Dodecanese Sailing Itinerary from Kos: A 7-Night Cruise to Pserimos, Kalymnos, Leros, Patmos and Lipsi
19 June 2027 - 26 June 2027
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
€ 13800
€ 12420
Book the entire yacht for a private trip
Included in the price
Entire boat rental
Dinghy with outboard engine
Bed linen, towels and blankets, one set per cabin per week
Air conditioning
Generator and water maker
Yacht additional fees
Mandatory additional expenses of EUR 400 per booking (Service Pack, confirmed on booking)
Security deposit: € 5,000, refundable
Fuel, provisions and mooring fees: not included
Extra services
Skipper: € 210 per night, € 1,470 for seven nights, plus food for the skipper
Cook: € 230 per night, € 1,610 for seven nights, plus food for the cook
Hostess: € 190 per night, € 1,330 for seven nights, plus food for the hostess
A large catamaran for up to twelve guests, with six cabins, air conditioning and plenty of room on deck and below for two families or a group of friends.
Generous in every dimension, this catamaran is made for group cruises. Six guest cabins are spread across the two hulls: four double cabins, each with its own bathroom, and two semi double cabins close to the saloon, for twelve guests in total. A separate cabin with a bunk bed is kept apart from the guest areas for a crew member. Twelve berths in total, all in the six guest cabins.
On deck, the wide cockpit with cushioned seating, a bimini and a sprayhood offers shade and shelter for long lunches and evenings, while the bright saloon and the galley, with a refrigerator and coffee maker, keep everyone together on board.
Air conditioning, a generator and an inverter keep the cabins comfortable on warm nights, solar panels and a water maker add independence between harbours, and electric winches and electric toilets make everyday life on board simpler.
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.
