The Colorful & Charming Town of Oia

Santorini Highlights Tour & Wine Tasting, Santorini

See Santorini's highlights on a driving tour featuring picturesque Oia, Prophet Elias Monastery and amazing caldera views

Overview

Discover Santorini's iconic sites and vistas on this half-day driving tour of the island. Along the way, learn all about the fascinating history of Santorini, including its ancient winemaking past.

Your guide will collect you from either your hotel or a central point in Fira. Υou’ll stop in charming Oia, Santorini's famous picture-perfect village. Enjoy the whitewashed facades and pastel-hued houses as you walk along twisting streets and soak in the scenery.

You will make your way to Prophet Elias Monastery, which sits atop the island's highest point and offers scenic panoramic views. Other stopping points include Santorini's medieval village and castle in Pyrgos and the quaint hamlet of Megalochori, amongst others.

You’ll visit a famous and prestigious winery to enjoy a wine tasting. As you sip, learn about the winery, the island's old vines, and the unique centuries-long winemaking process you'll only find in Santorini. Sit back with a glass of wine as you gaze out stunning views.
Read more about unique and interesting experiences in Santorini.

Know before you go

Duration
5.5 hours
Recommended for
All ages
Group
Small group, 10 people or less

Start times

  • Daily
    9:00 am, 3:00 pm

What's included

Local expert guide, roundtrip transfers, wine tasting

Traveler reviews

18 total ratings, 15 with reviews
4.9 out of 5
Feature ratings
Quality of Experience
5.0
Guides, Drivers and Staff
4.9
Transport
5.0
Lindsay
Lindsay C.
Twin Falls, ID | Reviewed on Sep 04, 2023

Harry our guide was adorable and Takis our driver an incredible driver.
We had a time confusion and they were very calm and flexible. Beautiful views and a fun experience! Read more

Harry our guide was adorable and Takis our driver an incredible driver.
We had a time confusion and they were very calm and flexible. Beautiful views and a fun experience!

Quality of Experience
Guides, Drivers and Staff
Give Harry and Takis our love!
Transport
S
Stephen W.
Canada | Reviewed on Jul 05, 2023

The tour guide made this enjoyable. Would of been nicer to maybe visit more vineyards. Sight seeing spots are nice though. Read more

The tour guide made this enjoyable. Would of been nicer to maybe visit more vineyards. Sight seeing spots are nice though.

Quality of Experience
Guides, Drivers and Staff
Transport
Nadia
Nadia J.
Charlotte, NC | Reviewed on Jun 11, 2023

We had so much fun on our wine tour with Harry!! Harry did an amazing job showing us Santorini, and the wine part was so fun too!! Harry was very professional but also really fun and showed us so many things around the island. The tour was a good mix of fun and learning!! Read more

We had so much fun on our wine tour with Harry!! Harry did an amazing job showing us Santorini, and the wine part was so fun too!! Harry was very professional but also really fun and showed us so many things around the island. The tour was a good mix of fun and learning!!

Tips for future travelers

It’s not a tour of wines it’s a tour of Santorini with wine tasting at the end

Quality of Experience
Guides, Drivers and Staff
Transport
Lisa
Lisa B.
Ivins, UT | Reviewed on Jun 03, 2023

Our guide was great. He was knowledgeable and friendly. We learned so much about the history of the island. We walked through iconic areas for the best photo opportunities. We were dropped at the winery while he waited outside. Wine tasting was at Artemis Karamolegos. There were 3 tastings and we talked them into 2 more! Very generous (we bought a bottle!). We got little nibbles for 2, even though they knew there were 3 of us. We had to ask for more food! They were very nice about it. Read more

Our guide was great. He was knowledgeable and friendly. We learned so much about the history of the island. We walked through iconic areas for the best photo opportunities. We were dropped at the winery while he waited outside. Wine tasting was at Artemis Karamolegos. There were 3 tastings and we talked them into 2 more! Very generous (we bought a bottle!). We got little nibbles for 2, even though they knew there were 3 of us. We had to ask for more food! They were very nice about it.

Quality of Experience
Organized and professional.
Guides, Drivers and Staff
Loved our guide!
Transport
Perfect!
M
Megan E.
Duxbury, MA | Reviewed on May 29, 2023

This is a must do in my opinion for anyone going to visit Santorini. It really does cover the whole entire island on a high level and then travelers can decide where they’d like to spend additional time. Our guide was absolutely amazing. He knew this island extremely well, and was able to give us lots of awesome information about the history, the highlights the best places to see the sunset, and even brought us to a secret place that the travelers and most tourist didn’t know about. It was a... Read more

This is a must do in my opinion for anyone going to visit Santorini. It really does cover the whole entire island on a high level and then travelers can decide where they’d like to spend additional time. Our guide was absolutely amazing. He knew this island extremely well, and was able to give us lots of awesome information about the history, the highlights the best places to see the sunset, and even brought us to a secret place that the travelers and most tourist didn’t know about. It was a really great experience for us.

