Greece is a popular destination for sailing enthusiasts, with its crystal-clear waters, scenic coastline, and numerous islands to explore. However, many sailors stick to the well-trodden routes and popular tourist destinations, missing out on the hidden gems that Greece has to offer.
If you’re looking for a unique sailing experience in Greece, consider going off the beaten track.
Off-the-beaten-track sailing in Greece means venturing away from over-tourism, crowded harbors, and touristy spots to explore the more secluded islands and beaches that few others visit. There are countless options for sailors looking to escape the crowds and discover the hidden treasures of Greece’s coastline.
Whether you’re a seasoned sailor or a first-time adventurer, sailing in Greece offers an unforgettable experience. With its stunning scenery, crystal-clear waters, and hidden gems, Greece is a paradise for those who love to explore the open seas.
So why not chart your own course and discover the hidden treasures of Greece’s coastline? Here are the best islands to escape the crowds this summer.
Off The Beaten Track Sailing In Greece: The Peloponnese
The Peloponnese is a sailor’s paradise, but is so often overlooked by people rushing through the Corinth Canal to reach the better-known Ionian or Sporades islands.
If you’re after a really unique sailing experience with (somewhat) reliable weather patterns and plenty of well-sheltered marinas and bays then the Peloponnese should be top of your list.
You will find plenty of remote anchorages along the way if you check the best apps for sailing before your trip, but here are some absolute must-stop destinations for anyone taking this route.
#1 Pylos
Pylos is a beautiful coastal town located in the southwestern part of the Peloponnese peninsula in Greece. With its picturesque harbor and crystal-clear waters, Pylos is the perfect destination for sailors and boating enthusiasts.
Sailing in Pylos offers an incredible opportunity to explore the stunning coastline, discover hidden coves and beaches, and experience the rich history and culture of the region.
One of the main attractions for sailors in Pylos is the natural harbor of Navarino Bay, which offers a sheltered and secure anchorage in shallow water with a sandy bottom. The bay is surrounded by hills and forests, and the water is calm and peaceful, making it an ideal spot for swimming, snorkeling, and other water activities.
The bay is also home to the impressive Navarino Castle, a fortress built by the Venetians in the 13th century that offers stunning views of the bay and the surrounding area. It’s free to enter, but make sure you’re a little careful when exploring as this site is not maintained. For the best views head up there at sunset.
Pylos town itself is also steeped in history, with many ancient ruins and archaeological sites to explore. One of the most impressive sites is the Palace of Nestor, an ancient Mycenaean palace that dates back to the 13th century BCE. The palace was discovered in the 1930s and is now open to the public, offering visitors a glimpse into the life and culture of the Mycenaean civilization.
There is a harbor in the town which you can use, but it’s worth noting that it has not been well maintained. The harbor is crowded with unused vessels and the bottom can be littered. If you prefer, you can anchor just outside the harbor. The anchorage has good holding but can become swelly in the wrong conditions. It’s best to visit here when the weather is calm.
#2 Methoni
Methoni is another great stop when sailing the Peloponnese. The anchorage here is well-sheltered and usually not too busy. You should have plenty of room to swing, and be able to stay here in most weather conditions.
One of the main attractions for sailors in Methoni is the Methoni Castle, a 13th-century fortress that dominates the town’s coastline. The castle is situated on a rocky promontory that juts out into the sea, and it offers stunning views of the surrounding area. The castle also has a small harbor, which provides a sheltered anchorage for smaller vessels.
Methoni is also known for its beautiful beaches, such as the long sandy beach of Methoni that stretches along the town’s coastline. The beach offers clear turquoise waters and is a great spot for swimming and sunbathing. Other nearby beaches include Lampes and Voidokilia, which are also known for their natural beauty and crystal-clear waters.
#3 Monemvasia
Monemvasia is an undiscovered gem and one of the best anchorages in all of Greece. It is a small fortified town located on a rocky island off the southeastern coast of the Peloponnese peninsula in Greece. You can anchor just below the rock for the most impressive view of the town, and although it isn’t the most sheltered, it is absolutely worth it for the photos alone.
If you find you arrive in not-so-favorable conditions you can use the harbor for a small fee. It’s small but well protected, with electricity and water. There is even a resident turtle or two, attracted by the fishing boats that unload daily.
Monemvasia itself is steeped in history, with numerous ancient ruins and historical sites to explore. The town’s main attraction is the Monemvasia Fortress, a well-preserved medieval fortress that dates back to the Byzantine period.
The fortress is situated on a rocky island connected to the mainland by a causeway, and it offers stunning views of the town and the surrounding area. Within the fortress, you can explore narrow streets and alleyways, ancient churches, and other historical buildings.
If you are feeling adventurous then make sure you trek all the way to the top of the rock where you’ll find the most incredible sunset views over the modern side of the town and the mountains beyond.
#4 Kyparissia
Kyparissia is the perfect off-the-beaten-track sailing destination in Greece. The little harbor is really well protected from most wind and swell directions. You can anchor out in the center of the harbor or use the town quay. Just be aware that the fishing vessels have priority, so you might be asked to move.
