The most beautiful week-long sailing routes in the Aegean Sea

The most beautiful week-long sailing routes in the Aegean Sea

Are you tempted to sail in Greece but not sure exactly where to head? Try one of our recommended 7-day itineraries in the Aegean for beginners to more experienced sailors.

The Aegean Sea is the most popular choice for sailors heading to Greece ⁠— it's easy to reach from Athens, temperatures are mild, winds are steady and predictable, and there are no tides or strong currents. The beautiful islands make for a wonderful sailing trip and, as they are not too far apart, you'll have time to explore several of them on your vacation. Take a look at 3 of our favourite routes.

1. The Cyclades: the most popular sailing destination

Route difficulty: Medium

Route: Athens — Cape Sounion — Kythnos (Kolona Bay) — Serifos — Kythnos (Agios Stefanos Bay) — Kea Island — Cape Sounion — Athens

Length: 142 NM

As the Cyclades are one of the most popular sailing destinations, it's no surprise that they're our top pick. Covering a total area of over 2,500 km², this archipelago is made up of 30 larger islands and around 190 islets. A favoured yachting destination due to their proximity to Athens (where most flight connections go), the islands are not too far apart and sailing there really offers a diverse array of experiences. Over a single holiday, you can visit several harbours and bays in a relatively short period of time.

In terms of sailing, our suggested route is of medium difficulty — there are no long crossings. However, there may be more powerful northerly Meltemi or southerly winds on occasion, making the sea around the Cyclades choppy and the route unsuitable for complete beginners. If the weather is good, it is perfect for a relaxing family cruise and our selected places (with the exception of Serifos) are relatively quiet. Overnight stays are mostly at anchor, but local marinas can be used if necessary. Your first night at anchor will be an unforgettable one, spent under Cape Sounion, overlooking the monumental Temple of Poseidon — sixteen Doric columns rising high above the sea.

Day 1: Athens -> Cape Sounion

Hire a boat in Athens, stock up on supplies and set sail for Cape Sounion, the southernmost tip of the Attica peninsula and a national park since 1974. As the route is only about 23 NM, it can be easily covered in one day and your reward will be a stunning sunset over the Temple of Poseidon, towering sixty metres above sea level. The beach below the cape is a popular tourist destination, but you won't have to fight your way in ⁠— simply dive into the turquoise waters directly from the deck of your boat. The bay below the cape can accommodate a large number of boats and provides excellent shelter from the northerly winds prevalent in July and August.

Temple of Poseidon in Sounion, Greece, at sunset

Temple of Poseidon in Sounion, Greece

Day 2: Cape Sounion -> Kythnos (Kolona Bay)

Set out early in the morning and hopefully, you'll catch a northerly breeze to carry you to your destination — Kolona beach on the island of Kythnos. This is the most picturesque beach on Kythnos and a great spot for true romantics. What makes it unusual is that the bay is split in half by a narrow sandy strip with ocean waters on both sides (a double-sided beach). Anchoring is possible on either side, so make the most of the day by taking a dip and relaxing. The bay is sheltered from all directions but you should still watch out for gusts from the north. If you don't feel like anchoring there overnight, head to the port of Merichas nearby to restock, and enjoy a nice meal at one of the local tavernas. Check out what delicacies to sample in Greece.

Day 3: Kythnos -> Serifos

The next stop on your voyage is Serifos, the island where the beautiful Danae gave birth to Zeus' son Perseus, one of antiquity's greatest heroes. You can dock your boat at the port of Livadaki, but make sure they have room for you in advance. Anchoring around Serifos is for more experienced skippers — the shallow waters and numerous cottages here can make it quite difficult to drop anchor. If you're looking for a bit of nightlife, the marina provides a nice base for visiting one of the discos in the centre. And while you're on Serifos, be sure to visit Chora, a picturesque village that is a typical example of Cycladic architecture.

Panoramic view of the double-sided Kolona beach in Kythnos, Greece, as seen from the islet of Aghios Loukas

Double-sided Kolona beach in Kythnos, Greece

Day 4: Serifos -> Kythnos (Agios Stefanos Bay)

With half the week behind you, it's time to start heading back. Land again on Kythnos, but this time on its eastern coast in the bay of Agios Stefanos, which can provide shelter from any potential Meltemi winds. The beach is partly sandy, partly pebbly and offers shade from the tamarisk trees. This is an ideal spot for spending an afternoon with children.

