Planning your next sailing holiday in Greece but keen to avoid the usual tourist hotspots? The Small Cyclades—often overshadowed by their larger neighbors like Mykonos and Santorini—offer a tranquil alternative for those seeking a truly off-the-beaten-path experience. Dotted across the Aegean Sea, these lesser-known islands boast unspoiled beaches, crystal-clear waters, and charming fishing villages. Whether you choose a yacht charter in the Cyclades or opt for a catamaran charter, the Small Cyclades promise a more laid-back pace, letting you immerse yourself in authentic Greek culture away from the crowds.
The Cyclades Islands in Greece are a world-famous sailing area, known for their whitewashed villages and the brisk Meltemi wind. The sailing season here runs from April to October, but the best time to sail the Cyclades is often at the edges of summer – in June or September – when you avoid the strongest Meltemi winds yet still enjoy long, sunny days. In mid-summer (July and August), the Meltemi can blow at full force, often north winds of Force 5–7 and sometimes gusting even higher. This provides exhilarating sailing for experienced crews and excellent sailing speeds, but it can also make certain routes challenging or uncomfortable during its peak. Many yachts will plan their itineraries to be on the leeward sides of islands or in sheltered harbors during Meltemi blows. By late August, this wind pattern starts to calm. June offers a great mix of warm weather (highs around 28°C), moderate winds, and fewer tourists, while September brings slightly cooler weather but a gentler Meltemi and beautifully warm seas from the summer heat. Outside the Meltemi season – in April, May and October – winds are lighter (coming from varying directions) and the weather is milder; during these shoulder months you’ll find a tranquil atmosphere in popular islands like Mykonos or Santorini, though some seasonal restaurants and beach clubs may be closed. Overall, if you seek lively sailing and don’t mind strong winds, July–August will provide it (just be prepared reefing sails); if you prefer more predictable breezes and quieter ports, aim for spring or early autumn when the Cyclades are at their most inviting balance.
Greece has clear requirements for bareboat charters, so you will indeed need a sailing license to rent a yacht in the Cyclades without a skipper. Greek Port Authorities require at least one certified skipper (captain) on board and one competent crew member over 18 as co-skipper. The skipper must hold a qualification such as an ICC (International Certificate of Competence) or a national equivalent (RYA Day Skipper, ASA 104 Bareboat, etc.) that is recognized by Greek authorities. The co-skipper doesn’t need a formal license, but will often need to sign a declaration attesting to their sailing ability (essentially acting as a first mate). Charter companies will ask you to present the original license upon embarkation and will retain a copy for the charter paperwork. They may also ask for a VHF radio license, though in Greece this is not always stringently enforced if the skipper’s license covers basic radio operation. If you do not have a valid license or enough experience, you can choose a skippered charter. In the Cyclades, many travelers opt to hire a local skipper or even a full crew, especially given the challenging winds – having an experienced captain who knows the Aegean means you can relax and safely reach all the iconic islands. In summary, for bareboat you must be licensed and prepared to document your skills, whereas a crewed Cyclades yacht charter is license-free (and stress-free) since the professionals on board handle the navigation and formalities.
Sailing through the Cyclades is not just a journey across the Aegean’s turquoise waters – it’s a voyage through Greek history, culture, and cuisine. Each island in the Cyclades has its own identity and traditions, offering yacht charter guests an ever-changing tapestry of experiences. Culturally, you can anchor off Delos to tour the extensive ancient ruins of Apollo’s sanctuary by day, then by night find yourself enjoying modern art galleries and chic nightlife in Mykonos. The smaller islands preserve authentic charm: on Paros and Naxos, you’ll wander through labyrinthine old towns with whitewashed houses and blue-domed churches, exactly as postcard-perfect as one imagines. Many Cycladic islands celebrate summer festivals – if you’re lucky, you might stumble upon a local panigyri (feast) with traditional music and dancing under the stars.
