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Santorini Shore Excursion: Private Caldera, Traditional Winery and Oia Village Tour


5 hours (approx.)

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See the highlights of Santorini on a 5-hour shore excursion, and explore the island from its half-submerged volcanic caldera to the summit of its highest mountain. With a private guide at your side, learn about Santorini’s volcanic history while visiting the caldera. Then, travel through the mountains to a monastery and sample local produce made by the resident monks. Try wine at a volcanic vineyard and winery, and then round off your day with free time in picturesque Oia village before returning to port.
Meet your private guide by the top of the cable car in Fira or at your Santorini hotel, and travel to the island’s caldera for your first stop of the day. A spectacular geological formation, the caldera is the volcanic remains of the original island that collapsed beneath the sea after a volcanic explosion thousands of years ago.

Stand at the edge of the caldera to pose for pictures against the backdrop of the Aegean Sea, and then continue by minibus to check out another of the island’s volcanic features: a dramatic-looking black-sand beach. If weather permits, take a stroll down Perissa – the longest beach on the island – and make the most of some free time to sunbathe on the warm shores and enjoy a bite to eat for lunch, if you wish. Or, if you prefer, you can skip the beach stop. Arrange with your guide on the day.

Later, travel to the peak of Profitis Ilias, Santorini’s highest mountain that stands some 2,000 feet (600 meters) above sea level. Gaze out at the island vistas surrounding you, and then follow your guide inside the ornate Greek Christian monastery perched at the mountain’s summit. Walk around the chapel, listening to the monks chanting, and savor samples of the dessert wine, honey and extra virgin olive oil that’s made on-site.

After learning about winemaking in the mountains, head down into the hills to visit a typical Santorini winery and volcanic vineyard where the local assyrtiko and vinsanto varietals are produced. Sample up to four glasses of the island’s distinctive light and acidic whites while learning how wine is produced in such a dry and unforgiving island environment.

From the hills, continue to Santorini’s poster-child village of Oia, the iconic whitewashed village that’s graced many a postcard. Take a stroll around the streets with your guide to get your bearings and learn about the village history, and then enjoy some free time to sightsee and shop at leisure. After making the most of your free time, meet your guide, and then finish your day with a drop-off at the port.

Worry-free Shore Excursion:We will ensure your timely return to Santorini Port for this activity. In the rare event your ship has departed, we will arrange for transportation to the next port-of-call. If your ship is delayed and you are unable to attend this activity, your money will be refunded. See our terms and conditions for full details.

Customer Review (34) see all review



We enjoyed the company of Stefano and all of his knowledge of the island, wineries and all he could give us in the time we had for the tour. We learned so much and had so much fun with him and all he showed us and shared about the history and current island workings! A+++++ Again, Thank YOU Stefano!!



What a beautiful island. Our guide, Gabriel, is a terrific guide. He has an excellent command of the English language and very easy to understand. He has a high energy level, very enthusiastic and entertaining. He took us to all the usual places folks want to see, but because we were in a small van we were able to get closer and spend as much time as we wanted to at the various places. As a result we weren’t so rushed as with big bus tours, we didn’t have to wait for the missing persons, etc.

If you have three or more folks in your party, it will probably cost you less to see and spend as much time as you like in the various spots on the island. We did go to Oia, the beach, a church high in the mountains to get a view of the island, and lastly to a winery where we were presented with five wines and a plate with many delectables to better sample the wine.

Christopher C


Amazing island and so much to see! Our tour guide Evangelo was great and really helped us to see the island. He took the time to show us the key spots Oia, Red Beach, monastery, winery among others and went out of his way to make sure we could photograph the beautiful island. Well done!



What a wonderful and amazing day. Our guide Demetrius was amazing, very accommodating, kind and knowledgeable of the island and Greece. We had a wonderful day and a beautiful tour of the island. The last thing we did was a wine tasting. The young lady who was our guide was one of the best.


Sales Points


  • Meeting point within walking distance from cruise port (top of cruise port's cable car)
  • Transport by air-conditioned Mercedes-Benz modern minivan
  • Private guide
  • Live commentary
  • Wine tastings at a traditional winery served with local cheese
  • Mineral water and soft drinks
  • Worry-free Shore Excursion Guarantee
  • Exclusion

  • Gratuities
  • Food and drinks, unless specified
  • Lunch / Meals (optional)
  • Cable car tickets for cruise ship travelers (6.00 Euros per person, per ride)
  • Additional Info

  • Confirmation will be received at time of booking
  • Meeting point for cruise passengers is top of cruise port's cable car. The guide will be holding a sheet with the Lead Passenger's name.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • Tour Grades Available

    Voucher Info

    You can present either a paper or an electronic voucher for this activity.

    Voucher Option

    EVouchers + Paper Vouchers accepted

    Departure point

    Traveler pickup is offered
    We pickup guests from all Santorini hotels & Airbnb's.
    If hotel is inaccessible by car due to restrictions, pickup will be held from a nearby location withing short walking distance.
    Cruise ship travelers: Meeting point is the top of the cable car. Your guide will hold a name board with travelers name on.
    Airport travelers: Pickup and drop off is possible from Santorini National Airport at no extra cost.


    • Santorini Airport, Greece


    • Cable car, Ipapantis 10, Thira 847 00, Greece

    Departure time



    Hotel Pickup



    5 hours

    Return Detail

    Booking EngineId

    The product will be confirmed immediately and the supplier will be sent a notification.

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