A relaxed, sun-splashed sailing holiday—your way.
There are few sailing routes in the Mediterranean as rewarding as the voyage from Rhodes through the Dodecanese islands. With steady winds, crystal-clear waters, charming harbors, and authentic Greek island culture, this region remains one of the best-kept secrets for yacht charters in Greece.
Whether you prefer the freedom of a bareboat charter or the comfort of a fully crewed yacht, sailing the Dodecanese offers a blend of adventure, relaxation, and discovery that suits sailors of all experience levels.
Let’s explore why this sailing route deserves a spot at the top of your next holiday plan.
Rhodes is the perfect gateway to the Dodecanese. As one of Greece’s most vibrant islands, it combines rich history with excellent marina facilities and easy international access.
Before setting sail, spend a day wandering Rhodes Old Town, a UNESCO World Heritage Site filled with medieval streets, cafés, and lively waterfront restaurants. Stock up on supplies, enjoy local cuisine, and prepare for the island-hopping adventure ahead.
From Rhodes, dozens of islands lie within comfortable sailing distances, making route planning flexible and enjoyable.
Unlike the busier Cyclades or Ionian islands, the Dodecanese feel authentic and unspoiled. Each island has its own personality, offering something different every day of your sailing journey.
Popular stops include:
Symi, famous for its pastel-colored harbor and elegant neoclassical houses.
Chalki, a peaceful island with crystal-clear waters and relaxed charm.
Tilos, known for untouched nature and quiet anchorages.
Nisyros, home to one of Greece’s most impressive volcanic craters.
Kos, offering lively nightlife and ancient historical sites.
Kalymnos, renowned for climbing, sponge-diving history, and friendly tavernas.
Distances between islands are manageable, allowing comfortable daily sailing while leaving plenty of time to swim, explore villages, and enjoy seaside dinners.
The Dodecanese offers excellent sailing conditions, particularly from May to October.
The region benefits from the Meltemi wind, which provides steady breezes ideal for sailing enthusiasts. At the same time, many routes allow for protected passages and calm anchorages, making the area suitable for less experienced sailors as well.
Summer temperatures remain warm but pleasant, and the sea stays invitingly clear throughout the season. With fewer crowds than other Greek sailing areas, you’ll often find peaceful bays all to yourself.
Every sailing holiday is different, and choosing the right yacht helps shape your experience.
Classic sailing yachts are perfect for travelers who enjoy authentic sailing. They offer performance, efficiency, and the thrill of navigating with the wind while maintaining comfortable living space onboard.
Catamarans are increasingly popular for families and groups thanks to their spacious layout, stability, and shallow draft. Large deck areas and multiple cabins make them ideal for relaxed cruising and social gatherings onboard.
For travelers wanting to cover more distance quickly or enjoy luxurious cruising, motor yachts provide speed, comfort, and style. They allow more time exploring islands and less time under way.
Not everyone wants the same type of sailing holiday, which is why charter options vary.
If you hold the appropriate sailing license and enjoy independence, a bareboat charter gives you complete freedom to design your route and pace.
A professional skipper handles navigation and mooring while you relax and enjoy the journey. It’s ideal if you want a stress-free experience or lack formal sailing qualifications.
A fully crewed yacht includes skipper, hostess, and sometimes a chef. This option transforms your trip into a floating boutique hotel, perfect for families, celebrations, or luxury escapes.
While routes remain flexible depending on wind and preferences, here is a popular one-week outline:
Day 1: Rhodes → Symi
A short sail brings you to Symi’s spectacular harbor. Enjoy sunset drinks along the waterfront.
Day 2: Symi → Tilos
Anchor in quiet bays and explore charming island villages.
Day 3: Tilos → Nisyros
Visit the volcanic crater and traditional mountain villages.
Day 4: Nisyros → Kos
Enjoy vibrant nightlife or relax in Kos’ historic town.
Day 5: Kos → Chalki
A peaceful harbor perfect for swimming and sunset dining.
Day 6: Chalki → Rhodes
Return toward Rhodes with stops in secluded bays.
Day 7: Rhodes Marina
Final swim, farewell dinner, and preparation for departure.
Of course, your itinerary can adapt to wind conditions and personal interests.
What truly sets the Dodecanese apart is the authentic island life you encounter along the way.
Expect small fishing boats in quiet harbors, family-run tavernas serving freshly caught seafood, and locals welcoming visitors with warm hospitality. Many villages remain largely untouched by mass tourism.
Highlights include:
Swimming in secluded turquoise coves
Fresh seafood dinners beside the sea
Visiting ancient ruins and medieval castles
Discovering volcanic landscapes
Enjoying peaceful sunsets in tiny harbors
Each day brings a new discovery.
The sailing season runs from April to October.
May–June: Warm weather, blooming landscapes, fewer crowds.
July–August: Peak season with lively atmospheres and steady winds.
September–October: Warm sea temperatures, calmer harbors, ideal sailing conditions.
For travelers seeking quieter anchorages, late spring and early autumn are especially appealing.
We offer a wide selection of modern, fully equipped yachts in Rhodes, including:
Sailing yachts
Catamarans
Motor yachts
Our fleet is available for:
Bareboat charters
Skippered charters
Fully crewed luxury experiences
Our local knowledge helps tailor routes, recommend hidden spots, and ensure your sailing holiday runs smoothly from arrival to departure.
Whether you seek adventure, relaxation, or family time at sea, we help create a sailing experience designed around you.
Sailing from Rhodes through the Dodecanese islands combines natural beauty, cultural richness, and unforgettable moments on the water. From colorful harbors to quiet anchorages, each island reveals a different side of Greece waiting to be explored.
With the right yacht and the right crew, your journey becomes more than a holiday—it becomes a story you’ll retell for years.
The wind is waiting. All that’s left is to choose your yacht and set sail.
SEVEN – Sailing & Tourism Services is authorised by:
Ministry of Culture and Tourism
Greek National Tourism Organization
License No : 0458E60000094101
Member of HYBA:
