7-day Itinerary between Samos, Patmos and Kalymnos aboard the Walkabout 43
Navigate the Dodecanese with Walkabout Charter: 7 days of sailing between Samos and Kos crossing the small islands of Agathonisi, Arki, Patmos, Lipsi, Leros and Kalymnos. An itinerary combining pleasant sailing, remote islands and authentic Dodecanese traditions plus fascinating UNESCO sites and traditional villages. Oceangoing Walkabout 43 yacht for sporty sailing and Mediterranean cuisine prepared by your skippers onboard for an exciting sailing experience in the heart of the Aegean.
Ideal for: Those who want to discover the most authentic Dodecanese, historical-religious sites (Patmos, Monastery of Saint John in Patmos UNESCO heritage, one of the most important in Orthodox Christianity) and remote islands like Arki and Agathonisi, far from mass tourism. Those seeking a balanced mix of sailing, culture and relaxation without challenging passages. Suitable for experienced sailors seeking a relaxed North Aegean itinerary, but also for those without sailing experience.
Destination: Dodecanese, Greece | Duration: 7 days/7 nights | Embarkation: Pythagorio (Samos) | Disembarkation: Kardamena (Kos) | Formula: Exclusive charter with skipper or Cabin charter.
Price and Available Dates: July 11, 2026 or check the cruise schedule.
Included Services Full details: Walkabout Charter Charter Conditions
⭐ Rating: 4.9/5 (based on 47 Google and TripAdvisor reviews)
Complete Guide
- 7-day Itinerary between Samos, Patmos and Kalymnos aboard the Walkabout 43
- Day-by-Day Itinerary
- Why This Itinerary
- FAQ
- How to Book
- Request availability and prices
Day-by-Day Itinerary
Day 1 – Pythagorio: Embarkation on Pythagoras’ Island / Agathonisi
Departure port: Pythagorio, Samos (37.6898°N, 26.9421°E) | Arrival: Agathonisi (37.4558°N, 26.9641°E) | Distance: 18 nautical miles (33 km) | Sailing time: 1 hour / 3 hours | Don’t miss: Picturesque port of Pythagorio, Eupalinos tunnel
Embarkation at 6:00 PM at Samos marina. Samos is the birthplace of mathematician Pythagoras. Those arriving in Samos before embarkation time can visit the ancient port, Eupalinos tunnel (6th century BC), Temple of Hera remains. Settling into Walkabout 43 cabins, safety briefing and itinerary presentation. Sailing to Agathonisi, small remote Dodecanese island with only 200 inhabitants. One of Greece’s least touristy islands, perfect to start the itinerary in tranquility. Anchorage in protected bay. Welcome aperitif and dinner onboard. Overnight at anchor.
Day 2 – Arki: The Fishermen’s Island
Arrival: Arki (37.3639°N, 26.7467°E) | Distance: 12 nautical miles (22 km) | Sailing time: 2-2.5 hours | Don’t miss: Tiny village with 50 inhabitants, bays with Caribbean waters | Activities: Relaxed sailing, snorkeling, authentic local life
Short sail to Arki, one of the smallest and most authentic islands of the Dodecanese. Only 50 permanent inhabitants, mainly fishermen. The island is practically unknown to mass tourism – here time seems to have stopped. Anchorage among the islets of the small archipelago. The entire “village” consists of a few white houses, 2-3 family-run tavernas and a small church. Afternoon dedicated to island exploration on foot (walkable in 1 hour), snorkeling in deserted coves accessible only on foot or by tender, total relaxation. Evening: dinner onboard prepared by your skippers. Overnight in protected anchorage.
Day 3 – Patmos: The Sacred Island
Arrival: Skala, Patmos (37.3318°N, 26.5521°E) | Distance: 10 nautical miles (19 km) | Sailing time: 1.5-2 hours | Don’t miss: Monastery of St. John UNESCO, Cave of the Apocalypse, medieval Chora | Activities: Sailing, monastery visit, Chora exploration
Sailing to Patmos, the sacred island of the Dodecanese where Saint John wrote the Apocalypse. Arrival at Skala port, dominated by the fortified monastery of Saint John the Theologian (11th century) from above. Mooring in port or anchorage in bay. Afternoon dedicated to visiting UNESCO sites (reachable by local bus or taxi or with a beautiful panoramic walk):
Monastery of Saint John the Theologian: Fortified monastic complex UNESCO heritage, one of the most important in Orthodox Christianity. Library with ancient manuscripts, precious Byzantine icons, ecclesiastical treasury, magnificent frescoes. Imposing architecture with fortified walls.
Cave of the Apocalypse: Where according to tradition Saint John received visions and wrote the Apocalypse in 95 AD. Place of intense spiritual pilgrimage.
Chora of Patmos: Medieval village perched around the monastery, with labyrinthine alleys, traditional whitewashed houses, Cycladic architecture. One of the most beautiful and best-preserved villages in Greece.
Evening: dinner at traditional taverna in Skala. Overnight in port or anchorage.
Day 4 – Lipsi: The Quiet Island
Arrival: Lipsi (37.2797°N, 26.7690°E) | Distance: 18 nautical miles (33 km) | Sailing time: 3-3.5 hours | Don’t miss: Sandy beaches, traditional villages, relaxed atmosphere | Activities: Sailing, swimming, relaxation, village exploration
Sailing to Lipsi, small quiet island with 700 inhabitants. Relaxed and authentic atmosphere, far from mass tourism. Lipsi is famous for its clean sandy beaches and crystal-clear waters – among the most beautiful in the Dodecanese. Anchorage near the main port or in one of the protected bays. Afternoon dedicated to swimming at the island’s most beautiful beaches (reachable by tender or on foot), snorkeling, total relaxation. Walk in the main village: traditional white houses, Orthodox churches, quiet local life. Evening: dinner at local taverna or onboard.
