szubrycht. “Without the pressure of scheduled tours or reservations, you can linger in places that captivate you, whether it’s a charming café, a hidden alleyway, or a conversation with a local. This flexibility also helps reduce stress—there’s no need to rush from one attraction to another, and you can truly soak in your surroundings.”

It could save you money

According to Jasmine Charbonier, founder of YourTampaBestie.com, unplanned travel actually saves money. “When you're not locked into advance bookings, you can take advantage of last-minute deals and local recommendations,” she explained. “I've scored luxury hotel rooms for 60% off by booking day-of, and found authentic restaurants that cost a fraction of tourist traps.”