14-Day Sailing from Rhodes
| Day | Port | NM |
|---|---|---|
| Saturday | Rhodes | – |
| Sunday | Symi | 23 |
| Monday | Nisyros | 32 |
| Tuesday | Kos | 21 |
| Wednesday | Leros | 27 |
| Thursday | Patmos | 20 |
| Friday | Lipsoi | 10 |
| Saturday | Levithia | 23 |
| Sunday | Kalymnos | 27 |
| Monday | Astypalea | 39 |
| Tuesday | Tilos | 53 |
| Wednesday | Chalki | 14 |
| Thursday | Rhodes (Lindos) | 49 |
| Friday | Rhodes (Marina) | 23 |
| Total NM | Check out at 09:00h | 361 |
The trip destinations
Day 1 – Saturday | Rhodes – Embarkation
Your charter begins from Rhodes, one of the Dodecanese’ most important yachting hubs and an ideal starting point for exploring the southeastern Aegean. Following embarkation and check-in, settle onboard, familiarize yourself with your yacht, and enjoy the vibrant atmosphere of Rhodes Marina.
If time allows, explore the UNESCO-listed Medieval City of Rhodes, where impressive fortifications, cobbled streets, and waterfront cafés create the perfect introduction to your sailing adventure.
Highlights
- Embarkation at Rhodes Marina
- Explore the Medieval City of Rhodes
- UNESCO World Heritage landmarks
- First evening onboard
Insider Tip
Arriving in Rhodes a day before embarkation allows you to explore the Old Town at a relaxed pace before your charter begins.
Day 2 – Sunday | Symi – 23 NM
A comfortable sail brings you to Symi, one of the most elegant islands in the Dodecanese. The approach by yacht is unforgettable, with colourful neoclassical mansions cascading down the hills surrounding the famous harbour.
Spend the afternoon exploring Gialos Harbour, enjoying waterfront dining, browsing local boutiques, or simply relaxing while admiring the island’s unique architecture.
Highlights
- Spectacular arrival into Symi Harbour
- Colourful neoclassical architecture
- Picturesque waterfront promenade
- Elegant dining by the sea
Insider Tip
Walk above the harbour in the evening for panoramic views and one of the best photo opportunities in the Dodecanese.
Day 3 – Monday | Nisyros – 32 NM
Today’s passage takes you to Nisyros, a fascinating volcanic island where dramatic landscapes meet authentic Greek island traditions. The famous Stefanos crater offers a unique opportunity to explore one of Greece’s most impressive natural formations.
Discover the charming village of Mandraki, with its whitewashed streets, traditional tavernas, and relaxed island atmosphere.
Highlights
- Visit Stefanos volcanic crater
- Explore Mandraki village
- Unique volcanic landscape
- Authentic island experience
Insider Tip
Visit the crater early in the day when temperatures are cooler and the landscape is at its most impressive.
Day 4 – Tuesday | Kos – 21 NM
Your journey continues to Kos, one of the largest and most vibrant islands of the Dodecanese. Combining ancient history, beautiful beaches, and lively waterfront areas, Kos offers a perfect balance between culture and relaxation.
Explore Kos Town, visit the Castle of the Knights, discover ancient landmarks, or enjoy the island’s excellent restaurants and cafés.
Highlights
- Historic Kos Town
- Castle of the Knights
- Ancient archaeological sites
- Vibrant marina atmosphere
Insider Tip
Explore Kos by bicycle, as the island offers one of the most enjoyable cycling networks in Greece.
Day 5 – Wednesday | Leros – 27 NM
Sail north to Leros, an island known for its sheltered bays, relaxed atmosphere, and distinctive Italian-influenced architecture. Less crowded than many neighbouring islands, Leros offers an authentic and peaceful sailing experience.
Explore Agia Marina, visit Lakki’s unique architecture, or enjoy the island’s charming waterfront tavernas.
Highlights
- Natural sheltered harbours
- Italian architectural influences
- Agia Marina waterfront
- Authentic island character
Insider Tip
Visit the Castle of Panteli in the late afternoon for breathtaking views across Leros and the surrounding islands.
Day 6 – Thursday | Patmos – 20 NM
Today’s destination is Patmos, one of Greece’s most atmospheric islands and an important spiritual destination. Home to the UNESCO-listed Monastery of Saint John and the Cave of the Apocalypse, Patmos combines history, culture, and natural beauty.
Explore the elegant streets of Chora, relax in Skala Harbour, or discover the island’s beautiful coastal scenery.
Highlights
- UNESCO World Heritage landmarks
- Monastery of Saint John
- Cave of the Apocalypse
- Charming Skala Harbour
Insider Tip
Visit Chora before sunset to enjoy spectacular views over the island and the Aegean Sea.
Day 7 – Friday | Lipsoi – 10 NM
A short sail brings you to Lipsoi, a peaceful island known for authentic Greek island life, crystal-clear waters, and a wonderfully relaxed atmosphere.
