Embark on an exhilarating sailing journey through the Dodecanese archipelago, a spectacular cluster of islands in the eastern Aegean Sea. Our adventure starts at Kos, a blend of ancient allure and modern charm, setting the stage for a 6-day exploration that promises more than just a voyage. Each day unveils a new island, each horizon tells a story, and the sea becomes your path to adventure and discovery. Get ready to sail, explore, and be enchanted.

Suggested 6-Day Sailing Itinerary From Kos 

The Aegean Sea provides favourable sailing conditions nearly year-round, but we suggest planning your Dodecanese trip in the autumn months. During this time, the sea remains warm enough for swimming, yet the daytime temperatures are not excessively high, making longer trips on the mainland comfortable. You will also avoid the dreaded Meltémi wind, which is typical in the area during the summer.

Getting to Kos, the starting point of the cruise, is straightforward. In September and October, numerous direct charter flights from Central Europe provide the quickest and most comfortable journey. Throughout the year, regular flights and reliable boat services connect the islands to Athens and other locations.

Charter boats are typically rented from Saturday to Friday, and our suggested itinerary takes this into account. You can extend your stay for a few days before setting sail or after the cruise ends. Even without a boat, there's certainly a lot to explore on-site.

Here are our suggested routes through Kos beaches:

Sailing Route From Kos - Recommendations 

Kos is one of the Dodecanese's two largest islands. The international airport (KGS) is located in its western part. The island’s capital, located at the northeastern tip, boasts an old harbour and a modern marina with a variety of charter boats. The marina is about 25 km from the airport, so a car or bus journey will take at least 45 minutes. 

The capital of the island of Kos, Greece, view of the city and marina at sunset, a popular destination in Europe
The capital of the island of Kos, Greece, view of the city and marina at sunset

In the marina, a small but well-stocked grocery store will deliver your groceries directly to your boat once you've paid. This way, before the skipper takes charge of the boat, the crew can conveniently stock up for the cruise without carrying the supplies. With any extra time before departure, they can enjoy a treat like a delicious Greek coffee at the café, conveniently located under umbrellas right in front of the main port building.

If you're spending a day in Kos, consider renting a car or booking a taxi to visit the Asklepion. This vast complex features the ruins of a famous ancient medical school and a temple dedicated to healing, where Hippocrates himself once taught.

Day 1: Kos - Kalimnos (20 nm)

Setting sail from Kos marina, we'll first go north, circumnavigate the island's northern tip, and then we'll head to the northwest. On the way, we'll pass by the island of Pserimos, which we'll leave either to our left or right side, depending on the current conditions. We'll head towards the deep bay near Vathys village on the eastern side of Kalimnos. 

This destination is quite popular, so try to arrive in the early afternoon. AA local at the dock often helps direct boats to an available berth and assists with anchoring. When the port fills up, boats are often tied up at the tip of the small pier in "packs." In such cases, it's wise always to tie up the cockpit and connect it to the neighbouring boat's end to ensure the crew's privacy. Additionally, this arrangement helps prevent damage if katabatic wind gusts occur at night, as it keeps the boats' masts from being too close to each other.

Marina Kos
Marina Kos

Along the shore, there are multiple stalls selling tourist items. One tavern is conveniently located right above the landing pier, while others can be found by walking a few hundred meters to the village centre.

In the area, you can go hiking to explore several small churches on nearby hillsides and cliffs. Alternatively, you can enjoy a relaxing time on the pebble beach next to the marina.

For a more urban experience, head to the harbour in Kalimnos' namesake capital, situated in a bay on the island's south side. There, you'll discover excellent shopping options and a variety of restaurants catering to all tastes and budgets.

Day 2: Kalimnos - Gyali (30 nm)

We'll depart from the bay and navigate along the south coast, heading towards the west of Kos, Greece. You can stop at the town harbour of the capital, Kalimnos, if you wish. Otherwise, we'll continue southwest to go around the western tip of Kos. Along the way, we can admire the view of Kos's east-west mountain ridge. The tranquillity on board may be occasionally interrupted by planes departing from Kos International Airport.

Vathýs Bay on the island of Kalimnos
Vathýs Bay on the island of Kalimnos

Our cruise destination will be the small islet of Gyali, known for its extensive pumice quarry. On the island's south side, there's a long pier and large buoys used by transport ships to load and carry away the mined material. It's important to sail cautiously in this area to avoid any ships manoeuvring to dock or depart.

Marina in Vathýs Bay on the island of Kalimnos
Marina in Vathýs Bay on the island of Kalimnos

We will spend the night at anchor east of the transport ship berth in the strait between Gyali and Agios Antonio's islands, in waters about 3-5 meters deep. The seabed here is covered in a thick layer of ground pumice, which is great for anchoring and gives the water a unique white appearance.   This location offers exceptional swimming in a sheltered, shallow bay with slightly warmer water than in other areas.

