Sailing in Greece
Greece is genuinely as pretty as a picture. Those stunning island views, the white sandy beaches and the whitewashed houses are all just as you probably imagined them. What that means is that you’ll get one of those ‘Wow’ moments, probably every day while sailing in Greece.
Finding a sailboat or catamaran rental to explore the stunning Greek islands is one of the best ways to see this fantastic country and it’s beautiful islands. There are over 6,000 islands in the Greek archipelago, with 227 of these containing permanent settlements. What this means is there are plenty of places to rent a yacht and get sailing in Greece.
Island Hopping
One of the most popular ways to explore the stunning Greek seas is by island hopping. Many use ferries to get between the most popular islands, but by using a private sailboat or catamaran rental you can see the best that Greece has to offer. Spend a few days, or a week, finding quaint fishing villages, mooring in bays lapped by crystal waters, and discovering your own slice of Greek paradise.
By enjoying a week on a sailboat or catamaran rental in Greece you’ll get to call the high seas home and visit a different port every day, if you choose. The Cyclades and the Dodecanese are two of the most famous islands for hopping with some of the most beautiful in the Mediterranean to explore at your leisure.
The Cyclades Islands
This archipelago is situated south of Athens, between the mainland and Crete. Some of the most famous islands in the Cyclades include Mykonos, Santorini and Paros. You’ll find plenty of opportunities to rent a yacht across the Cyclades and explore these beautiful islands as a day trip, or a longer charter.
The beauty of exploring when you rent a yacht in Greece is that you can choose what kind of sailing holidays you want. Looking for vibrant towns with nightlife and music? Mykonos is where many choose to go for a great party, with nightclubs and bars to tempt you into the early hours.
Prefer a more sedate and laid back feel on your sailing vacation? Set sail to Ios or Donousa to enjoy a slower pace of life and a more relaxed way to enjoy your glass of wine at sunset
Of course, Santorini is one of the picture postcard images of a Greek island. Arriving into the caldera of Santorini by chartered sailboat is one of the most unforgettable ways to experience this stunning island.
Dodecanese Islands
This cluster of islands sits closer to Turkey than to mainland Greece. The Dodecanese have a vibe all of their own, and some great opportunities for amazing sailing holidays in Greece. Hire a Sailo boat in Kos and explore neighboring islands such as Pserimos, Kalimnos and Nisyros. Some of these little explored islands make a great stop as part of either a day trip or to explore on a week-long sailing trip.
Like most places in Greece, many of the Dodecanese islands are dotted with old fortresses and fortifications, scenic walking routes and sleepy villages just begging for you to stop for a sundowner.
Another of the most popular places to explore is Rhodes, one of the biggest of the Greek Islands. The north coast of Rhodes is relatively unspoiled and a great place to moor your catamaran rental for some uninterrupted relaxation far from the madding crowds.
Island hopping between the Dodecanese and Cyclades islands is perfect if you rent a yacht from Sailo for a week or more. In fact, choosing the islands to stop at on your island hopping adventure could be the biggest challenge before you start your Greek island adventure.
Ionian Islands
On the western side of the Greek mainland, you’ll find the Ionian islands. This cluster includes some other familiar names such as Zakynthos (Zante), Corfu and Kefalonia.
Zakynthos is home to another of the most well known postcard images in Greece, with Navagio beach, known also as the shipwreck beach being a must visit. This is only accessible by boat, so why not arrive in style on your yacht charter and beat the crowds?
Rent a yacht from Corfu or Kefalonia is the perfect base for exploring the Ionian islands. If you’re looking for perfect seclusion then you’ll find plenty of opportunity to moor on your own private beach in the Ionian islands. Head to islands like Meganisi, Ithaka or even far flung corners of Corfu to find your own slice of Greek paradise.
No matter where you choose your starting point for sailing holidays in Greece, you’ll find plenty of choice for all types of sailboat charter with Sailo. From day trips, to weekly cruises aboard luxury yachts, you’ll find something to tempt you.
Top Sailing Itineraries in Greece
25 NM from last port
The first stop of your sailing in Greece brings you to the city of Methana. Get your camera ready to capture the striking landscape, home to 32 volcanoes! Take advantage and hike to one of the craters, or visit the volcanic beaches. Enjoy the hot springs, like the five sulfur springs at the center of the city.
16 NM from last port
Take a step back in time and visit one of the popular museums about the 1821 War of Independence in Spetses. Also, stop by the cathedrals or travel by horse-drawn carriage to admire the rows of mansions. As one might expect when you go sailing in Greece, the beaches on this island are beautiful, the crystal-clear waters, perfect for swimming and snorkeling.
32 NM from last port
Poros is home to both rich history and natural beauty. Stop by the ruins of Poseidon's Temple or the historic monument of Russian Bay. Make sure to hike up to the clock tower for the best views of the sunset. Try your hand at watersports and the water-ski school or take it slow and spend your time at one of the beaches.
