7-Day Itinerary to the Most Renowned Cyclades Islands aboard the Walkabout 43
Destination: Cyclades, Greece | Duration: 7 days/7 nights | Embarkation: Santorini | Disembarkation: Milos | Islands: Santorini, Folegandros, Polyaigos, Kimolos, Milos | Formula: Exclusive charter with skipper or Cabin charter | Highlights: Sporty sailing, coastal navigation, anchorages in secluded bays, authentic villages.
Price and Available Dates: AUGUST 1, 2026 – SEPTEMBER 5, 2026 or check the 2026 cruise schedule.
Included Services Full details: Walkabout Charter Rental Terms
⭐ Rating: 4.9/5 (based on 47 reviews on Google, TripAdvisor and Facebook)
Complete Guide:
- 7-Day Itinerary to the Most Renowned Cyclades Islands aboard the Walkabout 43
- Day-by-Day Itinerary
- FAQ
- Why Choose This Vacation
- How to Book
- Request availability and prices
Day-by-Day Itinerary
Saturday – Akrotiri, Santorini: Embarkation
Embarkation port: (36° 20.8065′ N, 025° 23.4442′ E) | Embarkation: 6:00 PM | Connections: Santorini Airport – 14 km from Akrotiri (25 minutes by taxi)
Embarkation at 6:00 PM, we will be anchored off Akrotiri. Settling into the cabins of the Walkabout 43, safety briefing, presentation of the itinerary. Then we move to the small lava island inside Santorini’s caldera. Dinner on board.
Sunday – Folegandros
Arrival: Folegandros (36° 37.6165′ N, 024° 53.1771′ E) | Distance: 30 nautical miles | Sailing time: 4 hours | Don’t miss: Exploring Chora and Kastro, sunset at Panagia Church | Activities:
The day begins with an unforgettable sail inside Santorini’s caldera. A unique experience sailing inside a volcano with views of the villages of Fira and Oia, hundreds of white buildings on black terrain.
Then a beautiful and long upwind offshore passage will allow us to reach Agkali, a splendid bay on the south coast of Folegandros.
Lunch on board and free afternoon. The evening program includes a long uphill walk to reach the Panagia church in time to admire one of the most spectacular sunsets in the Cyclades.
Then we descend to Chora for dinner at a taverna and to explore the dozens of alleys and the Venetian Kastro.
Then a long walk under the stars (or a taxi ride) will allow us to reach the boat for a well-deserved rest.
Monday – Firiplaka, Milos
Arrival: Firiplaka (36° 40.1825′ N, 024° 26.7376′ E) | Distance: 22 nautical miles | Sailing time: 3-4 hours
Another intense and fun broad reach-to-beam reach sail in a usually windy area allows us to reach a famous beach on the south coast of Milos. Firiplaka beach is famous for its chromatic contrast between turquoise waters and imposing volcanic cliffs made of variegated chalk in shades of red, green, pink and yellow.
We anchor in 3 meters depth on white sand, the water is so transparent that the boat seems to float in the air! Relaxing afternoon with long swims and walks on the beach.
Dinner on board.
Tuesday – Kleftiko and Kalamos, South Coast of Milos
Arrival: Kalamos (36° 39.9027′ N, 024° 27.7841′ E) | Distance: 12 nautical miles | Sailing time: 2 hours
Early wake-up today. Breakfast and then we depart for a short sail along the south coast of Milos. The goal is to arrive at Kleftiko before the boats bringing tourists from Milos.
Kleftiko is probably the most iconic place in Milos, a labyrinth of imposing white volcanic rocks emerging from the turquoise sea. It was historically used as a refuge by pirates, from which it takes its name.
After anchoring, the program includes a long dinghy tour to explore the Caves, some allow you to enter the rock for dozens and dozens of meters with a fantastic atmosphere and unforgettable light effects.
Then we head back along the south coast of Milos to arrive at another beach that’s a wonder of nature, Kalamos, where the volcanic and wild nature meets crystal-clear water and an untouched sea.
The beach is characterized by pebbles mixed with sand and extremely clear waters and the spectacular sand cascades, a fascinating natural phenomenon where on windy days the sand slides down the high rocks like a waterfall, creating a unique and evocative landscape.
It’s an ideal destination for those seeking solitude, as it’s difficult to reach by land. The afternoon passes admiring the scenery, swimming and snorkeling, and you can visit the Thermal Springs. The Kalamos area is known for its geothermal activity. Along the coast and in some inland areas, you can find hot water springs of volcanic origin, testimony to the “living” nature of Milos.
Dinner on board.
Wednesday – Polyaigos, The Island of Goats
Arrival: Polyaigos (36° 45.0097′ N, 024° 39.6730′ E) | Distance: 10 nautical miles | Sailing time: 2 hours
Today a short but intense sail takes us to Polyaigos.
Polyaigos is an authentic natural paradise and is considered one of the most spectacular and pristine islands in the entire Aegean, being the largest uninhabited island in the Cyclades. The sea is, as usual in these parts, crystal clear, and the rocky formations along the coast are multicolored. The erosion from wind and sea has created bizarre and spectacular shapes that are breathtaking.
Dinner on board and evening stargazing. Here we are far from inhabited centers and the night sky shows off all its splendor.