Day 5: Kythnos -> Kea island

As the wind will almost certainly be from the north, the 20 NM push to Kea Island will make for more interesting sailing. When you arrive, anchor and unwind with the many other yachts and boats in the sheltered bay of Koundouros.

Day 6: Kea -> Cape Sounion

It's time to say farewell to Greece, and preferably back exactly where you began ⁠— beneath the Temple of Poseidon. After all, Greece is synonymous with classical architecture and mythology.

Day 7: Cape Sounion -> Athens

Have breakfast at sunrise overlooking the Doric columns and make your way back to the marina. Your sailing adventure ends here.

What else should you know about sailing in Greece?

2. Sailing route around Lesbos for beginners

Route difficulty: Easy

Route: Mytilene — Saint Ermogenis — Tarti Bay — Eresos Bay — Sigri Bay — Molyvos — Mytilene

Length: 110 NM

The island of Lesbos (or Lesvos) is located in the north-eastern part of the Aegean Sea. With an area of 1,630 km² and a coastline of 320 km, it is the third largest island in Greece and the eighth largest island in the Mediterranean. Nobody wants to sail back and forth all the time and Greece provides ideal conditions for one-way sailing trips — you could easily spend a whole week cruising around one of its islands and Lesbos offers perfect sailing conditions. Plus, there is an international airport just a few kilometres from the capital Mytilene where you can rent a boat. So let's sail around this beautiful island, home of the ancient Greek poet Sappho and the birthplace of the feared Ottoman pirate Hayreddin Barbarossa.

As the route stays close to the island and the dreaded Meltemi is relatively mild in this part of the Aegean, it is easy enough for beginners. Still, caution is advised, particularly in light of the northerly winds and the cliffs that encircle Lesbos as a result of its volcanic origins.

View of the harbour and the town of Mytilene, Lesbos

Mytilene, Lesbos

Day 1: Mytilene -> Saint Ermogenis

The first crossing isn't long but, as always, you should buy some provisions before departure. On arrival, anchor in the bay of Saint Ermogenis, which offers welcome shelter against the northern winds. However, do keep in mind that it doesn't provide refuge from southerly winds. Enjoy lounging on the beach in the shade of the pine and olive trees and have dinner in the local tavern. A visit to the nearby church can be an interesting experience.

Day 2: Saint Ermogenis -> Tarti Bay

Set sail in the morning and enjoy bathing in the crystal-clear waters of Tarti Bay in the southern part of Lesbos. On the beach, take some refreshment in one of the tavernas or have a night out in the local bar, but be cautious of the rocks as you enter the bay. If you don't feel like spending the night at anchor, you can consider the nearby port of Plomari. If you are one of those who love typical Greek Ouzo, you've definitely come to the right place. Plomari is home to several distilleries and even a museum.

Day 3: Tarti Bay -> Eresos Bay

Eresos, the birthplace of the poet Sappho, is a popular hangout for lesbians, but there's something for everyone, especially beach lovers — Eresos boasts the most beautiful sandy beach on the island. The town itself, full of restaurants and bars, is also worth a visit.

Day 4: Eresos Bay -> Sigri Bay

The village of Sigri is located on the west coast of Lesbos. Directly in front of the village lies a bay well-protected against northerly winds, making it ideal for anchoring. We highly recommend a visit to the Natural History Museum of the Lesvos Petrified Forest.

Day 5–6: Sigri Bay -> Molyvos

After a few days at anchor, this time we recommend mooring in the harbour near the town of Molyvos. Not only will you be able to replenish your supplies, but once you are safely ashore, there's nothing stopping you from exploring the area. And there is plenty to discover. The town and the monumental Byzantine castle towering above it, is a UNESCO World Heritage Site.

We recommend staying in Molyvos for two days, reserving the second day for a trip to the nearby thermal springs of Eftalou — just a 10-minute taxi ride away. After alternately bathing in the cool sea and thermal waters, you'll truly feel reborn but don't forget to bring suitable footwear as there is a pebble beach.

Panoramic view of Molyvos or Mithimna, a picturesque traditional village on the Greek island of Lesvos.

