Imagine waking up in a quiet bay, diving into clear turquoise water before breakfast, and setting sail toward a new island every day. Sailing from Kos through the Dodecanese islands offers exactly that — a blend of adventure, relaxation, and authentic Greek charm.
Less crowded than many other Greek sailing destinations, the Dodecanese is ideal for travelers seeking real island life, beautiful anchorages, and unforgettable cruising routes. Whether you’re an experienced sailor or stepping aboard for the first time, this region offers the perfect sailing holiday.
With a choice of sailing yachts, catamarans, or motor yachts — available bareboat, skippered, or fully crewed — your journey can be as adventurous or as relaxed as you wish.
Kos is one of the best departure points in the Dodecanese for yacht charters. The island combines excellent marina facilities, international flight connections, and a lively atmosphere.
Before setting sail, you can explore Kos Town’s ancient ruins, medieval castle, and charming harbor cafés. Stocking up on provisions is easy, and the island’s vibrant waterfront is perfect for a final dinner ashore before heading out to sea.
From Kos, dozens of islands are within easy sailing distance, making route planning flexible and enjoyable.
The Dodecanese archipelago stretches along the southeastern Aegean Sea and offers incredible variety. Each island feels different, ensuring every day of your sailing trip brings something new.
Some of the most loved stops include:
Just a short sail from Kos, Kalymnos is famous for its sponge-diving heritage and friendly atmosphere. The island combines rugged landscapes with lively harbors and excellent local tavernas.
Leros feels peaceful and welcoming, with pretty waterfront villages and safe anchorages. Lakki Bay is one of the Mediterranean’s largest natural harbors and offers great protection in most conditions.
Small and relaxed, Lipsi is loved by sailors for its crystal-clear waters and charming harbor village. It’s perfect for slow evenings and swimming in secluded coves.
Known for the Monastery of St. John and picturesque Chora village, Patmos offers stunning views and peaceful anchorages. It blends history, culture, and natural beauty.
Further south, Nisyros offers a dramatic volcanic landscape. Visitors can walk inside the crater and explore traditional mountain villages untouched by mass tourism.
Distances between islands are comfortable, allowing you to enjoy relaxed sailing days without rushing.
The Dodecanese offers reliable sailing conditions throughout the main season from April to October.
The Meltemi wind provides steady breezes, particularly in summer, making the region exciting for sailing enthusiasts while still manageable for less experienced crews. Many routes also offer protected sailing options when needed.
Sea temperatures remain warm throughout the summer, and visibility underwater is excellent for swimming and snorkeling.
Compared to more crowded Greek regions, you’ll often find quiet bays and less busy harbors, even during peak season.
Your choice of yacht shapes your sailing experience. Fortunately, there are options for every style of traveler.
Perfect for those who enjoy traditional sailing, monohull yachts provide a true connection with the sea. They are efficient, fun to sail, and offer comfortable accommodation for families or groups.
Catamarans are ideal for travelers wanting extra space and stability. Wide decks, multiple living areas, and shallow draft allow access to beautiful shallow bays while offering great comfort onboard.
Motor yachts are ideal for guests wanting to cover greater distances quickly or enjoy a more luxurious cruising style. They provide comfort, speed, and convenience, allowing more time exploring islands.
Not every guest wants the same sailing experience, which is why different charter options are available.
Experienced sailors with proper qualifications can rent a yacht and explore independently, creating their own routes and schedule.
A professional skipper handles navigation and docking while guests relax and enjoy the journey. It’s perfect for those without sailing licenses or anyone wanting a stress-free trip.
For maximum comfort, choose a fully crewed yacht with skipper and hostess or chef. Meals, navigation, and daily operations are handled while guests focus purely on relaxation and enjoyment.
Weather conditions always influence routes, but a typical one-week itinerary might look like this:
Day 1: Kos → Kalymnos
Short sail, explore lively harbor and enjoy dinner ashore.
Day 2: Kalymnos → Leros
Swim stops along the way and evening in a charming marina town.
Day 3: Leros → Lipsi
Relaxed sailing and overnight in peaceful harbor.
Day 4: Lipsi → Patmos
Visit monastery, explore Chora village, sunset views.
Day 5: Patmos → Arki or small surrounding islets
Perfect swimming stops and quiet anchorages.
Day 6: Arki → Pserimos or return route toward Kos
Enjoy last swimming stops.
Day 7: Return to Kos Marina
Final swim, farewell dinner, and departure preparations.
This itinerary can easily adapt depending on wind conditions and personal preferences.
Beyond the sailing itself, what makes the Dodecanese unforgettable are the simple, authentic moments.
You’ll discover:
Family-run tavernas serving freshly caught fish
Quiet villages where time seems to slow down
Hidden beaches reachable only by boat
Friendly locals welcoming visitors
Stunning sunsets over calm harbors
Some nights you’ll dine ashore in lively towns, while others you’ll anchor alone in peaceful bays under a sky full of stars.
The sailing season runs from spring to autumn.
May–June: Warm weather, fewer crowds, green landscapes.
July–August: Lively atmosphere and reliable winds.
September–October: Warm sea, quieter harbors, excellent sailing conditions.
Many experienced sailors consider September one of the best months to sail the region.
We provide a wide range of modern yachts departing from Kos, including:
Sailing yachts
Catamarans
Motor yachts
Available for:
Bareboat charter
Skippered charter
Fully crewed charter experiences
Our local expertise allows us to recommend routes, hidden anchorages, and the best island experiences so your holiday runs smoothly from start to finish.
Whether you want adventure, relaxation, or quality time with friends and family, we help create a sailing holiday tailored just for you.
Sailing from Kos through the Dodecanese islands is more than a holiday — it’s a journey through some of Greece’s most authentic and beautiful islands. Every day brings a new harbor, a new swim spot, and a new memory.
Choose your yacht, gather your crew, and set sail toward an unforgettable Greek island experience.
The islands are waiting.
SEVEN – Sailing & Tourism Services is authorised by:
Ministry of Culture and Tourism
Greek National Tourism Organization
License No : 0458E60000094101
Member of HYBA:
