Top Sailing Itineraries: Greece

/ Published in Greece

Top Sailing Itineraries: Greece

With the start of the Greek sailing season only a few weeks away, we thought it’d be fitting to feature some of our charter guests’ favorite Greece sailing itineraries

Whether you experience exotic sailing in the Saronic Gulf or the Cyclades, Greece offers some of the most beautiful sailing in the world, an archipelago filled with quaint coastal villages, beautiful nature, world-class cuisine, and impressive historical sites. Navigare Yachting was awarded a 2023 Tripadvisor Travelers’ Choice Award for our exceptional sailing charters in our Greece destination, so you’re assured an unforgettable getaway with our highly-reviewed team.

At our Mediterranean bases, the check-in and checkout are on Saturdays and the minimum charter duration is 7 days (the check-in day and the checkout day together count as one day).

We’ve chosen to feature one sailing itinerary for 7 days and one for 14 days. On the destination page for Greece on our website, you can find an additional 7-day sailing itinerary which is simply a shorter version of the 14-day sailing route. For additional itinerary inspiration that may come in handy when you plan your Greece sailing charter, check out our blog (here and here).


7 DAYS The Saronic Gulf

Day 1 Saturday: Elliniko (Athens) - Perdika (Aegina)

After provisioning and checking in, it is time to board your yacht and begin your Greek sailing adventures. Sail in the southwest direction from Elliniko where our base is located to the picturesque island of Aegina and the fishing village Perdika. 

Many claim Perdika is the most beautiful village on Aegina and it’s clear to see why it has captivated visitors for centuries. Enjoy the relaxed atmosphere as you stroll the narrow streets framed with whitewashed buildings and enjoy a delicious seafood meal with a waterfront view. 

Across from Perdika, there are two islets called Moni and Angistri. The coves and caves in this area are teeming with sea life, so it’s a great snorkeling or diving spot. 

Day 2 Sunday: Perdika (Aegina) to Poros

The next day, leave Perdika and head to the island Poros and the fishing village with the same name. The island’s proximity to the mainland makes Poros a popular day-trip destination from Athens. The lively island vibes combined with the traditional Greek village charm have people returning to this place again and again. 

If you travel in the high season, make sure to arrive by early afternoon at the latest, to get a docking spot. Big yachts, small fishing boats, and everything in between share the same marina, so it fills up quickly. 

If you decide to eat dinner or lunch ashore in Poros, we highly recommend the restaurant, Oasis. The owner always gives our clients a warm welcome and is friends with some of our skippers. 

Day 3 Monday: Poros to Hydra 

Continue your sailing journey southeast to the island of Hydra. This is easily one of the most scenic islands in the Saronic Gulf, with beautiful nature and a fishing village that reaches from the harbor and up the hills. 

As you enter the bay, you will be greeted by a vibrant display of buildings, portside cafes and restaurants, and people. Cobblestone streets, churches, beautiful architecture, and donkeys make Hydra a memorable stop on your sailing trip. The absence of cars only adds to the allure and facilitates for pedestrians to walk the streets. Instead of motorized vehicles, the primary means of transportation are carriages drawn by donkeys and simply traveling by foot. Hydra has a relaxed and romantic atmosphere yet is also known for its nightlife. 

Day 4 Tuesday: Hydra to Spetses

As you sail further west, you will find the beautiful island of Spetses, a favorite destination among jet setters. Sophistication and elegance meet the traditional Greek island charm at this picturesque coastal village with the same name (Spetses). 

From the waterfront mansions and rare natural beauty to the small boutique shops and cafes framing the car-free streets, this island is likely to romanticize even the most well-traveled person. 

As you explore the outskirts of Spetses by foot or by bike, you can find some hidden beaches or coves, perfect for an afternoon swim, or simply to relax before the evening settles in and it’s time for a local dinner in the town or on your yacht.

Day 5 Wednesday: Spetses to Ermioni

As you turn around and make your way northeast, Ermioni is the ideal next stop on your sailing charter in the Saronic Gulf. 

Ermioni, a coastal city on the southeast side of the Argolid peninsula, has a rich history and culture yet is well-suited for tourists with a variety of restaurants, shops, and museums. 

Whether you decide to go paddle boarding in the bay or step ashore, visit a museum, and enjoy authentic Greek cuisine at a restaurant, Ermioni has something for everyone and embodies everything typical of a sailing vacation in Greece.

