Day-by-day estate-visit plans for Santorini: weekend, first-timer and deep-cellar editions.

Day-by-day plans

3-Day Santorini Wine Route: Pyrgos, Megalochori and Oia

  1. Day 1

    Morning
    Arrive Athinios port or Santorini airport. Transfer to Pyrgos. Late morning tasting at Santo Wines cliff-top facility with caldera-rim panorama and a flight covering Assyrtiko, Nykteri and Vinsanto.
    Afternoon
    Walk through Pyrgos village to the Profitis Ilias monastery viewpoint. Late-afternoon tasting at Hatzidakis Winery (organic) at Pyrgos Kallistis.
    Evening
    Sunset wine bar in Imerovigli or Fira. Dinner with a wine pairing at a caldera-rim restaurant.

  2. Day 2

    Morning
    Drive south to Megalochori. Morning visit to Boutari Santorini (Megalochori) for tasting of the estate's Santorini PDO range including the Mavrotragano red.
    Afternoon
    Tasting at the restored Venetsanos Winery on the caldera cliffside above Athinios port; a tour of the original gravity-flow vinification architecture is included. Optional walk-in tasting at Gavalas Winery on the way back through the village.
    Evening
    Dinner in Akrotiri or Megalochori. Optional sunset wine at the Akrotiri lighthouse.

  3. Day 3

    Morning
    Drive north to Oia. Morning tasting at Domaine Sigalas at Baxedes covering Assyrtiko single-vineyard bottlings and Mavrotragano reds.
    Afternoon
    Optional second tasting at Estate Argyros at Episkopi Gonia on the return drive south, focusing on the estate's old-vine Monosirto and library Vinsanto. Return to airport or Athinios for ferry departure.
    Evening
    Final sunset on the Oia caldera or return departure from Santorini.

2-Day Vinsanto Deep Dive: production, ageing and pairing

  1. Day 1

    Morning
    Tasting at Santo Wines focused on the cooperative's Vinsanto range, including 4-year and longer-aged expressions. The visit includes a brief education on the sun-drying process visible at the facility during the drying season.
    Afternoon
    Tasting at Estate Argyros at Episkopi Gonia, including the long-aged Vinsanto library bottlings. The estate's Vinsanto vertical covers 4-, 12- and 20-year-old bottlings.
    Evening
    Dinner with Vinsanto pairing course (often the dessert) in a caldera-rim restaurant.

  2. Day 2

    Morning
    Morning tasting at Boutari Santorini in Megalochori with the estate's Vinsanto range and the contrast with their dry Assyrtiko. Possible visit to Canava Roussos in Mesa Gonia for a heritage-canava perspective on Vinsanto production.
    Afternoon
    Return to base. Optional visit to the Wine Museum at Vothonas (subterranean cave museum) for the historical context of Santorini sweet wine production and Russian-trade history.
    Evening
    Final wine-paired dinner with multiple Vinsanto pours alongside Santorini food pairings (sweet-savoury contrasts, semi-aged kefalotyri cheeses, hazelnut and almond desserts).

1-Day Caldera-Rim Wine Bar Walk

  1. Day 1

    Morning
    Start in Fira at one of the central wine bars or tasting rooms (Mati Wine Bar or PK Cocktail Bar's wine list) for a morning glass of current-release Assyrtiko.
    Afternoon
    Continue north along the caldera path toward Oia, with shorter stops at Firostefani wine bars. Arrive Oia in the late afternoon.
    Evening
    Sunset glass of Vinsanto or aged Assyrtiko at an Oia caldera-rim wine bar with the sunset view, then bus back to base.

2-Day Ungrafted-Vine Vineyard Walk

  1. Day 1

    Morning
    Vineyard walk in the Pyrgos to Megalochori area through old-vine kouloura plantings, with a focus on observing the basket-training system and the volcanic ash substrate.
    Afternoon
    Cellar door tasting at Boutari Santorini in Megalochori with old-vine Assyrtiko and Mavrotragano. Optional second visit to Gavalas in the village.
    Evening
    Return to caldera-rim base for the evening. Light dinner with current-release Assyrtiko.

  2. Day 2

    Morning
    Vineyard walk in the Episkopi Gonia area, where Estate Argyros farms parcels of vines over 100 years old. Estate-led vineyard walks can be arranged in advance.
    Afternoon
    Cellar tasting at Estate Argyros with focus on the Monosirto and library Vinsanto bottlings.
    Evening
    Final dinner in Pyrgos or Imerovigli. Departure planning.

3-Day Wine and Akrotiri Archaeology

  1. Day 1

    Morning
    Visit the Akrotiri archaeological site in the south of the island. The on-site museum displays the carbonised grape remains and amphora residues that anchor the Bronze Age viticulture story.
    Afternoon
    Cellar visit at Hatzidakis Winery (organic) at Pyrgos Kallistis for the volcanic-soil context.
    Evening
    Dinner in Pyrgos with discussion of the Bronze-Age-to-modern continuity.

  2. Day 2

    Morning
    Visit the Museum of Prehistoric Thira in Fira (the major artefacts from Akrotiri excavations are displayed here). The Bronze Age frescoes and pithoi storage jars contextualise the Akrotiri site visited on Day 1.
    Afternoon
    Cellar visit at Santo Wines cliff-top facility above Pyrgos, with a Vinsanto-focused flight to connect the modern sweet wine to its ancient and Venetian-era trade history.
    Evening
    Sunset dinner with Vinsanto pairing in a caldera-rim restaurant.

  3. Day 3

    Morning
    Drive north to Oia. Morning tasting at Domaine Sigalas with focus on the modern producer renaissance and the role of Sigalas in the 1990s Mavrotragano revival.
    Afternoon
    Optional caldera boat tour to Nea Kameni (the active volcanic islet at the centre of the caldera) for the volcanic geology context, completing the loop from Bronze Age eruption to modern wine production.
    Evening
    Sunset and final dinner. Departure planning.

Book wine experiences in Santorini

See all 2264 bookable experiences in Santorini

Itineraries in Santorini, FAQ

When is the best time to visit Santorini for wine?

Peak wine-travel season in Santorini is spring through autumn, with harvest the standout window.

Do I need an appointment to taste at Santorini estates?

classified-growth and grand-cru estates require booking days to weeks ahead; smaller family domaines often take walk-ins midweek.

What hours do Santorini cellars and tasting rooms keep?

most estates open 10:00 to 17:00 by appointment, often closed Sunday and Monday.

How does tipping work at Santorini tastings?

tipping is not expected at tastings; buying a bottle from the cellar door is the customary thank-you.

What is the one wine to try in Santorini?

Ask the next local you meet what they would order. Santorini rewards trust.

← Back to Santorini wine guide