14 Day Cyclades & Little Cyclades Sailing Itinerary

Cape Sounio

Cape Sounio is renowned for its dramatic setting and the iconic Temple of Poseidon. Located at the southern tip of the Attica Peninsula, it offers a spectacular start to your cruising adventure, with panoramic views over the Aegean Sea. The area is steeped in history and surrounded by rugged coastlines, providing a perfect first stop as you embark on your journey. Cruise into this stunning location to take in the natural beauty and ancient landmarks that make Cape Sounio a must-see destination.

The day’s sailing

• 1 Hr 17 mins Sailing time
• 18 Nautical miles

Mooring

You’ll find mooring options at the nearby Lavrio Marina, which is well-equipped for yachts. The marina offers sheltered waters and easy access to the Temple of Poseidon and the surrounding area.

Things to do

Visit the Temple of Poseidon: Take a short walk from the marina to the temple, which sits atop a hill offering breathtaking views of the sea, especially at sunset.
Relax on the beaches: The nearby beaches, such as Legrena Beach, are perfect for a swim or a relaxing day by the sea.
Explore the ruins:Lavrio Marina provides water, electricity, and fuel stations. There are also shops, restaurants, and cafes for provisions and dining. The marina is known for its laid-back atmosphere and is an ideal starting point for the Cyclades Islands adventure. Discover ancient remnants of a once-thriving Greek civilization in this historically significant area.”

Facilities

Lavrio Marina provides water, electricity, and fuel stations. There are also shops, restaurants, and cafes for provisions and dining. The marina is known for its laid-back atmosphere and is an ideal starting point for the Cyclades Islands adventure.

Kythnos

Located south-east of Kea and north-west of Serifos, Kithnos (also spelt Kythnos) is typical of the arid, rugged islands found throughout the Aegean Sea. Its brown hills extend just over 1,000 feet high. Along the coast are numerous coves and bays, some of them quite beautiful with nearby sandy beaches. Exploring the indented shores aboard your graceful yacht marks a highpoint of Kithnos sailing. The ambience at the port towns and inland villages is laid-back, far removed from the bustle found on islands that are prime tourist destinations. The charm of Kithnos is just that – the quiet, traditional Greek villages, the intimate tavernas, the hospitality of a warm and hospitable people. Sailing in Kithnos waters is a journey to serenity, where the pace of life is slow and the subdued beauty is unforgettable.

The day’s sailing

• 4 Hr 10 mins Sailing time
• 25 Nautical miles

Mooring

No moorings are available. The two main ports are Merichas in a sheltered bay about midway down the west coast of the island, where the ferries come in, and Loutra, on the north-east side of the island. Loutra is about as well protected a harbour as you can find in the western Cyclades. The Kithnos coast has many scenic coves and bays, many of them beautiful and remote. Just a few miles north of Merichas are two bays (Sandbar Bay and Episkopi Bay) with picturesque anchorages and beaches. South of Loutra, about in the mid-coast of eastern Kithnos, is Stefanos Bay, which has a splendid sandy beach.

Dinghy dockage: Dinghy dockage is available.

Things to do

Renting a car or motor scooter is a great way to explore the winding roads and sleepy traditional villages of Kithnos. Of particular charm are Dryopida (the former capital) and Kithnos Town (Chora). Both are picturesque, with whitewashed houses and colourful painted trim. Dryopida is situated in a small, fertile valley and its centre is closed to vehicular traffic, making it a wonderful place to explore on foot. It’s occasionally closed to the public but if you’re lucky and find it open, a must-see is the nearly mile-long Katafiki Cave with its subterranean lakes. While you’re in Kithnos Town, check out the small but interesting Byzantine Museum. There are shops, tavernas, cafés, and restaurants on the narrow lanes and around the public squares of both villages. In Kithnos Town, you’ll see the ubiquitous Greek windmills, some ancient ruins, and numerous donkeys, which many local residents use to haul goods. Panagia Kanal Monastery perched on a cliff near the small seaside village of Kanala is interesting and beautiful, featuring some stunning murals and a superb view.

Facilities

Dockage, fuel, water, and Internet access are available. Bus service is available. Car and motor scooter rentals are available in Merichas.