Food is a highlight of a Cyclades yacht charter. The region’s cuisine is a quintessential Mediterranean diet with unique local twists. Almost every island produces its own cheese – sample Naxos’s buttery graviera, Paros’s tangy xinomyzithra, or the famed peppery kopanisti cheese of Mykonos. These pair beautifully with island-made wines (Santorini’s volcanic whites or Paros’s crisp whites). Seafood lovers will be in heaven: fishermen bring in fresh octopus, red mullet, and squid daily, which you’ll find grilled in seaside tavernas or simmered in savory local stews like kakavia fish soup. Don’t miss trying Santorini’s cherry tomatoes and fava bean purée, or Syros island’s sweet halva pie and unique San Michali cheese. Even simple dishes like a Greek salad burst with flavor here, thanks to sun-ripened tomatoes, capers (a Cycladic staple), and olives grown on these isles. Whether you’re dining aboard your yacht on a gourmet meal prepared by a private chef, or discovering a family-run taverna in a hidden cove on Serifos or Sifnos, the Cyclades will delight you with its culinary diversity. Amidst the iconic blue and white scenery, you’ll taste the true essence of Greek island life – rustic, flavorful, and filled with philoxenia (hospitality).
Navigating the Cyclades is straightforward as long as you adhere to general Greek maritime regulations. There is no special cruising permit required solely for the Cyclades beyond the national rules. Your charter yacht will come with a Transit Log (official sailing diary) and should be properly registered with Greek authorities – keep this documentation and your crew list on board at all times. Greek law requires you to notify port authorities when departing a port and sometimes upon arriving at the next, though in practice leisure yachts can move freely and just file the transit log at the charter base. One regulation to note is the Greek Cruising Tax (TEPAI), a fee for boats sailing Greek waters; if applicable, your charter company typically handles this fee and includes it in your booking.
Within the Cyclades, certain local regulations aim to protect specific areas. For example, around Delos, anchoring is restricted to specific bays and visiting hours for the archaeological site are daylight only (no overnight stay on Delos is allowed). Similarly, Rinia (the uninhabited isle near Delos) permits anchoring in its bays, but you should ensure you’re not in a protected zone or disturbing underwater antiquities (marked on nautical charts). Always avoid anchoring in clearly designated swimming areas – popular beaches on Mykonos, Paros, etc., are buoyed off in summer. The Meltemi wind itself imposes an informal “regulation”: during strong blows, local port authorities might direct yachts to remain in port for safety, especially ferries can be disrupted too. It’s wise to heed their advice or any gale warnings broadcast on the VHF. Also, note that dumping waste or sewage into these clear waters is strictly forbidden – use pump-out stations or holding tanks until offshore. Finally, respect any military restricted areas (for instance, the small island of Gyaros north of Syros has naval restrictions). The Cyclades are well-sailed, and information is readily available from port police or your charter briefing on island-specific rules. In essence, sail prudently, respect the environment, and follow standard Greek sailing laws – you will find cruising the Cyclades to be smooth sailing in every sense.
There’s nothing like taking off for an island retreat to catch some sun and sand and soak up the sunshine. But you’re not the only one with island life on the mind. Some locales are so hot and so noteworthy, that once you’re there … well, those crowded beaches don’t exactly make it feel like a retreat.
Everyone’s heard about partying in Mykonos, but if you’re after a holiday experience that offers a little more tranquillity and R&R, look to the lesser-known Greek islands: the Small Cyclades.
Unlike the main Cyclades, which attract millions of tourists every year, the small Cyclades are far less travelled and are a sort of “insider secret” among real travel fiends.
Why should you visit the small Cyclades?
For one, you’ll truly be able to enjoy the serene “island life” here. The Small Cyclades are among Greece’s smallest inhabited islands with populations only in the couple hundreds. Sailing around Greek islands like these allows you to slow down, take a break from your normal hectic schedule, and really soak in the simpler, more leisurely pace of life.
And there’s plenty to soak in. The Small Cyclades are abound with beautiful beaches, stunning hiking trails, and one-of-a-kind Mediterranean views.
What’s in store for you when you decide to take a step off the beaten path and travel to the Small Cyclades?
Iraklia is the largest island in the Small Cyclades. It’s also home to the Cave of the Sacred Icon of Agios Giannis, where you can explore stalactites and stalagmites by torchlight. Looking for a little more sun? Iraklia has eight breathtaking hiking trails whose cliffs offer perfect views of the other Greek islands.
The second most populated island in the Small Cyclades is Schinoussa. Home to ancient sites, like a Byzantine church and even a medieval castle, Schinoussa has a rich history that’s ripe for exploration. Here, you can enjoy your pick of secluded beaches, like Psili Ammos or Lioliou Beach, and then head to some of the delicious cafes and restaurants in Schinoussa’s three villages, Chora, Mersini, and Maseria.
Looking to have the best of both worlds when sailing the Cyclades?
