September is, for many, the most beautiful month of summer. The heat has softened, the sea remains warm, and the islands have regained their relaxed rhythm without the crowds and queues of August. If you’re planning a holiday in Greece in September, you’ll discover that this time of year offers the best of both worlds: a summer vibe with plenty of comfort when it comes to travelling.
In this guide, you’ll find the top islands to visit in September, perfect for both relaxation and exploration. You’ll also see how proper planning - including renting a car - can make your trip smoother and more memorable.
Santorini is one of the most famous islands for September holidays. At this time of year, hotel and restaurant prices are lower, and the streets of Oia and Fira are much calmer.
With a car rental at Santorini Airport, you can move freely around the island: visit colourful beaches like the Red Beach, taste local wines at traditional wineries, and discover charming villages such as Emporio and Megalochori.
The September sunsets are even more magical, with clearer skies and fewer camera flashes around you.
Rhodes is an excellent choice for a September trip. The temperature is ideal for exploring the Medieval City, its castles, and archaeological sites. Beaches such as Tsambika and Lindos remain beautiful yet far less crowded.
With a car rental at Rhodes Airport, you can easily reach Prasonisi - a windsurfing paradise - or uncover hidden coves for swimming.
September in Rhodes also brings cultural events and festivals that highlight the island’s traditions and history.
Crete is Greece’s largest island and in September it reveals a more authentic, relaxed side. Beaches like Elafonissi and Balos are quieter, while cities such as Chania and Rethymno take on a more local character.
With a car rental at Heraklion Airport, you can explore both the eastern and western parts of the island. Visit the Palace of Knossos, the villages of the Messara plain, or even drive all the way to Zakros.
Crete is ideal for those who want a mix of culture and nature, with endless options for food, hiking, and water activities.
Milos in September is perfect for those seeking peace and quiet. The sea temperature is just right, and its famous beaches - Sarakiniko and Kleftiko - are far less busy.
The island also offers boat tours and the chance to explore charming villages like Plaka and Pollonia, where the pace of life slows down in the post-peak season.
Moreover, the calm of September makes Milos ideal for enjoyable sunset walks, romantic dinners by the sea and more authentic experiences with the locals. It is a destination that combines relaxation, natural beauty and Cycladic atmosphere, ideal for a relaxing September holiday in Greece.
Paros in September combines the cosmopolitan atmosphere of summer with a more relaxed pace and less crowding. It is ideal for those who want to enjoy a vacation with an emphasis on gastronomy and authentic Cycladic hospitality.
In Naoussa and Parikia you will walk through lively alleys, try creative cuisine and local products, while the beaches of Santa Maria, Kolymbithres and Piso Livadi offer clear waters and options for water sports. At the same time, the villages of Lefkes and Marpissa take you on a journey to the traditional side of the island with a genuine Cycladic atmosphere.
Kefalonia in September is full of vibrant colors and its nature seems even richer. Myrtos remains impressive, while Assos and Fiskardo charm with their architecture.
With fewer crowds, excursions to the caves of Melissani and Drogarati become even more enjoyable.
It is the ideal season for leisurely walks in the villages, to taste local wines and flavors, but also to enjoy landscapes that combine mountain and sea.
Symi is a quiet destination with elegant, neoclassical architecture and clear, blue waters. September is the best time to enjoy it without the intense tourist traffic.
The walks in the picturesque harbor with its colorful mansions, the dives in small beaches reached by boat and the moments of relaxation in traditional taverns create a sense of authentic Greece.
If you're wondering what the advantages are of traveling in September, check out some of the main reasons that make this time ideal for a vacation on a Greek island:
Perfect weather: warm but not exhausting.
Lower prices compared to August.
The sea is still pleasantly warm.
Beaches and roads are quieter.
More authentic interaction with locals.
Getting around an island is easier and more comfortable with a rental car. With Let’s Drive, you can secure vehicles that suit your needs, whether you’re travelling solo, with a partner, or in a group.
If you’re heading to Crete, a car rental at Heraklion Airport is the ideal way to start exploring right away.
In Santorini, a car rental at Santorini Airport gives you access to every corner of the island, while in Rhodes, a car rental at Rhodes Airport brings you closer to unique places you wouldn’t discover otherwise.
For even more travel inspiration, check out our guide Where to Go on Holiday in September and find the destination that suits you best.
