Dodecanese: The Ultimate Sailing Adventure in Greece

Dodecanese sailing routes are made for explorers who crave challenge and cultural richness. To begin with, they offer the thrill of navigating through ancient waters and discovering Greece’s hidden gems. So, if you’re tired of the same old charter routes, this is the sailing trip for you.

Too often, skilled sailors settle for easy itineraries that don’t push their potential. But what if you could find a region with exhilarating conditions and rewarding discoveries?

In the Dodecanese, you’ll sail past medieval walls and fortresses in Kos or Rhodes. Drop anchor near Nisyros’ volcanic cliffs and explore Symi’s colourful neoclassical harbour. These islands combine open-water sailing with a blend of culture and nature.

Seafarer’s options let you tailor your sailing adventure to match your experience and style. Join a Flotilla Sailing holiday with support, or charter a yacht and take full control.

Looking for a thrilling sailing adventure? Let’s dive into the beauty of the Eastern Aegean islands.

Sailing the Dodecanese means combining natural beauty, reliable winds, and cultural depth. What’s more, this region offers consistent Force 3–6+ winds and some longer open-water passages. That’s why it’s ideal for intermediate to experienced sailors looking to stretch their skills.

The islands diversity is a sailor’s dream, offering something new at every stop. Explore Kalymnos’ ancient streets, then relax in the peaceful charm of Lipsi or Nisyros. These islands are rich with history—from Byzantine monasteries to Venetian ports—delivering meaning and magic at every anchorage.

Seafarer offers two ways to explore this area:

• Flotilla Sailing (from Kos): Join a sociable group of yachts led by a professional crew. Choose from two curated routes:
  • Kalymnos Route: Sail north to Kalymnos, Patmos, and Lipsi for sponge-diving heritage and sacred landmarks.
  • Symi Route: Cruise south to Symi, Tilos, and Nisyros for neoclassical harbours, eco-islands, and volcanic wonders.
• Yacht Charter (from Kos or Rhodes): Plan your own route—bareboat or with a skipper. Highlights include:
  • Rhodes to Kos Itinerary: Visit Symi, Nisyros, Tilos, Chalki, and Kos, finishing with Rhodes Old Town.
  • Kos North & West: Head to Patmos, Leros, Kalymnos, and remote gems like Arke, Levitha or Astypalaia on a two-week journey.

Therefore, whether you prefer some company and expert support or full autonomy, Seafarer ensures you experience the Dodecanese your way.

Flotilla sailing in the Aegean sea is ideal for intermediate and experienced sailors alike. It’s indeed for those seeking expert local knowledge ensuring you see all the best places. It offers the freedom to skipper your own yacht with our knowledgeable   lead crew, never far away. Your journey begins in Kos, a lively island known for its classical ruins and sandy beaches.

From there, you can choose one of two carefully curated routes. On the one hand, the Kalymnos Route takes you north to Kalymnos, known for its sponge diving heritage. It also includes Patmos, home to sacred monasteries, and peaceful, untouched Lipsi.

On the other hand, the Symi Route heads south to Symi, known for its colourful, neo-classical harbour. It also includes eco-friendly Tilos and Nisyros, home to a dramatic volcanic crater.

Each day averages 19 nautical miles of sailing, giving you time to explore and unwind. Moreover, yachts range from 34ft to 51ft with catamarans also available. A flotilla is perfect for couples, families, or groups seeking both challenge and comfort.

Note: While our flotilla offers defined north and south routes, itineraries may vary slightly based on weather and operating conditions. Your lead crew will keep you fully briefed each day.

Join our Dodecanese flotilla and enjoy an expertly guided adventure.

There’s something extraordinary about charting your own course, and the Dodecanese is the perfect Greek island group to explore. With Seafarer’s bareboat and skippered charters, you can explore on your own terms.

Indeed, confident sailors will thrive here. Force 3–6+ winds offer exciting sailing, with cultural gems and natural beauty at nearly every port. From Symi’s colourful harbour to Nisyros’ volcanic terrain, this journey is for travellers craving more than a holiday.

Choose bareboat for full autonomy or sail with a skipper for guidance and local insight. Our yachts and catamarans range from 34ft to 51ft—spacious, comfortable, and fully equipped for adventure.

The Dodecanese is quieter than the Cyclades, but every bit as spectacular.

Sailing through the Dodecanese feels like turning the pages of a living storybook. Given that, each island reveals a new chapter filled with culture, colour, and coastal beauty. From medieval fortresses to volcanic wonders, this region offers something extraordinary at every port.

This island group is unlike any other in Greece. You’ll discover the energy of Rhodes, where the Old Town brims with history and nightlife. Next, Kos welcomes sailors with sun-drenched beaches and ancient ruins. In Symi, on the other hand, neoclassical mansions rise from a stunning harbour that feels plucked from a postcard.

Patmos invites reflection with its monastic sites, while Nisyros surprises visitors with its active volcanic crater and whitewashed villages. And then there’s Halki, quiet and refined, with Venetian charm and crystal-clear waters.

Arki feels a thousand miles away, a hidden paradise in the Aegean Sea. Its blue lagoon and nearby Marathos islet create a picture-perfect escape.

Flotilla guests and private charters alike will discover the full diversity and magic of the Dodecanese islands.

May–June: Pleasant temperatures, lighter winds, and peaceful harbours make this the perfect time for relaxed exploration.

July–August: The Meltemi picks up, with stronger winds reaching Force 5–6+, ideal for experienced sailors seeking a challenge.

September–October: Late summer sailing offers warm seas, reliable breezes, and a tranquil, end-of-season charm.

Tip: Confident sailors will thrive in peak Meltemi season, while earlier and later months offer smoother conditions.

Greece offers a wealth of sailing opportunities, but each region caters to a different kind of sailor. Here’s how the Dodecanese compares to the Ionian Islands and Cyclades.

These islands feature stronger winds (Force 3–6+), ideal for adventurous, confident sailors. Its open-water passages and culturally rich islands provide a rewarding challenge.

In contrast, the Ionian Islands offer gentler winds (Force 2–4), short hops, and green, serene landscapes—perfect for beginners and families.

The Cyclades, while iconic, are best left to advanced sailors. The strong Meltemi winds (Force 5–7) and rugged coastlines make it thrilling but demanding.

So what? If you’re seeking cultural variety, thrilling conditions, as well as quieter harbours, the Dodecanese offers a richer sailing experience.

For a sailing experience full of adventure and history, the Dodecanese is unbeatable.

In conclusion, sailing the Dodecanese combines adventure, culture, and freedom across a chain of remarkable Greek islands. Enjoy open-water routes, historic harbours, and an island-hopping journey through captivating destinations.

Imagine anchoring in a quiet bay, strolling through medieval streets, or enjoying fresh seafood at a harbourside taverna. Choose flotilla support or independent chartering. Either way, your dream sailing holiday in the Dodecanese begins right here.

Don’t just dream it, chart it. Book your adventure now and sail beyond the ordinary.

To book or check availability get in touch with our experienced team on one of the links below.