09/28/2026
🇬🇷 DREAMING OF GREECE? SAVE THIS SANTORINI GUIDE.
Santorini is one of those places that really does look like the photos—whitewashed villages, blue-domed churches, dramatic cliffs and some of the most incredible sunsets in the world.
But there’s a lot more to Santorini than Oia at sunset. If Greece is on your travel list, here’s what I recommend:
✈️ GETTING TO SANTORINI
There are no nonstop flights from the U.S. or Canada directly to Santorini (JTR), so most travelers connect through Athens.
I actually love building Athens into the itinerary rather than treating it as just a connection. Spend a few days exploring the Acropolis, Plaka and incredible food scene, then continue to the islands.
From Athens, Santorini is about a 45–50 minute flight, or you can take the ferry from Piraeus—especially if we’re creating an island-hopping itinerary.
☀️ WHEN SHOULD YOU GO?
My favorite times are late May through early June and September into early October. You still get beautiful weather without quite as much of the peak-summer intensity. July and August are gorgeous, but they’re also the hottest, busiest and most expensive months. If your dream is a romantic Santorini experience without fighting the biggest crowds, shoulder season is your friend.
✨ THE BIGGEST GREECE TIP I GIVE MY CLIENTS:
Don’t plan Santorini in isolation.
Greece becomes an entirely different trip when the islands and mainland are paired intentionally. Depending on your travel style, we can combine Athens + Santorini with places like Mykonos, Paros, Naxos, Crete or Milos and coordinate the hotels, ferries, private transfers, experiences and those little details that make the entire journey flow.
Thinking about Greece for 2026 or 2027?
Tell me how you want Greece to feel—romantic, luxurious, adventurous, food-focused, relaxing or a little bit of everything—and I’ll help design the journey around you.
📩 Message me to start planning your Greece adventure.
