Dodecanese Islands Sailing from Kos: Flexible 7-Day Greece Itinerary
17 October 2026 - 24 October 2026
Dodecanese Islands, GR
7 days trip
5 places avaliable
Sailboat
Shared cruises may require a minimum number of guests.
Price may vary depending on the cabin type, occupancy and 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.
Island hopping sailing route in the Dodecanese from Kos, exploring Patmos, Leros, Kalymnos, Nisyros and Symi with short distances, steady winds and authentic Greek island life.
This Dodecanese Islands sailing itinerary from Kos offers one of the most flexible and complete sailing experiences in Greece, ideal for travelers looking to explore multiple islands within a single week while adapting the route to wind conditions and group preferences.
Located between the Cyclades and the Turkish coast, the Dodecanese archipelago includes more than 150 islands, with around 25 inhabited. Thanks to their proximity, sailing distances remain short, allowing more time for swimming, relaxing and exploring ashore. Starting from Kos Marina, one of the most strategic bases in the area, you quickly reach a network of islands that differ in landscape, atmosphere and cultural heritage.
The itinerary can naturally develop in two directions. The northern route includes islands such as Kalymnos, Leros, Lipsi and Patmos, known for their calm atmosphere, green landscapes and traditional villages. These islands are ideal for relaxed sailing, quiet anchorages and authentic local experiences. Alternatively, the southern route leads toward Nisyros, Tilos and Symi, where volcanic landscapes, less developed coastlines and unique harbor towns create a more remote and contrasting environment.
Sailing conditions in the Dodecanese are defined by the Meltemi wind, typically blowing from the northwest. This creates reliable and enjoyable navigation, especially from late spring to early autumn, with warm temperatures and very limited rainfall. The sea remains swimmable well into October, making this region ideal for extended sailing seasons.
Each day combines sailing, swimming and time ashore. Guests can anchor in protected bays, snorkel in clear waters and visit small fishing villages where local tavernas serve fresh seafood, grilled meats and traditional dishes. The cultural layer is equally strong, with traces of ancient civilizations, medieval castles and monasteries present across the islands.
This Greece sailing holiday in the Dodecanese is ideal for those who want a mix of nature, sailing and authentic island life, with the added advantage of a flexible route that adapts to conditions rather than following a fixed path.
Itinerary
Day1
Kos Marina
Your Dodecanese sailing holiday from Kos begins with afternoon boarding at Kos Marina, located in the heart of the island and within easy reach of nearby archipelagos. After meeting the skipper and settling into your cabin, a first short navigation takes you away from the main harbor into the surrounding waters. This initial sail offers the first opportunity to swim in the Aegean and get familiar with life on board. The evening is typically spent at anchor in a sheltered bay or in a nearby small port.
Day2
Kalymnos and Telendos Island
Sail north toward Kalymnos, an island known for its long maritime tradition and sponge diving heritage. The coastline offers multiple sheltered bays with clear water, ideal for swimming and snorkeling. A possible stop includes Telendos, a small island just off Kalymnos, where traditional tavernas serve fresh fish directly by the sea. This is one of the most authentic stops of the itinerary, with a slow pace and minimal tourism.
Day3
Leros and Lipsi
Continue toward Leros, characterized by green hills, small harbors and neoclassical architecture influenced by its Italian past. From here, sail to Lipsi, a small and peaceful island known for its clear waters and relaxed atmosphere. The day includes short sailing distances, multiple swim stops and time ashore in a compact village where everything is within walking distance.
Day4
Patmos or Remote Anchorages
Depending on wind and group preference, the route may continue toward Patmos, one of the most culturally significant islands in Greece, known for the Monastery of Saint John and its historic old town. Alternatively, for a more remote experience, the itinerary may include Levitha, a small and isolated island offering complete tranquility, with only a handful of inhabitants and untouched nature.
Day5
Sailing South or Continuing Exploration
The itinerary remains flexible, adapting to wind conditions and the desired pace of the group. The route may begin shifting south toward more volcanic and less visited islands or continue exploring the northern area with additional stops in hidden bays and quiet anchorages. The focus is on swimming, sailing and enjoying the natural environment.
