Santorini Sunset Caldera Cruise with Greek Dinner & Swim

Summary

Sail past red & white beach, swim thirassia island, sunset dinner on a wooden boat

You’ll step onto a traditional wooden boat at Oia’s Ammoudi Bay for a Santorini caldera sunset cruise with swimming at Thirassia Island, dinner cooked fresh on board, plus views of Red Beach and White Beach as you circle past volcanic cliffs. Expect laughter with your group, quiet moments at sunset, and flavors you might try to recreate back home.

What’s the experience like?

We’d barely climbed onto the old wooden boat in Ammoudi Bay when someone handed me a glass of local white wine — cold, just slightly salty from the sea air. The deck was warm under my feet. Our guide, Yannis, waved us over to the rail and pointed out Oia’s houses stacked up like sugar cubes behind us. I could smell grilled chicken already and I hadn’t even realized I was hungry yet. There were maybe twenty of us, all strangers but it didn’t stay that way for long — people started swapping stories before we’d even left the harbor.

First stop: Thirassia. The water there is this strange blue-green, so clear you can see your toes wiggling under you. I tried snorkeling (not my strong suit), mostly floated around while two kids did cannonballs off the side. Lunch happened right after — vine leaves stuffed with rice and lemon, beans in olive oil, that kind of food where you keep reaching for “just one more” even when you’re full. Yannis told us how his grandmother used to make those same dishes for Easter. I liked that.

We circled the volcano next — black rocks steaming quietly in the sun — and then drifted past White Beach and Red Beach. The cliffs looked almost unreal against the water; I kept thinking about how many colors there are here that don’t show up in photos. Someone tried to pronounce “Akrotiri” and got it totally wrong; everyone laughed except our captain who just grinned and shrugged. The wind picked up a bit by Black Mountain, but nobody seemed to mind. It felt good after swimming.

I lost track of time after that. At some point we anchored near these hidden coves — honestly, I don’t remember which one exactly — and dinner came out again: salad with tomatoes so sweet they tasted like fruit, more wine, fruit for dessert. The sun started dropping fast behind Oia’s cliffs and suddenly everyone went quiet for a minute or two just watching it go down over Santorini caldera. Even now I still think about that light on the water.

Step-by-step itinerary

Day 1 — Santorini Caldera Sunset Cruise

• Start cruise from Ammoudi Bay
• Swim and snorkel at Thirassia
• Enjoy lunch prepared on board
• Sail around the Volcano
• Sail past Black Mountain and Indian Rock
• Pass Venetian Lighthouse in Akrotiri
• Visit White Beach for swimming
• Swim and take photos at Red Beach
• End cruise at Vlychada's Port

Top questions

Does this Santorini caldera sunset cruise include hotel pickup?

Yes, transportation from and to your hotel is included by air-conditioned minibus or van.

Is dinner provided during the Santorini sunset cruise?

Yes, a traditional Greek dinner is prepared on board by the crew and included in your tour.

Can I swim during this Santorini caldera cruise?

Yes, there are stops for swimming and snorkeling at Thirassia Island and near Red Beach.

Are drinks included on this sunset cruise?

White local wine and soft beverages are included during the cruise.

Where does the sunset cruise start and end?

The cruise starts at Ammoudi Bay in Oia and ends at Vlychada Port.

Is snorkeling equipment provided?

Yes, use of snorkeling equipment and swimming aids is included in your tour.

Are vegetarian options available for dinner?

Yes, vegetarian options are available if requested when booking.

Is this Santorini cruise suitable for families with children?

Yes, infants can ride in prams or strollers; specialized infant seats are also available.

What’s included

Your day includes pickup from your hotel by air-conditioned minibus or van, all transportation between ports, use of snorkeling gear and swimming aids if you want them, plenty of local white wine or soft drinks throughout the trip, plus a full Greek dinner cooked right onboard with chicken fillet, dips like tzatziki, beans in olive oil, stuffed vine leaves, salad with local tomatoes, fresh fruit for dessert—and printed safety instructions in seven languages so everyone feels comfortable before setting sail.