Why Popular Isn’t Always Better: Rethinking Overrated Destinations for Discerning Travelers

In a world saturated with glossy “must-visit” lists and influencer-curated itineraries, it’s easy to assume that the most popular travel destinations are also the most worthwhile. But as someone who designs tailored travel for discerning clients, I’ve learned that popularity often comes at a cost: overcrowding, over-commercialization, and a loss of authenticity.

Luxury travel isn’t about ticking boxes. It’s about creating meaningful, seamless, and soul-filling experiences—and sometimes, that means skipping the obvious choice in favor of something more personal and under-the-radar.

Here are a few destinations that often get overhyped—and the alternatives I recommend instead.

Instead of Mykonos, Greece → Consider Ios

There’s no denying Mykonos has charm. But during peak season, it can feel more like a party hotspot than a serene Greek island escape. If you’re looking for whitewashed beauty, crystal-clear waters, and an elevated, laid-back vibe, Ios might be more your style.

Luxury Stay:

📍 Calilo (Ios) – A design-forward oasis carved into the cliffs of Ios, where art meets architecture and every suite feels like a secluded sanctuary. Perfect for travelers seeking barefoot luxury with a creative twist.

Instead of Santorini in Summer → Consider Naxos or Milos

Santorini’s caldera views are iconic—but they come with cruise ship crowds and premium pricing that doesn’t always reflect the experience. For a slower pace and stunning scenery, head to Naxos or Milos. You’ll still get the white villages and sunsets, but with far fewer selfie sticks.

Luxury Stay:

📍 Naxian Collection (Naxos) – Villas with private pools and full-service hospitality.
📍 Milos Cove (Milos) – A design-forward, clifftop sanctuary with views to rival Santorini—minus the chaos.

Instead of the Great Migration Crowds in the Mara → Consider Zambia’s South Luangwa & Lower Zambezi

The Great Migration in Kenya’s Maasai Mara is legendary—but during peak season, it also means crowded sightings, lines of vehicles, and a safari experience that can feel anything but serene.
For something more exclusive and equally awe-inspiring, head to Zambia. In South Luangwa and Lower Zambezi, you’ll find some of the most spectacular wildlife viewing in Africa—minus the traffic jam. Think leopards at golden hour, elephants crossing the river at sunset, and a level of intimacy with nature that’s hard to describe unless you’ve been there. (Trust me—I have.)

Luxury Stay:

📍 Sungani Lodge (South Luangwa) – Family-owned and beautifully remote, this is the kind of place where luxury meets true wilderness. The guiding is exceptional, and the experience is soulful, not staged.
📍 Lolebezi (Lower Zambezi) – Bold, modern, and tucked along the banks of the Zambezi River, Lolebezi offers sunrise views that stop you in your tracks and design details that feel both elevated and deeply connected to the land.

Instead of the Amalfi Coast in August → Consider Puglia in September

Don’t get me wrong—the Amalfi Coast is breathtaking. But in August? It’s crowded, hot, and often double the price. If you're looking for coastal charm, incredible cuisine, and romantic, rustic luxury—Puglia delivers all of that, with room to breathe.

Luxury Stay:

📍 Borgo Egnazia (Savelletri di Fasano) – An iconic property that blends tradition, elegance, and exceptional service.
📍 Masseria Torre Maizza (a Rocco Forte Hotel) – Set among olive groves, this masseria-turned-hotel is chic, tranquil, and delightfully Italian.

Looking for an alternative to the Amalfi Coast?

If you’re craving coastal beauty without the crowds, Puglia offers stunning seaside towns, incredible food, and authentic Italian charm—without the summer chaos. I break down why this region is one of my favorite under-the-radar picks in this guide to Puglia. 

What This Means for You

When we design your trip, we’re not just looking at what’s trending—we’re thinking about what’s true to you. We ask:

• What kind of traveler are you?

• What kind of experience are you craving?

• And how can we take that vision and elevate it?

The most memorable trips often happen in places you’ve never heard of—because they haven’t been filtered through a hundred Instagram stories. They’re quieter. More surprising. More you.

So next time you’re dreaming about where to go, remember: popular isn’t always better.

Let’s design something that feels like your version of luxury, not everyone else’s.

💌 Ready to plan a trip that’s anything but ordinary? Start by filling out our Trip Design Form—I’d love to create something unforgettable for you.