Day6
Nisyros, Tilos or Symi
The southern route includes Nisyros, known for its active volcanic crater, which can be visited on foot, offering a unique geological experience. Alternatively, the itinerary may include Symi, one of the most visually striking islands in Greece, with its colorful neoclassical houses surrounding a natural harbor, or Tilos, known for its untouched landscapes and slower pace. This day combines cultural exploration with some of the most distinctive landscapes in the Dodecanese.
Day7
Return to Kos
After a final morning sail, return to Kos Marina. Disembarkation takes place in the morning, marking the end of your Dodecanese sailing experience in Greece.
Important Note
This Kos sailing itinerary in the Dodecanese is intentionally flexible and may vary depending on wind conditions, sea state and the captain’s decisions. The route is adjusted daily to ensure optimal sailing conditions, safety and the best overall experience.
Cruise price details
Price per person
from € 890
Accomodation on selected shared cabin, check out single use and details
Cabin type
Double Cabin
Double cabin suite
10
cabin capacity
double bed
Use
Price/person
Shared
€ 890/
Single
€ 1290/
Included in the price
7 nights accommodation on board
Qualified skipper
Dinghy with outboard engine
Stand-up paddleboard (SUP)
Bed linen and towels
Final cleaning
Security deposit insurance
Travel price guarantee
Detailed pre-departure travel documents
Not included € 230 / person
Onboard kitty: approx. €230 per person/week, covering food provisions, fuel/diesel, marina and harbour fees and the yacht service package
Skipper’s share of onboard food expenses is divided among the guests
Flexible 40–47 ft Sailing Yacht Cabin Charter Experience
This sailing yacht roulette offers a flexible cabin charter experience on modern sailing yachts in the 40 to 47 ft range. The exact boat will be selected based on availability at the time of departure, allowing for a more efficient and adaptable organization of the trip.
While the specific model may vary, all yachts in this category provide a consistent level of comfort and onboard experience. Guests can expect well designed interiors, comfortable cabins, shared living areas and outdoor spaces suitable for relaxing, dining and enjoying life at sea.
These sailing yachts are designed for balanced cruising, combining ease of navigation with practical layouts that work well for both small groups and social cabin charter environments. Regardless of the final boat assigned, the standard of comfort, functionality and overall experience remains the same.
This solution is ideal for travelers who prioritize the sailing itinerary and overall experience rather than a specific boat model, while still ensuring a reliable and comfortable week on board.
Yacht
Model
2022 Sailboat Roulette: Oceanis 40.1, Oceanis 47 & Sun Loft
Length
12.9 m
Yacht services
Tender size
3.2 m
Accommodations
Max guests
6
Double cabins
3
Bathrooms
2
Private Bathrooms
No
Crew
1
Chef on board
No
Other facilities
Fridge - Hot water - Cooker with oven - Stereo - Pillows - Blankets – Bed linen – Towels - Cutlery - Glasses - Cups - Plates – Kitchen knives - Pots - Pans – 2 Italian espresso coffee makers – Coffee filters – Woode:n spoons – Containers – Lemon squeezer - Grater – Tin opener – Bottle opener – Salad bowls – Thermos flask – Tablecloth – Cabin & dining area fan
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?
Who Handles Cooking and Cleaning on a Yacht Charter?
On skipper-only charters, guests usually share cooking and cleaning duties, think salads, pasta, and good teamwork. If there's a hostess, light meals and tidying are included, but it's still a casual, collaborative vibe. On fully crewed yachts, you’ll enjoy full service with a chef and crew managing everything. Want to know what’s included in your setup? Read the full guide: Who takes care of cooking and cleaning on a sailing charter?
What Happens in Case of Bad Weather During a Sailing Holiday?
Summer sailing holidays rarely face major weather issues, but when the sea gets rough, skippers adjust the route for your 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
Shared cruises may require a minimum number of guests.
Price may vary depending on the cabin type, occupancy and 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.