Koufonisia is sometimes called the Mykonos of the Small Cyclades and is probably the most popular in this stretch of smaller Greek islands. A particularly great time to go is in late May or early June when you could catch the Fisherman's Festival, a feast celebrated on Koufonisia on the Saturday before Pentecost Monday, complete with traditional music, dancing, and, of course, great food.
Donousa is another stop in the Small Cyclades that you don’t want to miss while yacht chartering Greece. The main village is called Stavros, where you can check out the Church of Stavros with its striking blue dome, explore the villages’ taverns and cafes, and spend days visiting the islands’ four main beaches.
Ready to travel away from the crowds for a getaway that’s 100% relaxation and nowhere near the tourist traps?
The best time for sailing the small Cyclades is from June to mid-September when clear skies with sunshine are the norm, and you can count on an average temperature of 25C (77F).
Next, when preparing your Cyclades sailing itinerary, there are a few things you’ll want to keep in mind.
First, where to start from: You can begin your journey either from Lavrion, Paros, or Mykonos. Lavrion is on the mainland, so it is easily accessible from Athens International Airport. Paros and Mykonos, on the other hand, are in the heart of the Cyclades.
Because the Small Cyclades are further from the mainland, we recommend a two-week yacht charter and larger yachts.
A longer yacht charter simply gives you more time to cross the longer distance, so you’ll have more time to make stops along the way and hit the beach.
Next, you’ll also want to consider what kind of yacht to charter for sailing the Cyclades.
A larger yacht is key for sailing the Aegean Sea, as the Meltemi wind that blows in July and August would be too strong for smaller yachts. For your unique trip, a larger yacht might be a catamaran, which can easily cover more distances, or a larger sailing yacht if you’re looking for the ultimate and original sailing experience!
Not sure which one’s the right fit for you? Catamaran vs Monohull
Due to the larger distances and prevailing winds, you can’t explore all of the islands in a single trip—but the Small Cyclades are such a treasure trove of travel delights, that you’ll want to come back again and again!
Ready to brainstorm your Small Cyclades sailing journey? Check out below a few general guides for your itinerary. Of course, the final itinerary will depend on prevailing weather conditions.
Day 1: Lavrion – Kea (15 NM)
Embark from Lavrion Marina and set course for Kea, the closest Cycladic island to the mainland. Anchor in the protected bay of Vourkari and enjoy a peaceful evening among terracotta-roofed houses and authentic tavernas.
Day 2: Kea – Syros (35 NM)
Sail southeast to Syros, the elegant capital of the Cyclades. Moor at Ermoupoli harbour and explore neoclassical architecture, vibrant cafés, and the hilltop church of Ano Syros.
Day 3: Syros – Mykonos (20 NM)
Cruise to world-renowned Mykonos, where cosmopolitan charm meets Cycladic beauty. Anchor in Ornos or Tourlos Marina and enjoy the island’s stylish beach clubs, iconic windmills, and lively nightlife.
Day 4: Mykonos – Donousa (50 NM)
Sail off the beaten track to Donousa, a remote island beloved by sailors for its quiet beaches and bohemian flair. Anchor in Stavros Bay and enjoy a starlit night in one of the most untouched corners of the Aegean.
Day 5: Donousa – Koufonisi (15 NM)
Head southwest to Koufonisi, a postcard-perfect islet with turquoise waters and a charming fishing village. Swim in natural pools, stroll barefoot through the village, and unwind in absolute tranquillity.
Day 6: Koufonisi – Schinoussa (10 NM)
Make a short sail to nearby Schinoussa, a laid-back island with crystal-clear coves and a rustic Greek atmosphere. Anchor in the natural bay of Mirsini and dine on fresh seafood overlooking the anchorage.
Day 7: Schinoussa – Iraklia (8 NM)
Cruise to Iraklia, the smallest of the Lesser Cyclades, ideal for snorkelling, hiking, and a true escape from modern life. Visit the cave of Agios Ioannis or enjoy a secluded beach all to yourself.
Day 8: Iraklia – Paros (20 NM)
Set sail for Paros, one of the most well-rounded islands in the Cyclades. Anchor in Naoussa or Parikia and explore picturesque alleys, golden beaches, and buzzing nightlife with a traditional twist.
Day 9: Paros – Sifnos (30 NM)
Head west to Sifnos, an island celebrated for its whitewashed villages and renowned gastronomy. Discover the hilltop village of Apollonia or anchor near Vathi Bay for a peaceful overnight stay.
