Guide to Sailing in Greece: How to See Your Favorite Islands

The best time to visit Greek islands is in May, June, September, and October. The high travel season in peak summer can make the beaches feel crowded as it draws more people to the ports in search of sunset cruises or boat transfers between islands.

Some islands close hotels or resorts outside of summer, while others have a larger local population year-round. When considering the best time for sailing in Greece, the shoulder months of May and early June, as well as late September into October, can see the majority of islands still open, the weather warm, the sea calm, and generally fewer crowds.

Island hopping in Greece can introduce you to incredible island cultures, shaped by their specific histories. What may seem consistent under the Greek “umbrella” actually encompasses many elements particular to specific island regions. For example, the Cyclades, famous for Santorini and Mykonos, is home to the whitewashed walls and blue trim many associate with the best Greek islands, but the Dodecanese are known for bridging East and West with romantic medieval architecture.

When considering island hopping in Greece, it’s important to keep in mind your goals and expectations. Many of the islands are farther apart than travelers first understand. When traveling with a specific schedule in Greece, keep in mind transfer times; whether by ferry, which can range between 45 minutes to two hours, depending on the nearest islands; or by flight, which can also take more time than expected if the plane must first return to Athens.

Whether touching down on the Saronic islands close to Athens, exploring the celebrated Cyclades, or touring Crete, which is an island group of its own, consider what you want to see, how you want to experience Greece, and the types of excursions you will enjoy before expecting to quickly travel between the country’s renowned islands.

How to pick the Greek islands to visit during your trip will depend on the type of experience you want to have. There are over 6,000 islands spread over approximately 994 miles, so understanding which ones you want to visit and why will have a tremendous impact on your overall Greek island tour.

Santorini can be perfect for couples looking for romance, Rhodes can be an exciting island for families, and Crete is fantastic for adventure. Our guide breaks down the different archipelagos to help you decide on those to visit.

The Cyclades Islands are among the most famous in Greece, home to the likes of Santorini and Mykonos. The cluster is made up of 24 inhabited islands, while nearly 200 are uninhabited.

The Cyclades are the islands you see in pictures of Greece, where colorful bougainvilleas pop against whitewashed walls and blue domes crowd simple churches. Mykonos is known for its glamorous visitors and nightlife, while Santorini is famous for its scenic cliffs and impressive sunsets.

Among the cluster is Milos, whose popular beaches are drawing interested travelers away from the typical plunge pools of Santorini and Mykonos clubs.

The cluster in the Saronic Gulf is closest to Athens. They are easily reached by private charter or public ferry, and have a wide range of activities for all types of travelers.

Hydra is car-free and inspired famous artists like poet and musician Leonard Cohen. Spetses hosts green pine trees and the sound of clopping hooves from the horses pulling carriages near the waterfront. A clock tower dominates the skyline of Poros above the tree-shaded beaches.

The ease in visiting the Saronic Gulf islands makes a visit simple, quick, and a year-round excursion, without the logistical entanglements of hopping to or around other island clusters.

The Ionian cluster consists of seven main islands, but over 20 in total, crowned by the exotic landscape and history of Corfu.

Corfu’s Old Town is a UNESCO World Heritage Site with roots dating back to the eighth century BC. Olive trees with shimmering green and silver leaves blanket inland Paxos, while wild horses run free across the foothills of Mount Aenos on Kefalonia, the largest of the Ionian islands.

Charming beaches, surprising forests, and stories of Homer’s Odyssey give the Ionian islands a special touch unlike any of the other archipelagos in Greece.

With only 24 islands in the Sporades archipelago, only four of which are inhabited year-round, it’s easy to visit the more notable highlights of the collective when island hopping in Greece or looking to settle on a single island for a while. Alonnisos offers a lush green interior against the clear cobalt waters of the sea.

Skiathos is a fantastic place for family vacations, with adventurous children of all ages looking for magical woods and quiet beaches perfect for swimming. Skopelos offers romance in the unspoiled villages and rustic nature, while Skyros can feel like traveling to a remote and undiscovered corner of Greece, magnified by impressive views of the Aegean Sea and the medieval castle wall near the edges of the main town.

