Made up of around 220 islands and islets in the heart of the Aegean Sea, the Cyclades archipelago is the go-to destination for a sailing or catamaran cruise in Greece. A Cyclades cruise costs from around $1,780 per person (8 days / 7 nights), with the option to sail with a skipper, without a skipper, with a crew, or by cabin. If you want to charter a sailing boat in the Cyclades, you will sail between Santorini, Mykonos, Paros, and Naxos, taking in whitewashed villages, crystal-clear waters, and anchorages reachable only from the sea, an ideal setting for families and groups of friends. Prices are billed in euros and shown here in U.S. dollars for guidance only.
The types of boat to charter in the Cyclades
Choosing the right boat in the Cyclades comes down to your crew size, experience level, and how much comfort you want on board.
- The monohull sailing boat: the most common and most affordable option for a sailing cruise, perfect for experiencing navigation up close on the Aegean Sea.
- The catamaran: more stable, more spacious, and brighter, recommended for groups and for greater comfort on board. Discover our offers to charter a catamaran, with or without a skipper.
- The traditional vessel and the schooner: boats with real character, often offered as a cabin cruise, a fun, social way to explore the archipelago.
- The yacht: for a high-end cruise, with more space, comfort, and amenities on board.
The services we offer for your Cyclades cruise
Whether you're a seasoned sailor or a first-timer, we have options to match your style for sailing in the Cyclades:
- The cruise with a skipper: an experienced skipper handles all navigation, finds the best anchorages, and knows the archipelago inside out. An ideal option for enjoying the trip without taking the helm.
- The cruise without a skipper: for independent sailors who hold a license, complete freedom to plan your own itinerary and stopovers at your own pace across the Aegean Sea.
- The cruise with a crew: in addition to the skipper, you can have a cook and even a hostess, for a fully crewed, all-comfort experience on board.
- The cabin cruise: you book a private cabin aboard a sailing boat or a catamaran, shared with other travelers on a set itinerary. A sociable and affordable option: discover our departures for a cabin cruise in Greece.
How much does a cruise in the Cyclades cost?
An 8-day / 7-night cruise in the Cyclades costs from $1,780 per person, across all options (with a skipper, without a skipper, with a crew, or by cabin). The table below gives a rough idea according to the type of boat; the price then varies depending on the season and the model.
| Type of boat | Price per person (8 days / 7 nights) |
|---|---|
| Traditional vessel | $4,060 |
| Yacht | $3,340 |
| Sailing boat | $1,910 |
| Schooner | $1,780 |
Our insurance recommendations
- Cancellation insurance: it covers every member of the crew, whereas individual insurance or coverage through your bank card will only cover the holder.
- Deposit waiver: at 5.5% of the charter price, this coverage lets you recover a significant part of your deposit in the event of navigation-related damage (at anchor or alongside).
Request a personalized quote from our advisors.
Where to sail in the Cyclades?
The Cyclades archipelago brings together some of the most beautiful islands in Greece, separated by short distances: often 10 to 30 nautical miles between two stopovers (barely 10 nautical miles between Paros and Naxos). Here are the must-sees:
- Santorini: the most famous island in the archipelago, of volcanic origin. Whitewashed houses, blue domes, colored-sand beaches, and spectacular sunsets over the caldera. Plan a stop with our Santorini yacht charter.
- Mykonos: the lively, cosmopolitan island, between bustling beaches, nightlife, and seaside tavernas. See our Mykonos yacht charter.
- Paros: between tradition and modernity, with the lanes of Parikia, the fishing harbor of Naoussa, on Paros, and well-known kitesurfing and windsurfing areas. Discover our Paros yacht charter.
- Naxos: the largest island in the archipelago, between mountains, long beaches, and ancient sites such as the Portara.
- Milos: the gem of secret beaches, with the white rocks of Sarakiniko and the sea caves of Kleftiko.
- Sifnos: the foodie stopover, renowned for its local cuisine and traditional villages.
A few nautical miles from Mykonos, the island of Delos, the mythological birthplace of Apollo, is a UNESCO World Heritage Site. To plan your route stage by stage, take inspiration from our sailing itineraries and our selection of the most beautiful islands in the Cyclades.
When to go on a cruise in the Cyclades?
