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 >
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 >
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 >
Discover the very best of southern Sicily and the Val di Noto on our suggested 7-day itinerary, with plenty of pool and beach time so you can relax as well as explore. Read more >
‘Eating well gives a spectacular joy to life and contributes immensely to goodwill and happy companionship.’ So wrote the iconic Italian designer Elsa Schiaparelli, and, having spent a joyous (gluttonous?!) week exploring the latest Simpson Travel collection in Puglia, Destination Specialists Éva and David agree that she was definitely onto something... Read more >
We love all of Italy from the peaks of the Alps to the heel of the boot, but for summer holidays, it has to be Puglia. Come with us and discover why… Read more >
For an unforgettable celebration, nothing compares to hosting a party at a magnificent villa in Italy. Read more >
It’s all about latitude of course, so you don’t need us to tell you that Crete is likely to be considerably sunnier than Cambridge in April! Read more >
Italy's Panzano is rapidly becoming the toast of Tuscany. Find out how this small town in Chianti has garnered such a big reputation and why we're so excited to be at the heart of it. 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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