Greece from the water, one deck at a time.
Which caldera catamaran actually stops long enough to swim. What the Balos boat out of Kissamos costs. Whether the open bar earns its money. Reviews of the sailing trips you can book in Greece.
The caldera, Balos, Kleftiko, Delos: four days under sail.
One boat day per island group. What each costs, and what the people who were on deck said afterwards.
01The caldera dayCatamaran Tour with BBQ Dinner, Drinks, and MusicThe big Santorini catamaran, with the volcano, the hot springs and dinner cooked on the stern.
02The Crete dayBalos & Gramvousa Luxury Catamaran Sailing CruiseOut of Kissamos to Balos and Gramvousa. The pink-sand lagoon everybody comes back with photographs of.
03The Milos dayKleftiko Sailing Day Trip with Snorkeling and LunchAdamas to Kleftiko, where the white rock is cut into arches and there is no road down to any of it.
04The Mykonos dayYacht Cruise to Rhenia and Guided Tour of DelosThe crossing to Delos and Rhenia, sacred ruins in the morning and an empty bay for lunch.
Santorini sails inside a drowned volcano. Pick your deck.
Every boat out of Vlychada and Ammoudi crosses the same flooded crater, then splits: the black cone and the sulphur spring, or the red and white beaches and a long lunch. What separates them is the head count, whether the bar is open and how much water time you actually get.
★★★★★★★★★★ 4.6 · Catamaran Tour with BBQ Dinner, Drinks, and Music
Catamaran daysShade, a swim ladder, lunch off the stern grill.
Open bar aboardPoured all afternoon, with no tab at the end.
Sunset sailingsOia from the water, while the path above is shoulder to shoulder.
Private chartersYour own boat, your own route, nobody else on deck.
All 65 Santorini sailings →
Santorini, Crete, Milos, Mykonos: the harbours worth sailing out of.
A caldera you can swim inside, a pink lagoon at the far west of Crete, the white coves of Milos, the crossing to Delos, the Athens riviera at six in the evening. Six places, and the best boat day out of each.
In Greece the lunch is half the reason to sail.
Grilled off the back of the boat, or a buffet laid out below deck. Some sailings pour drinks all afternoon; some hand you a bottle of water and a fruit plate. This is where the difference in price actually goes, so it is worth reading before you book.
Greece’s most-booked sailing trips.
The full Greek sailing list →The sailings more travellers take than anything else on the Greek coast, from the caldera catamarans down to a morning out of Heraklion.
1
Catamaran Tour with BBQ Dinner, Drinks, and Music
Review of Santorini’s 5-hour catamaran cruise with swimming, BBQ, wine, music, hotel pickup, and sunset views for $93.
From · $93
Read our review →
2
Luxury Catamaran Day Trip with Meal and Open Bar
from $129
3
Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar
from $133
4
Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar
from $117
5
Dia Island Sailboat Cruise with Swimming and Meal
from $95
6
Catamaran Caldera Cruise with Meal and Drinks
from $70
7
All-Inclusive Catamaran Cruise with Lunch and Drinks
from $83
8
Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset
from $181
Catamaran, sailboat or private charter: what a Greek day aboard buys.
Every catamaran cruise →
A catamaran is flat, shaded and steady, which is why most of Greece sails on one. A monohull heels over and actually sails. Semi-private cuts the head count; a charter removes it. The boat matters, but the number of people on it matters more.
Catamaran, shade and a swim ladder
Two hulls, a flat deck, a net at the bow to lie on and a ladder off the back. Groups run twenty or so on the big Santorini boats, fewer everywhere else.
Semi-private, eight or so guests
The same route with a third of the passengers, which means a say in where the boat stops and a swim stop that is not a queue for the ladder.
Private charter, your own route
Priced for the boat rather than the seat, so it turns reasonable once there are six of you. The skipper comes with it, so no licence and no paperwork.
What a day on a Greek boat actually costs.
Every sailing trip on the site, grouped by the per-person price. The cheap end is a morning out of Heraklion; the top end is a boat with nobody else on it.
Morning sails to Dia, the Sithonia coves, the short hops off the Cretan and Corfiot coasts.
The standard full day: caldera catamarans, the Balos boat, Kleftiko and Poliegos with lunch aboard.
