Charter a Yacht in Greece and explore Santorini, Folegandros, Milos, Sifnos, Paros, Naxos, Koufonisia, and Ios on this Cyclades sailing itinerary
Yacht Charter Day 0 – Arrive in Santorini | Yacht Charter Day 1 – Santorini to Folegandros | Yacht Charter Day 2 – Folegandros – Kimolos – Milos | Yacht Charter Day 3 – Milos to Sifnos | Yacht Charter Day 4 – Sifnos – Antiparos – Paros | Yacht Charter Day 5 – Paros to Naxos | Yacht Charter Day 6 – Naxos – Koufonisia – Schoinousa | Yacht Charter Day 7 – Koufonisia to Ios | Yacht Charter Day 8 – Ios to Santorini return
The itinerary includes Folegandros, where you will visit the charming port of Karavostasi and then follow on to the lesser-known island of Kimolos with scenic, unspoiled beaches. The volcanic island of Milos is next on our Greek island sailing trip, where you will explore Sarakiniko beach. From there, we set sail for Sifnos to taste local delicacies and explore golden sand beaches and various cultural attractions. In Paros, you cannot miss a visit to Kolymbithres and, of course, strolling through the iconic villages of Naoussa and Parikia. Nearby, the island of Antipaxos offers an entirely different experience with remote beaches you will enjoy from your private yacht. Not far from Paros, the largest island in the Cyclades, Naxos, awaits, with its Venetian fortresses and dreamy sandy beaches. After, we head to Koufonisia, a paradise for snorkelling and diving enthusiasts. You will end your Cyclades yacht charter holiday with a visit to Ios, known for its excellent nightlife and abundance of traditional churches, before making your way back to Santorini.
All our Greek yacht charter holidays can be expanded to include more islands and destinations in the Cyclades and other Greek island complexes based on your needs. Check out more of our itineraries for sailing in Greece here:
Cyclades Sailing Itinerary
Yacht Charter Day 0 – Arrival in Santorini
Santorini is the starting point of our yacht charter cruise across the Cyclades.
The beauty of Santorini cannot be overstated. If you’re looking for the ideal vacation destination, it is among the top picks globally. With houses perched on top of rugged cliffs and unique geological formations shaped after the volcanic eruption thousands of years ago, Santorini continues to enchant all visitors that arrive on its shore.
Visitors have the option to arrive early and spend a few days exploring the island. Alternatively, you can also choose to spend time here after the end of this yacht charter cruise.
The volcano and views of the caldera take center stage, so for the best experience, book a caldera-view hotel in Fira, Oia, or Imerovigli.
> Sailing in Santorini – important information:
- The safest anchorage is Vlyhada public marina
- Plenty of shoals at the entrance
- The caldera is incredibly deep – no anchoring possible
> Sailing in Santorini – don’t miss:
- A visit to the picturesque village of Oia with views of the Caldera
- Tasting Saganaki cheese, fava dip, and white eggplants
- A romantic dinner at a winery and a taste of the local Vinsanto
Yacht Charter Day 1 – Santorini to Folegandros
The island of Folegandros, nestled between Milos and Santorini, is our first stop for the trip.
Only a few hours from other popular destinations, Folegandros fills like another place. The dry climate and rough winds that hit its shore historically isolated the island, and only a tiny local population of fewer than 300 people stays year-round. Visitors arrive here for a taste of the old ways – traditional food, secluded beaches, and the friendly welcome of the locals.
The two main anchorages for yacht charters are Karavostasi and Ormos Vathi; they are also the best sheltered from Meltemi winds. The best beaches are Vorina on the east and Katergo to the south, which requires a half an hour walk to reach unless you are arriving by boat.
