14 Day Cyclades and 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

To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.

Kythnos

Kythnos is a tranquil island, known for its unspoiled natural beauty and traditional villages. Located between Serifos and Paros, Kythnos is an ideal spot for those seeking peace and authenticity, with stunning beaches and crystal-clear waters.

The day’s sailing

• 4 Hrs 10 mins Sailing time
• 25 Nautical miles

Mooring

Kythnos offers several mooring spots, including the well-protected Loutra Harbor, which is perfect for yachts. Loutra is also known for its thermal springs, which are a unique feature of the island.

Things to do

Thermal Springs of Loutra: Take a dip in the famous hot springs, known for their therapeutic benefits.
Hike to the traditional villages: Explore the charming village of Chora, with its narrow streets, whitewashed houses, and beautiful views.
Relax on secluded beaches: Enjoy the quiet beaches like Kolona, which is accessible by boat and perfect for swimming and sunbathing.

Facilities

Loutra Harbor has basic amenities such as water, electricity, and fuel stations. There are also tavernas and cafes nearby where you can enjoy local Greek delicacies. The island is less touristy, so it offers a more serene, authentic experience.

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

Anchoring option

Things to do

Snorkelling,Shopping,Swimming,Exploring

Facilities

Rubbish,Restaurants,

Discover Kythnos

Visit Katafiki Cave
Katafiki Cave is one of the largest and most famous caves in Greece, which was used as a shelter by locals from invasions. You will get the opportunity to walk the narrow paths and discover several archaeological sites.

Relax in the Thermal Springs
Head over to Loutra and relax in the renowned thermal springs, which are rich in iron and sulfer making the perfect free spa treatment.

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.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

Milos is famous for its unique volcanic landscapes and incredible beaches. The island boasts over 70 beaches, each with its own distinct charm. Milos is also home to rich history, with impressive archaeological sites and crystal-clear waters.

The day’s sailing

• 2 Hr 50 mins Sailing time
• 17 Nautical miles

Mooring

The main harbor in Milos, Adamas, provides excellent mooring options for yachts. It’s a busy port with easy access to the island’s attractions and sheltered waters.

Things to do

Explore Sarakiniko Beach: Visit the otherworldly Sarakiniko Beach, known for its white volcanic rock formations and turquoise waters.
Visit the Catacombs of Milos: Explore these ancient burial sites, one of the most important early Christian archaeological sites in Greece.
Discover the ancient theater of Milos: The ruins of this ancient theater offer great views and insight into the island’s past.

Facilities

Adamas Harbor has comprehensive facilities, including water, electricity, fueling stations, and a variety of restaurants and shops. There are also banks, pharmacies, and ATMs, making it a convenient stop for yacht charterers.

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.

Ios

Sail to Ios, one of the top party Greek islands, renowned for its vibrant restaurants, bars and clubs. As well as the party atmosphere, Ios offers pristine beaches, magnificent views and mythological history.

Mooring

Anchoring option

Things to do

Snorkelling,Shopping,Swimming,Exploring

Facilities

Water, Taxi,Restaurants, Bars,Electricity, Laundry,Ice,Gift shop,ATM

Discover Los

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

Mooring buoy

Things to do

Snorkelling,Shopping,Swimming,Exploring

Facilities

Water,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.

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 mins Sailing time
• 12 Nautical miles

Mooring

Mooring buoy

Things to do

Snorkelling,Shopping,Swimming,Exploring

Facilities

Water,Taxi, Restaurants,Provisioning, Restaurants,Provisioning, Restaurants,Provisioning

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.

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

Anchoring option

Things to do

Snorkelling,Shopping,Swimming,Exploring

Facilities

Water,Taxi,Restaurants,Electricity.Fuel

Kythnos to Serifos

Serifos is known for its multiple award-winning beaches and white-washed cubed houses contrasting with the natural landscape. After a day at the beach, stroll through the cobblestone narrow alleys and have a drink at one of the many bars in the islands capital, Serifos Chora.

Mooring

Lazy line on a town quay or in Marinas

Things to do

Snorkelling,Shopping,Swimming,Exploring

Facilities

Water,Restaurants,Electricity

Discover Serifos

Visit Serifos Piazza Square
This cosy square, situated in Chora, the capital of Serifos, is the perfect lunch spot with several ouzeries and tavernas. As the capital is perched on a hill, you will get amazing views of the Aegean sea, and the perfect spot to watch the sunset.

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

Snorkelling,Shopping,Swimming,Exploring

Facilities

Water,Restaurants, Electricity,Fuel

Discover Kea

See the Stone Lion of Kea
A short hike from Loulida is one of the most popular sights of the island, dating back to 600 BC.

Dive amongst the shipwrecks
Kea is a diving paradise with two shipwrecks to explore: the British liner HMHS Britannic, one of the largest liner wrecks in the world, and the S/S Burdigala, a luxury liner built in the late 19th century. Snorkelling is a must too, with colourful marine life.

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.