Serifos

One of the hidden gems of the Cyclades is Serifos, which combines rugged, natural landscape with impressive white-washed cubed architecture. The capital, Chora is built on a steep mountain with narrow alleyways, bougainvillea-filled courtyards, colorful houses and stunning Aegean sea views. Walk up the stairway to the Venetian castle that includes the chapels of Agia Varvara, the Saviour, Agios Konstandinos and Agios Ioannis.

On the southeastern side of Serifos is the quaint port of Livadi, which is the tourist centre with an abundance of bars and restaurants. You will also find beautiful beaches such as Megalo Livadi, Aghios Sostis, Psili Ammos, Aghios Ioannis, Koutalas and Sikamia. West of Koutalas beach is the famous limestone Cave of Koutalas, with impressive stalactites and stalagmites. On a rust-coloured hillside above Megalo Livadi beach is the mining museum, where you can learn about Serifos past and main source of income. The hill is lined with old rail tracks, wagons and tunnels.

The day’s sailing

• 2 Hr Sailing time
• 12 Nautical miles

Mooring

You can anchor in the bay or go stern or bows – to the jetty off the village on the Southeast side of the bay.

Things to do

Enjoy swimming in one of the many beaches, or explore the maze of alleyways in the Capital. Learn about the history of Serifos and visit the mining museum and Venetian castle, and take in the spectacular views at sunset.

Facilities

Water, Restaurants, Bars, Gift Shop, ATM, Fuel

Sifnos

Cosmopolitan Sifnos is renowned for its rich culinery heritage, local crafts, traditional architecture and beautiful beaches. Once a gold and mining location, it has since developed a reputation for offering the finer things in life. Despite this sense of luxury, Sifnos has kept its low profile, providing a peaceful, relaxing atmosphere for all visitors to enjoy.

Sifnos main town, Apollonia is the place to go for entertainment, including locally organised festivals with lively music and delicious food. Be sure to indulge in the traditional cuisine consisting of chickpea soup, mastelo (lamb or goat baked on vine branches) and salad with capers.

The day’s sailing

• 1 Hr 40 mins Sailing time
• 10 Nautical miles

Mooring

The entrance is difficult to identify until you get there, when the cliffs on either side open up to amphitheatre of the bay. Use only the anchor to stay at the bay in the North side.

Things to do

Visit the 17th Century Monastery of Chrissopighi, which is the most important pilgrimage site on the island. There is also the Church of the Seven Martyrs, a picturesque small blue domed church surrounded by emerald waters. Or go swimming in one of the many beaches including Kamares, Platys Gialos and Vathy. 

Facilities

Water, Restaurants, Bars, Gift Shop

Milos

Shaped by its volcanic past, Milos is an extordinary island with the most exotic landscape and incredible beaches, scattered with red, pink and orange volcanic rocks. Sarakiniko and Kleftiko beaches present impressive white rock formations with eroded caves and emerald waters.

Stroll around the charming, colourful Little Venice, where the ancient port of Milos used to be, and catch the sunset. Or head towards the east of the island where you can discover the eerie atmosphere of the old sulphur mine with old train tracks, carriages and iron bridges.

The day’s sailing

• 2 Hr 50 mins Sailing time
• 17 Nautical miles

Mooring

Go stern or bows.You can berth on the West side. Avoid the ferries.

Things to do

Absorb the Med sunshine on one of the 40+ beaches and their volcanic splendor, or wander round colorful fishing villages, Klima and Firopotamos, where you will find white-washed houses with vibrant shutters and boat yards.

Facilities

Taxi, Restaurants, Car hire, Bars, Electricity, Fuel

Kimolos

Today, you will set sail for the charming island of Kimolos, known for its peaceful atmosphere and picturesque landscapes. Located just north of Milos, this island offers pristine beaches and clear turquoise waters. The quaint village, with its narrow streets and whitewashed houses, provides an authentic Greek experience. As you explore, you’ll find wonderful spots for swimming and relaxation. Kimolos is a haven for those seeking tranquility away from the more tourist-heavy spots in the Cyclades.