> Sailing in Folegandros – important information:
- Two main anchorages: Karavostasi and Ormos Vathi
- Night approaches not recommended for Karavostasi
- Most beaches on the island are only reachable by boat
> Sailing in Folegandros – don’t miss:
- The walk to the medical castle for panoramic views and the Church of Panagia
- A swim at Agali beach
- Snorkelling at Katergo beach with crystal clear waters
Yacht Charter Day 2 – Folegandros – Kimolos – Milos
From Folegandros, we set sail north towards the island of Kimolos, located right next to Milos, which is our next stop on this trip.
Next to Kimolos, we find the tiny island of Agios Efstathios and the much larger island of Polyaigos, the largest uninhabited island in the Aegean Sea, named after the active population of goats that occupy the space. Here, Mediterranean seals (Monachus Monachus) give birth to their young. The island is a designated protected site under the Natura 2000 network.
Plenty of non-organized sandy beaches can be found in Kimolos, offering carefree moments for all.
From Kimolos, the island of Milos is less than 1,5 hours away or about 12 nautical miles.
With more than 40 beaches to choose from, picturesque fishing villages, and enchanting landscapes, Milos is a place that can’t be missing from your Greek islands itinerary across the Cyclades. The “syrmata” houses of Milos on the coastal village of Klima are unique to the area and traditionally used by fishermen. Nowadays, some operate as accommodation units. The brightly colored doors on the water acted as garage doors for the fishermen’s boats.
> Sailing in Milos – important information:
- The largest port is Adamas
- There are only limited mechanical repairs on Milos. Fuel and water are available.
- Volcanic island with very dramatic coastline worth exploring in full
> Sailing in Milos – don’t miss:
- Exploring Sarakiniko beach
- A visit to Klima and the picturesque fishing villages
- Sailing around Kleftiko for the famous Caves of Mylos
Yacht Charter Day 3 – Milos to Sifnos
National Geographic called Sifnos “The Cyclades’ hottest food scene,” and we couldn’t agree more.
One of the best-kept secrets of the Cyclades, Sifnos has a flourishing culinary scene and the ambiance required to enjoy it all in. Modest in size, Sifnos is easy to explore and easier to fall in love with.
There is something here for everyone; long stretch of golden sand beaches like Platys Gialos, Chrissopigi, and Kamares and secluded beaches like Vroulidia and Dialiskari. There are also plenty of cultural and historical attractions on the island for those interested. You can visit the Archaeological Museum, the churches of Panagia Chrissopigi, the Church of Seven Martyrs, and the windmills and pigeon houses scattered around the island.
> Sailing in Sifnos – important information:
- Easy approach, except for possible meltemi winds
- Ormos Kamares is the only port on the island
- There is water and electricity available on the quay at Kamares
> Sailing in Sifnos – don’t miss:
- Visit the church of Seven Martyrs
- Swim at Platys Gialos beach
- Explore the village of Kastro
Yacht Charter Day 4 – Sifnos – Antiparos – Paros
From Sifnos, we are ready to head towards Antiparos and then Paros.
Antiparos is less than 5 nautical miles from Paros and a popular day trip option for travelers. However, it is also an excellent place to explore on its own. The main feature that attracts visitors here is the beaches. Sandy, with crystal clear waters, the beaches of Antiparos are remote and nudist-friendly. An excellent place for diving and snorkeling. Saint George Beach on the southwest boasts incredible views and is one place not to be missed.
Arriving in Paros, it is clear why this island captivates the heart of so many travelers and has quickly risen in status among the greats, such as Mykonos, Santorini, and Naxos. The cosmopolitan vibe and picturesque fishing villages combine traditional elements with luxury amenities and a vibrant nightlife in a refreshing and unexpected way.
It is worth spending an afternoon strolling through the streets of Parikia and Naoussa, the two most popular settlements on the island.
> Sailing in Paros – important information:
- Parikia is the main commercial harbor – approach can be tricky with lots of low-lying reefs
- Plenty of anchorages including Naoussa Bay, Ayios Ioannis, Plastira and Aliki
- Very popular destination during the Greek summer season
> Sailing in Paros – don’t miss:
- Stroll around Parikia and Naoussa villages
- A swim at Kolymbithres – you can also try watersports!
