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  • Destinations

    Destinations

    France

    France

    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
    • Crete
    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
    • Paxos
    • Zakynthos
    • Sivota & Epirus

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

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    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
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    Teen-friendly villas
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    Family villas
  • Hotels

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    Adult-only hotels
    Romantic hotels for two
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    • Couples holidays
    • Beach holidays
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Luxury Greek Island holidays

Picture the quintessential Greek holiday scene: small white pebble coves and soft sandy beaches; friendly harbourside tavernas and silvery olive groves; tiny hamlets, historic towns and peaceful churches. Our carefully chosen Greek Island destinations and handpicked collection of luxury villas and boutique hotels offer all this and more. 

Often described as stepping back in time, the Greek Islands offer a heady combination of ancient landscapes, stunning coastlines and picturesque fishing villages. And yet within this mix of fascinating history and rich culture, a Simpson Travel luxury villa or hotel holiday allows you to experience the Mediterranean at your own pace, which can be as slow as you want it to be.

Which Greek Island is for you?

While the blue seas, stunning views and pine-scented countryside are part of all our Greek Island destinations, there are distinguishing features that give each island its own identity.

Explore the UNESCO-listed Corfu Town or ancient ruins of Knossos in Crete; tap into the exclusive tranquillity of Meganissi or the simplicity of a beach holiday on diminutive Paxos – whichever you choose, there’s a unique Greek Island holiday waiting to happen. You may prefer Skopelos and Kefalonia as featured in the movies, or the Homeric history of Ithaca, but for a family holiday with young children, our crèches and children’s clubs on Lefkada and Zakynthos tick many boxes. After all, with professional nannies on standby, mummies and daddies can have some well-earned time out.

Things to do on the Greek Islands

When you want to venture further afield than your own private villa swimming pool or the peaceful garden of your boutique hotel, you’ll be spoiled for choice. Hire a boat and find a secluded bay far away from the modern world. Explore the winding streets of pretty villages or go walking through pine forests and ancient olive groves. A Greek Island holiday with Simpson Travel allows you to experience the authentic Mediterranean – and that includes the food: freshly caught fish, hearty meat dishes and shining Greek salads that can be consumed leisurely with a carafe of wine at a table overlooking the sea.

This is your Greek Island holiday – so what will it be?

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Simpson Kids

Whether you're travelling with babes in arms, toddlers, school-age children or teens, our Simpson Kids programme will help you find the perfect holiday to suit your family. From hotels with expert childcare to villas with complimentary infant packs and garden games for the kids, we have everything you need for a stress-free family holiday.
Simpson Family Holidays

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Mousses Crèche and Kids' Clubs

Lefkada, Greece

Villa | Bedrooms 2-3 | Sleeps 2-6

  • 12 delightful 2-3 bedroom villas
  • First-class childcare with fully qualified nannies
  • Large gated swimming pool
  • Spacious and secure lawned gardens

Prices are based on 2 sharing for 7 nights

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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  • Departs 05 May 2024

Prices
from

£796pp Total price £1,591
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  • Departs 06 Oct 2024

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Villa Palekastro

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to Kouremenos Beach
  • Beautiful views
  • Gentle stroll to nearest taverna
  • Authentic Crete at its best

Prices are based on 2 sharing for 7 nights on Tuesday 30 April 2024

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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    Included option varies by selected accommodation, arrival airport & date

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Prices
from

£801pp Total price £1,602
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  • Villa

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from

£385pp Total price £770
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Simply Simpson

The simple things in life often give the greatest pleasure and we believe our Simply Simpson Collection offers the chance to experience a more authentic taste of local living in some of the most idyllic locations in the Mediterranean. Take time to discover our comfortable, no-frills accommodation and join us on the road less travelled.
Simply Simpson

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Apothikes Beach Suites

The Gulf of Mirabello & South East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2-4

  • Magical beachfront location
  • On Crete's unspoilt southern shore
  • Four comfortable self-catering suites
  • Nearest taverna 1min walk

Prices are based on 2 sharing for 7 nights on Tuesday 30 April 2024

Package holiday

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Prices
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£811pp Total price £1,622
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  • Suite

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from

£395pp Total price £790
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Kyparissi