Day 5 – Leros: The Island with Italian Flavor
Arrival: Panteli, Leros (37° 8.689’N, 26° 51.751’E) | Distance: 10 nautical miles | Sailing time: 2 hours | Don’t miss: Capital Lakki with Italian rationalist architecture | Activities: Downwind sailing, discovering Italian past
Leros is a unique island in the Dodecanese for its Italian heritage. Between 1912 and 1943, the Italians transformed the island into a strategic naval base, building the city of Lakki (Porto Lago) according to rationalist architecture principles. Today Lakki remains one of the best-preserved examples of Italian urban planning from the fascist period, with its monumental buildings, wide tree-lined streets and rationalist squares creating an almost surreal atmosphere.
A stop in a quiet bay then we anchor at Panteli, a traditional fishing village dominated by the Venetian castle of Panagia. From here you can reach Lakki to admire Cinema Paradiso, the Municipal Market and the Governor’s Palace, or discover hidden small bays like Vromolithos and Alinda. In the evening, we’ll dine onboard with views of the windmills and illuminated castle.
Day 6 – Kalymnos: The Sponge Island
Arrival: Pothia, Kalymnos (36.9477°N, 26.9820°E) | Distance: 15 nautical miles | Sailing time: 2 hours | Don’t miss: Colorful capital Pothia, sponge fishing tradition, climbing, maritime museum | Activities: Longer fun downwind sailing, city exploration, local culture
Longest sail of the itinerary to Kalymnos, the fourth largest island in the Dodecanese. Famous worldwide for its millennia-old tradition of sponge diving and for being an international sport climbing destination (spectacular crags). Arrival at Pothia, island capital with colorful houses cascading down the hillside. Mooring in port. Afternoon and evening dedicated to exploration: maritime museum with sponge diving history, fishermen’s quarter, natural sponge shops (typical souvenir), local market. Evening: dinner at local taverna with Kalymnos specialties (fish, grilled octopus, local cheeses).
Day 7 – Kardamena (Kos): Toward Hippocrates’ Island
Arrival: Kardamena, Kos (36.7632°N, 27.1331°E) | Distance: 25 nautical miles (46 km) | Sailing time: 4-5 hours | Don’t miss: Sandy beaches, lively town evening | Activities: Sailing, beach relaxation
Sailing to Kos, crossing the channel between Kalymnos and Kos. Arrival at Kardamena on the south coast of Kos, beach resort with sandy beaches. Mooring in port or bay. Afternoon dedicated to relaxation after days of sailing: swimming at nearby sandy beaches, snorkeling, reading in the cockpit. Kardamena also offers nightlife options for those who want it (bars, restaurants, music). Special farewell dinner onboard or at local taverna. Review of the week’s sailing in the Dodecanese.
Day 8 – Kos: Hippocratic Heritage / Disembarkation
Disembarkation port: Kardamena, Kos (36.7632°N, 27.1331°E) | Disembarkation: 9:00 AM | Don’t miss: Kos town, Asklepion, Hippocrates’ plane tree, Knights’ castle | Connections: Kos Airport (KGS) – 8 km from Kos town, 25 km from Kardamena
Last breakfast onboard. Disembarkation operations. Before transfer to airport, recommended excursion to Kos town (15 km from Kardamena, reachable by taxi or bus):
Asklepion: 4 km from Kos town, ancient sanctuary and medical school where Hippocrates taught, father of modern medicine. Archaeological site on three terraces with spectacular views of the sea and Turkish coasts. Among the most important archaeological sites in Greece.
Kos town: Historic center with Castle of the Knights of Saint John (14th century), ancient agora, Hippocrates’ plane tree (millennia-old tree under which according to tradition he taught), Ottoman mosque, Italian quarter (Kos was Italian 1912-1943).
The itinerary stops are subject to changes due to weather conditions or other unforeseen circumstances that prevent or make sailing uncomfortable to reach them or for mooring. Any modifications to the itinerary are made exclusively to ensure better vacation organization and to guarantee the safety and comfort of our guests.
Why This Itinerary
Authentic Dodecanese + UNESCO Patmos + Remote Islands
Perfect itinerary to discover the Dodecanese beyond the main tourist islands (Rhodes, Kos). Focus on small authentic islands: Arki (50 inhabitants), Agathonisi (200 inhabitants), quiet Lipsi. Spiritual and cultural component: Monastery of Saint John in Patmos UNESCO heritage, Cave of the Apocalypse. Unique sponge fishermen tradition in Kalymnos.
Walkabout 43 perfect for these waters: pleasant sailing suitable for beginners too, boat stability and speed with sustained Meltemi, autopilot for comfortable sailing.
Dodecanese Cuisine and Expert Skippers
Skippers prepare daily dishes with fresh local products.
Skippers with sailing experience in the Dodecanese.
FAQ
Is it suitable for beginners without experience?
Yes! This is one of the accessible itineraries for those who have never sailed. Close islands, many protected bays, generally calm sea. Skippers handle everything and teach you gradually. Perfect also as a first itinerary in Greece.
➕ More questions? Check the complete FAQ on sailing cruises or contact us directly.
How to Book
- Personalized Quote: Receive within 24h: detailed quote, confirmed availability, contractual conditions.
- Confirmation: Pay deposit to block booking | Balance 30 days before departure.
- Book flights: Walkabout Charter provides info for flights, ferries and transfers.
- Trip Preparation: Receive: recommended equipment list, communicate special dietary requirements.
- Embarkation! See you in Pythagorio Sunday at 6:00 PM – your Dodecanese adventure begins!
Sailing between forgotten bays and millennia-old monasteries. Where the sea is still blue. Walkabout Charter takes you there!
Request availability and prices