Caldera sunset cruise + Fira to Oia hike

We used the caldera sail as a way to avoid the chaos of the cruise ship crowds. People complain that Oia is “so crowded.” And it is…while the cruise ships are in town. If people only come on a cruise ship, I can understand why they think it’s overrated. But in the morning and in the evening/night after the cruise ship crowd has departed it’s just as magical as you are imagining.

So, we chose the sunset cruise (which leaves early afternoon if I remember right. Instead of the hotel pick up, we chose to walk down ALL the steps to Ammoudi Bay (not nearly as easy as it sounds! Wear good shoes and give yourself plenty of time!) We had some appetizers and drinks at one of the seaside restaurants at the bottom…lovely! The catamarans pick up right by the restaurants. After the sail, the company has vans waiting to take you back up the hill to your hotel (which you will appreciate.) Then we walked the now quiet moonlit streets to a late dinner at a restaurant on the cliffside overlooking the caldera with some new friends from the sail. Amazing and memorable! (Sorry it’s been a couple of years so no specific restaurant recs.)

Just to add…another smart way to avoid the cruise crush is to hire a private guide for a few hours and explore the less traveled parts of the island. There are some charming villages with local artisans and pretty squares, and it’s fun just to wander there with no crowds. The Akrotiri archeological dig is worth an hour, and our guide ended the day by taking us to a cliffside happy hour that was well worth the climb for the lovely sunset views enjoyed to classical music. Very memorable!

One tip here though…do your research and have an idea of where you want your guide to take you. Ours started out with what I think was his “canned” itinerary (lighthouse, Akrotiri, Red Beach, Black Beach, etc.) and some things were fine. But we had seen the Red Beach from our caldera cruise the day before, and we made a whole drive out to Black Beach just to glance at black sand. I felt the day slipping away on things that had little for us personally. If you want to go to Imerovigli and wander the town, make sure your guide knows at the beginning so he can plan accordingly.

As far as restaurant recommendations, my advice is to really use your hotel concierge. I was able to email them several times back and forth in the months we were planning our trip. They were happy to arrange a private car to pick us up from the airport, make dining recommendations and reservations and answer any general questions. Maybe ask them about what leg of the hike they suggest for your needs. On the day we hired our guide, our concierge arranged a very authentic lunch in one of the nearby villages (about a 30 min walk) so we got to do a little of the Fira walk and our guide picked us up from there. Have a great trip!

Hi Jannypanny

Thank you for your detailed reply.

Since you say you walked down the steps from your hotel to Ammoudi Bay , I assume you were staying in Ola. Can you please tell me at which hotel you were staying ? I am asking, so as to get an idea about the drop back in the van . Since it’s a common van to drop off all the people on the boat, I was wondering how long will it take to get back to the hotel.
Also, from what I read about the sunset cruise, a dinner is served onboard. Did your sunset cruise not include a dinner ?
In your opinion do you feel it’s better to take the sunset cruise rather than the day cruise ?

And yes, we are also taking a guided tour around the island.

Thanks for your help.