The short answer: for most visitors, a catamaran is the better choice in Santorini. Its two hulls make it far more stable in the caldera’s afternoon breeze, its flat deck offers several times the lounging space of a monohull sailboat, and its low swimming platform makes getting in and out of the water easy for every age. A traditional sailboat rewards purists who want to feel the boat heel under sail — and don’t mind trading comfort for it.

Stability: the Caldera Test

Santorini’s caldera is a spectacular but breezy amphitheatre — the meltemi wind builds most afternoons in summer. A catamaran rides that breeze on two hulls, staying flat and reassuring; a monohull leans (sailors say “heels”), which is romantic for twenty minutes and tiring for five hours. Guests prone to seasickness consistently do better on a catamaran — one reason we sail Lagoon catamarans on every one of our Santorini boat tours.

Space: Where Will You Actually Sit?

A 44ft catamaran like ours is over 7 metres wide, with deck mattresses at the bow, a permanently shaded T-top, and enough rail for everyone when the volcano or the cliffs of Oia come into view. A sailboat of the same length is a narrow wedge by comparison — beautiful, but with one good sunbathing spot and a queue for it. On a semi-private cruise capped at 15 guests, that width is what makes “semi-private” feel private.

Swimming: the Platform Matters

Every good Santorini itinerary is built around swim stops — Red Beach, White Beach, the hot springs beside Nea Kameni. A catamaran’s swimming platform sits at water level: you step off, you climb back on, no drama. Boarding a monohull from the water is closer to a fitness assessment. Families, older travellers and nervous swimmers feel the difference immediately.

The Romance Argument

Purists are right about one thing: a heeled-over monohull under full sail is the prettier picture from shore. But you will be on the boat, not looking at it — and from on board, the picture is the caldera itself. For proposals and honeymoons, the stable deck of a private catamaran wins on practical romance: champagne glasses stay upright. (Ask the couples on our yacht proposal cruise.)

So Which Should You Book?

Choose a catamaran if you want comfort, space, easy swimming and a group that ends the day relaxed rather than rearranged — whether semi-private at sunset or privately chartered. Choose a monohull sailboat only if the sailing itself, not Santorini, is the point of your day. In this caldera, we think the island deserves top billing.

Frequently Asked Questions

Which is better if I get seasick?

The catamaran, decisively. Two hulls damp the roll that single-hulled yachts amplify, the caldera is sheltered water to begin with, and the crew keeps seasickness remedies aboard. Morning departures are the calmest of all.

Is a catamaran really that much more spacious?

Yes — the wide beam creates bow trampolines, a shaded cockpit and walking room that no monohull of similar length can offer. On a five-hour cruise with meals and swim stops, that space is the difference between a deck and a bench.

Isn't a heeling monohull the more authentic sail?

For sport sailing, arguably. For a day built around swimming, a cooked lunch and glasses that stay upright, the catamaran's level ride wins — authenticity is small comfort with wine in your lap.

What boat do your cruises actually use?

A Lagoon 440 sailing catamaran named Summer Wind — shaded cockpit, trampolines, cabins and a freshwater deck shower — on every departure from Vlychada Marina.