Dodecanese Sailing Itinerary from Kos: A 7-Night Cruise to Pserimos, Kalymnos, Leros, Patmos and Lipsi
14 November 2026 - 21 November 2026
Dodecanese Islands, GR
7 days trip
12 places avaliable
Catamaran
Price may vary depending on the cruise date.
Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
A one week sailing holiday from Kos around the northern Dodecanese, with swim stops at Pserimos, sheltered harbours on Kalymnos and Leros, time ashore in Patmos and Lipsi, and a return to Marina Kos.
This one week cruise starts and ends at Marina Kos and explores the northern Dodecanese, the chain of islands that lies between Kos and the open Aegean, close to the Turkish coast. The route is a loop: it heads north through sheltered channels, reaches Patmos at the far end and returns by a slightly different line, so that almost every night is spent in a new harbour or bay.
Legs between the stops are generally short, so there is usually time for swimming, walks ashore and long lunches on deck, depending on the stops chosen, wind and sea state. In summer the wind often builds in the afternoon, so crossings are best made in the morning, and the plan can be adjusted from day to day according to weather and sea state.
The first stop is Pserimos, a small island with a sandy bay and clear water. Kalymnos follows, rugged and dry, with sheltered inlets, then Leros, whose indented coastline offers some of the best natural harbours in the Aegean. Lipsi and the quiet bay of Emporios on Kalymnos add peaceful anchorages with sandy beaches nearby.
Ashore, Pothia on Kalymnos shows the working life of the island of sponge divers, while Skala, the port of Patmos, is the gateway to Chora and the Monastery of Saint John, both listed by UNESCO. Leros adds its Italian rationalist architecture and the castle above Pandeli, and Lipsi is a small harbour village with a relaxed evening atmosphere.
Life on board follows the rhythm of the sea: a morning swim, a sail to the next island, lunch at anchor and an evening in a village harbour or a quiet bay. Every night of the week is spent on board, with a different view each morning.
Itinerary
Day1
Marina Kos and Pserimos
Boarding takes place at Marina Kos, with time to settle in and attend the briefing at the base. If time and weather allow, the boat then crosses the short channel to Pserimos, a small island with a sandy bay and clear water, for a first swim and the first night at anchor.
Day2
Pserimos to Kalymnos
After a morning swim, leaving either Marina Kos or the anchorage at Pserimos depending on where the first night was spent, the route continues north to Kalymnos, the island of the sponge divers. Depending on wind and sea, the night is spent in the harbour of Pothia or in the sheltered bay of Vathy, with time ashore for a walk and dinner in a local taverna.
Day3
Kalymnos to Leros
A sail north leads to Leros, whose deep bays make some of the best natural harbours in the Aegean. The night is spent in Lakki, with its Italian rationalist waterfront, or in the village of Pandeli, below the castle, with tavernas along the quay.
Day4
Leros to Patmos
The crossing to Patmos takes the route to the far end of the loop. The port of Skala is the gateway to Chora, the hilltop town, and to the Monastery of Saint John, both listed by UNESCO, with views over the surrounding islands.
Day5
Patmos to Lipsi
A short sail south leads to Lipsi, a small and quiet island with a pretty harbour, white houses and sandy beaches close to the village. It is a relaxed stop for swimming, a walk and an evening at one of the quayside restaurants.
Day6
Lipsi to Emporios, Kalymnos
Leaving Lipsi, the route heads toward Kalymnos with a last swim at an anchorage chosen along the way. The night is spent at Emporios, a quiet bay on the north west side of Kalymnos, with the weather deciding the final choice of anchorage.
Day7
Back to Kos and last night at Marina Kos
The final sail leads back to Kos and Marina Kos, where the boat is prepared for return. The last night is spent on board and disembarkation takes place the following morning.
Important Note This itinerary may vary depending on weather conditions, sea state and operational requirements. The person in charge of the boat may adjust the route, anchorages and overnight stops, following the briefing at the base, to ensure safety and comfort.
Cruise price details
Entire yacht price
€ 3200
€ 2688
Book the entire yacht for a private trip
Included in the price
Entire boat rental
Dinghy
Basic boat equipment
Bed linen, towels and blankets, one set per person
Yacht additional fees
Mandatory additional expenses of EUR 720 per booking (Service Pack EUR 320 and Obligatory Insurance EUR 400, non refundable, confirmed on booking)
Security deposit: € 1,000, refundable, by Visa or Mastercard
Fuel, provisions and mooring fees away from the base: paid by guests as used
Extra services
Skipper: € 1,750 for the 7 nights, plus € 30 per day for food
Hostess: € 1,540 for the 7 nights, plus food
Early check-in at 14:00: € 150
Sunday check-in at 10:00: € 150
Wi-Fi, unlimited data for up to 6 users: € 80 per week
A bright and spacious catamaran for a group of friends or two families, with six double cabins, a generous cockpit and a saloon that opens onto the deck.
Spread over two hulls and a wide central saloon, this catamaran gives everyone on board plenty of room. Six double cabins sit in the hulls, so every couple or pair of friends has a private place to retire to, with four bathrooms shared out between them. Twelve berths in total, all in the six double cabins.
The cockpit is the heart of daily life on board, with cushioned seating and a bimini for shade during long lunches. Inside, the saloon and galley connect directly to the outdoor area, so cooking and conversation happen together.
Under way, the steady platform of a catamaran makes sailing relaxed even for guests who are new to the sea, and it makes it easy to anchor in sheltered bays. An autopilot, a chart plotter and solar panels take care of the everyday work of the voyage.
What to pack for a sailing holiday?
Pack smart for your yacht charter: choose a soft bag instead of a hard suitcase, bring lightweight layers, reef-safe sunscreen, and non-slip shoes for onboard use. A couple of swimsuits and motion sickness remedies can also make a big difference. Each boat has limited storage, so pack light, but wisely! Need help building the perfect list? Read our full guide: What to pack in a suitcase for a yacht charter
What’s a Typical Day Like on a Yacht Charter?
Start your day with a swim in a quiet bay, sail to hidden beaches or seaside villages, and enjoy a slow lunch on deck. Afternoons mean snorkeling, sunbathing, or exploring ashore. As the sun sets, your boat anchors in a scenic cove or near a harbor, ready for a relaxed dinner and a night under the stars. Curious about the full experience? Discover more in our guide: What’s a typical day like on a sailing holiday?
What Happens in Case of Bad Weather During a Sailing Holiday?
In the Dodecanese the summer breeze can freshen in the afternoon, and when the wind or sea picks up, the person in charge of the boat adjusts the route for safety. Expect protected bays, marina stops, or a change in plan. These moments often lead to unexpected gems: local towns to explore, time to relax on board, or cozy dinners ashore. Curious about how crews handle these changes? Read the full FAQ: What to do in case of adverse weather conditions or changes to the itinerary
Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