Day 6 Thursday: Ermioni to Aegina

Return to the beautiful island of Aegina and this time visit the coastal city with the same name. The city of Aegina is the capital of the island and offers a glimpse into the past. Well-preserved historical buildings and impressive churches (such as the St. Nicholas Church) will transport you back to a time when a lot of wealth was invested in the city. 

For the history enthusiast, this place features several well-preserved archeological sites on the hill outside of the city, such as the Archeological Site of Palaiochora of Aegina, the Chapel of Saint Nicholas, and the Holy Monastery of the Holy Trinity. 

Instead of visiting the city of Aegina, another option is to go back to Perdika a second time if you want to explore it further. 

Day 7 Friday: Aegina to Elliniko (Athens)

Once you are done exploring Aegina, make the last sailing trip across the Saronic Gulf back to our base in Agios Kosmas Marina in Elliniko. 

The checkout is the following day, but we recommend returning to the marina on Friday by 6 pm. Fill up the tanks either this night or the following morning before checking out. 

In the meantime, spend a relaxed afternoon in Elliniko, an authentic, less touristy part of Athens. Perhaps spend a few hours here and go for a walk in the modern Ellinikon Experience Park or make a trip to the city of Athens. Here is more inspiration for things to do in Athens

Saturday: Checkout

After breakfast, disembark and check out by 9 am. 

More information about check-in and checkout is available here

14 DAYS The Cyclades

Day 1 Saturday: Elliniko (Athens)

Provision and check-in at our base in Agios Kosmas Marina in Elliniko. Spend your first night onboard the yacht in the marina and enjoy Elliniko for a few hours. 

Day 2 Sunday: Elliniko (Athens) to Cape Sounion

After breakfast the next morning, set sail and follow the coastline of the Attica peninsula in a southward direction until you reach Cape Sounion where the Temple of Poseidon is located. Akra Sounio, while not a harbor, is a good nearby bay to anchor. Admire the temple from a distance, perhaps from one of the lookout points, or make the short walk to the top of the cape to explore it. It’s also a great day to enjoy the waters by swimming or through watersports activities. Return to the boat for the night. 

Day 3 Monday: Cape Sounion to Loutra (Kithnos)

Continue your sailing journey south to Loutra, a quaint village on the island of Kithnos. Loutra is a beautiful village, with traditional whitewashed buildings and a harbor lined with restaurants serving up delicious Mediterranean meals. Their outdoor seating areas reach to the water’s edge on the beach. 

At the south end of the village, there is a beach featuring hot springs, that form little natural hot tubs by the shoreline. This is a perfect opportunity to enjoy the water if you are going in the shoulder season before the rest of the ocean has warmed up. The water in the springs is also said to have healing properties.

Day 4 Tuesday: Loutra (Kithnos) to Finikas (Siros)

Set sail to the east towards the island Siros, which is the capital island of the Cyclades. There is a village on its southwest coast, called Finikas, where you can dock or moor your boat. 

While Finikas is nice, we recommend a visit to the city of Ermoupoli on the opposite coast of Siros. It’s not hard to get there from Finikas as both buses and taxis travel between the two cities. Ermoupoli is a unique picturesque city with brick houses, and streets and plazas made of marble! Walk the fancy streets, admire the architecture, and get a glimpse of the rich (literally!) history of this place through museums. Return to Finikas and your boat for the night. 

Day 5 Wednesday: Finikas (Siros) to Mykonos

Sail the 25 nautical miles from Finikas to the famous island of Mykonos. From the harbor where the ferries dock, the town of Mykonos is 2 km south and you can get there either by walking, renting a bike, or taking a taxi. As you may have guessed, this city can get uncomfortably crowded, especially in the summer months, but if you enjoy lively nightlife, you have come to the right place. 

You may then travel a little further south to the city of Dilos, which is far less crowded than Mykonos and has a very rich history. Legend has it that the sun god Apollo was born here and it just so happens that Dilos has a track record of being one of the sunniest places in the world.

Day 6 Thursday: Mykonos to Paros (Lefkas)

Next, set sail to the island of Lefkas and the coastal village of Paros. Walk the tiled streets between the whitewashed houses so typical of Mediterranean coastal cities. Here you can find plenty of cafes and boutiques where you can buy some handcrafted gifts. 

