6 Best Santorini Hikes

Evening Experiences, Guided, Hiking & Trekking, Santorini, Tour Reviews

Santorini: Caldera Trail Guided Hike and Sunset Viewing

/ August 6, 2026

1.Santorini: Caldera Trail Guided Hike and Sunset Viewing

Hike Santorini’s caldera rim with a guide, enjoy a traditional picnic, then watch a 360 sunset view above Oia.

Santorini: 4hr Small Group Caldera Hike from Fira to Oia

/ August 17, 2026

2.Santorini: 4hr Small Group Caldera Hike from Fira to Oia

Small-group Santorini caldera hike from Fira to Oia with an English guide, snacks, and water. Up to 12 people, about 4 hours.

★ 5.0

“My husband and I booked this hike to see such amazing sceneries, little did we know, it’s only us and our tour guide Kathrin, who i would recommend, if people are trying this kind of activities. She was very knowledgeable and accommodating. Good vibes and lots of interesting stuff we learned from her about Santorini.”

75 reviews4 hours (approx.)From $120.68by SantoriniExperts

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Hiking & Trekking, Private, Santorini, Tour Reviews, Tours

Santorini’s Famous Fira to Oia Hike: A Private tour Adventure

/ August 29, 2026

3.Santorini’s Famous Fira to Oia Hike: A Private tour Adventure

Private Fira to Oia hike with pickup, snacks, and an English guide. Walk the caldera villages and finish in Oia with photo help.

★ 5.0

“This hiking tour from Fira to Oia was a delightful experience! Our guide, Sergiu, was wonderful – so sweet, knowledgeable, and a great conversationalist, making the easy hike even more enjoyable. The trail offered absolutely beautiful views at every turn. Highly recommend this tour with Sergiu for a relaxed and scenic way to see Santorini!”

49 reviews3 to 4 hours (approx.)From $132.16

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Hiking & Trekking, Santorini, Tour Reviews, Walking Tours

Santorini Caldera Walk Hiking Experience Fira-Oia

/ September 2, 2026

4.Santorini Caldera Walk Hiking Experience Fira-Oia

Hike Santorini’s caldera rim from Fira to Oia with hotel pickup, free water, and an English guide for epic cliff views.

★ 4.5

“Excellent hike. George was an awesome tour guide. Hike was tough but very doable. He may it easy and was very supportive during hard parts of it.”

41 reviews4 hours (approx.)From $161.77by Pigaia travel

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Dining Experiences, Dinner Experiences, Evening Experiences, Food & Drink, Hiking & Trekking, Santorini, Tour Reviews, Wine Tours

Santorini: Night Hike, Wine Tasting, and Greek Dinner

/ September 3, 2026

5.Santorini: Night Hike, Wine Tasting, and Greek Dinner

A guided Santorini night hike from Fira toward Imerovigli, ending with Assyrtiko and Vinsanto wine tasting plus a traditional Greek dinner.

★ 4.5

“The tour was a great experience with a very friendly guide. For us it was the best activity and the best meal (4 excellent courses with delicious wines) of the whole holiday! We wouldn't want to miss it and can recommend it to anyone who wants to have a good time.”

40 reviews3 hoursFrom $182by Trekking Hellas Santorini

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Cruises & Boat Tours, Hiking & Trekking, Private, Santorini, Tour Reviews, Volcano Hikes

Caldera Private Cruise & Volcano Hike

/ September 14, 2026

6.Caldera Private Cruise & Volcano Hike

Private Santorini cruise from Ammoudi with volcano hike, snorkeling stops, hot springs, and calmer small-group sailing.

★ 5.0

“2 hour trip is not enough. We didn't get the chance to see the volcano properly (walking up takes about 25 min, and we were given 30 for overall) and neither had time to get even close to the thermal waters, the crew took us there pointed finger and sailed away. Although we were 15…”

31 reviews3 hours (approx.)From $330.39by Spiridakos Sailing Cruises

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