The day’s sailing

• 50 mins Sailing time
• 5 Nautical miles

Mooring

Anchoring & mooring options

Facilities

Kimolos Port (Psathi): Offers basic facilities including water, electricity, and a few tavernas nearby.
Anchoring at Prassa Beach: It’s perfect for those looking for a peaceful overnight stop, but be aware that there are limited facilities here.

Folegandros or Sikinos

Next, you have the choice to visit either Folegandros or Sikinos, two stunning islands with unique charm and relaxed atmospheres.

Folegandros: Known for its dramatic cliffs, beautiful Chora, and stunning views, Folegandros offers a calm and quiet escape. The island’s rugged beauty is complemented by its authentic vibe, and the central town is filled with traditional white houses.

Sikinos: A lesser-known gem, Sikinos offers a laid-back experience with a rich history. The island’s small villages, ancient ruins, and pristine beaches make it a perfect destination for those seeking a peaceful retreat.

Mooring

Anchoring & mooring options

Facilities

Folegandros:
Karavostasis Port: A small, well-protected harbor suitable for yachts. Facilities include water, electricity, and tavernas.
Anchoring at Agali Bay: This anchorage has limited amenities.

Sikinos:
Alopronia Port: A quaint harbor that offers basic facilities such as water and electricity. The town is close by for provisions.
Anchoring at Agios Georgios Bay: Facilities are minimal.”

Ios

Ios is famous for its lively party scene, however it offers so much more than this, from the magnificent views, to the breathtaking landscape and clifftop villages. Get lost in the cobblestoned alleyways of the capital, Chora and climb up to the Odysseas Elytis Theatre, which resembles ancient Greek theatres and is the perfect spot for sea views. Worth a visit is Skarkos Hill, the island’s largest, award winning Bronze Age archaeological excavation site.

If you would prefer to be amongst the vibrant atmosphere, visit Mylopotas beach, a 1km long sandy beach with Far Out Club based at the end.

The day’s sailing

• 3 Hr Sailing time
• 18 Nautical miles

Mooring

Pay attention to the ferries that are coming and going and the waves they cause. Go stern or bows – to in the basin.

Anchoring is an option.

Things to do

Visit the most significant church on the island, Panagia Gremiotissa which is built on the highest spot of Chora, offering amazing views. The lighthouse is a famous site which should not be missed at the ports entrance, as well as the Harbour of Adamantas – the second biggest natural harbour in Greece.

You can also enjoy: Snorkelling, Shopping, Swimming, Exploring

Facilities

Taxi, Restaurants, Bars, Electricity, Laundry, Ice, Gift Shop, ATM

Discover Ios

Party at Mylopotas beach
The secluded Mylopotas beach is one of the most popular beaches, where travellers often visit the renowned Far Out Club at the end of the beach.

Visit Odysseas Elytis Theatre
Named after a famous Greek poet, the open air amphitheater of Odysseas Elytis resembles ancient Greek theatres and is the perfect place to watch local performances and festivals.

Small Cyclades (Irakleia, Koufonisia, Schoinousa)

The Small Cyclades, a group of 32 islands and islets are considered the true hidden gems of the Cyclades. Today, only four islands remain inhabited – Iraklia, Schinousa, Koufonisia and Dhenoussa.

Iraklia is the largest of the islands and home to the Cave of the Sacred Icon of Agios Giannis, about 2 hours walk from the main port. Koufonisia is the go-to fashionable destination of the Small Cyclades where the Old Town is lined with cafes and restaurants. Dhenoussa sits apart and offers a more secluded, peaceful experience.

The day’s sailing

• 2 Hr Sailing time
• 12 Nautical miles

Mooring

The entrance is difficult to see from the North. There is no much space for the yachts to go bows – to inside the short mole. Use a trip line on the anchor.

You can also enjoy: Snorkelling, Shopping, Swimming, Exploring

Things to do

The Small Cyclades is where you can kick back and relax with a book; enjoy a siesta; swim in the crystal clear waters; go spearfishing round the islets Aspronisi, Ofeidousa and Argilos and indulge in taverna meals.

Facilities

Restaurants, Bars

Discover Small Cyclades

Nearby Islets Schinousa
The islets Aspronisi, Ofeidousa and Argilos are located at the northern part of the island and can be visited by boat. You should not miss the opportunity to explore them and swim in their charming, cooling waters which are ideal for snorkelling or spear fishing.

