The Algarve, Portugal
Best for: Dramatic beaches and gourmet pitstops

With highs of around 23°C, Portugal’s southern coast remains sun-kissed well into October. Think caramel cliffs, hidden sandy coves, and relaxed lunches of grilled sardines with chilled vinho verde. Perfection. The light is magical at this time of year – and we’ll be chasing it for all it’s worth.
Stay: Vila Vita Parc – a luxurious cliff-top resort with lush gardens, infinity pools, Michelin-starred dining, traditional Portuguese details and slick contemporary design.
Crete, Greece
Best for: Ancient history with a side of turquoise seas
Greece’s largest island offers warm seas (around 25°C) and sunshine perfect for exploring the Palace of Knossos or hiking the Samaria Gorge without the summer crush. Evenings are best spent in candlelit tavernas, dreaming amidst the bougainvillaea, which spills in abundance over whitewashed walls. Bliss.
Stay: Cayo Exclusive Resort & Spa – a sleek, eco-conscious hideaway with private plunge pools, panoramic sea views, and an interior scheme worthy of a design magazine.
Malta
Best for: Compact culture-hopping and late-season swims

With highs of 25°C, Malta offers up history, architecture, and sea in a way that feels almost cinematic (no surprise then that it is perennially popular amongst Hollywood filming crews). Stroll the walled streets of the atmospheric Mdina, explore Valletta’s golden limestone facades, and take a boat to Comino’s Blue Lagoon.
Stay: The Phoenicia Malta – a glamorous Art Deco-meets-Mediterranean icon in Valletta with manicured gardens and a stunning infinity pool overlooking the harbour.
Sicily, Italy
Best for: Food lovers and culture vultures
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Sicily’s 22°C October weather is perfect for wandering ancient ruins, sampling fresh cannoli, gorging on arancini, and exploring bustling markets without the stifling summer heat. Autumn brings a harvest of grapes, olives, and citrus – perfect for scoffing one’s way around the island, from the majesty of Palermo to the laid-back holiday vibes of Siracusa.
Stay: Villa Igiea, Palermo – Rocco Forte hotels never misfire, and this restored Art Nouveau palazzo with lavish interiors, a serene pool, and sweeping views over the Bay of Palermo is yet another case in point.
Madeira, Portugal
Best for: Nature lovers who still want luxury

Madeira’s lush hills and warm seas (around 22°C) make it a year-round beauty. Spend days hiking levada trails, visiting botanical gardens, or just sipping poncha on a sun terrace.
Stay: Savoy Palace – a striking contemporary hotel with dramatic ocean views, a rooftop infinity pool, and interiors that channel tropical glamour.
Cyprus
Best for: Serious sun-seekers in autumn

With temperatures often nudging 27°C, Cyprus delivers a genuine summer feel in October. Beach days are still in full swing, but if you do want a dose of cooler mountain air, just zip up to the Troodos and bask in the glorious panoramic views.
Stay: Anassa – an achingly elegant resort with whitewashed villas, serene pools, and an Aegean-meets-Riviera vibe that epitomes understated luxury.