14-Day Sailing from Athens
| Day | Port | NM |
|---|---|---|
| 1 Saturday | Lavrion Olympic Marina, Athens – Kythnos | 23 |
| 2 Sunday | Serifos | 24 |
| 3 Monday | Sifnos | 20 |
| 4 Tuesday | Kimolos (Psaronisi) | 10 |
| 5 Wednesday | Milos (Kleftiko) | 20 |
| 6 Thursday | Santorini | 53 |
| 7 Friday | Ios | 25 |
| 8 Saturday | Koufonisia | 25 |
| 9 Sunday | Naxos | 22 |
| 10 Monday | Paros | 12 |
| 11 Tuesday | Mykonos | 22 |
| 12 Wednesday | Syros | 18 |
| 13 Thursday | Kea | 38 |
| 14 Friday | Lavrion Olympic Marina, Athens | 15 |
| Total NM | Check out at 09:00h | 312 |
The trip destinations
Day 1 – Saturday | Lavrion Olympic Marina, Athens – Kythnos – 23 NM
Your journey begins from Lavrion Olympic Marina, one of the most strategic departure points for the Cyclades. After embarkation and check-in, the route opens directly toward Kythnos, offering an elegant first passage into the Aegean.
Kythnos welcomes guests with understated Cycladic beauty, quiet bays, and authentic island character. Its calm anchorages and relaxed atmosphere make it an ideal first stop, allowing everyone to settle into the rhythm of life onboard.
Highlights
- Smooth departure from Lavrion
- First Cycladic island experience
- Relaxed anchorage and swimming waters
Insider Tip
Complete provisioning early in Lavrion, so you can depart comfortably and enjoy your first evening in Kythnos without rushing.
Day 2 – Sunday | Serifos – 24 NM
Sailing to Serifos introduces a more dramatic and authentic side of the Cyclades. The island is known for its rugged landscapes, golden beaches, and striking hilltop Chora overlooking the Aegean.
Serifos offers a refined simplicity that feels untouched and genuine. Guests can enjoy swimming in clear waters, explore the harbor of Livadi, or visit Chora for panoramic views and a beautifully atmospheric evening.
Highlights
- Authentic Cycladic atmosphere
- Hilltop Chora with panoramic views
- Beautiful beaches and clear waters
Insider Tip
Visit Chora before sunset; the views over the island and sea are among the most memorable in the western Cyclades.
Day 3 – Monday | Sifnos – 20 NM
Sifnos is one of the most elegant islands of the Cyclades, celebrated for its refined villages, whitewashed architecture, and exceptional gastronomy. The sail from Serifos is comfortable and rewarding, leading to an island where tradition and style coexist beautifully.
Guests can explore Apollonia, Kastro, or the charming seaside villages, each offering a different expression of Cycladic charm. Dinner ashore is a highlight, as Sifnos is considered one of the finest culinary destinations in the Aegean.
Highlights
- Elegant villages and Cycladic architecture
- Renowned local gastronomy
- Refined yet authentic island atmosphere
Insider Tip
Reserve dinner in advance during high season, as Sifnos’ best restaurants are highly sought after.
Day 4 – Tuesday | Kimolos (Psaronisi) – 10 NM
A short sail brings you to Kimolos and the nearby waters of Psaronisi, offering a quieter and more secluded Cycladic experience. The island is known for its soft colors, peaceful atmosphere, and volcanic coastline.
This day is ideal for swimming, relaxation, and enjoying the simplicity of a less crowded island. Kimolos has a gentle charm, with traditional streets, calm bays, and a sense of authenticity that feels increasingly rare in the Cyclades.
Highlights
- Short and relaxed sailing day
- Peaceful volcanic scenery
- Quiet swimming stops near Psaronisi
Insider Tip
Use the shorter distance to enjoy a longer swim stop before heading ashore for a relaxed evening.
Day 5 – Wednesday | Milos (Kleftiko) – 20 NM
Milos is one of the most visually impressive islands in Greece, and Kleftiko is its most iconic natural landmark. The sail brings you to a coastline shaped by volcanic rock, sea caves, and extraordinary turquoise waters.
Kleftiko offers an unforgettable swimming and exploration experience, with dramatic white formations rising from the sea. This is a day designed around nature, photography, snorkeling, and the pure beauty of the Aegean.
Highlights
- Iconic volcanic scenery of Milos
- Swimming and snorkeling at Kleftiko
- Sea caves and dramatic rock formations
Insider Tip
Arrive early at Kleftiko for calmer conditions and fewer boats, especially during peak season.
Day 6 – Thursday | Santorini – 53 NM
A longer and spectacular passage brings you to Santorini, one of the most iconic destinations in the world. The approach by yacht is unforgettable, as the volcanic caldera rises dramatically from the sea.
Santorini combines extraordinary scenery with refined hospitality, elegant dining, and world-famous sunset views. Whether admiring the cliffs from onboard or exploring the island ashore, this stop adds a truly cinematic dimension to the itinerary.
Highlights
- Dramatic arrival into the caldera
- World-famous volcanic scenery
- Exceptional sunset atmosphere
Insider Tip
This is a long and weather-sensitive passage, so departure timing should be carefully planned with the skipper.
