On the heels of exploring the blue-washed walls of Morocco, my wanderlust is still sailing strong—this time straight into the heart of the Aegean.
There’s something undeniably magical about the Greek Isles—whitewashed villages, turquoise waters, ancient ruins, and sun-soaked days that stretch into slow, golden evenings. And while I haven’t made it there yet, the idea of sailing from island to island aboard a small boat has firmly anchored itself in my top 25 travel dreams.
It’s a dreamy escape I can’t stop picturing: the wind in my hair, a glass of wine in hand, watching the sun dip below the sea near Santorini while the sails gently flutter. Not a cruise, not a ferry—but a small-group sailing trip, where spontaneity rules and hidden coves become your own private paradise.
🌊 The Allure of the Aegean
There are over 6,000 islands and islets in Greece—only about 200 of them are inhabited. Which means there’s a whole world of discovery waiting beyond the crowds of Mykonos or Santorini.
Imagine hopping from quiet ports like Syros, Amorgos, or Folegandros—places where time slows and the streets are lined with lazy cats, wildflowers, and the scent of grilling souvlaki. That’s the adventure I’m craving. One filled with salty swims, cliffside sunsets, fresh feta, and the rhythm of waves as my lullaby.
🧭 Wander Tip: How to Book a Small-Group Sailing Trip
Whether you want to keep things relaxed or a bit adventurous, here are a few things to consider:
🛥️ Start with a Reputable Company
Look for sailing tour companies that specialize in small-group, 8–12 passenger trips. A few top-rated options:
- G Adventures – Sailing Greece
- Intrepid Travel – Greece Sailing Adventure
- MedSailors – Greek Islands Explorer
These companies offer routes through the Cyclades (Santorini, Ios, Paros), Saronic Gulf (Hydra, Poros), and even the Dodecanese (Rhodes, Symi) depending on the season and experience you’re after.
📅 Book in Shoulder Season
Late May to early June or September are ideal. Fewer crowds, warm weather, and better deals—plus the Aegean Sea is perfect for swimming.
🎒 What to Pack
- Soft-sided luggage (space is tight on boats!)
- Light layers + swimwear
- Reef-safe sunscreen + sunglasses
- Water shoes for rocky beaches
- Travel towel + dry bag
☀️ Final Thoughts
Sailing the Greek Isles isn’t just about the destination—it’s about the journey. The quiet conversations on deck, the laughter over shared meals in hidden tavernas, the rhythm of nature and tide leading the way.
One day, I’ll board that boat with nothing but a backpack and an open heart. Until then, I’ll keep the dream alive—and the sea close to mine.
What’s your ultimate “sail-away” destination?
Let me know in the comments—and come back next Wednesday for another inspiring travel dream from my wanderlist.