Tips for future travelers

My only advice for future travelers is that this is a walking tour where you will need to be able to walk up and down many steps and navigate some uneven terrain so if that is a challenge for you, it might not be your best option

Quality of Experience
Amazing overall quality of experience. If there was anything at all that we would change, we found ourselves definitely anxious to wrap up the day after 5 1/2 hours. If the company had offered a bottle of wine to watch the sunset with that would have enhanced the experience but all we had was a bottle of water, and we started feeling very hungry and ready to get back.
Guides, Drivers and Staff
Excellent driver and tour guide for this experience!
Transport
Very safe and efficient driver in a very comfortable van
Carole
Carole D.
Arvada, CO | Reviewed on Oct 07, 2022

Vasili was fabulous Read more

Vasili was fabulous

Quality of Experience
B
Barbara C.
Palm Desert, CA | Reviewed on Oct 06, 2022

Vasili was our best guide of the trip. Extremely helpful, knowledgeable , friendly and good English. A joy to be with for a day Read more

Vasili was our best guide of the trip. Extremely helpful, knowledgeable , friendly and good English. A joy to be with for a day

Quality of Experience
Guides, Drivers and Staff
Transport
Lori
Lori H.
Miami, FL | Reviewed on Sep 26, 2022

Belos (sp), our guide was great! Fun and interesting. Nice day. We enjoyed. Read more

Belos (sp), our guide was great! Fun and interesting. Nice day. We enjoyed.

Quality of Experience
Guides, Drivers and Staff
Transport
Jazmine
Jazmine S.
La Mirada, CA | Reviewed on Sep 17, 2022

I thought we were just going on a wine tour but I was shocked to know we had a whole guided tour of everything. I was so excited while he explain everything and took us to different locations. I love the tour guide, gelato, sunset, and wine. Also met another amazing couple there. Read more

I thought we were just going on a wine tour but I was shocked to know we had a whole guided tour of everything. I was so excited while he explain everything and took us to different locations. I love the tour guide, gelato, sunset, and wine. Also met another amazing couple there.

Quality of Experience
Guides, Drivers and Staff
Transport
Anita
Anita M.
Canada | Reviewed on Aug 30, 2022

Excellent guide!! Read more

Excellent guide!!

Quality of Experience
Guides, Drivers and Staff
Transport

Itineraries with Santorini Highlights Tour & Wine Tasting

History and Culture in Athens and Santorini - 7 Days

Get to know ancient Athens and get a taste of island life on Santorini with this weeklong itinerary. Sample volcanic wine varietals in centuries-old vineyards, take a mythological tour of the capital, take a cooking class based on ancient Greek culinary methods, and more.

Cultural Cyclades: Mykonos, Naxos, Ios, Santorini - 12 Days

Visit four distinct islands in Greece's most famous archipelago with this 12-day itinerary. Shop the glamorous boutiques of Mykonos, take a cooking workshop on cultural hotspot Naxos, experience village life on tiny Ios, and soak in the sun (and sunsets) of Santorini. Along the way, you'll enjoy lots of Greek history, glorious beach time, and pretty ferry rides across the Aegean sea.

Discover Athens, Mykonos, Santorini & Crete - 13 Days

From Athens to the islands, you'll experience some of the best Greece has to offer with this itinerary. Travel back in time in the capital as you visit historic sites like the Acropolis and Delphi. Then make your way to the beaches of vibrant Mykonos, Delos' sacred ruins, and Santorini's volcanic hills. End your island-hopping adventure in Crete, where you'll discover fascinating ruins and hike the stunning Samaria Gorge before returning to Athens.

Taste of the Cyclades and Crete - 16 Days

The glittering Cyclades span hundreds of miles, with centuries of history under their belt. Your trip through the island chain will start in glamorous Mykonos before a stop at relaxed Paros for lazy days of beaches and tavernas. Continue to Naxos and Ios, making your way to the volcanic sunsets and cliffside architecture of Santorini. Finally, head to Crete, where excellent cuisine and hospitality await.

Greek Panorama in Athens, Mainland Greece, The Cyclades, and Crete - 19 Days

Travel almost the entire length of Greece on this fun itinerary. You'll start with the myths of Athens, then travel to the modern nightlife mixed with traditional farms of Mykonos and Santorini. The ferry to Crete will take you back to the Palace of Knossos and era of stone villages, then return to Athens to use the city and neighboring Nafplio as your base for expeditions to even more ancient monuments.