My Favourite Way to See Santorini

I’ll never forget the first time I sailed away from Santorini at sunset. I was determined to find the best vantage point on the ship. I remember darting up two flights of stairs with my camera banging against my side, only to find the top deck already lined with fellow passengers. Everyone was hushed, holding their places, waiting for that golden moment.

I squeezed in along the rail. Next to me was an older couple holding hands, whispering in Italian. Further along, a family with teenagers were snapping selfies, laughing even as the wind whipped their hair into chaos. My own hat nearly flew straight off the side—it was that gusty. I remember the sharp tang of sea spray on my lips and the faint smell of sun lotion still clinging to my shirt.

What I love about Santorini is that it’s beautiful from every angle—but from the sea, it’s magic. The cliffs rise like a giant amphitheatre, stacked with whitewashed houses that catch the dying light like tiny lanterns. You can hear the deep, muffled churn of the ship’s engines and the creak of ropes in the breeze. The caldera turns molten gold, and even the loud talkers fall quiet. The air smells faintly of warm stone and saltwater. It feels like the whole ship is holding its breath.

My ritual now is simple: a glass of crisp, cold Assyrtiko wine in hand, standing right at the rail. The rim of the glass feels chilled in my fingers, the wine dry and citrusy, a perfect match for the sea air. I always remind myself: put the camera down for a minute. Just watch. Don’t stay inside. Don’t let yourself get distracted. Take it all in, properly.

The first time I did that, I remember thinking: This is why I do this job. Not just to advise on holidays & cruises, but to share experiences that genuinely change how you see the world.

🌟My Practical Tips for Your Own Santorini Sail Away

✅ Best Time to Cruise for Sunsets
Late April through early October is ideal. High summer (June–August) means longer daylight and blazing sunsets that seem to last forever, but it can be busy. Spring and early autumn offer softer light and fewer crowds on deck. If you’re a photographer, that “golden hour” glow is stunning throughout the season. crowds.

✅ Arrive on Deck Early
Plan to head up 30–45 minutes before departure to claim a rail spot. The best vantage points tend to fill quickly—especially on big ships. Bring your camera, but also remember to put it down and simply soak in the view.

✅ Dress for the Wind
Even on the hottest summer days, the breeze at sail-away can be surprisingly cool and gusty. A light scarf or jacket is perfect. And watch those hats—I’ve nearly lost mine more than once!

✅ Drink Recommendation
Santorini’s signature Assyrtiko wine is crisp, citrusy, and bone-dry—perfect for pairing with the salty sea air. Most ships will have a Greek wine on the list; if not, even a chilled Sauvignon Blanc will do. My personal ritual? Sip slowly and toast the island as it fades behind you.

✅ Recommended Tours Before Departure

Santorini isn’t just about the sail-away—it’s about what you do before you get back on board.

Private Caldera Cruise – One of my favourite ways to see Santorini before sailing away is by joining a private caldera cruise. These smaller boats take you right inside the ancient volcanic crater. Expect dramatic views of the sheer cliffs from sea level, stops for swimming in volcanic hot springs (the water is warm and tinted reddish from minerals), and time to snorkel in crystal-clear coves. Many tours include local wine, grilled seafood lunches, and expert guides who share the island’s volcanic history. It feels intimate, scenic, and completely different from the crowded bus tours.

🛥️ Top Tip: Book a morning or early afternoon slot so you have time to return to the main port in time for your cruise ship’s all-aboard time. Private tours can often customize pickup and drop-off around your schedule.

Winery Visits – Santorini is famous for its volcanic soils, which give its wines their crisp minerality. My personal recommendation is Santo Wines, perched on the cliff with panoramic views of the caldera. It’s an unbeatable photo stop—and the tasting flights are generous. Ask for Assyrtiko (dry white) and Vinsanto (sweet dessert wine).
Oia Photo Stop – It’s the postcard-perfect spot with those blue domes and narrow marble alleys. But be warned—Oia gets crowded, especially in peak season. Head there early if your schedule allows, or consider Firostefani or Imerovigli for similar views with fewer crowds. Always factor in your return time to the tender port so you don’t cut it too fine!

✅ And my own Pro Tip
Some ships offer live commentary during sail away. Listen in—but don’t forget to stand there, feel the breeze, and truly soak it in.

✨ Your Turn!

Have you ever watched the sun set as you sail away from Santorini? What did you love most about it? Or do you have another port where the sail-away took your breath away?

👉 Share your favourite sail-away memory in the comments below—I’d truly love to hear your story.

If you’re dreaming of your own Santorini sunset sail-away, I’d love to help you make it your story.

📩 Message me today to start planning your Mediterranean cruise.

If you’re dreaming of your own Santorini sunset sail-away, I’d love to help you make it your story.

Want to experience your own Santorini sail-away at sunset? I’ll help you choose the right cruise line, cabin, excursions, and timing for a seamless Mediterranean adventure.