Best Tours in Santorini: Catamarans, Volcano, Wine & Kayaking

Santorini’s caldera is one of the most striking marine environments in the Mediterranean — a flooded volcanic crater where the sea is warm, the cliffs are sheer, and every viewpoint feels designed for a photograph. The island’s best experiences happen on the water. Here are the tours worth booking, with prices, operators, and honest notes on what each delivers. All prices are approximate as of 2026.

Catamaran Cruises

A catamaran cruise is the defining Santorini experience. The standard route circles the caldera from Vlychada or Ammoudi Bay, stopping at Nea Kameni (volcano), the Palea Kameni hot springs, Thirassia (the quieter sister island), and Red Beach. Most tours include lunch and open bar.

Santorini Sailing runs a full-day catamaran from EUR 130 per person (8 hours, max 20 passengers). Their sunset catamaran is EUR 95 (5 hours, open bar, BBQ dinner on deck). Both depart from Vlychada Marina.

Sunset Oia Sailing operates a premium smaller-boat experience (max 12 people) from EUR 160 per person for the sunset tour. The smaller group makes the BBQ deck feel genuinely social rather than chaotic.

Catamaran Santorini (operated by Spiridakos Sailing) lists group catamaran day tours from EUR 99 per person, including snorkelling gear. Private charter starts at EUR 950 for the boat (up to 8 people, half day).

Duration: 5–8 hours
Difficulty: Easy — occasional ladder climbing from the water to get back on board
What’s included: Snorkelling gear, lunch or BBQ dinner (depending on tour), open bar, guide
Best season: May–October. July and August can be rough in the afternoon on exposed boats — morning departures (9am) are calmer.

Volcano Boat Tours

Nea Kameni, the active volcanic island at the centre of the caldera, is reachable only by boat. Traditional wooden caïque boats run short trips (2.5–3 hours) that include the volcano walk and a stop at the sulphur hot springs at Palea Kameni, where the water turns orange-brown around you.

Sunset Tours Santorini runs shared volcano boat trips from EUR 20–25 per person. It’s a no-frills ferry with a lot of passengers — good value if you want to say you’ve walked on the volcano.

Fira Boat Trips operates smaller group options from EUR 35 per person (max 20), with a longer time on the volcano for those who want to reach the summit crater.

For a private hire, local caïque operators at the Fira Skala port charge around EUR 150–200 for a half-day boat with skipper (up to 6 people). Worth considering for families or those who want to control the itinerary.

Duration: 2.5–4 hours
Difficulty: Moderate — the volcano walk is on uneven, loose rock; not suitable for flip flops
What’s included: Boat transfer, guide (on better tours), swim stop at hot springs
Best season: April–October. The volcano is accessible year-round but winter seas can delay trips.

Wine Tasting Tours

Santorini produces some of Greece’s most distinctive wines. The volcanic soil (ash and pumice) stresses the vines to near-death, concentrating the Assyrtiko grape into something minerally, high-acid, and unlike anything from the mainland. A wine tasting tour gives context to what’s in the glass.

Santorini Wine Tour (operated through Wineroads) runs a 4-hour guided tour of 3 wineries from EUR 95 per person, including transportation. The route typically covers Domaine Sigalas (Assyrtiko specialist), Estate Argyros (the island’s largest biodynamic producer), and a smaller boutique winery. 6 wines minimum, with food pairing.

Santo Wines Cooperative on the caldera cliffs in Pyrgos offers self-guided tastings from EUR 20–30 depending on the flight. Their terrace has the famous sunset views — book an 8pm slot in summer.

Wine Lovers Santorini runs a private tour with a sommelier from EUR 180 per person (minimum 2). Includes transportation, access to 4 wineries, and a cheese and charcuterie board.

Duration: 3–5 hours
Difficulty: Easy
What’s included: Transportation, tasting fees, food pairing (varies by tour)
Best season: September–October brings harvest season — some wineries allow guests to help pick grapes. Summer works but is busy.

Caldera Kayaking

Sea kayaking along the caldera wall is quieter and more intimate than any boat tour. You paddle at water level past volcanic rock, reach caves and sea arches inaccessible by caïque, and swim in water that’s 20–25°C in summer.

Santorini Kayak runs a 3-hour guided sea kayak from Ammoudi Bay, paddling north along the caldera base to a secluded cave cove, from EUR 65 per person (max 10 kayakers). All equipment included, no experience necessary.

Fira Kayak Tours offers a sunrise paddle starting at 6:30am from EUR 55 — the caldera light at that hour is exceptional and the water is completely flat.

For experienced paddlers, Kayak Santorini offers a 5-hour semi-circumnavigation of the caldera from EUR 95, reaching spots the boats can’t access. Rated intermediate — Meltemi wind awareness required.

Duration: 2–5 hours
Difficulty: Easy to intermediate depending on tour
What’s included: Kayak and paddle, buoyancy aid, guide, snorkelling gear (most operators)
Best season: May–October. Morning departures are essential in summer to avoid the Meltemi afternoon wind.

Oia Sunset Tour

Watching the sunset from Oia’s castle ruins is Santorini’s most famous activity — and its most crowded. Doing it as part of a guided tour (often combining a village walk with the sunset viewpoint) adds context to what you’re seeing and gets you better positioned than the general scrum.

Santorini Sunset Tours runs a 3-hour Oia guided walk and sunset from EUR 45 per person. The guide covers the history of the Venetian fortress and explains the blue dome churches — both often photographed, rarely understood.

Private Oia Sunset Photography Tour operators charge EUR 100–150 for a 2-hour session with a photographer-guide who knows the angles. Worth it if photography is the purpose of the trip.

Booking Tips

Book catamaran tours at least a week ahead in July and August — good operators sell out. Wine tours can typically be arranged with 48 hours’ notice except during harvest week (late September). Kayak tours run with minimum 2 bookings; confirm ahead in shoulder season (May and October). For volcano boat trips, same-day booking is usually possible but choose the smaller group options over the mass-ferry versions — the experience is noticeably different. Already on the island and looking for what’s still available this week? Our last-minute tours page tracks current availability across Santorini and the rest of Greece, updated twice daily.

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See Also

• Santorini Island Guide — full island overview beyond just the tours
• Where to Stay in Santorini — Fira, Oia, and Imerovigli options
• Santorini Itinerary — how to structure 3–5 days on the island
• Milos vs Santorini — if you’re deciding between the two Cycladic volcanic islands
• Best Tours in Mykonos — comparing what’s on offer a ferry ride away
• Greek Island Hopping Itinerary — building Santorini into a wider Cyclades circuit