17 NM from last port
The Greek city of Aegina has an abundance of attractions to visit. The most notable site is the Temple of Athena which has remained in pristine condition and offers the best, hilltop view of the island. Continue on a cultural path by touring one of the many museums or the ghost village of Paleochora. You can also choose to drop anchor on your boat charter in Greece and hang by the busy marina or walk to the beaches for a more relaxing day.
13 NM from last port
Enjoy a relaxed sailing back to your home port. After a week in the Land of Gods, we know you’ll want more so make sure to check our itineraries in the Ionian islands and the Dodecanese archipelago. We are looking forward to welcoming you back on a Sailo yacht charter in Greece!
29 NM from last port
The beautiful island of Poros is home to both rich history and natural beauty. Dock your Sailo boat charter in Greece at the Poros Town harbor. Visit the impressive ruins of Poseidon's Temple and the beautiful Monastery of Zoodohos Pigi. Make sure to walk up to the clock tower for the best views of the island. For the best dinner in town, make a reservation at the waterfront Apagio Taverna!
46 NM from last port
Kythnos is first island you will visit in the western Cyclades. The island has over 70 beaches, many accessible only by boat. The one we love and also the most famous is the golden sandy beach of Kolona, located on the crescent-shaped isthmus on the northwest coast. We recommend choosing the Loutra harbor on the northeast coast of the island as your overnight anchorage spot.
23 NM from last port
Some might say this island outshines both Santorini and Mykonos. Serifos has a dramatic peaked landscape, beautiful beaches and a spectacular deep-blue Aegean, perfect for snorkeling and diving. Visit Chora town and walk up to the 15th century Venetian castle for a coffee with a fantastic view. Going back to your boat charter in Greece in port Livadi, you can rest on the beach and have dinner at one of the waterfront tavernas.
31 NM from last port
Sailing in Greece is a fantastic mix of going back to the beginning of the modern civilization, stunning natural beauty and friendly people welcoming you with some of the most delicious foods in the world. Your next stop in the Cyclades is Paros - the more affordable sister of the famous Mikonos. Parikia, the chic bayside capital, is the boating hub of the Cyclades.
30 NM from last port
Enjoy yourself in the famous Mykonos, the jet-set center of the Cyclades. Walk around the port, visit the windmills, eat at amazing restaurants or bars, and go shopping for souvenirs at the local markets. Our favorite Mykonos chill-out spot when going sailing in Greece is the elegant Buddha Bar Beach. Relax, try the signature cuisine and take in the breathtaking view over the Aegean sea.
60 NM from last port
Leaving behind Mykonos and its bohemian atmosphere, your next stop is on Kea - the closest of Cyclades to mainland and one of Athenians’ favorite weekend getaway. Drop anchor on your yacht charter in Greece in the small harbor of Vourkari (or the main port Korissa), go for a stroll along the colorful streets of Ioulida, and enjoy some beach time.
15 NM from last port
The fantastic Cape Sounion is considered by our local team in Greece the best spot to witness a breathtaking sunset over the Saronic Gulf. Anchor in the large bay of Anavissos and go visit the beautiful Temple of Poseidon, voted in top three historical attractions in Greece.
17 NM from last port
Your second stop in Poros could be very well a quest to find some of the best beaches in the Cyclades. For a relaxed day on board of your Sailo yacht charter in Greece and a quiet overnight, drop anchor in the small cove of Yerolimenas, on the westernmost end of the island. Or choose the Russian Bay as your base for the night and spend you day at Love Bay - the most beautiful beach on Poros.
17 NM from last port
Our last stop is the famous Aegina island, located in the middle of the Saronic gulf. Choose one of the two ports: Aegina or Perdikas to drop anchor on your boat charter in Greece and explore the island. A popular weekend destination for the locals, Aegina offers a good selection of fresh seafood waterfront restaurants in both Aegina town and Perdika. Do not miss the chance to visit spectacular 5th century Temple of Aphaia, and the impressive Byzantine Paleohora ruins.
13 NM from last port
The end of your sailing trip brings you back to Alimos. Your short ride back to Athens will bring a change of pace from the quieter destinations you have explored during your sailing in Greece on a Sailo yacht. Large and lively, Athens is the perfect place to spend some time adjusting to the city life before heading home.
30 NM from last port
Drop anchor at Kamares - the only harbor on the beautiful island of Sifnos - and take the bus to visit the 17th-century Chrisopigi monastery, built on top of a rocky cape. Spend a relaxed afternoon on the nearby Apokofto beach or head back to Kamares for dinner at one of the local tavernas. This island is particularly known for the traditional art of pottery and for its fine cooking.
