Large Group Holidays in September
- By Simpson Travel
- 07 Aug 2026
- Where to go
Search by property or destination…
More peaceful than peak, with better prices and availability for large villas, September is the sweet spot for group holidays with friends or a multi-generation break. Read more >
Discover our guide to the most-loved and must-see places around Stoupa in the Peloponnese as well as more unusual activities further off the beaten track Read more >
Whether you’re planning a last-minute holiday or getting organised a year or more in advance, here’s everything you need to about booking a holiday to Meganissi. Read more >
Did you know that we can arrange a private chef to cook for you in 180 of our villas in Greece, Turkey, Italy, Mallorca and France? Take your holiday to the next level of indulgence - and it's not as expensive as you might think. Read more >
Organising a large villa holiday for a group? We can help you find just what you need with a hand-picked collection of villas for 8 to 20+ guests. Read more >
Small and undeveloped despite superb beaches and a vibrant little capital, Skopelos feels like the perfect Greek island if you like a side order of sophistication along with your green and unspoilt landscapes... Read more >
Kalkan is the perfect place to enjoy doing very little, very well. Find out how to spend the perfect day in this glamorous small resort. Read more >
Inspired by the past, building for the future and with a new-found appreciation of France, our founder Graham Simpson explains what's keeping him busy in 2026. Read more >
Crete has everything you could possibly want from a Greek island destination; when it comes to uncovering its secrets, the only problem is where to begin… our A to Z of Crete is here to help. Read more >
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‘[Simpson Travel] specialise in the sort of magical, unspoilt destinations my family loves’ Author: The Telegraph
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‘So how did we find the near-perfect villa in Mallorca? The first step was to approach… Simpson Travel… we needed expertise, not just blinding choice.’ Author: Sunday Times Travel Magazine, The Villas Handbook
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‘Where Simpson [Exclusive] really excels is in its first-hand knowledge of properties and destinations’ Author: House & Garden
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‘Simpson [Exclusive] delivers holidays that combine sunshine, five-star luxury and friendly service’ Author: House & Garden
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Our stay was also infused with his thoughtful brand of hospitality, matched with that of the experienced tour operator (Simpson Travel). Author: Claire Irvin, The Times
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