There's an Oia most people never see because they're facing the wrong way. You'll walk it with me, through the back lanes where the village still works like one, past the blue domes everyone photographs and into the streets that explain where they come from. I'll show you how a captain's neighborhood had to be laid out, and we'll move at a pace made for talking. Art is the Ariadne's thread tying it all together. Painters live and work in Oia even now, and you'll see their work, starting with Panos Karamitsos, whose LILOPAS paintings fill the gallery at Domus K 1885. The house itself is part of the story: a 19th-century Sea Captain's House, restored room by room, with a herb garden and pistachio trees at the back. That garden is where we finish. Kadio Sigalas, the first Santorini woman to become a shipping tycoon, lived here. You'll sit under the trees for a guided tasting of Greek wines with small bites of cheese—Santorini's Assyrtiko-Aidani first, then its mainland cousins—while the house's story unfolds around you. This is for you if you'd rather come home talking about the painter whose work you stood in front of than the photo everyone else covets. You arrive on your own, but you don't taste alone.
Oia Art Walk: Quiet Lanes & Sea Captain's House
Walk Oia's back lanes with a local host and meet the artists who still live here. The walk ends at Domus K 1885, a restored Sea Captain's House, with a tasting of Greek wines in the garden where Kadio Sigalas once lived.
Available: April to December
Language: English, Spanish, Greek, Portuguese on request
Good for: couples, friend groups, families
Min participants: 1
Accessibility: Contact the host for accessibility information
Animals: Check with the host
Why we love this experience
- Culture:
This is where the experience is entirely rooted. Maria walks guests through the Oia that most visitors never reach — the lanes behind the blue domes, the neighbourhoods that explain how the village was laid out around a captain's trade, the art that is still being made here by painters who live and work on the island today.
- Community:
Maria is a year-round resident of Santorini who has built a trusted circle of local people, places, and stories over many years. Domus K 1885 is part of that circle — a local, family-rooted space run by people committed to keeping Oia's real history visible and alive. The experience does not route guests through internationally owned venues or tourist infrastructure; it moves through spaces that belong to the community and benefit from continued local engagement.
- Participation:
You walk at a pace made for talking. You stand in front of paintings and learn who made them and why.
- Rhythm:
The walk moves through back lanes deliberately chosen to reduce congestion in Oia's busiest arteries. The pace is explicitly designed for talking, not ticking off sights. The experience avoids the most congested summer peak.
About the host
Mission
My mission is to connect visitors with "my people" — the circle of locals who love this island and work to keep its quieter side alive.
Impact
Experiences are built around a trusted circle of local producers, artists, winemakers, and cultural spaces that she has known for years. Her approach actively steers away from the island's most congested routes, designing days around quieter timing and smaller places that reflect Santorini beyond its busiest surface. She describes this openly as reducing unnecessary congestion and supporting smaller local producers. She is also a member of One Planet Journey as a Deep Travel Ambassador, reflecting a conscious alignment with values of slow, place-respecting travel.
Organisation
Santorini by Maria
Location
Oia, Greece
Google MapsThe precise location will be communicated by the host when booking the experience
Contacts host for booking
This host will handle your booking directly.
Good to know
This experience works for solo travelers, as you'll be interacting with local hosts who don't hurry you along. But it's also perfect for groups of friends who wish to chat or couples wanting some quiet time in the garden at the end.
Ask us anything
Do you have any questions before booking? Do not hesitate to contact us by filling out the form.
Curated accommodation
Where to stay nearby
Cycladica Cave Houses
In their own words, "Cycladica is an expression of our family’s respect for the culture, architecture and environment of the Greek islands. We welcome our guests into historical houses that we have restored and often lived in ourselves." The owner's mother - the architect Voula Didoni - was behind a lot of Oia's post 1956-earthquake restoration.
Book your stay directly
Related experiences
