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Holidays in historic towns and villages in Italy

For a holiday with the rich heritage of times gone by, you’ll find a wealth of interesting buildings and artefacts in the historical towns and villages of Italy. Even better, these engrossing locations are never too far away from our luxury villas in the Tuscany and Umbria regions.

Asked to compile a list of Italy’s most notable historical locations, many of us would include Rome, Florence, Pisa, Siena and Venice. While these cities can certainly help to bring history to life when you visit, there’s a multitude of smaller towns and villages across Italy that are also worth seeing.

For example, in Tuscany alone, Arezzo has an impressive Duomo and a tradition of gold-smithery that makes it one of the richest towns in the region. Also set within the beautiful Tuscan landscape, the hill-topping Cortona dates back to Etruscan times and was chosen by St Francis of Assisi as the site of his first monastery.

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La Madonnina

Tuscany, Italy

Villa | Bedrooms 1-2 | Sleeps 2-4

  • Two delightful 2-bedroom apartments, one studio cottage
  • Stunning views
  • Beautiful gardens
  • Complimentary welcome meal

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Apartment

Prices
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$551pp Total price $1,101
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Casa Brilli

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Comfortable refurbished villa
  • Set in an extensive manicured garden
  • Ideal for two families travelling together
  • Delightful outdoor pergola

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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$590pp Total price $1,179
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Casa Momi

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming property for two
  • Comfortable and spacious
  • Stunning views across rolling hills
  • Radda in Chianti 5-minute drive

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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$591pp Total price $1,181
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La Casa dei Mandorli

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming bijou Chianti villa
  • Stunning views
  • A romantic interlude
  • Beautiful sunset terrace

Prices are based on 2 sharing for 7 nights on Saturday 30 April 2022

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$948pp Total price $1,895
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Casa al Colle

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Elevated, spacious retreat
  • Stunning panoramic views
  • Comfortable interiors
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

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$958pp Total price $1,915
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Simpson Kids

Whether you're travelling with babes in arms, toddlers or school-age children, 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.
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Villa Passione

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Stylish and comfortable barn conversion
  • Extensive garden with small lake
  • Cooking classes available
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 30 April 2022

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$1,041pp Total price $2,081
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Villa Mille Desideri

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 11

  • Beautifully positioned villa
  • Breathtaking views
  • Comfortable and welcoming
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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$1,684pp Total price $3,367
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Casetta Carina

Tuscany, Italy

Apartment | Bedrooms 2 | Sleeps 3

  • Contemporary and comfortable apartment
  • Ideally located to explore Chianti
  • Magnificent large private swimming pool
  • Shops/restaurants/supermarket 10-minute drive

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

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$787pp Total price $1,574
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Villa Donatella

Umbria, Italy

Villa | Bedrooms 5 | Sleeps 6-9

  • Calming and welcoming country house
  • Spacious and comfortable
  • Captivating views
  • Excellent location to explore Umbria

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,432pp Total price $2,863
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Simpson Kids

Whether you're travelling with babes in arms, toddlers or school-age children, 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 Kids

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Villa Da Vinci

Tuscany, Italy

Villa | Bedrooms 7 | Sleeps 13

  • Exceptional manor house
  • Spacious and comfortable
  • Set in the heart of Chianti
  • Outstanding views

Prices are based on 2 sharing for 7 nights on Saturday 9 October 2021

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  • Villa

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$3,064pp Total price $6,127
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Simpson Travel in the press

  • ‘[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

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Travel advice from the Foreign Office

For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

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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  • Destinations

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    France

    France

    • Côte d'Azur
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    • The Dordogne & South West
    • Vendée
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    • Ile de Ré

    Mallorca

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    • Villas with childcare
    • Luxury villas
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    • Large group villas
    • Villas together
    • Romantic villas for two
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    • Teen-friendly villas
    • Beachfront villas
    • Villas with heated pools
    • Villas near the beach
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    Back

  • Hotels

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    • Simpson Hotels
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    Back

  • Holiday inspiration

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    Holiday Types

    Holiday Types

    • Couples holidays
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    • Car-free holidays
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    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
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    Family Holidays

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    • Holidays with childcare
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    Collections

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    Be Inspired

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    • Give the gift of travel
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