Can I do a Flying Dress Photoshoot in Santorini while on a Cruise?

Nov 9, 2025

Date Visited: August 2025

Ship: Virgin Voyages – Resilient Lady

Port Stop: Santorini, Greece

Booked with: https://www.santorini-flying-dress.com/

Perfect For: Content creators, couples, bucket-list moments, wine lovers, and adventurers in sturdy shoes 😅

Woman in a red flying dress on the cliffs of Oia in Santorini

✨ A Flying Dress Photoshoot in Oia (Bucket List: ✔️)

When planning our Greek Isles cruise with Virgin Voyages, I knew Santorini was going to be the busiest day of the trip; and also one of the most iconic. With four cruise ships docked, crowds were a certainty. So I did what any planner would do: I booked my flying dress photoshoot in advance, coordinated everything with the team, and made sure we had an early start.

street view of crowd in streets of santorni in summer

#TravelMore TIP: If you're sailing Virgin Voyages, you cannot pre-schedule your tender boat time until you're on the ship; and they often fill up FAST and I was worried that if I waited, I may not make my photoshoot meet time.

To guarantee we made it ashore early, I booked a low-cost ship excursion (~$35 pp) with the earliest tender available. It was SO worth it. Standby lines were already hours long by 7:30 AM! (Picture to the right is of us walking through the streets in Oia!!)

🚤 Getting Ashore & Making Moves

Our tender dropped us at a different dock than the usual cable car. We were then bussed into Fira, where we let our tour guide know we’d be venturing off on our own for the day.

After a quick coffee and pizza breakfast (don’t judge, Greece brings out the YOLO), we met our private driver and headed to Oia for the photoshoot.

💃 The Dress, The Heat, The Hills of Oia

Let’s talk logistics:

I changed into my dress in the basement of a restaurant.
Walked a half-mile uphill in the sun to the cliffs.
It. Was. HOT.

But oh my Santorini, it was worth it.

We shot at 6+ iconic spots with sweeping views of whitewashed buildings and blue domes. If you're planning this shoot:

Tips for Future Flying Dress Goddesses:

Wear velcro rollers or a heat wand and leave hair pinned until the cliffs to fight frizz.
Bring a hand fan and makeup setting spray.
Choose shoes you can walk in (I had tennis shoes on and slid them off for the shots).
Remember: Photoshop saves the day if sweat wins the battle. I was able to look through over 300 photos to pick my top 20 for edits. The end album was well worth the wait and will be on our travel wall forever.

🍷 Post-Photoshoot Greek Delights

After the shoot, our driver took us back to Fira, but not before dropping us at his cousin’s café (yes, really). We enjoyed a leisurely lunch of local food and Santorini white wine with a view; one of those spontaneous gems you can't plan for, but always remember.

🐴 When the Cable Car Fails You… Take the Donkey Trail

We wrapped up with some quick shopping before heading to the cable car line…which was over TWO HOURS long. So we chose the other option: the 500-step donkey trail.

🛑 Warning:

It’s steep, slippery, and scattered with donkey droppings.
You WILL encounter donkeys (some charging).
But it’s doable; just wear grooved shoes or hiking sandals and take it slow.

We made it in 30 minutes and hopped the next tender back to the ship, hot-tub ready and full of stories.

🧳 Kristin’s Cruise Tips for Santorini:

Tip	Detail
🚤 Tender Early	Book a cheap early excursion just to secure the first tender boats ashore.
📸 Flying Dress	Coordinate your photographer & dress vendor ahead of time, and be ready to walk.
🥵 Heat Prep	Plan for intense heat if visiting in summer - hair, makeup, and hydration matter.
🐾 Skip the Cable Car	If the line is long, the donkey trail down is the lesser of two evils—but not for the faint of heart!
📞 Book in Advance	Santorini gets swarmed with cruise ships - every minute counts if you want photos without crowds.