The best time is May-June and September: calm seas, fewer crowds, and temperatures of 68 to 75°F (20 to 24°C). The sailing season runs from May to October. In July and August the archipelago is at its hottest and busiest: it is also the peak of the meltemi, the northerly wind that typically blows Force 5 to 7 on the Beaufort scale, with gusts that can exceed Force 8 in the channels between the islands. It's a wind that experienced sailors love, but it demands confidence at the helm.
| Month | Air temperature | Sea temperature |
|---|---|---|
| May | 68°F (20°C) | 66°F (19°C) |
| June | 75°F (24°C) | 72°F (22°C) |
| July | 81°F (27°C) | 75°F (24°C) |
| August | 81°F (27°C) | 77°F (25°C) |
| September | 75°F (24°C) | 75°F (24°C) |
| October | 68°F (20°C) | 72°F (22°C) |
Indicative seasonal averages (air and sea).
Sailing conditions in the Cyclades
Sailing in the Cyclades is demanding but accessible: short distances between the islands, varied anchorages, and favorable sailing conditions, provided you have a little experience or take a skipper on board. The main factor remains the meltemi: at the height of summer, it means choosing your stages carefully and favoring sheltered bays when the wind is strong.
Most boats anchor in coves or moor alongside the quays of fishing harbors. Some small harbors have limited depth and few berths in high season; catamarans, with their shallow draft, reach shallow coves more easily. Book your evening anchorages ahead of time, especially in July and August.
Do you need a license to sail in the Cyclades?
Yes. To rent a boat without a skipper in Greece, you need a recognized sailing license (such as the ICC, International Certificate of Competence) and a VHF radio operator's certificate. The regulations also require a second experienced crew member on board. If you don't hold these documents, a skippered charter requires no license at all.
If you would rather sail with peace of mind, opt for the cruise with a skipper: you enjoy the archipelago with no administrative requirements. For the full details of the documents required, see our FAQ on boat licenses and regulations in Greece.
What to do during your Cyclades cruise?
Beyond the sailing, the Cyclades offer plenty of activities to share as a group:
- Water sports: snorkeling and diving around Milos and Paros, paddleboarding and kayaking to secluded coves, kitesurfing on Paros and Naxos thanks to the meltemi, or sea fishing for a dinner of fresh fish on board.
- Cultural activities: visiting the ancient sites of Delos, wandering the white lanes of Santorini and Sifnos, discovering the architecture typical of the Cyclades.
- Relaxation and nature: swimming at white-sand beaches such as Kolymbithres on Paros, peaceful anchorages, and panoramic walks, in particular along the paths from Fira to Oia on Santorini.
Frequently asked questions about cruising in the Cyclades
How much does it cost to charter a yacht in the Cyclades?
A cruise in the Cyclades costs from $1,780 per person for 8 days / 7 nights, up to $4,060 on a traditional vessel. On top of the charter price, budget for extras such as the skipper's fee (on a skippered charter), fuel, the end-of-trip cleaning package, and the security deposit.
What is the meltemi wind in the Cyclades?
The meltemi is a dry northerly wind that blows across the Cyclades from June to September, typically Force 5 to 7 on the Beaufort scale, with gusts exceeding Force 8. It's strongest in July and August.
What is the difference between a bareboat charter and a crewed charter?
A bareboat charter means you rent the boat without a captain and sail it yourself (a license is required). A crewed charter includes a professional skipper, and optionally a cook or hostess.
Where do cruises in the Cyclades depart from?
Most Cyclades sailing trips depart from Lavrio or Piraeus, both within a 30 to 45 minute drive from Athens International Airport (ATH) by car or taxi. Some itineraries also depart directly from islands in the archipelago.
When is the best time for a cruise in the Cyclades?
The best time is May-June and September: calm seas, temperatures of 68 to 75°F (20 to 24°C), and fewer crowds. The sailing season runs from May to October.
Can you go to the Cyclades without knowing how to sail?
Yes. You can explore the Cyclades without any sailing experience by booking a skippered yacht charter or a cabin cruise: a professional skipper handles all navigation.
How do you finalize the booking of your boat in the Cyclades?
As soon as we receive your request, an advisor will contact you by phone to understand your plans, then send you boat suggestions by email. Once the boat is chosen, you pay a deposit in your customer area to confirm the booking and secure the boat.
Ready to set sail? Start your search among our boats available in the Cyclades and get a personalized quote within a few hours.