Sail the Santorini caldera on a private 44‑ft boat while a WSET sommelier guides you through six local wines, swims at Thirassia, and enjoys a freshly prepared Greek meal. Choose a daytime or sunset cruise for a different perspective on volcanic cliffs and warm Aegean water.
More ways to explore the area's outdoor wonders
You step onto a 44‑ft sailboat in Vlychada as the Aegean wind picks up and the white cliffs of Santorini fall away to the north. The boat slips past black‑sand shores and the carved faces of pumice cliffs, sails filling while a sommelier uncorks the island’s signature wines. Glasses of Assyrtiko and Nychteri awake on deck as the caldera’s rim watches you circle its ancient mouth.
Difficulty
easy
Duration
5–6 hours
Fitness Level
Minimal fitness required — able to board a small tender and stand on deck for tasting and short swims
Wildlife
History
Santorini’s dramatic caldera formed from a massive Minoan‑era eruption; the volcanic soils shaped a distinct viticulture tradition, including the famed Assyrtiko grape and Vinsanto production.
Conservation
Operators avoid disembarking on fragile islets and discourage reef‑damaging sunscreens; take all waste ashore and follow crew guidance to protect marine habitats.
Reserve your spot on the Private Sailing & Wine Tasting on a Sailboat with a Sommelier today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Bring sea‑sickness medicine
The Aegean is generally calm but the caldera can get choppy; take medication beforehand if you’re prone to motion sickness.
Sun protection is crucial
Wide‑brim hat, high SPF sunscreen (reef‑safe), and polarized sunglasses will keep you comfortable during long exposure on deck.
Wear non‑slip deck shoes
Soft‑soled shoes or boat shoes improve traction on wet decks and when boarding from tenders.
Carry ID for pickup and drinking rules
Bring your passport or ID for hotel/port pickup and remember anyone under 18 cannot be served alcohol under Greek law.
Reef‑safe sunscreen
Protects skin and local marine life during prolonged sun exposure.
summer
Non‑slip deck shoes
Improves grip when moving on wet boat surfaces and boarding.
Light windbreaker or boat jacket
Keeps you warm on open water, especially at sunset or in spring breezes.
spring
Seasickness meds or patches
Useful if you are susceptible to motion sickness on open water.