Island Hopping in Greece: Why Santorini Should Be Your Last Stop, Not Your First

Let me save you from the mistake I made on my first Greek island-hopping trip: don't start with Santorini.

I know, I know. Those white-washed buildings cascading down cliffsides, those impossibly blue domes, those sunsets that break the internet—Santorini is the Greece of your Pinterest boards and travel fantasies. But here's the thing: if you go there first, everywhere else will feel like a letdown.

The Santorini Effect

Santorini is Greece on performance-enhancing drugs. It's been so perfectly curated for Instagram that it barely feels real. And that's not a criticism—it's genuinely stunning. But it's also expensive, crowded, and designed for tourists in a way that the other islands aren't.

When you start there, you set an impossible standard. Suddenly, charming Naxos feels "too quiet." Authentic Paros seems "underdeveloped." You've peaked too early.

The Right Way to Island Hop

After three trips to Greece, here's the route I wish I'd taken the first time:

Start in Paros – This is Greece before it knew it was supposed to be photogenic. Marble-paved villages, family-run tavernas where the owner's grandmother is making moussaka in the back, beaches that locals actually use. It's the perfect introduction because it feels real.

Move to Naxos – Bigger and more diverse than Paros, Naxos has mountains, ancient ruins, and the best food in the Cyclades (fight me). Spend a day hiking to mountain villages where old men play backgammon in kafeneions unchanged since 1960.

Hit Milos – If Santorini is the supermodel of Greek islands, Milos is the naturally beautiful girl who doesn't know it yet. Volcanic rock formations, hidden pirate coves, lunar landscapes that feel like another planet. Rent a boat and spend a day exploring caves.

End in Santorini – Now you're ready. You've seen authentic Greece. You've eaten real Greek food (not the tourist-menu version). You've swum in empty coves and gotten lost in villages where no one speaks English. Santorini becomes the grand finale it deserves to be—a spectacular, over-the-top celebration of everything that makes Greece magical.

What to Actually Do in Santorini

Once you get there (at the end of your trip, remember), here's how to do it right:

Skip Oia for sunset – Yes, it's iconic. It's also a shoulder-to-shoulder mob scene. Instead, watch from Imerovigli or rent an ATV and find your own clifftop spot.

Eat in Pyrgos – The hilltop village has all of Oia's charm with 10% of the tourists. Selene Restaurant does modern Greek cuisine that'll ruin you for hotel breakfast buffets.

Hike Fira to Oia – The 10km coastal trail is the best way to see the caldera without fighting crowds. Start early, bring water, and stop at every viewpoint.

Stay in Imerovigli – Quieter than Fira, cheaper than Oia, still has the cave hotels and infinity pools. Book a place with a hot tub and spend at least one evening just soaking and staring at the Aegean.

The Ferry Reality Check

Greek ferries are an adventure unto themselves. They're mostly reliable, occasionally delayed, and always an experience. Book tickets in advance during high season (July-August), but don't stress about exact times—Greeks certainly don't.

Pro tip: the slow ferry is half the price and twice the fun. You'll meet backpackers, island-hopping retirees, and Greek families hauling mysterious amounts of luggage. Plus, the deck views are unbeatable.

Why This Order Matters

Travel is all about contrast and crescendo. If you start with the most spectacular destination, everything else becomes "not as good as Santorini." But if you build up to it—if you earn those caldera views by first experiencing the Greece that exists beyond the Instagram grid—then Santorini becomes transcendent.

It's the difference between eating dessert for dinner and savoring it after a perfect meal. Both are delicious, but only one leaves you truly satisfied.

So save Santorini for last. Trust me on this one. Your future self, watching the sunset from a cliffside hot tub after a week of island adventures, will thank you.