Ithaca, Greece

Villa | Bedrooms 1-2 | Sleeps 2-4

  • Five charming suites
  • Wonderful position overlooking Kioni
  • Private terraces and balconies
  • Sea views

Prices are based on 2 sharing for 7 nights on Sunday 5 May 2024

Package holiday

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  • Return flights from London Gatwick Airport
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    Included option varies by selected accommodation, arrival airport & date

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Prices
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£811pp Total price £1,622
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Mochlos Waterside

The Gulf of Mirabello & South East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Romantic waterfront studio
  • Uninterrupted sea views
  • Set in the charming village of Mochlos
  • Tavernas/cafés 1min walk

Prices are based on 2 sharing for 7 nights on Tuesday 23 April 2024

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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    Included option varies by selected accommodation, arrival airport & date

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Prices
from

£839pp Total price £1,677
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from

£423pp Total price £845
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Muses Beach Villas – Erato

Palekastro & Far East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas
  • Close to Palekastro

Prices are based on 2 sharing for 7 nights on Tuesday 15 October 2024

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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Prices
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£873pp Total price £1,746
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£367pp Total price £734
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Villa Sonatina

Rethymno & Central Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful contemporary villa
  • Set in peaceful olive grove
  • Wonderfully unspoilt
  • Distant sea views

Prices are based on 2 sharing for 7 nights on Tuesday 16 April 2024

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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Prices
from

£880pp Total price £1,759
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Simply Simpson

The simple things in life often give the greatest pleasure and we believe our Simply Simpson Collection offers the chance to experience a more authentic taste of local living in some of the most idyllic locations in the Mediterranean. Take time to discover our comfortable, no-frills accommodation and join us on the road less travelled.
Simply Simpson

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Arethusa Cottage

Ithaca, Greece

Villa | Bedroom 1 | Sleeps 2

  • Simply Simpson
  • Romantic open-plan cottage
  • Private pool and garden
  • 5min drive to Vathy

Prices are based on 2 sharing for 7 nights on Sunday 5 May 2024

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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Prices
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£886pp Total price £1,772
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Muses Beach Villas – Cleo

Palekastro & Far East Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Beachfront location
  • Authentic Crete
  • Short walk to tavernas
  • Close to Palekastro

Prices are based on 2 sharing for 7 nights

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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  • Departs 30 Apr 2024

Prices
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£890pp Total price £1,779
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  • Departs 15 Oct 2024

Prices
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£412pp Total price £823
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Villa Adagio

Rethymno & Central Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful contemporary villa
  • Set in peaceful olive grove
  • Wonderfully unspoilt
  • Distant sea views

Prices are based on 2 sharing for 7 nights on Tuesday 30 April 2024

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
  • Car hire or transfers

    Included option varies by selected accommodation, arrival airport & date

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Prices
from

£902pp Total price £1,804
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Why travel with us..?

Talk to one of our experts

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A brand you can trust

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See what others say about us

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Reviews

Simpson Travel in the media

  • ‘[Simpson Travel] specialise in the sort of magical, unspoilt destinations my family loves’ Author: The Telegraph

  • ‘So how did we find the near-perfection that was Villa Cabanellas 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

  • ‘The Simpson Travel check-in at Heathrow’s Terminal 5 was seamless.’ Author: Family Traveller, Katy Hill

  • ‘Where Simpson [Exclusive] really excels is in its first-hand knowledge of properties and destinations’ Author: House & Garden

  • ‘Simpson [Exclusive] delivers holidays that combine sunshine, five-star luxury and friendly service’ Author: House & Garden

Awards

  •  Silver British travel awards 2017
  • Award - Telegraph 2018
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  • Award - Conde Naste Traveller 2020
  • Award - Conde Naste Traveller 2021
  • Award - Conde Naste Traveller 2022
  •  Silver British travel awards 2021/22
  • Runner up Telegraph travel awards 2023

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For up-to-date advice and information on travel from the UK, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500. For travel from countries outside the UK, please visit your corresponding government website.

The air holidays and flights shown are ATOL protected by the Civil Aviation Authority. Our ATOL number is ATOL 5858. ATOL protection extends primarily to customers who book and pay in the United Kingdom. Find out more about ATOL. Simpson Travel is the trading name of Far & Wide Ltd.

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