Icy waters and snow have replaced the long, sweltering days of summer. Some sailors prefer the challenge of cold weather and set sail eagerly. Others, however, are not as inclined, in which case a sabbatical to the Mediterranean climate of Greece may be in order.


The average daily temperature in Greece during the warm season, June through September, is 83 degrees Fahrenheit. The short cold season averages a temperature that rarely dips below 60 degrees. Greece and all of its island wonders are optimal destinations to travel to during the winter. This guide brings you the five best locations to island-hop in Greece that will keep the captain, crew, and passengers entertained no matter the length of the journey. 

Santorini of the Cyclades Islands

Santorini is known for romantic getaways, stunning sunsets, and amazing island-hopping. With beaches of red and black sand, surrounded by crisp blue and white architecture, this island is at the top of any vacationer’s list. The steep cliffs, clear waters, and green fields of the island, along with stunning sunsets, complete the renowned landscape. Explore Perissa and Oia, book a catamaran charter, or rent kayaks for an adventure in Santorini. Yachting and cruising among the islands will make for a relaxing vacation on Santorini. 

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Crete Island in Greece

The largest of the Greek islands, Crete will host any boater with ease. Renting a boat in Crete is a great way to spend time on the island. The population of approximately 650,000 is spread across the island, enticing travelers with culture, tasty cuisine, secluded villages, and tourist attractions. If you are cruising the shoreline, pristine beaches and crystal clear water are in abundance. Kayaking is also a popular daytime attraction while island exploration and day excursions by watercraft offer endless exploration. 

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Mykonos of the Cyclades Islands

Boasting the best beaches in the country and a lively nightlife, boaters that choose to visit Mykonos will have the best of both worlds. Catamaran charters are popular in Mykonos and are great for day trips and island hopping. Beautiful beaches, immaculate waters, and dreamy landscapes will optimize relaxation while the fast-paced evenings, full of fine dining and dancing, will entertain all night.

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Hydra, Saronic Gulf

Hydra Island’s ban on high-rise buildings, cars, and motorbikes is only one of the reasons it attracts locals and travelers alike. The island’s largely uninhabited interior sets the stage for quaint villages on the shores of the island. A smattering of small monasteries, galleries, and museums in 18th-century mansions demonstrates the quiet pace of everyday life on Hydra. Most of the beaches are rocky or pebbly, but that does not stop sunbathers from choosing a favorite and lounging in the sun. 

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Milos of the Cyclades Islands

Milos is an island defined by its landscape of prominent sea-shaped rocks in gold, brown, and sandy-white hues. The island’s beaches add more color in splashes of red, white, gray, and gold. White-washed fishing villages or quiet towns make perfect day excursions while exploration of the many coves the island has to offer is a viable option by watercraft.

Alonnisos of the Sporades Islands

Alonnisos boasts Greece’s first national marine park. The main city where you can rent a boat is Patitiri. The stark white, cubed architecture of the villages, the pine forests, and rolling green hills set it apart from many of its neighboring rocky islands. Various coves and bays offer refuge from the open (yet tranquil all the same) sea while white beaches against the turquoise waters make for a memorable landscape. Nearby islands include Skopelos and Skiathos and both make for great day trips.

Kastelorizo of the Dodecanese Islands

Kastelorizo is the smallest of the Greek islands and it is inhabited year-round. It is also the furthest from Athens. Small, colorful houses complement the turquoise sea and white beaches that surround the Island. Kastelorizo excursions include the Blue Grotto, a sea cave lit by refracted sunlight, and St. George for sunbathing or snorkeling. Hiking is abundant in the interior, and the local fares will not disappoint.

Ithaca of the Ionian Islands

The island of Ithaca lives up to its mythological history as the homeland of Homer’s Odysseus. A gem in the turquoise sea, this island is both lush, covered with dense forests, as well as barren, boasting intermittent sand dunes. This island makes for a perfect educational pit stop on any boater’s island-hopping adventure, riddled with hiking and cycling paths that wind through the scenery sprinkled with ruins. 

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Syros of the Cyclades Islands

While Syros has a favorite of tourists in the past, Athenians have recently been taken with its charm. This tiny island is brimming with Greek fare, music, and culture. Outside of the small port cities that line the coasts, climbing the stairs to the top of St. George Church presents a breathtaking panoramic view of the six neighboring islands. After descending to the shorelines, visiting the islands closest to Syros is the next step.

So if you are a warm-blooded sailor, and want to dock for a day in a small village or stay anchored as sea in a small cove to get away from the chilly winter, Greece is the place for you. The diversity of the Greek islands, the robust culture and history as well as the fare make for a great escape for any boater.