Day 7 – Friday | Ios – 25 NM
Leaving Santorini, the route continues to Ios, an island that combines beautiful beaches, whitewashed architecture, and a lively yet stylish summer atmosphere. The sail offers a refreshing change of pace after the dramatic scenery of the caldera.
Ios is ideal for guests who enjoy both relaxation and energy. During the day, its beaches provide excellent swimming, while the evening can be spent exploring Chora, with its charming alleys, restaurants, and vibrant island mood.
Highlights
- Beautiful beaches and clear waters
- Charming Cycladic Chora
- Lively evening atmosphere
Insider Tip
For a quieter experience, enjoy dinner early in Chora before the island’s nightlife becomes more energetic.
Day 8 – Saturday | Koufonisia – 25 NM
Koufonisia offers one of the most relaxed and enchanting atmospheres in the Cyclades. Known for its luminous turquoise waters, sandy coves, and barefoot elegance, it is a destination that feels intimate and effortlessly beautiful.
The island is perfect for swimming, paddleboarding, and slow exploration by tender. Its small scale and refined simplicity make it a favorite stop for guests seeking natural beauty without excess.
Highlights
- Turquoise waters and sandy coves
- Relaxed barefoot island atmosphere
- Excellent swimming and tender exploration
Insider Tip
Explore the coastline by tender if conditions allow; some of the most beautiful spots are best approached from the sea.
Day 9 – Sunday | Naxos – 22 NM
Naxos brings a richer and more varied Cycladic experience, combining impressive landscapes, long beaches, historic monuments, and authentic local culture. The sail from Koufonisia is scenic and rewarding.
The island’s harbor town offers a lively waterfront, traditional tavernas, and the famous Portara, one of the most recognizable landmarks in the Cyclades. Naxos is also known for excellent local products and a warm, welcoming atmosphere.
Highlights
- Arrival at one of the largest Cycladic islands
- Portara and historic harbor town
- Local cuisine and authentic island life
Insider Tip
Visit the Portara at sunset for one of the most beautiful views of the itinerary.
Day 10 – Monday | Paros – 12 NM
A short sail brings you to Paros, one of the most elegant and versatile islands of the Cyclades. The island offers a refined balance of traditional villages, golden beaches, stylish restaurants, and vibrant harbor life.
Naoussa is especially atmospheric, with its old fishing harbor, boutique shops, and sophisticated dining scene. Paros is ideal for guests who want both authentic Cycladic charm and a polished island lifestyle.
Highlights
- Short and comfortable sailing day
- Elegant atmosphere in Naoussa
- Beaches, villages, and refined dining
Insider Tip
Reserve dinner in Naoussa during high season, as the best waterfront restaurants fill quickly.
Day 11 – Tuesday | Mykonos – 22 NM
Mykonos introduces a cosmopolitan and glamorous energy to the itinerary. Known for its iconic whitewashed town, luxury beach venues, boutique shopping, and vibrant nightlife, it is one of the most famous islands in the Mediterranean.
Beyond its social scene, Mykonos also offers beautiful bays and classic Cycladic scenery. Guests can choose between a lively evening ashore or a more relaxed experience onboard, depending on the mood of the charter.
Highlights
- Iconic Cycladic architecture
- Luxury dining, shopping, and nightlife
- Cosmopolitan island atmosphere
Insider Tip
Plan reservations in advance for beach clubs, restaurants, and transfers, especially in July and August.
Day 12 – Wednesday | Syros – 18 NM
Syros offers a sophisticated contrast to Mykonos, with Ermoupoli standing as one of the most elegant towns in the Aegean. Its neoclassical architecture, marble squares, and cultural atmosphere give the island a distinctly refined identity.
The harbor arrival is impressive, with pastel buildings rising amphitheatrically above the sea. Guests can enjoy elegant cafés, boutique shops, and a quieter, more cultured evening ashore.
Highlights
- Neoclassical elegance of Ermoupoli
- Cultural and architectural interest
- Refined evening atmosphere
Insider Tip
Walk through Miaouli Square and the Vaporia district in the evening for the most elegant side of Syros.
Day 13 – Thursday | Kea – 38 NM
The route begins its return toward Athens with a longer passage to Kea, also known as Tzia. The island is loved for its earthy landscapes, discreet elegance, and relaxed atmosphere close to the mainland.
Kea offers a calm and authentic final island stop, with beautiful bays, traditional villages, and a sophisticated but low-key character. It is the perfect place to slow down before the final return to Lavrion.
Highlights
- Rewarding return passage
- Relaxed final Cycladic island stop
- Elegant simplicity and scenic bays
Insider Tip
Enjoy a quiet dinner in Vourkari, one of Kea’s most charming waterfront areas.
Day 14 – Friday | Lavrion Olympic Marina, Athens – 15 NM
The final sailing day brings the yacht back to Lavrion Olympic Marina, completing a rich and dynamic Cyclades itinerary. The short return allows time for a final swim, a relaxed breakfast onboard, or a calm morning under sail.
Upon arrival, guests complete refueling and check-out procedures while reflecting on a journey that included volcanic landscapes, cosmopolitan islands, hidden bays, and some of the most iconic destinations in Greece.
Highlights
- Short return sail to Lavrion
- Final swim opportunity
- Completion of a full Cyclades route
Insider Tip
Return with enough time for refueling and marina procedures, as Friday arrivals can be busy during the charter season.