Day 7 Friday: Paros (Lefkas) to Schinousa

Arriving at the island of Schinousa is like finding a peaceful oasis in the lively Greek archipelago. Enjoy tranquility combined with the typical Greek charm. The relaxed vibes are usually combined with calm weather, even when the Meltemi winds are blowing. 

Next to the Schinousa, there is another island called Iraklia, and to the west of Iraklia in a bay, you find a buoy. If you look down in the shallow water where the buoy is floating, you will see a small plane from World War II on the bottom of the sea floor.

Day 8 Saturday: Schinousa to Chora (Amorgos)

Sail east from Schinousa to the island of Amorgos. Up on the hill on the east coast, there is a beautiful village called Chora that’s worth a visit. There is a pretty lighthouse down at the harbor and an impressive whitewashed monastery attached to the side of a mountain, but the roads there can be a bit slippery, especially after the rain. Overall, Chora is the perfect place to just walk the cobblestone streets, and enjoy the Greek local cuisine and the scenic views.

Day 9 Sunday: Chora (Amorgos) to Ios

If you are into the Greek nightlife scene, you will be happy with the next stop: the party island, Ios. Choose from a variety of pubs, bars, cafes and restaurants. Ios also features nice sandy beaches and some historical sites such as Odyseas Elytis Amphitheater and the Tomb of Homer. 

Day 10 Monday: Ios to Kamares (Sifnos)

On your sail north, stop by the port town Vathi in Sifnos and then make your way to Kamares (also Sifnos) a short sail north of Vathi. Kamares is a larger port city where you can go for a swim in the clear water, enjoy the culinary delights, or hike in the mountains.

Day 11 Tuesday: Kamares (Sifnos) to Serifos

26 nautical miles north of Sifnos is the island Serifos. Enjoy the sand beaches here with crystal clear blue water, do some watersport activities, or go snorkeling. In the port town of Livadi, you can have dinner by the water at one of the restaurants in the harbor. Some of the tables are right by the shoreline so the waves are only a few feet away.

Day 12 Wednesday: Serifos to Kithnos

From Serifos, you continue to sail north back to the island of Kithnos. Here you can stop by some secluded bays and beaches for some watersports activities or make a stop in a harbor, for example, the harbor of Merihas. 

Merihas is a small fishing village that has kept its traditional look throughout the years. While the people here may not speak English very well, they are very hospitable and warm, so it’s not hard to communicate with them. 

If you are interested in history, you may enjoy a trip to the ancient ruin of Vryokatsro, or the scenic whitewashed monastery, Panagia Flambouriani, built on a hill south of Merihas with a beautiful view of the bay. 

Day 13 Thursday: Kithnos to Kea

The next day, continue about 20 nautical miles north from Kithnos, to the gorgeous island Kea. Make a stop here and anchor or moor either in the main port of Coressia or in the Vourkari Bay. 

This is an interesting place if you are a diver as the sea bottom in this area has many shipwrecks. The lack of tourists in this city only adds to its mysterious vibes. The reason that this place has not been a typical tourist destination is that getting here has been tricky for centuries due to the absence of a connecting ferry line from Athens, even though it is the closest Cycladic island to the Greek mainland. 

If the weather allows and if the radar predicts light north winds, stay in the southwest bay of Kea and go for a morning swim in the clear water the next day. 

Day 14 Friday: Kea to Ellinko

It’s 35 nautical miles from Kea to Ellinko in Athens where our base is located, so you don’t need to stress to get back. The checkout is the following day, but we recommend to return to the marina on Friday by 6 pm. Fill up the tanks either this night or the following morning before checking out. 

For the rest of the day, you are free to explore Elliniko, which is a wonderful, less touristy neighborhood of Athens. Walk in the modern Ellinikon Experience Park and enjoy dining at authentic restaurants at local prices. Here is more inspiration for things to do in Athens

Saturday: Checkout

After breakfast, disembark and check out by 9 am. 

More information about check-in and checkout is available here

Since 2001, over 350,000+ charter guests have set sail with Navigare - it’s safe to say that your yachting adventure will be in capable hands. With 12 exotic locations worldwide, the possibilities are endless! Whether you're an experienced sailor or a first-time adventurer, Navigare Yachting opens up a world of exploration, discovery, and sailing that comes with complete peace of mind.

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