Pick the right boat and Greece changes shape.
Which catamaran stops long enough to actually swim. What the Balos run out of Kissamos costs. Whether four of you are better off on a shared deck or hiring the whole boat. Reviews of every sailing trip you can book in Greece.
Four Greek boat days worth building a week around.
The sailings that fill first, what a seat costs and which port each one leaves from.
01SantoriniCatamaran Tour with BBQ Dinner, Drinks, and MusicThe caldera day almost everyone books. Past the red and white cliffs, into the hot springs, then dinner grilled on deck while Oia lights up.
02CreteDia Island Sailboat Cruise with Swimming and MealOut of Heraklion to Dia, an empty rock with three bays on its south side. The swimming stops are the trip; the sailing is how you get between them.
03MilosMilos & Polyaigos Full-Day Sailboat Tour with LunchA full day around Milos and uninhabited Polyaigos, finishing at Kleftiko where the white arches come straight out of the water.
04MykonosYacht Cruise to Rhenia and Guided Tour of DelosAcross to Rhenia for the beaches, then Delos for the ruins. The one Aegean day that puts an archaeological site and a swim stop on the same ticket.
Santorini from the water beats Santorini from the queue.
The caldera rim is shoulder to shoulder by six in the evening. The water below it is not. Four kinds of Santorini sailing, what it costs to get aboard each one, and how much time you really spend in the sea.
★★★★★★★★★★ 4.6 · Catamaran Tour with BBQ Dinner, Drinks, and Music
Catamaran dayShade, a swim ladder and lunch grilled behind the helm.
Open barDrinks poured all afternoon, so nobody counts rounds.
Sunset sailOia goes gold from below while the cliff queues for it.
Whole boatSkipper, route and departure time are yours to set.
Every one of the 65 Santorini sailings →
The Greek sailings more travellers book than any other.
Every Greek sailing trip we have reviewed →Eight boats carry more people here than anything else afloat. What a seat costs, how long each one is out, and which port it leaves from.
1
Catamaran Tour with BBQ Dinner, Drinks, and Music
Spend five hours aboard the 74-foot Ocean Voyager or 80-foot Tahiti catamaran, with hotel pickup, hot-spring swimming, Red and White Beach stops, a fresh barbecue, unlimited white wine and soft drinks, and music. Choose morning light or a sunset sail through Santorini’s caldera.
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
In Greece the boat feeds you, and that decides the day.
Grilled on the stern, eaten at anchor, usually with the bar left open behind it. Most of this fleet sells the meal as hard as the route, so it pays to know what all-inclusive covers before you hand over a card.
What a seat on a Greek boat really costs.
Every trip on the site sorted by the price of one seat. The bottom band is a half-day hop out of a ferry port; the top is a premium catamaran with a crew of three.
Half-day hops, shared sailboats and the Dia Island runs out of Heraklion.
The standard Greek boat day: catamaran, a meal on deck, three or four swim stops.
Premium catamarans, small-group sailings and crewed yachts with a proper galley.
Six Greek coastlines, and the boat day each one is known for.
Caldera cliffs at anchor, a pink lagoon at the far west of Crete, the white rock of Kleftiko, the channel across to Delos, the Athens riviera and the long run to Symi.
The meltemi, the swim ladder and the words open bar.
Greek sailing has four facts that decide whether a booking works. The meltemi blows hardest through July and August and cancels Cycladic departures at a few hours notice, so leave a spare day at the end. Most trips anchor in open water, which means getting in and out down a ladder with no beach to stand on. All-inclusive here normally means the meal plus the bar, with hotel transfers charged separately. And the smaller the boat, the earlier it goes.
- 01Dia Island Sailboat Cruise with Swimming and Meal★★★★★★★★★★ 4.8 · 2,579 reviews · from $95
- 02Shared Mykonos Sail Cruise to Delos and Rhenia Islands★★★★★★★★★★ 5.0 · 705 reviews · from $151
- 03Sailing Trip to Dia Island with Lunch & Swimming★★★★★★★★★★ 4.8 · 517 reviews · from $100
Charters in Greece are quoted per boat, not per head.
Six of you on a charter can come in under the price of six seats on a shared catamaran, and the route is yours. The figures below are what the boat costs for the day, with the number it takes.
Three things that only happen on a Greek deck.
Turquoise water and a swim ladder exist everywhere. Swimming into a volcanic vent, sailing under a mined-out white arch and anchoring off a pink lagoon do not.
The caldera and the hot springs
Santorini sits inside a drowned volcano, so the anchorage is a flooded crater and the swim stop is a sulphur spring off Palea Kameni. Boats moor outside the shallow bay and you swim the last stretch, through water that goes from cold blue to warm rust in about ten metres. It stains a pale swimsuit, which nobody mentions at the booking desk.
- 1Catamaran Caldera Cruise with Meal and Drinks★★★★★★★★★★ 4.7 · 2,255 reviews
- 2Catamaran Caldera Cruise with Meal and Drinks★★★★★★★★★★ 4.8 · 980 reviews
- 3Santorini All-inclusive Catamaran Cruise with Thirassia Stop★★★★★★★★★★ 4.5 · 348 reviews
Kleftiko, on the far side of Milos
The south-west corner of Milos is mined-out white rock, cut by the sea into arches and tunnels, with no road to any of it. Pirates used the coves as a hideout and the name still says so. Boats slow to pass under the arches and drop a ladder into water that reads about four metres deep and looks like one; the smaller sailboats get inside where a catamaran cannot follow.
- 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
Balos and Gramvousa
From Kissamos, at the western end of Crete, a morning under sail reaches a Venetian fort on a bare rock and a lagoon where the sand runs pink and the water rarely gets past your waist. The road in is famously punishing, which is exactly why the boat is the sensible way to arrive. Both fit in one day if the fort is climbed before the lagoon fills.
- 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
Crete is long enough that the boat is the shortcut.
Two hundred and fifty kilometres of coast, two ports that matter and a road network that turns forty sea miles into most of a day. Sail out of Heraklion for Dia, out of Kissamos for Balos, out of Chania and Rethymno for the afternoon coves.
- 1Sailboat Cruise to Dia Island with Drinks & Lunchfrom $35
- 2Private Half-Day Sailing Trip to Dia Islandfrom $459 per boat
- 3Balos Gramvousa Sailing Cruise with Lunchfrom $229
Athens, Mykonos, Naxos, Santorini, Milos, Crete: two weeks of ports.
NaxosThe Greek boats reviewed most recently.
Browse every sailing review →
Private Sailing Cruise to Dia Island with Meal & Water Activities
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Dia Island Private Sailing Cruise with Full Meal
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Kleftiko Semi Private Sailing Cruise with Lunch
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Lindos: Full-Day Private Sailing Cruise
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Private sailing to Dia Island with Lunch
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Dia Island: Semi-Private Full Day Sailing Trip with meal
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Rhodes Fully Private Yacht Experience- Day Cruise | Sunset cruise
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Private 5-Hour Cruise on Brand-New 2023 Motor Yacht in Mykonos (Voreus)
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Catamaran Day Cruise – Swim, Snorkel, Food & Drinks!
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Private Luxury Sailing Trips to Dia Island
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Daytour Sailboat with Lunch/drinks in Lindos area
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