Sunset during a sail to the island of Gyali
Sunset during a sail to the island of Gyali

Day 3: Gyali - Rhodes (60 nm)

This will be the longest journey of our trip and is expected to take the entire day. Thus, we plan to set sail as early as possible, heading to towards the northeastern tip of Rhodes, where the capital is. Our route will take us between the islands of Tilos to the west and Symi to the east.

Pumice quarry on the island of Gyali
Pumice quarry on the island of Gyali

It's wise to contact a marina in Kos, Greece, before you set sail. Try calling Mándraki Marina in Rhodes to book a berth for the evening. It's often difficult to secure a spot without a reservation, even in October, which is outside the high season. However, if you cannot get a reservation, there’s no need to worry.

Entrance lighthouse of Mandraki marina on the island of Rhodes
Entrance lighthouse of Mandraki marina on the island of Rhodes

Instead of the old marina near the town centre, you'll need to use the newer Rhodes Marina, located a few kilometres to the south. The old town is still easily accessible on foot from this marina. If we have some energy left after our long cruise, we can take a stroll, though we'll plan the main tour for another day.

Day 4: Rhodes - Symi (20 nm)

We'll spend the first part of the day sightseeing. The old harbour is where the "Colossus of Rhodes," one of the seven wonders of the ancient world, once stood. Just a few minutes' walk from the harbour, we can reach the historic city walls and enter the city through one of its gates.

Fortifications of the old town of Rhodes
Fortifications of the old town of Rhodes

The old town is a beautifully preserved medieval fortress, originally established as a base for the Crusaders on their journeys to the Holy Land. Visiting during the off-peak season might mean fewer tourists, making it a more enjoyable experience. You can spend the whole day exploring the labyrinth of narrow streets, stone houses, and palaces, constantly finding new sights, nooks, and crannies. The area is full of tourist shops and restaurants, offering something for every taste.

After fully experiencing the city and all its attractions, we'll set sail again. Our next destination is on the northwest towards the island of Symi, which we had passed by the previous day.

Panormítis Bay with the pilgrimage monastery of Archangel Michael on the island of Sými
Panormítis Bay with the pilgrimage monastery of Archangel Michael on the island of Sými

Located on the southern tip is the bay of Panormítis, marked by a lighthouse that's visible from afar on its northern shore. Keep the lighthouse to your port side as you approach and enter the large inner bay. This natural harbour is perfect for anchoring in about 5 meters of water, offering ample space for everyone.

Day 5: Symi - Nisyros (30 nm)

The 6-day journey around Kos continues. We'll visit the pilgrimage monastery of St. Michael the Archangel, situated just off the bay's eastern shore. This monastery has a long history, but its present form is the result of a major reconstruction in the late 18th century. In front of the monastery's entrance, there's a small concrete pier used mainly by motor boats transporting tourists from Rhodes on half-day excursions. We'll likely need to take a boat to reach the shore.

In addition to the monastery and museum, there is a small convenience store, a café, and a restaurant. It's also worthwhile to take a walk along the path that follows the bay's north shore, leading to the harbour entrance and the lighthouse that stands watch over it.

Following our walk along the shore, we'll get ready to sail northwest towards the island of Nisyros. This crossing should take about 6 hours. Our destination is the small port of Paloi on the northern coast. Those who arrive early can dock at the town pier, surrounded by a long line of tavernas and shops. Late arrivals may need to settle for a spot on the opposite dock, constructed along the inside of the breakwater.

Páloi port on the island of Nisiros
Páloi port on the island of Nisiros

You'll find a car rental office in the harbour's western part. This is a great spot to visit in the evening to arrange a car for your trip inland the next morning.

Day 6: Nisyros - Kos (20 nm)

Nisyros is an island created by a single large volcano. While the volcano is no longer active, you can still see various post-volcanic features inside the crater. The best way to get to the visitor centre in the centre of the crater is by rental car. If we dock early, we can get to the site before it officially opens, helping us avoid the crowds of tourists who come for day trips from nearby islands, particularly Kos.

Inside the crater of the volcano on the island of Nisiros
Inside the crater of the volcano on the island of Nisiros

The volcanic activity in this region is linked to the subduction zone where the African plate is sliding beneath the southern edge of the Aegean tectonic plate. Consequently, earthquakes are also common in the Aegean area.


If time allows, we can proceed from the crater's interior along the unpaved road to the island's south to explore that part of the crater too. However, we must remember to account for our return trip to Kos and the scheduled arrival time at the marina for returning the boat.

The Best Yacht Booking Services

For your 6-day Kos expedition, Boataround provides an outstanding sailing experience. We have a range of options, letting you choose your ideal mode of transportation. Feel free to get in touch with us today!

Frequently Asked Questions 

What If I Want a Skippered Cruise?

If you're more interested in a cruise with the expertise of a seasoned skipper rather than navigating independently, explore our cruise offerings. You'll often find voyages through the Dodecanese available there.

How many nautical miles will I cover during the journey?

In a week, you'll cover approximately 180 nautical miles, taking you to several islands and showcasing the best attractions the Dodecanese has to offer.

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