The Northeastern Aegean Islands sit closest to Turkey and feel secretive. Because they are harder to reach, they can seem more rewarding, offering a glimpse into the authentic spirit, history, and heritage of Greece, including a timeless connection to the cluster’s mythological origins.

Five of the 13 islands offer the most alluring beaches and natural wonders, as well as cultural highlights featured in remains of Venetian and Ottoman fortified villages dating back to the 14th century.

From petrified forests to the rumored birthplace of Greek goddess Hera, the Northeast Aegean islands are the epitome of adventure and discovery.

Crystal-clear waters, sand and pebbled beaches, archeological mysteries, and medieval monuments represent the timeless treasures of the 12 large Dodecanese islands, home to the likes of Rhodes and Kos.

History, adventure, and culture combine around the cluster as visitors look for rock-climbing expeditions, the remains of medieval strongholds, or introductions to local cuisine in a family-friendly environment.

The archipelago’s secluded position makes the islands far less crowded and touristy than the Cyclades, for example, but with wonderful beaches, fantastic nature, and eclectic heritage seen through the different architectural styles, the islands are not just for Greek island enthusiasts.

Greek islands have a variety of nature, culture, and luxuries, but our list of the best represents the most popular to visit and the different reasons travelers enjoy them:

• Crete
• Naxos
• Paros
• Santorini
• Rhodes
• Milos
• Tinos

Find more about Greece’s best islands and which you should visit with our list of Greek Island trip ideas and inspiration.

Greece is celebrated for its summers, but the best Greek islands to visit in winter include the likes of Santorini and Crete. When considering where to go in Greece in winter, you have to compare the experience you want against the capacity of the places you are thinking of visiting.

Santorini has become a year-round destination, with many cruise ships visiting off-season. This has resulted in plenty of restaurants, shops, and excursions remaining open throughout the year. Crete is the largest and most southern Greek island, known for its unique culture and warm weather along the coast and lowlands, no matter the month.

Places like Hydra, Poros, and Rhodes have great heritage and gorgeous scenery, but will most likely be cold and damp. Greece’s reputation as a year-round summer destination can misguide travelers into thinking the country is a perfect Mediterranean beach escape no matter the month, but winter can be cold. However, there are plenty of great islands to visit and explore even without visiting the beaches.

The Saronic Islands are in the Saronic Gulf off the Athenian coast, making them the best Greek islands to visit close to Athens. Aegina, Poros, and Hydra. You could take a day tour there to explore the history and beautiful scenery, or escape the urban expanse of Greece’s capital city.

Islands like Santorini and Mykonos are also very easy to reach from Athens. Flights between Athens and Santorini take an average of 50 minutes and those between Athens and Mykonos average 45 minutes. Ferries take longer and their routes can vary depending on sea conditions. The fastest ferry between Athens and either Mykonos or Santorini is around two-and-a-half hours.

The Greek islands are diverse culturally and topographically, and the best Greek island to visit for first-timers can feel like the realization of a dream. Romance, adventure, ancient and medieval history, remote beaches, or traditional life, each island has its own particular charm. The best islands for first timers include:

• Santorini
• Mykonos
• Crete
• Rhodes
• Naxos
• Hydra
• Syros

The best Greek islands for families with kids include Crete, Rhodes, and Santorini, as well as lesser-known islands. When considering which are great for families, you can balance adventure and charm with beaches and mythology with our list:

• Crete
• Rhodes
• Delos
• Paxos
• Milos
• Santorini
• Naxos
• Alonissos

Learn more about what each individual island has for your kid-friendly trip by finding more detailed information on the best Greek islands for families to visit.

The best Greek islands for couples and honeymooners enhance romance. With exceptionally clear waters, gorgeous sunsets, and charming villages steeped in history, visiting one of the following islands can accentuate passion and turn the dream of a Greek island into a reality:

• Santorini
• Monemvasia
• Symi
• Rhodes
• Milos
• Crete

Your list of the most romantic places in Greece for couples can take you beyond the islands for a richer and more secluded exploration with your partner.