One of the main attractions for sailors in Kyparissia is the Kyparissia Castle, a 13th-century fortress that dominates the town’s coastline. The castle is situated on a rocky promontory that offers stunning views of the surrounding area and the harbor below.
Another popular spot in Kyparissia is the nearby beach of Ai Lagoudis. The beach is a long stretch of sand with crystal-clear waters and is a great spot for swimming and sunbathing. The beach is also surrounded by hills and forests, which makes it an ideal spot for hiking and exploring. It’s popular with locals and Greeks who holiday here, but you’ll find very few tourists.
Kyparissia is also known for its rich history and cultural heritage. The town has a long and storied past, with ancient ruins and historical sites scattered throughout the area. One of the most impressive sites is the ancient city of Messene, which is located a short distance from Kyparissia. Messene is an incredibly well-preserved ancient city that dates back to the 4th century BC and is a must-visit destination for history buffs and culture lovers.
Overall, sailing in Kyparissia offers an unforgettable experience, combining natural beauty and rich history. It’s perfect for anyone wanting a little taste of real local life.
Off The Beaten Track Sailing In Greece: The Cyclades
The Cyclades are home to some of Greece’s most popular islands, but it’s also possible to find quieter, more secluded islands here and they are some of the most beautiful in Greece. Home to the Meltemi winds, you should be aware before you head here.
For experienced sailors, the Cyclades is the perfect cruising ground. It’s dotted with plenty of islands, all with a huge range of well-protected anchorages. If you visit during the summer months it is very likely that you will get some pretty decent northerly winds to push your boat (and its crew) to the limits. You will want to keep your storm sails at the ready!
For less experienced sailors the Cyclades is better avoided, or visited in the shoulder season. The Meltemi winds blow for days at a time with wind speeds often reaching 40+ knots.
Regardless of your experience, if you’re sailing in this area make sure you have a well-thought-out route and be prepared to be flexible. Make sure you have scouted out anchorages on the south side of the islands you’re visiting.
#5 Serifos
If you’re chartering from Athens then Serifos is a great option. The island boasts crystal-clear waters, picturesque bays, ports, and often ideal weather conditions that make it a perfect spot for sailing enthusiasts.
Although you might experience the Meltemi here, it tends to blow less severely. If you’re keen to experience some windy conditions without the intensity or build up of waves and swell then Serifos is a great island to add to your itinerary.
One of the highlights of sailing in Serifos is the chance to explore its many secluded coves and beaches, which are only accessible by boat. Some of the most popular spots include Koutalas Bay, Sykamia Beach, and Vagia Bay, all of which offer tranquil and idyllic settings for swimming, snorkeling, or simply relaxing on the deck of your sailboat.
Chora, the island’s capital, is built on a hill and features narrow alleys, white-washed houses, and stunning views of the Aegean Sea. Livadi is the main port of Serifos and offers plenty of restaurants, cafes, and shops where sailors can stock up on supplies.
The harbor here is small and can be crowded with charter boats, but you can anchor just outside in a protected bay. Just be aware that the holding isn’t the best. Make sure you’re anchored in sand before heading to shore!
#6 Kimolos
Kimolos is a small island in the Cyclades found just next to the more popular island of Milos. In fact, there are three islands all within very short sailing distance of each making this area a bit of a sailors’ playground.
If the weather is looking suspect for one anchorage it’s easy to duck out to another, and the three islands are close enough to offer decent protection from waves.
One of the main attractions for sailors in Kimolos is the island’s stunning beaches. Kimolos is known for its unspoiled natural beauty and pristine beaches, which are among the best in the Cyclades. Some of the most popular beaches include Prassa, Aliki, and Bonatsa, all of which offer crystal-clear waters, soft white sand, and stunning views of the surrounding area. The beaches are also relatively uncrowded, which makes them ideal for swimming, sunbathing, and other water activities.
Another popular spot for sailors in Kimolos is the island’s picturesque harbor. The harbor is situated in the main town of Kimolos, and it offers a sheltered anchorage for boats. The town itself is a charming and picturesque village, with narrow streets and whitewashed buildings. The harbor is also home to numerous tavernas and restaurants, where you can sample local specialties such as fresh seafood, grilled meats, and traditional Greek dishes.
The main chora in Kimolos is a short walk up the hill and has fantastic views of Milos and beyond. You’ll love exploring the white-washed streets and quaint little alleyways which have a unique charm.
#7 Astypalea
Astypalea is a little out of the way, which is probably the only reason it doesn’t make it onto more people’s Greek island-hopping routes. It’s thought to be an unspoiled Santorini, and it’s easy to see why.
The only negative thing about this island (in a sea of positives!) is that it’s pretty far off most people’s usual sailing routes. If you head down here during the summer months then you should be prepared to wait a while for a decent weather window to sail north again.
The Meltemi winds and leftover swell can have you pinned down on this island for a lot longer than you’d expect, so if you charter here then don’t put yourself under any time pressure!
