14 Day Cyclades and Little Cyclades Sailing Itinerary
Take the helm and enjoy our recommended two-week bareboat sailing holiday itinerary around the Cyclades islands, the most popular island group in the Aegean Sea. The name “Cyclades” refers to the islands forming a circle around the island of Delos, and these islands are some of the most beautiful in the world! Set sail from our Athens base and experience stunning sandy beaches, distinctive white and blue architecture, friendly locals, folk music and breath-taking landscapes as you island hop your way around the islands taking on the adventure one day at a time!
Highlights
- Fantastic Saronic Sailing
- Sacred Island of Delos
- Little Venice in Mykonos
- The Temple of Poseidon in Sounio
- Serifos Cave of Koutalas
- Great hiking, diving and snorkelling
- Katafiki Cave in Kythnos
Day 1
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.
Day 2
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 min Sailing time
- 25 Nautical miles
Day 3
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
Day 4
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.
Day 5
Serifos to Sifnos
Sifnos was once a thriving gold and silver mining location and has since developed a reputation for being cosmopolitan yet traditional. This picturesesque island is renowned for its cuisine and local crafts so indulge and immerse yourself in all that Sifnos has to offer.
Mooring
Mooring buoy
Things to do
Snorkelling,Shopping,Swimming,Exploring
Facilities
Water,Restaurants,Bars,Electricity,Fuel,Gift shop,ATM
Discover Sifnos
Visit the Monastery of Chrissopighi
This 17th Century Monastry was built on a craggy rock and is the most important pilgrimage site on the island. It has been painted beautiful shades of pink and orange, making it a stunning photo stop.
Day 6
Sifnos to Milos
Milos is the most exotic island in the Aegean Sea and the most impressive with yellow, orange, white and red volcanic rocks scattered across over 70 beaches – Palaiochori, Papafragas, Gerontas, Firiplaka, Tsigrado, Plathiena beaches are definitely worth a visit!
Mooring
Mooring buoy
Things to do
Snorkelling,Shopping,Swimming,Exploring
Facilities
Water,Restaurants,Bars,Electricity,Fuel,Gift shop,ATM
Discover Milos
Visit the Pirate Caves
The caves – Papafrangas, Sarakiniko, Katergo – were used as hideouts for pirates of the Middle Ages, where traces of their ships are found next to the caves. In Sarakiniko, you will experience a spectacular landscape with white rocks of different shapes.
Stroll around Little Venice
Wander around this quaint hamlet, level with the water, where the ancient port of Milos used to be.
Day 7
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 The
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.
Day 8
Small Cyclades (DHENOUSSA - IRAKLIA – SKHINOUSA – KOUFONISIA)
Small Cyclades is a chain of small islands in the eastern part of the Cyclades. There are many Small Cyclades but only four are inhabited: Donousa, Iraklia, Skhinousa and Koufonisia. Spend your day exploring the islands, swimming in the crystal clear waters and enjoying a siesta. These peaceful islands offer ultimate relaxation after visiting party central, Ios.
Things to do
Snorkelling,Shopping,Swimming,Exploring
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.
Day 9
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.
Day 10
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.
Day 11
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
Day 12
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.
Day 13
Kea
Kea (or Tzia as it is also known as) stands out from the other Aegean islands for its rich flora, rare plant species, olive groves and vineyards. Discover 60km of exciting hiking trails leading to monuments, buildings, hidden coves, caves and beaches. It is also home to the largest oak forest in the Cyclades making it a great spot for birdwatching.
Mooring
Mooring buoy
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.
Day 14
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.
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