Stop off at the Cave of the Sacred Icon of Agios Giannis
This is Iraklias most interesting walking destination, around 2 hours from the main port. The entrance leads to a sequence of caves with an abundance of stalagmites and stalactites.”

Paros-Antiparos

In the heart of the Aegean Sea is Paros, which combines traditional elements such as the architecture, quaint villages and historical monuments with the lively nightlife and bustling beaches. Paros stretches across 120km of coastline and has endless blonde-sand beaches at the bottom of lush mountains, perfect for kitesurfing and windsurfing.

Head to the capital and cultural hub, Paroikia and immerse yourself in the buzz of the sophisticated bars, restaurants and tavernas. Or explore Paros Environmental and Cultural Park, which is approximately 80 hectares of walking trails,remarkable rock formations, caves and hidden coves.

The day’s sailing

• 5 Hr Sailing time
• 30 Nautical miles

Mooring

Berth stern or bows – to in the inner harbor or in calm weather off the outside the mole. Use the anchor. Be careful the ferries.

Mooring buoys available.

Things to do

Enjoy watersports along the stretch of coastline; visit Frankish Castle in Paroikia or explore the vast area of Paros Park.

You can also enjoy: Snorkelling, Shopping, Swimming, Exploring

Facilities

Taxi, Restaurants, Provisioning, Bars, Electricity, Fuel, Ice, Gift Shop, ATM

Discover Paros

Explore Paros Environmental and Cultural Park
Situated on the Agios Ioannis Detis peninsula, this park is an area of approximately 80 hectares of remarkable rock formations, caves, hidden coves and seashores with crystalline waters.

Mykonos

Widely known as the ‘Ibiza of Greece’, you can expect a vivid party scene, award-winning restaurants, lively bars, designer boutiques and incredible beaches. The trademark of Mykonos is the windmills in front of Little Venice, an 18th centure district which is the most picturesque part of the main town and the perfect spot to watch the sunset.

The dry, windy climate of Mykonos attracts watersports enthusiasts who enjoy surfing, windsurfing and kitesurfing on the many beautiful beaches. One of the main attractions of the Cyclades is the sacred islet of Delos, which was the island of God Apollo and is considered one of the most important archealogical sites in Greece.

The day’s sailing

• 4 Hr 10 mins Sailing time
• 25 Nautical miles

Mooring

You can berth stern or bows – to or alongside on the South side of the basin. Some berths with laid moorings on the pontoons. Otherwise go alongside or stern- to where convenient.

Mooring buoys available.

Things to do

Dine and go shopping at Mykonos capital, Hora where Matoyánni Street is filled with designer stores, cafés and restaurants. Or stroll around the charming Little Venice and have a cocktail along the waterfront.

You can also enjoy: Snorkelling, Shopping, Swimming, Exploring

Facilities

WiFi, Showers/Toilets, Restaurants, Provisioning, Bars, Electricity, Fuel, Ice, Gift Shop, ATM

Discover Mykonos

Visit Little Venice
A romantic, picturesque area of the main town, and is a great spot to have a drink and enjoy the sunset from one of the many bars along the waterfront.

Explore the sacred islet of Delos
Delos is one of the most important archealogical sites in Greece. Under the Ministry of Culture’s guidance, vessels need special permission to dock. Overnight stays are prohibited.

Syros

Whilst there is so much to do in Syros, it is the quieter, calmer island of the Cyclades. The classy capital Ermoupoli is stately and grand with marble paved squares, neoclassical buildings, and catholic and orthodox churches. Vaporia is the attractive area of Ermoupoli, where glamorous receptions and lavish balls were held in the numerous Venetian mansions.

In the southern part of Syros, you will find the most popular beaches – Kini, Galissa, Delfini, and Dellagratsia. Or you can head north to Grammata and the Grey Cave with inscribes of wishes and prayers covering the rocks dating back to Roman and Byzantine times.

The day’s sailing

• 2 Hr 30 mins Sailing time
• 15 Nautical miles

Mooring

Go stern or bows – to the mole or alongside the inner mole. You will need to use your anchor although there are plans to re-lay moorings.

Anchoring option.

