Santorini Private Sail & Wine Tasting: Sunset and Day Cruises with a Sommelier
Sail the Santorini caldera with a WSET-certified sommelier aboard a private 44-ft sailboat. Taste six Santorini wines, swim at Thirassia, and choose a sunset or daytime cruise with transfers and a cook-on-board Greek meal included.
The Experience
Before You Go
Book the sunset slot early
Sunset departures fill quickly—reserve at least a few days ahead to secure a private evening cruise for optimal caldera light.
Protect swimwear from sulfur
Avoid swimming at the hot springs with your best suit; the sulfur can stain or degrade fabric—use an older suit if you intend to go in.
Pack non-slip footwear
Bring deck-friendly shoes for safe boarding and moving around the sailboat during maneuvers and when stepping ashore at Thirassia.
Stay hydrated and pace tasting
Sip water between wine pours, and plan to eat the onboard meal before the tasting intensifies to avoid light-headedness on deck.
Local Knowledge
Hidden Gems
- •Photograph the Indian’s Face rock formation from the water for a unique perspective
- •Quiet tavern on Thirassia—ask the crew for a recommendation to extend the island visit
Wildlife
- •Mediterranean shearwater (seabird)
- •Loggerhead sea turtle (Caretta caretta)
Conservation Note
Operators commonly avoid landing on fragile volcanic islets and advise against swimming in hot springs to limit environmental and equipment damage; respect local rules to protect marine life.
Santorini’s caldera formed after the massive Bronze Age Minoan eruption that reshaped the island and created the mineral soils that define local vineyards.
What to Bring
Sunscreen (SPF 30+)Essential
Strong Aegean sun reflects off water—high-SPF protection is essential.
Deck shoes or sandals with gripEssential
Non-slip soles help with boarding and moving safely on wet surfaces.
Light wind jacket
Evenings on the caldera can be cool; a windproof layer adds comfort.
Swimwear and quick-dry towelEssential
Bring a suit for the Thirassia swim stop and a towel for returning to the boat.
Common Questions
Are transfers included?
Yes—hotel, port or airport pickup and drop-off are included; total door-to-door time is about six hours.
Can under-18s participate in the wine tasting?
Minors may attend the cruise but cannot consume alcohol under Greek law; tasting is restricted to adults.
Will we stop at the hot springs?
The route passes the hot springs and you’ll see the sulfuric water, but cruises usually do not stop to swim there due to crowding and sulfur effects on swimwear.
Is the cruise suitable for pregnant travelers or those with heart issues?
This tour is not recommended for pregnant guests or travelers with serious cardiovascular conditions; consult your physician before booking.
Book This Experience
Check AvailabilityDuration
5–6 hours (5-hour cruise; ~6 hours with transfers)
Location
Vlychada, South Aegean
Difficulty
easy
Fitness Level
Suitable for travelers of average fitness; must be able to step on/off a dock and stand on a moving boat.
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