The Sunset Sailing (Yacht) Proposal
Your own catamaran — not a group cruise — sails into the caldera, drops anchor as the cliffs glow gold, and gives you the question with only the crew nearby.
The caldera, all to yourselves
You board a private catamaran with just a skipper and host aboard, sail beneath the coloured cliffs, and anchor in the caldera as the light turns gold. Away from every crowded terrace, you ask — and the photographer captures it from the deck.
Champagne and canapés follow as standard; many couples stay aboard for a full dinner served after the reveal, once the anchor is down and the sun has set. Read the full yacht proposal guide for route, timing and planning detail.
What's included
- Private catamaran charter (skipper & host)
- Sunset timing into the caldera
- Champagne, canapés or full dinner option
- Onboard styling & reveal moment
- Photography from boat & optional drone
Want more? Add drone film, a musician on deck or transfers from our services — or see the yacht & catamaran setting in our locations guide.
Ideal for couples who want…
- Complete seclusion — no crowds, no passers-by
- A proposal and a celebration in one evening at sea
- Dinner on the water after the "yes"
- The caldera cliffs as a backdrop instead of a viewpoint
Prefer solid ground? See The Caldera / Cliffside Proposal. For your own terrace with a chef, see The Private Villa Proposal.
How the moment unfolds
- Late afternoon
You board
Departure from Vlychada marina or Ammoudi Bay — we confirm the exact point and timing when the charter is set.
- First hour
The sail
You cruise the caldera coast past the coloured cliffs and volcanic islets, glass in hand.
- Golden hour
The question
The anchor drops, the cliffs glow, and you ask — photographed from the deck.
- After "yes"
Celebrate aboard
Champagne and canapés, or a full dinner served on board as the light fades.
Departure & route
Private charters usually leave from Vlychada marina or Ammoudi Bay below Oia, then sail the caldera coast. Compare settings.
Weather plan
The summer meltemi can make the caldera choppy, so every sail includes an agreed plan — a calmer morning sail, a sheltered stretch of coast, or a styled cliffside terrace.
Price
From €3,400 for the catamaran package. A larger private motor yacht is a bespoke commission, quoted individually. See the cost guide.
About this package
From €3,400. That covers the private catamaran charter with skipper and host, sunset timing into the caldera, onboard styling and the reveal, champagne with canapés or a full dinner option, and photography from the boat. A larger private motor yacht is quoted individually.
Yes — the catamaran is booked exclusively for you, with its own skipper and host. It is never a shared group cruise.
Santorini’s summer meltemi can make the exposed caldera choppy, so every sail includes a weather plan agreed in advance: a calmer morning sail, a sheltered stretch of coast, or a styled cliffside terrace instead.
Ready to ask on the water?
Tell us your date and we’ll check the charter.