As travellers increasingly seek to avoid summer's extreme heat and crowds, shoulder season—the period between peak and off-season—has become the preferred window for exploring Europe's islands. Booking data from major travel agencies shows a surge in demand for Spain, Italy, Portugal, and France during September and October, driven by pleasant temperatures and better value. For those looking beyond cities, we've curated a list of the best islands for a 'second summer' escape, including one where rain is likely but the atmosphere more than compensates.
Crete: Greece's Largest Island Shines in Shoulder Season
Crete, one of Greece's approximately 6,000 islands, is renowned for its crystal-clear waters and stunning beaches, with Elafonissi Beach recently named the best in Europe. But the island offers far more than sunbathing. As Greece's largest island, Crete boasts extensive hiking trails, exceptional cuisine, top-tier vineyards, ancient monasteries, and charming stone towns. The shoulder season provides ideal conditions: balmy temperatures without the summer heat, and significantly fewer visitors.
Must-see attractions include Preveli Monastery for breathtaking views, Toplou Monastery for Cretan wine tasting, and the epic Samaria Gorge for an unforgettable trek. Crete is also notably affordable compared to other Greek islands, making it a budget-friendly choice. In late September, direct flights from London can be as low as £75 return.
Pantelleria: The 'Navel of the Mediterranean'
Closer to Tunisia than mainland Italy, the Sicilian island of Pantelleria offers a painterly landscape of brooding black cliffs, turquoise bays, and emerald coves. Early autumn is the ideal time to visit: the heat has mellowed, beach crowds have thinned, and the harvest is in full swing. Homer famously called Pantelleria the 'navel of the Mediterranean,' and its unique geography makes it a special destination. The island is known for spectacular sunsets—a vast red sphere against indigo, violet, yellow, and pastel blue—and on clear days, North Africa is visible on the horizon.
During shoulder season, visitors can taste the island's acclaimed wines at Donnafugata, relax in the natural springs at Gadir, and take a speedboat to explore the craggy coastline's hidden coves.
The Aran Islands: Rugged Beauty and Celtic Heritage
Located off Ireland's wild western coast, the Aran Islands—Inis Mór, Inis Oírr, and Inis Meáin—are not for sunseekers, but they offer a unique experience. Home to around 1,200 people who speak both Irish and English, these islands are known for their serene, spiritual atmosphere, limestone landscapes crisscrossed by stone walls, blue flag beaches, dramatic cliffs, and ancient monastic sites. Visitors can surf, stroll, or cycle by day, then enjoy traditional Irish music in local pubs each evening.
Access is via ferry from Galway City or Doolin Harbour in Clare. For a memorable trip, visit in late October to celebrate Samhain, the ancient Celtic harvest festival that inspired modern Halloween. Return to the mainland for the Púca Festival, which brings this heritage to life with music, myth, and fire shows.
Lefkada: The 'Greek Caribbean' with Empty Beaches
Nicknamed the 'Greek Caribbean' for its iridescent ocean and stunning beaches, Lefkada is a star of the Ionian Islands. Home to some of Greece's most breathtaking beaches—Porto Katsiki and Milos regularly rank in Lonely Planet's top 10—Lefkada remains relatively undiscovered by British tourists. During shoulder season, world-class beaches like Kathisma and Egremini are virtually empty, yet the water is still warm for swimming, and hillside tavernas remain open.
Dining is remarkably affordable: giant plates of saganaki (fried cheese with honey), calamari, mussels, and grilled octopus with glasses of chilled red wine cost as little as €16 per head. Lefkada is the only Greek island accessible by car, via a causeway from Preveza airport, which is served daily by budget airlines like Ryanair and easyJet from April to October. In winter, the easiest route is to fly to Athens, then take a €40 bus to the island, a journey of four to five hours.
Madeira: The 'Hawaii of Europe' in Autumn Splendour
Madeira, with its majestic mountains, forest trails, and natural pools, is often called the Hawaii of Europe. Autumn is arguably the best time to visit: temperatures rarely stray from 20°C to 24°C, the ocean remains swimmable, and the lush landscape bursts into rich colours. Local delicacies such as custard apples, passionfruit, and chestnuts are in season, and summer crowds have largely departed. By October, direct return flights from London with easyJet are just £124.
Whether you're seeking sun, culture, or rugged adventure, these European islands offer the perfect shoulder-season escape in autumn 2026.