One of the best things about sailing in Astypalea is the variety of places to explore. There are many coves and bays around the island where you can drop anchor and enjoy a swim or a picnic.
Some of the most popular spots include Livadi Bay, Maltezana Bay, and Koutsomiti Beach, all of which are known for their crystal-clear waters and scenic surroundings. But there are numerous other secluded anchorages to explore if you prefer a little peace.
In addition to the natural beauty of the island, Astypalea is also home to some charming and traditional villages that are worth visiting. Chora, the island’s capital, is built on a hill and features narrow streets, whitewashed houses, and stunning views of the sea. Make sure you visit the traditional Greek windmills that line the lower streets.
Off The Beaten Track Sailing In Greece: The Dodecanese
The Dodecanese has some of the best cruising grounds in the whole of Greece, but because places like Santorini and Corfu are generally better known it tends to be a little overlooked.
During the summer months, you will get some strong winds from the Meltemi, but less so than the Cyclades.
The season tends to extend a little longer here, with decent weather for sailing well into October and even November (though swimming gets a little chillier!) You won’t be wrestling with strong northerlies in the shoulder months but you might experience a few violent storms instead.
Here are some of the best islands to head to for some off-the-beaten-path sailing in the Dodecanese.
#8 Patmos
Patmos has some beautiful anchorages on its southern shores that are well-protected and quiet. The island is an interesting shape, with many small bays tucked into larger bays, offering great shelter from swell and waves.
If you’re into freediving and spearfishing then Patmos has some great fishing spots too. You don’t need to venture far from most anchorages here to find an abundance of underwater life.
Patmos is home to some charming and traditional villages that are worth visiting, such as Chora, Skala, and Grikos. Chora is the island’s capital and is famous for its beautiful architecture and narrow streets, while Skala is the main port of Patmos and offers plenty of restaurants, cafes, and shops where sailors can stock up on supplies.
One of the main attractions for sailors in Patmos is the island’s rich history and cultural heritage. The Monastery of Saint John the Theologian, located in Chora, is a UNESCO World Heritage Site and is one of the most significant religious sites in Greece.
The cave of the Apocalypse, where Saint John the Theologian wrote the Book of Revelation, is also located on the island and is a must-visit destination for history buffs.
#9 Lipsi
Lipsi is a beautiful and unspoiled Greek island located in the Aegean Sea, and it’s an ideal destination for sailing enthusiasts. The island boasts crystal-clear waters, picturesque bays, and charming ports that offer a unique and unforgettable sailing experience.
One of the main attractions for sailors in Lipsi is the island’s peaceful and unspoiled atmosphere. The island is relatively untouched by mass tourism and offers a tranquil and authentic Greek island experience. The locals are friendly and welcoming, and the island’s traditional way of life is still very much alive.
Lipsi is also home to several charming villages, such as Lipsi Town and Kambos, that are worth exploring on foot. Lipsi Town, the main port of the island, offers plenty of restaurants, cafes, and shops where sailors can stock up on supplies. Kambos, on the other hand, is a picturesque village located on a hill and offers stunning views of the surrounding sea.
There are also several small rocky outcrops surrounding Lipsi that are a half an hour’s sail away. You can day anchor by them for some incredible snorkeling and free diving, with a few exciting swim-throughs. Or simply enjoy having the white stone beaches all to yourself!
#10 Kalymnos
Kalymnos is best known as a climbing destination, so if you’re keen to explore a little on land after a good days sail then head here.
The landscape on Kalymnos is breathtaking and will appeal to climbers and hikers alike. Even if you’re not one for exercise on foot then you’ll be keen to get up high and take in the views.
There are several charming villages in Kalymnos, such as Pothia, Massouri, and Myrties. Pothia is the island’s capital and offers a lively atmosphere, with plenty of shops, restaurants, and cafes. Massouri and Myrties, on the other hand, are more laid-back villages that offer stunning views of the surrounding sea.
The island is famous for its sponge diving tradition, which dates back to ancient times, and visitors can learn more about this fascinating industry at the Kalymnos Maritime Museum.
Conclusion: Off The Beaten Track Sailing In Greece
Greece is known worldwide for its idyllic islands, crystal-clear waters, and picturesque ports, making it one of the most popular destinations for sailing enthusiasts. However, many of the more well-known islands can get crowded, especially during the peak season.
For those looking for a more peaceful and authentic sailing experience, as you can see there are plenty of lesser-known Greek islands that offer unspoiled natural beauty, traditional Greek culture, and tranquil sailing conditions.
Overall, sailing in the lesser-known Greek islands offers a unique and authentic Greek island experience that combines the joy of sailing with the beauty of the Aegean Sea.
These islands are a perfect spot for those who want to experience the real Greece and explore some of the hidden gems of the Aegean.
Emily Nancolas is the author of the travel blog Two Get Lost, where she writes about her sailing adventures living on board a 38ft sailboat in the Mediterranean. Emily sailed the Greek islands for four years, visiting some of the more remote and beautiful destinations in this beautiful country and immersing herself in Greek culture.
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