- Visiting Antiparos island
Yacht Charter Day 5 – Paros to Naxos
Leaving the charming beaches of Paros behind, we hop over to Naxos, only a few hours to the east.
Naxos is the largest island in the Cyclades and also the greenest. The natural beauty of the island is only surpassed by its rich history and cultural sights, including the Portara, a huge door that sits at the entrance of an unfinished temple, and the Venetian fortresses – the Tower of Fragopoulos, one of the oldest fortified towers, and the Tower of Glexos, part of the Castle of Naxos in Chora.
With incredible, long, sandy beaches like Plaka, Agios Georgios, and Agios Prokopios, Naxos is a favorite for yacht charters that want all the options!
> Sailing in Naxos – important information:
- Naxos Marina near the commercial harbor offers a sheltered spot for yacht charters
- Lots of stores for provisioning
- Finding space during peak season is often an issue
> Sailing in Naxos – don’t miss:
- Walk to Portara to enjoy a sunset
- Indulge in kitesurfing and other wind sports at Mikri Vigla
- Hike to Mount Zas
Yacht Charter Day 6 – Naxos – Koufonisia – Schoinousa
On Day 6 of this Greek yacht charter itinerary across the Cyclades, we set sail for Koufonisia.
Koufonisia is comprised of two islands: Kato (Down) and Ano (Upper) Koufonisi.
The latter is where most of the activity and amenities are centered and where visitors can find tavernas and accommodation. Kato Koufonisi is uninhabited and is a yacht charter’s paradise, with countless majestic spots for diving, snorkeling, swimming or simply lounging and admiring the turquoise waters.
After soaking in the scenery and glistening waters, it is time to head to Schoinousa. This tiny island off the south coast of Naxos is only 9 square kilometers in size, meaning you can walk around it in less than one hour. Schoinousa is the kind of place where time sits still, and there is no need to check the clock.
If you prefer to spend your days by the beach and dining on local delicacies, this is a great place. Options abound, including Piso Ammos, Livadi, Almyros, and Tsigouri. The island is frequented by celebrities and other well-known personalities that wish to relax while staying away from the crowds of nearby Naxos.
> Sailing in Koufonisia – important information:
- Narrow entrance with limited berths for visiting yachts
- The harbor of Parianos provides good shelter
- You can walk to the village (about 15-20min)
> Sailing in Koufonisia – don’t miss:
- Excellent beaches and coves everywhere you turn
- Most visitors spend time in or around the water
- Visit Glaronissi Islet
Yacht Charter Day 7 – Koufonisia to Ios
Ios rose to fame as one of the top Greek party islands for local and international visitors. While that is still very much the case, Ios has a lot more to offer, including beautiful beaches and, according to the legend, more than 365 churches, one for each day of the year.
If visiting cultural and religious sights is not on your list of top things to do, Ios will surprise you with its charming Chora – a maze of blue painted windows and doors – stunning beaches and deserted coves. Mylopotas Beach is the most well-known spot on the island, with a long stretch of golden sand, water sport rental services, and a scuba diving center for those who prefer to stay active.
> Sailing in Ios – important information:
- The Port of Ios known as Yialos is the only port
- Excellent shelter but busy and crowded during peak summer period
- Other anchorages include Milopotamos Bay, Koumbaras Bay and Manganari Bay
> Sailing in Ios – don’t miss:
- Swim at Mylopotas and Manganari beach
- Explore the charming Chora village
- Hike to Gremiotissa church
Yacht Charter Day 8 – Ios to Santorini
It is always hard to say goodbye, but returning to Santorini makes the end of this yacht charter trip a little bit easier to handle.
The complex of the Cyclades includes more than 220 islands and uninhabited islets, so it doesn’t matter how many times you visit; there is always something new to discover.
From here, you can continue your Greek holiday in Santorini or extend your sailing trip with another charter. Don’t forget to check out our itineraries for the Ionian and Dodecanese, where you can discover new and unexpected destinations for your Greek holiday.