YachtSailingYachtSailing

Sailing destination

Santorini

Island group
Cyclades Islands
Best time to sail
May – October
How
Private crewed catamaran
Explore Santorini

Arriving by sea changes Santorini completely. You anchor below the cliffs or off the red and white beaches on the quieter south coast, swim in water still warm from the volcano beneath it, and only go up to the rim - Fira or Oia - for dinner and the sunset, timed to skip the day-tripper crush. It's the one Cycladic island that genuinely looks like nowhere else.

How your week works

There's no fixed route - your week bends to you.

Every charter is private and fully custom. Your captain shapes each day around the weather, the sea and what you feel like - more swimming or more towns, an early start or a slow morning. Anything you read here about Santorini is inspiration, not a schedule; you can change plans anytime on board.

Planned with you daily

The route is set together, each morning.

Weather-led

Always the calmest, most beautiful option.

Your call

Linger longer wherever you fall in love.

The character of Santorini

Black volcanic cliffs rising straight out of a flooded caldera, whitewashed villages balanced along the rim, and a sunset in Oia that draws a crowd every single evening of the season.

For guests who want the postcard - the cliffs, the blue domes, the sunset - without the cruise-ship crowds around it.

What you do here

How it fits a week

One dramatic night mid-itinerary - the caldera sunset, dinner on the rim, back to the boat to sleep. Nothing here is fixed - your captain places Santorini wherever it works best for your weather and your mood.

Highlights

What to see & do in Santorini

Santorini1

Beaches & swimming

Anchor below the caldera cliffs, or off a quieter south-coast beach

Santorini2

Sunset views

Sunset in Oia, timed to beat the crowds up top

Santorini3

Beaches & swimming

Swim the red and white volcanic-sand beaches

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Dinner On The

Dinner on the caldera rim in Fira or Oia

Frequently asked questions

01Is the itinerary fixed, or can we customize our route? +

All our trips are fully customizable. There is no fixed itinerary. The final route is shaped together with you, based on your preferences (how many hours you wish to sail per day, sightseeing or relaxation, hiking, swimming, local cuisine, etc.) and - most importantly - the weather at the time of your trip. The captain adjusts the plan daily to keep the experience relaxed, safe and enjoyable, and you can stay longer at places you love.

02Cyclades or Saronic Islands – what’s the difference and which do you recommend? +

The Cyclades offer iconic whitewashed villages, dramatic landscapes and longer open-water crossings - ideal for experienced cruisers and classic Greek scenery. The Saronic is calmer, greener and closer to Athens, with short hops between historic islands - perfect for relaxed sailing and families. We recommend based on your dates, group and pace.

03Can we visit Santorini, Mykonos, Naxos, or other specific islands in one week? +

Yes - within reason. A one-week route comfortably covers a cluster of nearby islands. Combining far-apart highlights (e.g. Mykonos and Santorini) is possible but means longer sailing days. We’ll design a realistic route that includes your must-see islands without rushing.

04What happens if the weather is bad? Will the trip be canceled? +

Trips are very rarely canceled. The captain monitors conditions daily and adapts the route to keep you in sheltered, comfortable waters. Safety and enjoyment always come first, and the flexible itinerary means there is almost always a great alternative nearby.

05Are prices per person or for the entire boat? +

Prices are for the entire boat - you charter the whole catamaran for your group, not per person. This makes it excellent value for families and groups of friends sharing the experience.

06What additional costs should we expect beyond the yacht price? +

Typical extras include fuel, marina/port fees, food and drinks, and the crew gratuity. We provide a clear breakdown in advance so there are no surprises, and you can choose your provisioning and dining preferences.

07How many islands will we visit during the week? +

Usually 5–7 islands or anchorages in a week, depending on distances and your pace. We balance moving and relaxing so you experience variety without spending all day at sea.

08Can we decide where to stop each day, or is it decided in advance? +

Both. We agree a flexible plan before departure, then fine-tune it day by day with your captain based on weather and what you’re enjoying. You stay in control of your holiday.

Explore more in the Cyclades
Cyclades
Cyclades
Mykonos
Mykonos
Paros
Paros
Naxos
Naxos
Read on the blog

Choose: Mykonos or Santorini with a sailing boat?

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Santorini Sailing - Experience Santorini with a sailing boat.

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Santorini by Catamaran: Should You Sail There From Athens?

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Our fleet

Featured yachts

Baccarat, 45 ft

Comfortable and effortlessly enjoyable - four cabins for up to eight guests aboard a Lagoon 450 Flybridge, refit in 2024. Generous deck space for sun-filled days and easy evenings at sea.

Staterooms 4 • Up to 8 Guests • Refit 2024

from / week
€5,000
View

Baron, 52 ft

Understated luxury and easy comfort across sun-filled decks and calm anchorages - six cabins for up to ten guests, refit in 2025. A quietly confident catamaran built for slow mornings and long lunches at anchor.

Staterooms 6 • Up to 10 Guests • Refit 2026

from / week
€11,500
View

Casino Royale, 50 ft

Nimble and welcoming, ideal for exploring the Cyclades at your own pace - six cabins for up to ten guests, refit in 2024. Light enough to feel quick, roomy enough to feel generous.

Staterooms 6 • Up to 10 Guests • Refit 2024

from / week
€7,600
View
View all yachts
Santorini
Plan your sailing holiday

Ready to explore Santorini?

Talk to our team and we'll tailor the perfect one-week catamaran itinerary around Santorini - skipper, hostess and all.

Ask an advisor

Get in touch

Contact usSend an enquiry, a real advisor replies personally Arrange a video callPick a time that works for you Call us+30 693 723 4566 WhatsApp usAlso available on the same number