September & October Sun Holidays

Thinking you might like to escape post-summer, but still fancy somewhere sunny in autumn? Here’s a roundup of some of Further Afield’s favourite places for September and October sun holidays, taking in Italy, Spain, Portugal, Greece, Malta and Turkey:


Heading to the land of wine and olives in autumn still means sunny days and warmer nights, but without the frantic crowds of summer.

Trullivistas, Puglia (self-catering, sleeps 4)

A stone farmhouse in Puglia, surrounded by olive groves and incredible views, Trullivistas also has a beautiful pool. October and even November can be lovely here, perfect for exploring this fascinating region or simply chilling. SAVE 15% ON REMAINING WEEKS – use the code PugliahFA15off when you book.

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Casa Castagno, Tuscany (self-catering, sleeps 2-4)

Head to Tuscany and soak up the last of the summer’s warmth at this stone-built Tuscan farmhouse for two or four. Surrounded by fascinating towns and cities as well as 12 acres of its own woodland, it really is the best of both worlds. Wood burner if it’s chilly, pool for when it’s not. SAVE £100 ON REMAINING SEPTEMBER WEEKS – quote Further Afield when you book.

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Casal dei Fichi, Le Marche (self-catering, sleeps 2)

These six holiday apartments in beautiful countryside near the Italian coast are the ideal escape. Each beautifully equipped and with a village just a stroll away, fresh produce is readily available so you can cook up a storm. Weekly pizza nights are a treat to be savoured and you their gourmet break in November a brilliant plan.

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The Greek islands in September and October offer a totally different vibe. Still stunning and chilled out, they also mean quieter beaches and a chance to totally recharge.

Galini Breeze, Crete (self-catering apartments for 2 or a villa for 6)

On the classic Greek island destination of Crete, adult only, modern and stylish Galini Breeze is a superb option for escaping it all on an October sun holiday. All with great views and only five minutes’ walk to bars and restaurants, it’s a guaranteed winner.

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My Little Place on the Hill, Kefalonia (self-catering for 2 or 2+2)

Alex and Vicky have created the perfect blend of cool, laid back but super-friendly accommodation at My Little Place on Hill. With direct flights, September is a great time to head to this corner of paradise. Pool, nicely appointed suites (some catering for +2 children), beaches, towns and villages to explore as well as the island’s capital, Argostoli, just 12km away.

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Pino di Loto, Syros (B&B)

The view from this B&B on Syros means you may end up not leaving, with heavenly sunsets creating lasting memories. Although, if you make use of the amazing cocktail bar those memories might become slightly clouded. Charming rooms and two new suites with private terraces and plunge pools create an intimate and relaxed escape from real life.

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With easy connections and a warm autumn (even winter) climate, southern Spain is one of the best places to go on holiday in October.

El Nispero Dulce, Alcaucín (B&B)

A friendly and discreet little B&B in the hills between Malaga and Granada, El Nispero Dulce makes for a nice little escape. Great views, a pool and suppers on offer, with Kris and Rene as your charming hosts, mean that you might not want to explore, but if you do there’s lots on offer.

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Finca Los Pinos, Villanueva del Rosario (B&B)

With just two rooms, this oasis in the Spanish plains is a total treat. Individual style, homegrown fare and a location perfect for exploring the region (including Granada, Malaga and Cordoba) – plus Julie and Terry’s welcome – mean this should be on your list. A FREE BOTTLE OF CAVA AWAITS FURTHER AFIELD TRAVELLERS.

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Exotic and sultry Turkey has long been one of the best hot holiday destinations in October, as with its warm autumn weather it makes for a perfect escape later in the year.

Tas Otel, Alacati (B&B and villas)

In the lovely coastal town of Alacati, this converted mansion offers the very best combination of hospitality and charm. Beautifully decorated, with antiques and artworks and a lovely garden and pool, you can hole up and recharge (made easier by daily afternoon teas…). Head out and explore the town when you have the strength, guided by Zeynep’s knowledge.

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Whether on the mainland or the islands, city or beach, Portugal offers a superb October sun holiday. We’ve selected our favourite autumn escape:

Savoy Saccharum Resort and Spa, Calhera (Boutique Hotel)

Bigger and grander than some of our properties, we’re huge fans of this stylish retreat. With an inclusive and friendly welcome, this boutique hotel – with its infinity pool, bars and restaurants – on Madeira makes a wonderful autumn escape. The in-house spa is superb and the sunsets truly memorable.

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South of Italy, sunning itself in the Mediterranean are Malta and its group of islands. With temperatures in September and October still bikini-friendly but with enough culture to keep everyone happy, it’s a great choice.

Julesy’s B&B (B&B)

In a stunning, historic mansion in the Three Cities area of the island, this charming B&B is the ideal base for exploring the delights of Malta. Valletta is a boat ride away and the numerous beaches and coves of the island are easily accessed. The rooftop terrace at Julesy’s is the perfect spot from which to take it all in.

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Check out Dar tal-Kaptan Boutique Maison, our other Maltese gem.

If nothing here has excited your travelbuds, then remember you can always contact us directly for advice and travel ideas.


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