Why Sailing in September is the Smartest Holiday Choice

We’ve been trained to believe that July and August are the only real months to unplug—but what if there were a better way? A time when the sea is still warm, the sun still shines, but the crowds have gone home and prices have quietly dropped?

More and more travellers are rethinking the traditional calendar and discovering the magic of taking a sailing holiday in September. If you’ve ever wished for quieter beaches, more space onboard, and the freedom to explore without the summer frenzy, then late summer sailing in the Mediterranean might just be the holiday you didn’t know you needed.

In this article, we’ll dive into the five reasons why September is the ideal month to sail—and reveal the best places to go, both in Europe and beyond. Get ready to see the Mediterranean (and the world) from a whole new perspective.

5 Reasons Why Sailing in September is a Brilliant Idea

1. The Sea is Warmer and More Pleasant

The Mediterranean Sea is at its warmest in September, thanks to a summer of continuous sun exposure. With average water temperatures between 23°C and 26°C, diving in is not just refreshing—it’s enjoyable! Whether you're planning on snorkelling in the Aeolian Islands or swimming in the turquoise bays of the Cyclades, you’ll find ideal conditions for every water activity.

2. Comfortable Air Temperatures and Calmer Winds

Gone are the scorching heatwaves of July and August. In September, you can expect mild daytime temperatures and pleasantly cool evenings. In areas like the Cyclades or the Turkish Riviera, northern winds such as the Meltemi begin to ease, providing more predictable and relaxing sailing conditions. This makes it a great month for both beginners and experienced sailors planning a Mediterranean sailing itinerary in September.

3. Less Crowds, More Authenticity

Ports, anchorages, and coastal towns are significantly less crowded. This means easier mooring, quieter beaches, and more availability for last-minute berths. Local restaurants and taverns are more relaxed too—giving you the chance to chat with locals, receive personalised recommendations, and enjoy genuine hospitality. A late summer sailing destination becomes a true escape from the tourist rush.

4. A Better Selection of Boats

With peak demand behind us, September boat rental deals are plentiful. Whether you're dreaming of a sleek monohull, a spacious catamaran, or a luxury yacht, you’ll find greater availability and more options at every price point. This is your chance to select the ideal boat for your group size and itinerary, without compromising on comfort or style.

5. More Value for Money

Everything is simply more affordable. From the boat rental itself to marina fees and dining out, September is known for competitive pricing across the board. Many charter companies offer discounts and flexible packages, allowing you to upgrade your vessel or enjoy premium experiences—like a gourmet dinner on the coast or a private skipper—without breaking the bank.

Enjoy the peaceful silence of a secluded bay — all from the comfort of your own sailboat this September.

Top 5 Destinations to Sail in September in Europe

1. The Cyclades, Greece – Mild Winds and Sunny Days

Known for strong summer winds (Meltemi), the Cyclades are far calmer in September, making it the ideal time to explore iconic islands like Mykonos, Paros, and Naxos. With crystal waters and charming whitewashed villages, sailing holidays in September in Greece become much more enjoyable and accessible.

2. Turkey’s Turquoise Coast – Serenity and History

From Bodrum to Göcek, the Turkish Riviera offers stunning coves, ancient ruins, and warm hospitality. September is perfect for sailing here: the sea is still warm, the ports are quieter, and the sunsets over Lycian tombs or natural bays are unforgettable.

3. Tenerife, Canary Islands – Eternal Spring All Year Round

The Canary Islands offer a unique opportunity for year-round sailing. In September, Tenerife’s mild trade winds and moderate seas make for a smooth sail. Explore black sand beaches, volcanic landscapes, and authentic towns—all while enjoying a climate that's always spring-like.

4. Mallorca, Balearic Islands – Culture and Hidden Coves

With its dramatic coastline, hidden calas, and lively villages, Mallorca is one of the best places to sail in September. Temperatures are still high, but the summer crowds are gone. Visit Sóller, Pollença, and the Cabrera Archipelago for a varied and culturally rich itinerary.

5. Aeolian Islands, Italy – Volcanoes and Crystal Waters

September is the best time to explore this UNESCO-protected archipelago. Enjoy quieter moorings, perfect weather for volcano hikes in Stromboli, and snorkelling in Filicudi. The archipelago feels wild and luxurious at the same time—ideal for late summer sailing lovers.

September views over the Aeolian Archipelago

Bonus: Best Places to Sail in September Outside Europe

Seychelles – Tropical Bliss in Late Summer

While Europe slowly welcomes autumn, the Seychelles enter one of their best sailing seasons. Expect calm seas, light breezes, and stunning anchorages around Praslin, La Digue, and Mahé. Sailing in September in the Seychelles is perfect for a tropical escape.

Tahiti & the Society Islands – Exotic Adventure

September marks the dry season in French Polynesia. From Raiatea to Bora Bora, this is the moment to discover lagoon sailing, snorkel in coral gardens, and meet a rich local culture. The weather is pleasant, and the ocean brims with marine life.

British Virgin Islands – Off-Peak Charm

Though still part of the Caribbean hurricane season, the BVI can be a good choice for experienced sailors in early September. You’ll find deserted beaches, reduced prices, and perfect winds around Tortola, Norman Island, and Virgin Gorda. Be sure to check weather forecasts and insurance coverage if you go!

The best sunsets await you in September 

Set Sail with Master Yachting

Not sure where to start? At Master Yachting, our team of sailing experts is here to help you choose the perfect destination and the right boat for your sailing holiday in September. Whether you're looking for a sleek sailboat, a spacious catamaran, or a luxury yacht, we'll guide you step by step based on your budget and crew preferences.

Explore our vast selection of boats available around the world and reach out for a free, no-obligation quote. Sailing in September isn’t just possible—it’s the smartest choice you can make.

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