One of the most common planning mistakes I see—especially among smart, well-traveled people—is they come to me trying to fit too much into one trip. More cities, more hotels, more highlights. On paper, it looks efficient. In reality, it often does the opposite.

Here’s the insider truth: fewer stops almost always lead to a better travel experience.

Why We’re Tempted To Pack It All In

When time is limited, there’s a natural urge to maximize it. Add bucket lists, social media inspiration, and the feeling that “we might not be back,” and suddenly a trip becomes tightly packed with constant transitions.

What often gets overlooked is how much energy those transitions take. Packing and unpacking. Transfers. Delays. Check-ins. Navigating logistics in unfamiliar places. Even the smoothest travel days quietly chip away at the experience. Which leads to travel fatigue, where chances of enjoying the trip dwindle at rapid speed.

What Slowing Down Actually Gives You

When you reduce the number of stops, something shifts.

You wake up knowing where you are. You recognize your surroundings. Meals linger instead of feeling scheduled. Wandering becomes intuitive rather than strategic. The destination starts to feel familiar—in the best way.

Practically speaking, fewer stops, better travel also means:

• Less time spent in transit
• Better use of your travel budget
• More flexibility when plans change

But the real benefit is how the trip feels: calmer, fuller, and more enjoyable.

Where Cruises Quietly Get This Right

This is also why cruising can work so well for travelers who want to see a lot without feeling fragmented.

You unpack once. Your room stays the same. The logistics of getting from place to place fade into the background. Instead of managing the journey, you wake up somewhere new to explore!

For travelers who value ease and continuity, cruises offer a surprisingly elegant way to experience multiple destinations without the constant reset that comes with frequent hotel changes.

This is a fantastic example of that! These cities could never be seen in 13 days in land based travel!

A Better Question to Ask

Rather than asking, “How many places can we fit in?” try asking:

• Where do we want to feel settled?
• What is the ideal pace?
• How much moving around actually enhances the trip?
• What are the priorities?
• What would make this journey feel smoother?

Once we learn these answers (and maybe a few more), we can make suggestions based on our experience, to craft an amazing trip without feeling you’ve compromised at all! Seeing less—or seeing smarter—more thoughtfully, almost always leads to experiencing more.

If you’d like to learn more, I’m always happy to talk