THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Swap the daytime crowds for a quieter, after-dark walk along the caldera edge, then sink into a guided tasting of Assyrtiko and Vinsanto paired with traditional Santorinian dinner. This three-hour evening tour blends geology, local wine culture and easy hiking with hotel pickup.
Swap the daytime crowds for a quieter, after-dark walk along the caldera edge, then sink into a guided tasting of Assyrtiko and Vinsanto paired with traditional Santorinian dinner. This three-hour evening tour blends geology, local wine culture and easy hiking with hotel pickup.
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Book directly with TREKKING HELLAS for the best rates and real-time scheduling.
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Operated by TREKKING HELLAS · Fira, South Aegean
The cobbled lanes of Fira are quieter at dusk: shutters click closed, stray cats pad between whitewashed houses, and the caldera edge throws a long shadow across the Aegean. A small group gathers under a ferryman’s lamp, and the guide checks headlamps before they step onto the Fira–Imerovigli section of the famous trail. The sun—still a fierce coin of orange—sinks behind the rim and Santorini, unhurried, begins to glow with thousands of scattered lights.
easy.
3 hours.
Suitable for most fitness levels; you should be comfortable walking 3 km on uneven terrain and climbing short stone steps.
The walking segment covers roughly 3 km and takes about 45–90 minutes depending on pacing and stops; the full tour is about 3 hours including wine tasting and dinner.
Yes—guests sample four Santorinian wines including Assyrtiko and Vinsanto, and a traditional local dinner is served at the restaurant in Imerovigli.
Yes—the tour provides roundtrip hotel pickup and drop-off from most hotels on Santorini; confirm exact pickup point when booking.
The hike is family-friendly for older children used to walking on uneven ground, but the operator advises the tour is not recommended for pregnant travelers and those with serious back or heart conditions.
The tour may be canceled in case of bad weather; full refunds are available if canceled at least 24 hours before departure or if the operator cancels due to conditions.
Yes—bring a government-issued ID if you plan to drink, as staff may check for age compliance during the tasting.
Santorini’s dramatic cliffs are the result of one of the largest volcanic eruptions in the Mediterranean; the island’s volcanic soils are central to its ancient and modern wine culture.
Stick to marked trails to limit erosion on fragile volcanic soil and support local tavernas and wineries that follow sustainable farming practices.
TREKKING HELLAS operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with TREKKING HELLAS
Book directly with TREKKING HELLAS for the best rates and real-time scheduling.
Reserve Now