28 NM from last port
Conde Nast Traveler once called Folegandros “Greece's most beautiful undiscovered island.” Moor at Karavostasi - the island’s only harbor - or choose the quieter southern bay Vathi to anchor your Sailo boat charter in Greece. Everything on this island is within walking distance.
30 NM from last port
The famous and probably one of the most photographed islands in Greece will welcome you with a fantastic panorama of whitewashed architecture on the backdrop of the most amazing azure Aegean sea. Island doesn’t offer too many secured anchorages. We recommend checking anchorage off the little pier in Ayios Nikolaos bay and take the ferry to Thira - the main island and the one you’d want to be on at sunset.
40 NM from last port
When you go sailing in Greece, every stop on your itinerary has something unique to offer. Amorgos has dazzling dramatic rocky landscape. While not the best island for beach-going, Amorgos is a destination where you will enjoy walking to admire the authentic architecture, diving or rock-climbing. Don’t miss the 11th-century Monastery of Hozoviotissa, with a breathtaking cliffside site and a fantastic view of the Aegean sea.
Starting Point
Lavrion (Lavrio) is the starting point of your sailing adventure in the Cyclades. Hop aboard your Sailo boat charter in Greece and get ready to enjoy the natural beauty, rich historical heritage, the wonderful people and the delicious Mediterranean cuisine of the Greek islands.
23 NM from last stop
Merichas is located on the western side of Kythnos - one of the low-key islands in the Cyclades, with a laid-back atmosphere and a typical landscape of rolling hills, green valleys and beautiful coves and beaches. Hop on the local bus for a short trip to the picturesque town of Chora. Go for a stroll along the narrow streets and small squares to admire the authentic Cycladic architecture.
50 NM from last stop
The beautiful town of Ermoupolis is the capital of Syros and the Cyclades. The remarkable rich historical tradition of Ermoupolis can still be admired in its well-preserved neoclassical architecture: old manors, marble paved streets and squares, and monumental churches. Visit the impressive Miaouli Square, built in the 19th-century and considered one of the most beautiful neoclassical squares in Greece.
27 NM from last stop
Mykonos - the jet-set center of Cyclades - is a mix of glam and glitz St Tropez style with and nonstop party Ibiza atmosphere. Your stop on Mykonos is the perfect chance to enjoy fine dining at one of the many chic restaurants around and later join the happy crowd at one of the many clubs opened till morning.
44 NM from last stop
Leave behind the glamorous Mykonos and set sail on your Sailo yacht charter in Greece to one of the less touristic islands in the Cyclades - Andros. Check out Batsi port as a quieter alternative to Gavrion, the main harbor on the island. Visit the lovely Batsi village and beach, and the close-by ancient town of Paleopolis. Check out the local stores for souvenirs and have a quiet dinner at one of the tavernas overlooking the bay and the charming little fishing port.
25 NM from last stop
The typical landscape of Cyclades changes quite a bit on Kea island - your last stop before heading back to your home port Lavrion. The whitewashed houses with blue rooftops are replaced here with the summer houses of Athenians, painted in earthy colors. Drop anchor in Korissia and visit Ioulia, the capital of the island. For a dinner with a sweeping view of the Aegean sea, try To Spiti Sti Hora tavern on top of a hill overlooking the town.
11 NM from last port
Your first stop will be the little port town on Palairos, located on mainland at the southern end of the Lefkas channel. Unpretentious and still retaining the traditional Greek village feeling, Palairos has a pebbly beach and a lot of hidden coves for you to explore. Have dinner at one of the waterfront tavernas and get ready to set sail in the early morning.
16 NM from last port
Kalamos is a little island with a dramatic landscape of high mountains and steep cliffs almost plunging into the deep-blue waters of the Ionian sea. A popular overnight stop for sailing enthusiasts, the island offers two anchorage spots: the main port located close to Kalamos town, and the small Episkopi harbor on the northern side of the island (safe only on settled weather). No matter which one you’ll choose, there’s a walking distance between the two of them so you can wander around and enjoy the unspoiled landscape.
5 NM from last port
Go for a relaxed short sail to Kastos - a small island with only one village located on the SE side. Take in the beautiful scenery - lush green hills and azure, crystal clear waters, secluded bays and pebbly wild beaches. Enjoy a delicious Greek meal at one of the waterfront tavernas.
10 NM from last port
The peaceful Meganisi is welcoming you with a serene, typical Greek atmosphere. Sail around the island and drop anchor to go for a swim and relax on board of your Sailo yacht charter in Greece. Anchor for the night in Port Vathi, close to the picturesque village with the same name and take a stroll along the beach.
16 NM from last port
Your next stop is the beautiful village in Sivota on the Lefkada island, well known for its natural beauty, the long sandy beaches nearby and the blue crystalline waters, perfect for swimming. Enjoy dinner at one of the waterfront tavernas and make the best of your last night of your sailing in Greece.
