14 Day Cyclades & Little Cyclades Sailing Itinerary

Cape Sounion Bay

Few places showcase the natural beauty and rich history of Greece quite like Cape Sounion. Perched on the towering cliffs of the Attica Peninsula, the area’s biggest attraction is the legendary Temple of Poseidon. Composed of worn white marble, these restored ruins date all the way back to 440 B.C. when the original temple was built to honor the legendary god of the sea. Look close and you might find the mark of George Lord Byron, a famed romantic poet and frequent visitor to Cape Sounion. Nearby are the ruins of the Temple of Athena, goddess of wisdom.

Overlooking the beautiful Saronic Gulf, the views from the Cape are absolutely stunning. Stay and watch the sunset for a photo-worthy finish to your day.

The day’s sailing

• 3 Hr Sailing time
• 18 Nautical miles

Mooring

No moorings are available. Anchor in Cape Sounion Bay on the west side of Cape Sounion. Nearby Legrana Bay is a good alternative anchorage.

Dinghy dockage: Dinghy dockage is available.

Things to do

Merely anchoring in Cape Sounion Bay and admiring the Temple of Poseidon from the comfort of your yacht is an experience in itself, the quintessential Greece you read about in glossy brochures. Many sailors like to take the dinghy ashore and climb the trail leading up the cliffs to walk through the ruins of Poseidon’s grand temple. Sunsets are magnificent, but the view of the coast and the Cyclades Islands in the distance is stunning at any time.

Facilities

No facilities for yachts are available.

Temple of Poseidon

As the sun sinks low in the sky, turning the Aegean Sea into a glimmer of oranges and reds, crowds gather atop the 196-foot cliffs on the southwest end of the Attica Peninsula at Cape Sounion. The people look out to sea, then shift their gaze to the ghostly white marble columns of the Temple of Poseidon, a sacred place for the Greeks in 440 B.C., when they began to build this grand homage to the god of the sea. Originally, there were more than 30 columns, and a massive statue of Poseidon presided over the grounds. Today, about half the columns are still standing, but they make no less of an impressive sight from the cliff tops. From the bay below, where yachts frequently anchor, the temple remains a landmark for mariners, bathed in the subtle glow of the setting sun or in the glaring light of day.

Kythnos

Located southeast of Kea and northwest of Serifos, Kythnos is typical of the acrid, rugged islands found throughout the Aegean Sea. Its brown-colored hills extend just over 1,000 feet in height. 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 Kythnos 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 Kythnos is just that – the quiet, traditional Greek villages, the intimate tavernas, the hospitality of a warm and inviting people. Sailing in Kythnos 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 northeast side of the island. Loutra is about as well a protected harbor 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 Kythnos. Of particular charm are Dryopida (the former capital) and Kythnos Town (Chora). Both are picturesque with whitewashed homes and colorful painted trim. Dryopida is situated in a small, fertile valley and its center is closed to vehicular traffic, making it a wonderful place to explore on foot. Although it is occasionally closed to the public, 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 Kythnos 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 Kythnos 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

At the western edge of the Cyclades, you will find the mountainous isle of Kea, its steep slopes carpeted in forests and scrubby brush from the abundant springs and streams, quite rare in the archipelagos fanning out into the Aegean from mainland Greece. As you go sailing in Kea waters, approaching from the Saronic Gulf, the green heights become plain long before you reach the coast. The main port of the island is Korissia. A selection of low-key cafés, tavernas, and restaurants are in the port and the nearby village of Vourkari, as well as a number of shops. Historic sites and religious monuments are fascinating to explore, and the island is also popular for its more than 30 hiking trails that were once part of the ancient road system linking the villages of the island. The beaches are superb. Kea sailing is a rich and varied adventure in an idyllic setting.

The day’s sailing

• 3 Hr 20 mins Sailing time
• 20 Nautical miles

Mooring

Moorings are available. The port of Korissia is situated at the south end of Nikolaos Bay, on Kea’s northwestern shore. It’s a picturesque and quiet harbor, where you can find dockage. The north side of Nikolaos Bay has excellent anchorages, all of them scenic and secluded. On the east coast, you will find a wonderful anchorage at Poleis Bay.

Dinghy dockage: No dinghy dockage is available

Things to do

Renting a bicycle or a motor scooter at Korissia is a great way to explore Kea. Bus service is also available to take you from Korissia to the other villages, including the island’s capital, most commonly called Kea Town or Kea Chora. There you will find the ruins of an ancient settlement, a selection of churches and monasteries, and possibly the most noteworthy and certainly impressive site on the island. You walk a short distance to the northeast from Kea Town along a winding path and suddenly come upon the enormous stone Lion of Kea. The creature is 23 feet long and was carved in the 6th century B.C. The Archaeological Museum of Kea is also worth visiting. Just outside Korissia is an ancient acropolis, where you can explore the ruins of homes and temples. Also near the port are five popular beaches. All of them are scenic. Some have beachside bars and cafés, while others are simply gorgeous expanses of golden sand.

Facilities

Dockage, fuel, and water are available at Korissia at the south end of Nikolaos Bay.

Kea Island

Kea isle is blessed with abundant springs and streams, making it one of the most beautiful of the Cyclades. In the time of ancient Greece, it was known as the Water Island and called Ydroussa. Water nymphs were said to live there. In Greek mythology, the story goes that the gods became jealous of Kea’s exquisite beauty and they sent a fierce lion to ravage the island, robbing it of water and driving away the nymphs. Ultimately, Zeus restored the water and Kea once again was beautiful. The nymphs returned. In the 6th century B.C., an unknown stone carver with a sense of humor fashioned a 23-foot-long smiling lion near present-day Kea Town. The Lion of Kea is the most visited destination on the island.

Athens Base

The Zea Marina is much more than just a place to dock your boat. This 4.7-square-mile facility is the epicenter of everything from coffee shops and bars to cafes, markets, and more. Stroll along the waterfront and watch as the sun shimmers off the glistening Bay of Zea. If you’ve got some time, there are plenty of things to do around the city of Piraeus. Get a fascinating glimpse of Grecian history at the Archaeological Museum of Piraeus or the Nautical Museum of Greece; marvel at the massive Church of Saint Nicholas and its beautifully intricate interior; or pull up a chair at a harbor-side café and watch as the boats move in and out of the bay.

As you can see, there are plenty of things to do around Zea Marina, but if you’re looking to explore the most famous city in all of Greece, it’s definitely recommended that you take the 10-minute drive into Athens. The birthplace of Western civilization, Athens is now a vibrant and modern city that still preserves much of its important past.

Visiting the Acropolis is an absolute must. Take the short walk up to the ancient high city and explore famous historical structures like the Parthenon, the Temple of Athena Nike, the Erectheion, and the nearby New Acropolis Museum.

If you’re looking to learn more, head over to Museum Mile, a long strip of museums that starts at Syntagma Square and includes the National Archaeological Museum, home to the world’s finest collection of art and sculpture from Ancient Greece.

The day’s sailing

• 3 Hr 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.”