Crete
Crete is an island with a lot to see and do. Some of the great beaches include Elafonissi, Falasarna and Preveli. If you don’t mind putting in a bit of effort, Balos Lagoon in the Kissamos area is difficult to get to, but well worth it for the crystal warm water, white sand and rugged beauty. If you like animals, Aquaworld Aquarium is a popular site, which can be visited until October 31. They have a large variety of marine species, and only take in animals that are in need of care. For a scenic experience visit Samaria Gorge National Park, often said to be one of the most beautiful national parks in Europe. In early September, you can attend the Labyrinth Musical Workshop with classes and events to learn about local and world music. Furthermore, in mid-October you can celebrate their annual Chestnut Festival, a fun day honoring the arrival of fall and chestnut-inspired foods.
Ios
While known as a wild party island, Ios calms down considerably by September. That’s not to say there isn’t nightlife – you’ll still be able to party and have fun – but it won’t be as crazy as when the backpackers arrive in the summer. For many, this is a blessing, as it offers a chance to explore the beauty of the island in a more peaceful manner. When I went, I stayed at Far Out, which has a hotel, bungalow and camping option literally right across from Mylopotas Beach. Ios is often touted as having the “Top 10 Beaches in Europe” when surveys are done, so exploring this and Maganari Beach is a must. Until mid-October, you’ll be able to enjoy water sports like windsurfing, waterskiing, wakeboarding, kneeboarding, kayaking, surfing, banana boats and tube rides. Other worthwhile activities include boutique shopping and admiring the whitewashed buildings in Chora, visiting the Venetian castle of Paleocastro and seeing Homer’s Tomb, the resting place of one of the greatest Greek poets in history.
Mykonos
This cosmopolitan destination is one of the most popular of all the Greek Islands, and for good reason. Because it tends to get overcrowded in the summer, visiting during shoulder season is a good idea. Visit the destination’s iconic windmills, stroll through the charming streets and get a cocktail in Little Venice, take in panoramic views from Armenistis Lighthouse, visit the Byzantine Church of Paraportiani and get educated at the Folklore Museum. And of course, a visit to one of the many beaches, like Panormos, a quiet beach with a mountain backdrop, Platis Gialos, a beach featuring calm water and a plethora of eateries and Elia, a clothing optional beach, is a great way to waste away the days in a beautiful setting.
Paros
Paros is the second-largest island in the Cyclades, and features unique beaches, each of which has a different vibe. For example, Santa Maria has a Caribbean Island feel, while Kolymbithres Beach is unspoiled with unique rock formations, colorful water and no music or fancy lounge chairs to take away from the untouched feel. Other fun activities include visiting the first century Panayia Ekatondapiliani Cathedral, the old-world village of Lefkes and the Marathi Marble Quarries, which features a high-quality marble only found in Paros.
Naxos
Naxos is the largest island of the Cyclades, with opportunities for relaxation, adventure, culture and history. If you want to experience true paradise, head to Plaka Beach. This isolated beach features fine white sand, turquoise waters, barely any wind and even a clothing-optional section. For those seeking adventure, head to Agios Prokopios Beach where you can partake in water sports or sign up for a snorkeling or diving trip to see marine life and shipwrecks. For a bit of history, check out the iconic Portara, a marble gate from sixth century B.C., on the islet of Palatia in Naxos Harbor. It is the sole remainder of a temple dedicated to Apollo. And, for great photo opportunities, the Castro, or old walled city, is elevated above the harbor, awarding excellent views.
Delos
According to mythology, Delos was the birthplace of Apollo and Artemis, and there are many opportunities to explore this part of history. Visit the three temples of Apollo, the sacred lake where Apollo was born and The Alter of Dionysos. You’ll also get the chance to visit Cleopatra’s House, named after the two headless Cleopatra statues found inside. A theatre from the second to third century B.C., the Archeological Museum of Delos and the Avenue of Lions, a street from seventh century B.C., lined with ancient lion statues, are also worthwhile sites to check out.
Corfu
Located in the Ionian islands, Corfu has a history of being controlled by foreign powers like the British and the Venetians. Its rich history combined with its natural beauty make this a destination for all types of travelers. Moreover, the rainy season doesn’t come until November, so those looking to go in September and October will still be able to enjoy the sunny weather. During a visit to Corfu, make sure to explore the various villages on the island. There is Nymphes, full of waterfalls and legends of bathing nymphs and Roda, a mix of traditional fishing village and modern tourism. Moreover, Lakones features 18th and 19th century homes and churches while Kynopiastes has old mansions from the 17th and 19th centuries, a 17th-century monastery, a marble church and a museum dedicated to the olive tree. For something historical and peaceful, the British Cemetery offers a tranquil garden, hundreds of British graves and over 200 years of history. And, of course, the many beaches can keep you occupied for hours. Wine lovers will be able to take part in the annual Arillas Wine Festival, in September .
Rhodes
One of the largest Greek Islands, visitors to Rhodes will experience beaches, a medieval town, archeological sites and a rich history that goes back to Neolithic times. This island often has more than 300 days of sunshine per year, making it a great destination even during shoulder season. Travelers love visiting Rhodes for the mix of sandy and rock beaches, all with different atmospheres. While Lindos is a sandy and trendy beach, Gennadi is a popular surf spot. Additionally, Faliraki is a mix of sand and rock and is the island’s only legal nude beach, although tanning in the nude is tolerated in some areas of Tsambika. For some adventure with stunning views, climb to the top of Mount Attavyros. The climb takes about two to three hours and will take you up 3,986 feet in elevation. Moreover, some historical sites of the island include the Acropolis of Lindos, the medieval fortress and city sites of Ancient Rhodes, the Church of Panagia and the Palace of Grand Master of Knights. Some events to check out include Timiou Stavrou, a Greek dancing festival taking place from September 13 to 14, and the religious festival of Aghios Loukas on October 17.
Skiathos
Part of the Sporades Islands, Skiathos is a mix of cosmopolitan luxury and medieval history. While the main strip is more loud and boisterous, the other areas feature great hikes and quiet retreats. For some medieval history, visit Kastro, which was the largest medieval town from the 12th century until 1830. It was built upon a cliff sticking out into the ocean at the north end of the island, and although today the site is mostly ruins, it still offers expansive views of Skiathos and its surroundings. For a bit of relaxation, head to the beach. A beautiful sandy beach that allows nudity is Banana, which is actually composed of three beaches – Little Banana, Nameless Banana and Big Banana. Moreover, Koukounaries is the most popular and thought to be the “best in the Aegean,” Kanapitsa is good for water sports and Asselinos is quiet and romantic. My personal favorite beach on the island, however, is Lalaria. It is only accessible by boat, and features gray marble pebbles, unworldly rock formations and crystal clear water you can see through even in the deep areas.
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