11 NM from the last port
Set sail to the enigmatic little island of Pserimos and drop anchor in the cove on the western side. Walk up this island without streets to one of the soft white sand beaches and relax for the day. Our personal favorite beach is Grafiotissa - half an hour walk from the village.
21 NM from last port
Head to Leros and drop anchor on your yacht charter in Greece at the main port - Lakki. Set foot to this unusual Greek town with a 1930 modern architecture style. The seafront is dominated by monumental buildings, the streets are wide and the entire city landscape tells a story about the Italian occupation during WWII.
43 NM from last port
Your stop on Astypalaia - the butterfly-shaped island very close to Cyclades - is the chance to relax on one of the off-the-beaten track islands in the Dodecanese. Enjoy the spectacular landscape, the fantastic beaches (insider tip: Kaminakia is the most beautiful one) and walk up to the 13th-century castle for a breathtaking view over the island and the bluer-than-blue Aegean sea.
18 NM from last port
Get a day away from the hoards of tourists coming ashore from the big cruisers and visit the rather remote Tilos - Greece’s “green island”. The entire island is a nature reserve, where you will get the chance to see rare orchids and endangered species of birds. Spend your day in privacy on one of island’s beaches and head to Livadia for fresh seafood dinner at one of the local tavernas.
35 NM from last port
Sailing in Greece is a permanent discovery of new and fascinating places, each unique in its own way. The picture-perfect Symi has by far one of most charming ports in Greece. The harbor is located on the backdrop of 19th-century neoclassical manors built on abrupt slopes. Check out the two main beaches: Ayios Yiorgos Disalonas or Marathounda - both accessible only by boat.
14 NM from last stop
Your first stop will be in the middle of the Saronic gulf, on Aegina island. You can choose to drop anchor in Aegina harbor or in Perdikas, 3.5 miles SSE of the main port. Visit the island’s most impressive landmark: the 5th-century BCE well-preserved temple of Aphaia or go for a stroll along Aegina’s waterfront. Try the pistachios, the almonds or the figs locally produced.
26 NM from last stop
The car-free island of Hydra is a popular vacation spot for both Greeks and boating enthusiasts from around the world. The uplifting charm of Hydra town, the sun-drenched beaches and the crystalline waters of the Aegean are the perfect backdrop for a relaxed summer day on your yacht charter in Greece. In the evening stop by at the Pirate Bar to enjoy a drink and homemade traditional Greek meal.
15 NM from last stop
Set sail to one of the most protected harbors in the region - Porto Cheli - nicknamed “The Peloponnesian Riviera”. Go for a relaxed sail to admire the typical jet-set decor: majestic vacation mansions, private white-sand beaches, and mega-yachts lining up the shores. Drop anchor and head to Nikki Beach where you can hang around with the locals, grab a street meal and take a hike to the archaeological sites of Ancient Halieis and the Franchthi cave.
22 NM from last stop
Nafplio is one of our favorite Greek cities and a must on list your places to visit while sailing in Greece. The charming seaport, with the impressive Palamidi Venetian fortress overlooking the bay, is gate to a romantic little town. Enjoy a walk along the narrow cobbled streets to admire the Venetian mansions, stop for coffee at one of the many chic cafes and shop for souvenirs.
23 NM from last stop
Set sail to the the gorgeous eastern coast of the Peloponnese and drop anchor at Plaka, the small town harbor. Located at the foot of mount Parnon, the region is famous for the sweet “tsakóniki” aubergine. Don’t miss the chance to taste the local dishes and burn those calories with a session of watersports!
10 NM from last stop
Kyparissi is a quaint village with beautiful beaches and spectacular ocean views on the backdrop of high mountains. Drop anchor on your boat charter in Greece and take a stroll around the little harbor, go for a hike to Taverna Tiris (the beach below is also a very good overnight anchorage).
13 NM from last stop
The fortress town of Monemvasia is perched on a little peninsula. Explore the main town to admire the superb mix of Byzantine, Venetian and Ottoman influences. Or choose from one of the 50 beaches and hidden coves, perfect for sunbathing and swimming. The region is also famous for the Malvasia grapes (used to make the Madeira wines), so make sure you stop by one of the local tavernas and try the local wine!!
41 NM from last stop
Spetses island is internationally recognized for the role played in Greece’s war against the Ottoman Empire - it was the first of the Greek islands to raise the revolution flag. Besides the rich historical heritage, the island is also known for the quiet atmosphere, the pristine beaches hidden in coves lined up by lush green pine trees.
12 NM from last stop
The last stop of your sailing in Greece will be in Poros - “The Island of Poseidon”. Check out the ruins of the Doric temple dedicated to the mighty god of all seas, dating back to year 520 BCE. Go for a walk along the lively waterfront, shop for souvenirs and stop by at the family-owned Apagio Taverna to hang with the locals over a delicious home-cooked meal.