Day 10: Sifnos – Serifos (15 NM)
Sail to Serifos and anchor in the crescent-shaped bay of Livadi, framed by steep hills and a dramatic Chora perched above. Explore its untouched charm and enjoy dinner with sweeping sunset views.
Day 11: Serifos – Kythnos (20 NM)
Cruise north to Kythnos and drop anchor at Kolona Bay, where a sandy strip connects the main island to a rocky islet. Swim between two beaches or visit the thermal springs in Loutra village.
Day 12: Kythnos – Lavrion (25 NM)
Sail your final leg back to Lavrion, enjoying a last dip in a hidden bay along the way. Return to the marina for your final evening onboard and a celebratory farewell dinner.
Day 13: Lavrion (Check-out)
Disembark at Lavrion Marina after 12 nights of unforgettable sailing through the Cyclades. Depart with lasting memories of azure waters, Cycladic sunsets, and the timeless charm of the Greek islands.
Day 1: Paros – Koufonisi (25 NM)
Depart from Paros and set sail southeast to Koufonisi, one of the most enchanting islands in the Small Cyclades. Drop anchor near the harbour and enjoy the island’s crystal-clear waters, natural swimming pools, and barefoot island charm.
Day 2: Koufonisi – Schinoussa (10 NM)
Sail a short hop to nearby Schinoussa, a quiet and unspoiled paradise ideal for swimming and disconnecting from the world. Anchor in Mirsini Bay and enjoy a peaceful evening under the stars.
Day 3: Schinoussa – Iraklia (8 NM)
Continue your slow exploration to Iraklia, the smallest and most tranquil of the Lesser Cyclades. Hike to the Cave of Agios Ioannis or simply enjoy the serenity of your anchorage in Livadi Bay.
Day 4: Iraklia – Ios (20 NM)
Set sail for Ios, where traditional Cycladic beauty meets vibrant island life. Anchor in the sheltered bay of Ormos and explore the hilltop Chora with its winding alleys, whitewashed chapels, and lively tavernas.
Day 5: Ios – Folegandros (20 NM)
Cruise southwest to Folegandros, one of the Cyclades’ most romantic and dramatic islands. Anchor in Karavostasis port and take a taxi or hike up to the breathtaking clifftop Chora for sunset drinks.
Day 6: Folegandros – Paros (30 NM)
Enjoy a scenic sail back to Paros, passing the sparkling Aegean and nearby islets. Return to the marina or anchor near Naoussa or Parikia for a final evening filled with Cycladic charm and fresh Greek cuisine.
Day 7: Paros (Check-out)
Disembark in Paros after a week of relaxed sailing through the Cyclades. Depart with unforgettable memories of hidden beaches, charming villages, and the quiet elegance of the Lesser Cyclades.
The Cyclades archipelago in Greece is a classic sailing ground known for its whitewashed island villages and the brisk Meltemi winds – and it offers bareboat, skippered, and crewed charters for your adventure. Seasoned sailors often opt for bareboat charters in the Cyclades to test their skills in the Aegean breeze, charting courses to famous isles like Mykonos, Paros, and Santorini on their own and enjoying the freedom to discover secluded bays beyond the tourist spots. If you’re less experienced or simply want a more relaxed holiday, skippered sailing charters are a smart choice in this region; a local skipper will expertly handle the Cyclades’ winds and crowded summer ports, taking you to the best tavernas and anchorages so you can just enjoy the island-hopping without worry. And for those craving a high-end Greek Isles experience, fully crewed yachts (from sailing gulets to sleek motor yachts) are at your disposal – your crew will provide a seamless private yacht cruise around the Cyclades, complete with gourmet meals and insider knowledge, letting you soak up the sun and scenery in total comfort.
The Small Cyclades are ideal for both first-time and seasoned sailors seeking a calm yet captivating voyage. Chartering a bareboat lets confident sailors navigate at their own pace, while a skippered or fully-crewed catamaran charter offers ease for those preferring a laid-back holiday. From scenic coves and friendly local tavernas to authentic island communities rarely seen by mass tourism, the Small Cyclades deliver a genuine taste of Greek hospitality. Add in mild sailing conditions for most of the season, and you have the recipe for a truly enchanting yacht charter getaway in the heart of the Cyclades.
Need help picking your yacht charter and planning your itinerary? Get in touch with a consultant from Yacht4less for a free quote.