Traditional village on the Greek island of Lesbos

Day 7: Molyvos -> Mytilene

After a relaxing day at the spa, it's time to say farewell and begin your return journey, which can be a little more challenging. Turkey is not far away, so make sure you remain in Greek territorial waters. And study the charts carefully, keeping an eye on your position — there are rocks along the way, often hidden underwater, and you don't want to return the boat with a damaged hull.

YACHTING.COM TIP: Interested in sailing in Greece? Take a look at our guide to the top 7 sailing destinations in Greece for the best places to visit by boat. Greece is really worth visiting! Thanks to the largely sandy seabed, it's also a great place to drop anchor, so you won't be solely reliant on marinas and buoys. Greek people are also very friendly and not just after your money. In fact, frequently they don't charge you at all for a few hours at the jetty — a welcome change from other tourist destinations. 

3. Dodecanese archipelago: cruise around the island of Kos near Turkey

Route difficulty: Difficult

Route: Kos  Pserimos — Leros — Astypalaia — Tilos — Kos

Route length: 219 NM

Another so-called one-way option is to circumnavigate the island of Kos. This time, however, the route won't be sticking to just one island but will take in others of the Dodecanese archipelago, including a voyage on the open sea and a night crossing. Geographically, Kos is actually closer to Turkey than to mainland Greece and although the charter boat will likely come equipped with a Turkish flag, make sure you try to stay within Greek territorial waters. After all, Turkey is not in the EU and this could be seen as illegally trespassing. On your voyage, you might even encounter one of the destroyers defending the Turkish border and although according to COLREG rules, you have right of way when crossing the path of these massive vessels, we don't recommend it...

Blue white Greek flag and wind in a Greek harbour full of ships, Kos, Greece

A harbour full of boats on the island of Kos

Day 1: Kos

Stroll around the island's capital (or rent a bike from one of the many rental shops), stock up on supplies and don't forget to use the services of local stores that will gladly deliver your purchases to the pier.

Day 2: Kos -> Pserimos

As the crow flies, the island of Pserimos is about 8 NM from Kos and it is virtually uninhabited (there is a single village in the southern part of the island with around 80 permanent inhabitants). Anchor in the bay on the eastern side of the island, where you'll probably be by yourselves, to enjoy some peace and quiet. If you like diving, don't miss a visit to the nearby wreck of a Syrian transport ship sunk in 1997.

Day 3–4: Pserimos -> Leros -> Astypalaia

Your next stop will be the island of Leros, about 34 NM away. Dock at the pier in the town of Lakki, recharge your batteries, buy supplies and prepare for the night crossing to the island of Astypalaia located 23 NM southwest of Kos. If you have any concerns about the trip, take a look at our article on how to sail at night. After an exhausting night at the helm, relax on one of the island's beautiful beaches or explore the local rock formations. But expect to set sail early — you've got another 62 NM to Tilos.

Day 5–6: Astypalaia -> Tilos

The picturesque islet of Tilos is definitely worth the slight inconvenience of a longer crossing. Moor at the town pier in Livadia, where they are frequently generous enough to forget to ask you to pay. If there is not enough room, you will have to anchor stern-to at the pier with your bow at anchor (learn everything you need to know about this manoeuvre here). Grab some delicious seafood at one of the local tavernas and don't miss a visit to the nearby monastery.

The ruins of the abandoned village of Mikro Chorio on the Greek island of Tilos.

Ruins of the abandoned village of Mikro Chorio on the Greek island of Tilos

If you want to experience something unique and some authentic Greek culture, plan your trip so that you'll be here on July 27. That's the feast day of St. Panteleimon, the island's patron saint, ⁠on which the locals organize a feast to commemorate him at the Monastery of Agios Panteleimon in the mountains. The event can be reached by bus from Livadia — the ride through the winding mountain roads on a crowded bus is an experience in itself. Built on a cliff above the sea and on the site of a sacred spring, locals flock to the monastery, dancing and eating traditional Greek food, and have no problem welcoming tourists into their midst. Perhaps your greatest accomplishment here will be not tripping over or stepping on someone's foot during the traditional Greek circle dance. And don't forget that the tempo of the music is ever increasing.

Day 7: Tilos -> Kos

With your crowning moment behind you, it's time to head back to Kos to return the boat, about 47 NM away. May Saint Panteleimon accompany you on your final voyage and let's hope you'll be back in Greece again soon.

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