A Round Trip on Santorini – May 2021

Santorini Small-Group Hiking Trip (May 2021): Flexible, Scenic, Unforgettable

Trip summary

Our May 2021 journey to Santorini was a special experience. Traveling as a small group allowed us to adapt the daily plan to everyone’s pace and interests. Not everyone can or wants to tackle the longest caldera hikes—and that’s exactly the strength of our tailor-made walking holidays: we listen, we adjust, and we make sure every guest enjoys the island to the fullest.

Even though we didn’t cover every originally planned route or the most remote viewpoints, the week was gorgeous from start to finish. Participants discovered Santorini’s essentials—from the whitewashed villages of Oia and Imerovigli to the dramatic caldera rim, plus key historical highlights and the island’s distinctive volcanic landscapes.

This trip reaffirmed what we value most: it’s not just about ticking off sights, but about sharing the moment. Every tour is different—and each one has its own magic.

Highlights at a Glance

Small group and flexible itinerary tailored to ability and interest

Iconic villages: Oia, Imerovigli, and views across the caldera

Time to explore historic sites and volcanic scenery

Stress-free pacing with photo stops and café breaks

Personal guidance with an eye for geology, culture, and the best viewpoints

Who This Trip Suits

Travelers who prefer small groups and personal attention

Guests who want adaptable walking distances rather than fixed, strenuous routes

Photographers and nature lovers who enjoy unhurried exploration

Why Choose Our Santorini Walks

Tailor-made pace: We shape each day around the group’s energy

Local insight: Hidden corners beyond the usual postcard spots

Quality over quantity: Fewer “must-do” checklists, more real moments

 

May 21, 2021: Arrival with stunning views of Greece!
May 22: Private Caldera Hike
May 23: First excursion with the guests to Thira & Oia
May 24: Visit to the Ancient Thera excavation site
May 25: Visit to the mountain village of Pyrgos
May 26: Visit to Oia
May 27: Visit to Emporio
May 28: Thira and Perissa
May 29: Akrotiri & return flight

Santorini Photos