Thursday – Kimolos, The Beautiful Chora
Arrival: Kimolos (36° 47.1731′ N, 024° 35.0012′ E) | Distance: 5 nautical miles | Sailing time: 1 hour
We move slowly sailing along the fantastic coast of Polyaigos, then we anchor in one of the most beautiful bays in the Cyclades, a true natural pool with crystal-clear waters and white sand, sheltered from the Meltemi. Here an afternoon of pure relaxation awaits us: refreshing swims and time to enjoy the unspoiled beauty of the island.
In the afternoon, we set sail for nearby Kimolos, an authentic and welcoming island, where it feels like diving into the most traditional Greece. Once we arrive, we’ll dedicate ourselves to visiting the picturesque village of Chorio, with its white houses, narrow alleys and the peaceful atmosphere that invites you to slow down and enjoy every detail.
The evening ends with dinner at a typical local taverna, where we’ll savor the traditional and genuine dishes of Greek cuisine, immersed in the pleasant and relaxed atmosphere of Kimolos.
Friday – Adamas, Milos
Arrival: Adamas (36° 43.5045′ N, 024° 26.9172′ E) | Distance: 14 nautical miles | Sailing time: 2-3 hours
The day’s program depends on the wind. If calm, we depart in the morning for Sarakiniko, a natural spectacle of white rocks sculpted by wind and sea, creating a unique lunar landscape, with turquoise waters ideal for a swim.
Otherwise, we stop at the beaches south of Kimolos for lunch and then in the afternoon, we’ll head towards Adamas, a picturesque and lively port, the main maritime center of Milos. Adamas is famous for its welcoming atmosphere and animated waterfront, where you’ll find bars, cafés and restaurants overlooking the harbor waters. Here we prepare for a special evening, climbing up to the castle and monastery to admire the sunset from an exceptional viewpoint, enjoying breathtaking views over the entire island and the Aegean.
The day concludes with a visit to Plaka, the chora of Milos, located on a hill. Plaka is an enchanting and authentic village, with cobblestone streets, white houses and flowered balconies. Its traditional tavernas are perfect for tasting local flavors, while Plaka’s evening atmosphere, with soft lighting and views over the Aegean, makes dinner a memorable experience, immersed in the beauty and authentic charm of the Cyclades.
Saturday – Adamas
Disembarkation port: Adamas (36° 43.5045′ N, 024° 26.9172′ E) | Disembarkation: 9:00 AM | Connections: The port where ferries dock is located one hundred meters from where we disembark. The airport is 5 km away (10 minutes by taxi).
Last breakfast on board. Disembarkation procedures.
The itinerary stops are subject to changes due to weather conditions or other unforeseen circumstances that prevent or make navigation uncomfortable to reach them or for mooring. Any itinerary modifications are made exclusively to ensure better vacation organization and to ensure the safety and comfort of our guests.
FAQ
Is it suitable for those without sailing experience?
Absolutely yes. This area of the Aegean can present challenging sea passages due to the Meltemi, which can blow with intensity. If you have no sailing experience, the experienced skippers will put you at ease and take complete care of managing the boat. The distances between islands are limited (never more than 3 hours of sailing) and there are numerous protected bays with calm waters where you can anchor in shelter. The Walkabout 43 is stable and comfortable. Experienced skippers ensure safety and share their passion for sailing by teaching the basics.
When does the Meltemi blow?
The Meltemi in the Cyclades is generally sustained. It blows mainly July-August with intensity 5-6 Beaufort, making sailing sporty and fun. June and September typically have lighter winds.
Can the itinerary be modified?
Yes, the itinerary is indicative. Skippers adapt it based on weather, group preferences and opportunities. The only constraint is embarkation in Santorini on Saturday and disembarkation in Milos the following Saturday. You can spend more time on certain islands, discover alternative bays, add unplanned stops.
Consult the complete sailing cruise FAQ or contact us directly.
Why Choose This Vacation
Why Choose This Vacation
The Most Renowned Cyclades Islands + Thrilling Sailing + Unspoiled Nature
Ideal itinerary for those who want to visit the most renowned islands of the Cyclades while discovering hidden bays away from mass tourism. Experienced sailors will appreciate the sailing boat’s qualities with a perfect balance between fast and sporty sailing and anchorages in protected yet crystal-clear waters.
Walkabout 43 and Food & Wine
The Walkabout 43 is the perfect boat for this itinerary: comfortable for life on board, safe even with the Meltemi, fun to sail. Three double cabins and 2 single berths in the dinette, two bathrooms, spacious cockpit with teak swim platform to enjoy the sea.
Your skippers will prepare traditional Mediterranean dishes with local ingredients purchased on the islands.
Skippers with deep knowledge of the Cyclades, the best hidden bays, authentic tavernas frequented by locals, and the area’s marine weather conditions.
How to Book
- Personalized Quote: Receive within 24h: detailed quote, confirmed availability, contractual conditions.
- Confirmation: Pay the deposit to lock in the booking.
- Book flights: Walkabout Charter provides info for flights, ferries and transfers.
- Trip Preparation: Receive recommended equipment list, communicate special dietary needs.
- Embarkation! Your Sporades adventure begins!
The Most Spectacular Islands of the Aegean. Walkabout Charter Takes You There!