Greece is famous for its coastline and ancient history, and the best islands for beaches can give you both. Greece’s incredible beaches can be found on the mainland and across the wide spread of islands that include our favorites:

• Mykonos
• Santorini
• Naxos
• Corfu
• Milos
• Zakynthos
• Kefalonia
• Ios

How to travel around Greece can be as easy as renting a car or as luxurious as island-hopping with a private catamaran. Depending on where and how you travel, you can choose slower options between island groups or their faster counterparts to travel farther.

The Greek islands are scattered across three different seas, the Aegean, Mediterranean, and Ionian. Even islands considered clustered together can still be positioned far from each other. A number of smaller or less popular islands may not have airports, while famous islands may have longer waits for flights or ferries because of their popularity. The easiest and fastest ways to travel around the Greek islands include:

• Plane
• Ferry
• Private boat

One of the best ways to experience traveling the Greek islands is by combining flights and private boats. You can fly to the nearest island airport before boarding a boat and sailing around the closest archipelago. Many islands do not have flights connecting one another unless the flight first stops in Athens.

Ferry routes to the most popular Greek islands are important for planning your travel logistics. By knowing where you want to go and how to get there, you can better plan your schedule. When traveling from Athens, the Piraeus port is nearly 30 minutes from the city center without traffic. The most popular ferry routes include:

• Athens and Santorini
• Athens and Mykonos
• Crete and Santorini
• Rhodes and Crete
• Mykonos and Santorini
• Between the Cycladic Islands
• Rhodes to the Cyclades

Whether looking for perfect island beaches or a marina in which to anchor for the day, the best time for sailing Greek islands is from April to October. How you want to experience the water, culture, and Mediterranean lifestyle can play a part in when you choose to visit, but spring, summer, and fall in Greece give you plenty of options.

Famous islands open their beaches and resorts around May, while small islands with year-round populations are less crowded and the seas much calmer. This can give you an easier, more inviting sailing journey, in addition to a more well-rounded travel experience.

Sailing in Greece is not hard. When doing so, guided by a qualified skipper, you can easily enjoy the relaxing atmosphere of the Mediterranean lifestyle and gorgeous islands. Local knowledge of the coastlines, rocks, and sea will help you feel secure during your excursion.

Whether on a boat for a day, a week, or a month, the elements are unpredictable, with possible storms or strong winds, shallow waters or rugged coastlines, making a knowledgeable guide and crew that much more important for the success and comfort of your trip.

Greece has four main sailing areas. Although the country has more than 6,000 islands, the most popular clusters share a few characteristics. Known for their natural beauty, accessibility, and cultural heritage, the following clusters are the main sailing areas in Greece:

• Ionian Islands
• Sporades Islands
• Dodecanese Islands
• Cyclades Islands

The catamaran is the most popular boat choice for sailing in the Greek islands. A catamaran has two parallel hulls and is larger than a typical sailboat, making it much more comfortable to travel long distances.

A catamaran is also much faster than a smaller sailboat that relies solely on the wind. Due to their size, traditional sailboats make it more difficult to navigate rough seas and there is less room to walk around the vessel to enjoy the scenery comfortably.

When island hopping in Greece, you need at least eight days. Sailing in the country gives you a more authentic experience and a richer introduction to the importance of sea life throughout the nation’s history.

From visiting a cluster of gorgeous islands to leaping out into the crystal-clear waters at a hidden bay, sailing the Greek islands is a perfect opportunity to relax and enjoy the combination of welcoming traditions, surprising scenery, and unique culture specific to each island.

While we recommend at least eight days for your Greece sailing tour, you can speak with a Greece travel specialist to plan the perfect island-hopping tour, -tailored to your preferences, style, and goals.

Whether looking for unique Greek islands to visit or discovering the best ones for couples, our Greek island travel guide offers comprehensive information to help you learn more about the possibility of sailing Greece’s islands, before speaking with a travel specialist. From which are located close together to which may offer a more comfortable experience outside of the typical high season, you can embrace the wonders of the Greek islands at your pace and according to your travel style.

Learn more about the types of experiences you could have with our Greece vacations and tours or Greek island-hopping tours, or find more information about where to go, what to do, and more with our Greece travel guide.