Things to do

Try the local soft and chewy sweets called loukoumia, flavoured with rosewater, pistachios and almonds. Or visit the industrial museum in Ermoupoli, where you will see exhibits on shipping, industry and history of the capital.

You can also enjoy: Snorkelling, Shopping, Swimming, Exploring

Facilities

Taxi, Restaurants, Bars, Electricity, Fuel

Kea

Kea (also known as Tzia) is one of the closest islands to Athens, renowned for its scenic beauty, charming villages, and rich history. Cruising into Kea offers the perfect blend of relaxation and exploration, with traditional Cycladic architecture and a range of ancient sites to discover. The island is also known for its excellent hiking paths, making it a great destination for those looking to enjoy both its natural beauty and cultural heritage.

The day’s sailing

• 1 Hr 47 mins Sailing time
• 25 Nautical miles

Mooring

The main harbor of Kea, Korissia, is well-equipped for yachts, offering mooring spots in a calm, sheltered bay. The town is small, but it provides a peaceful atmosphere and easy access to the island’s attractions.

Things to do

Hike to the ancient Temple of Athena: Take a hike to this ancient site, where you can enjoy stunning views and explore the ruins.
Wander through Ioulida: The island’s charming capital, Ioulida, has narrow streets and traditional Cycladic architecture, perfect for exploring on foot.
Relax at the beaches: Enjoy the peaceful beaches of Kea, such as Gialiskari and Otzias, perfect for swimming and sunbathing.

Facilities

Korissia Harbor offers water, electricity, and fueling stations. The town has a few tavernas, cafes, and small shops where you can stock up on provisions. Kea is a quieter island, ideal for those seeking a more peaceful stop.

Athens Base

Zea Marina is much more than just a place to dock your boat. This expansive 4.7-square-mile facility is the hub for everything from coffee shops and bars to cafes, markets, and more. Enjoy a leisurely stroll along the waterfront and watch the sun shimmer off the sparkling Bay of Zea. If you have some time, there are plenty of things to do in and around the city of Piraeus. Take a fascinating dive into Grecian history at the Archaeological Museum of Piraeus or the Nautical Museum of Greece, marvel at the magnificent Church of Saint Nicholas with its intricate interior, or relax at a harbor-side café and watch the boats cruising in and out of the bay.

While there’s plenty to enjoy around Zea Marina, if you’re eager to explore one of the world’s most iconic cities, take the 10-minute drive into Athens. Known as the birthplace of Western civilization, Athens is a vibrant, modern city that still preserves much of its rich historical heritage.

A visit to the Acropolis is a must. Take a short walk up to this ancient high city and explore famed structures like the Parthenon, the Temple of Athena Nike, the Erectheion, and the nearby New Acropolis Museum.

For those wanting to dive deeper into Greece’s history, head to Museum Mile, a collection of museums starting at Syntagma Square, including the National Archaeological Museum, home to the world’s finest collection of art and sculpture from Ancient Greece.

The day’s sailing

• 1 Hr 20 mins Sailing time
• 18 Nautical miles

Mooring

The Moorings has its own private docks at the Zea Marina. Arriving in Zea, call the base and assistance with docking will be provided.

Dinghy dockage: No dinghy dockage is available

Things to do

Walk along the waterfront and choose from a variety of bars, restaurants and shops. Enjoy the sights and dining in the surrounding town of Piraeus. There are several places to each along the scenic coasts of Mikrolimano and Piraiki including sumptuous seafood restaurants and harbor side tavernas.

Facilities

All facilities at Zea Marina are available for yachts and guests of The Moorings. These include fresh water and electricity, showers, laundry, WiFi, shopping and entertainment.

The Acropolis

Perhaps the most famous site in all of Athens, The Acropolis was built on a flat-topped rock that rises 490 feet above the city streets below. This ancient high city includes a number of structures that were integral to ancient Greek culture and the birth of Western civilization, as we know it. Walk amongs the towering marble columns of the Parthenon and marvel at the attention to detail that many consider the high point of Greek art. Explore the Temple of Athena Nike and learn about the revered goddess of victory in war and wisdom. Just outside the city, the new Acropolis Museum will give you an inspiring glimpse into the lives of the ancient Greeks.”