Enjoy swimming in beautiful bays, exploring the village, and dining at traditional waterfront tavernas serving fresh local cuisine.
Highlights
- Authentic island atmosphere
- Crystal-clear swimming bays
- Traditional waterfront tavernas
- Peaceful harbour setting
Insider Tip
Stay for the evening and experience Lipsoi after the day visitors leave, when the island becomes especially peaceful.
Day 8 – Saturday | Levitha – 23 NM
A rewarding sail takes you to Skyros, one of the most unique islands of the Aegean. Arriving at the organized port of Linaria reveals a distinct character blending culture with rugged landscapes.
Highlights
An exciting offshore passage across the open Aegean Sea.
A welcoming, well-organized, and traditional harbor experience.
Striking contrasts between rugged rocks and authentic villages.
Insider Tip
Take some time to explore the island beyond the port area for a deeper cultural experience.
Day 9 – Sunday | Kalymnos – 27 NM
Your next destination is Kalymnos, an island famous for its centuries-old sponge-diving tradition, dramatic coastline, and authentic maritime character. Today, Kalymnos is also internationally recognised as one of the world’s premier rock-climbing destinations.
Explore the lively harbour, discover local sponge workshops, or enjoy traditional cuisine overlooking the sea while experiencing the island’s unique atmosphere.
Highlights
- Historic sponge-diving heritage
- Vibrant harbour atmosphere
- Traditional waterfront tavernas
- Authentic island culture
Insider Tip
Visit a traditional sponge workshop to discover the craft that shaped Kalymnos’ identity for generations.
Day 10 – Monday | Astypalea – 39 NM
Today’s longer passage rewards you with arrival at Astypalea, known as the “Butterfly of the Aegean” due to its distinctive shape. Combining Cycladic elegance with Dodecanese traditions, Astypalea is one of the region’s most beautiful and atmospheric islands.
The impressive Venetian Castle overlooking the whitewashed Chora creates one of the most spectacular views in the Aegean, especially during sunset.
Highlights
- Whitewashed Chora
- Venetian Castle
- Traditional island architecture
- Panoramic Aegean views
Insider Tip
Climb to the castle shortly before sunset for breathtaking views over the harbour and surrounding islands.
Day 11 – Tuesday | Tilos – 53 NM
Today’s passage brings you back towards the western Dodecanese and the peaceful island of Tilos. Known for its untouched landscapes, authentic villages, and environmentally conscious way of life, Tilos offers the perfect opportunity to slow down and reconnect with nature.
Enjoy swimming in beautiful bays before spending a relaxing evening in Livadia Harbour, where traditional hospitality and local charm remain central to island life.
Highlights
- Peaceful natural surroundings
- Traditional harbour of Livadia
- Beautiful swimming bays
- Authentic island atmosphere
Insider Tip
Tilos is an excellent location for evening walks and stargazing thanks to its peaceful atmosphere and limited light pollution.
Day 12 – Wednesday | Chalki – 14 NM
A short and enjoyable sail brings you to Chalki, one of the Dodecanese’ most elegant hidden gems. Famous for its colourful neoclassical waterfront and relaxed pace of life, Chalki offers a beautifully authentic island experience.
Spend the day exploring the picturesque harbour, swimming in nearby bays, or enjoying the peaceful rhythm of this charming island community.
Highlights
- Elegant harbour setting
- Colourful neoclassical architecture
- Relaxed island atmosphere
- Traditional waterfront dining
Insider Tip
Enjoy dinner by the harbour during sunset, when Chalki’s colourful buildings create a magical atmosphere.
Day 13 – Thursday | Lindos (Rhodes) – 49 NM
Your final destination before returning to Rhodes Marina is Lindos, one of the most iconic villages in Greece. Dominated by its ancient Acropolis and surrounded by stunning coastal scenery, Lindos perfectly combines history, architecture, and natural beauty.
Explore the narrow whitewashed streets, swim beneath the Acropolis, or enjoy panoramic views across the Aegean from this unforgettable destination.
Highlights
- Ancient Acropolis of Lindos
- Traditional whitewashed village
- Crystal-clear swimming waters
- Spectacular coastal views
Insider Tip
Visit the Acropolis later in the afternoon when temperatures are cooler and the views over the bay are at their most impressive.
Day 14 – Friday | Lindos – Rhodes Marina – 23 NM
Your final sailing day returns you to Rhodes Marina, completing an unforgettable two-week journey through the Dodecanese. Enjoy one last opportunity to experience the open waters, with a possible final swim stop depending on weather conditions.
After returning to the marina, enjoy your farewell evening in Rhodes, reflecting on a remarkable adventure filled with volcanic landscapes, historic harbours, secluded anchorages, and authentic Greek island experiences.
Highlights
- Final sail through the Dodecanese
- Return to Rhodes Marina
- Farewell evening in Rhodes
- End of an unforgettable two-week voyage
Insider Tip
Complete refuelling and final onboard preparations before your last evening, allowing for a smooth and stress-free disembarkation the following morning.