Semi-private decks, luxury cats, and the charters where the boat is yours until sundown.
Three Greek sailings you cannot do anywhere else.
Warm water and a good boat exist all over the Mediterranean. Swimming inside a volcano, a cove cut into white rock at Kleftiko, and lunch off an island nobody lives on do not.
The Santorini Caldera
The bay is the flooded crater of the eruption that took the middle of the island away. Boats cross to the black cone of Nea Kameni, then anchor off Palea Kameni where a warm sulphur spring runs into the sea and you swim to it from the boat. The water changes colour and temperature within a few metres, and the cliffs stand three hundred metres over the mast.
- 1Catamaran Caldera Cruise with Meal and Drinks★★★★★★★★★★ 4.7 · 2,255 reviews
- 2Catamaran Caldera Cruise with Meal and Drinks★★★★★★★★★★ 4.8 · 980 reviews
- 3Caldera Classic Catamaran Cruise w/ Meal & Drinks★★★★★★★★★★ 4.8 · 379 reviews
Kleftiko and the sea caves
The south-west corner of Milos is soft white volcanic rock that the sea has cut into arches, tunnels and coves, with no road down to any of it. Pirates used it, which is where the name comes from. It is a couple of hours under sail from Adamas and the trip is off whenever the north wind gets up, so the boats leave early and the good days go first.
- 1Kleftiko Sailing Day Trip with Snorkeling and Lunch★★★★★★★★★★ 4.8 · 713 reviews
- 2Half-Day Morning Catamaran Cruise to Kleftiko★★★★★★★★★★ 4.8 · 362 reviews
- 3CATAMARAN Kleftiko Poliegos & Round of Milos Lunch with Openbar★★★★★★★★★★ 5.0 · 242 reviews
Delos and Rhenia
Delos was the sacred island of the Cyclades and is now a ruin field with a warden, a museum and no residents. The site shuts in the afternoon and nobody sleeps there, so the boats out of Mykonos run to the site clock, then cross to Rhenia next door for lunch and a swim in a bay with nothing built on it.
- 1Dia Island Sailboat Cruise with Swimming and Meal★★★★★★★★★★ 4.8 · 2,579 reviews
- 2Sailboat Cruise to Dia Island with Drinks & Lunch★★★★★★★★★★ 4.8 · 1,405 reviews
- 3Corfu Island Sailing Trip with Snack and Soft Drinks★★★★★★★★★★ 4.8 · 851 reviews
Four Greek sailings that will not wait for you.
Most of a Greek summer can be arranged from a taverna table the night before. These four run on one departure a day, a fixed closing time, or a wind that makes the decision for you.
- 01Kleftiko Sailing Day Trip with Snorkeling and LunchThere is no road to Kleftiko and the boats turn back when the meltemi gets up. The settled days sell out well before the windy ones.
- 02Balos & Gramvousa Luxury Catamaran Sailing CruiseThe Kissamos boats run to a published timetable, and the lagoon has the whole day’s arrivals standing in it by lunchtime. The early departure is the one worth having.
- 03Yacht Cruise to Rhenia and Guided Tour of DelosDelos closes in the afternoon and nobody stays the night, so the crossing runs to the archaeological site’s clock rather than to yours.
- 04Santorini Catamaran Cruise with Greek Meal, Open-Bar and SunsetOne sailing a day, timed to the sunset, on islands where that is the thing everybody came for. August books out weeks ahead.
When the north wind blows, the Cyclades boats stay tied up.
July and August bring the meltemi down the Aegean and it does two things: it cancels or reroutes the exposed sailings out of Milos, Mykonos and Paros at a few hours’ notice, and it turns an open crossing into a wet one. There are two answers. Take the morning departure, before it fills in, or sail somewhere sheltered: the caldera, the Cretan north coast, the Ionian, the Halkidiki coves.
By place, the Cyclades to the Cretan coast
Athens, Mykonos, Santorini, Milos, Crete: a first Greek sailing week.
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Chrissi Island Yacht Cruise with Lunch & Snorkeling
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Daily Sailing experience between Naxos and Paros coastline
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Chios: Sailing Boat Cruise to Oinouses with Meal & Drinks
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Private Sailing Cruise with Snorkel, Lunch & Drinks
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