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  • Destinations

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • Pollensa & Puerto Pollensa

    Greece

    Greece

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

    Turkey

    Turkey

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

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
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    Romantic villas for two
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    Teen-friendly villas
    Beachfront villas
    Villas with heated pools
    Villas near the beach
    Villas near a restaurant
    Family villas
  • Hotels

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    • Couples holidays
    • Beach holidays
    • Large group holidays
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    • 10 night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Walking holidays in Greece
    • Special Interest Holidays

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    • Easter holidays
    • Half-term holidays
    • Multi-gen holidays
    • School Summer Holidays

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Luxury honeymoons in Italy

Is there a better place than Italy for a honeymoon? A country of breathtakingly beautiful landscapes with some of the finest wines in the world, home to both Casanova and Michelangelo and birthplace of the Renaissance - this world-renowned destination puts couples in the mood for love more stylishly than most.

Few places have the power to stir hearts and minds like the awe-inspiring cities and rolling landscapes of Tuscany. Yet the lesser-known regions of Umbria and Puglia are increasingly catching the eye of discerning travellers in search of la dolce vita (the sweet life) and offer equally atmospheric alternatives for a memorable honeymoon.

Couples have an open invitation to lose themselves in medieval hilltop villages and towns, only to find the finest art and architecture around every corner; spend hours over a romantic lunch or dinner accompanied by the best local wines or follow ancient walking trails through some of the loveliest landscapes ever painted – and at the end of if all, there’ll be a luxury villa, hotel or apartment to welcome you home.

A honeymoon in Italy is a celebration from start to finish – and an idyllic destination to appreciate your own amore to the full.

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Casa Papa

Tuscany , Italy

Villa | Bedrooms 2 | Sleeps 2-4

  • Our most popular Tuscan property
  • Charming hillside villa
  • Classic Tuscan views
  • Outdoor kitchen with barbecue and pizza oven

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£520pp
Total price £1,040
View details
Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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Masseria Specchia

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stunning Simpson Exclusive
  • Understated luxury
  • Huge grounds
  • Set in beautiful Salento

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,395pp
Total price £2,790
View details
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Villa Vita

Umbria , Italy

Villa | Bedrooms 3 | Sleeps 2-6

  • State-of-the-art design
  • Stunning roof-top living area
  • Heated 12m swimming pool
  • Pool-side gym room

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£1,552pp
Total price £3,103
View details
Simpson Secrets

Our search for exceptional villas occasionally leads us along the road less travelled to find hidden gems just too lovely to leave behind. Aimed at the adventurous at heart, each Simpson Secret offers a unique take on what a holiday off the beaten track can be.
Simpson Secrets

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Simpson Secret – Puglia

Puglia , Italy

Villa | Bedrooms 2 | Sleeps 4

  • Stunning nature reserve location
  • Comfortable country villa
  • Unique natural rock pool
  • Walking distance to beach

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£811pp
Total price £1,621
View details
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Le Guardie

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming renovated cottage, perfect for couples
  • Designer interiors
  • Hot tub
  • Fully air-conditioned

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£850pp
Total price £1,700
View details
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Villa Favorita

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 8

  • Elegant historic villa
  • Spacious and comfortable
  • Heated swimming pool
  • Exceptional outdoor area

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£1,715pp
Total price £3,430
View details
Go to property page

Villa Bellosguardo

Tuscany , Italy

Villa | Bedrooms 3 | Sleeps 8

  • Superb views over Florence
  • Exceptionally rare holiday rental
  • Air-conditioned
  • Roof-top lounge, hot tub & summer kitchen

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£7,855pp
Total price £15,710
View details
Go to property page

La Casa dei Mandorli

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic bijou Chianti villa
  • Stunning views
  • 10m private infinity pool
  • Beautiful sunset terrace
Reserve now for 2025 with a fully refundable deposit of £500

Use our Advanced Registration service to secure your 2025 holiday with a deposit of £500, fully refundable when prices are published

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Villa Aurora

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stylish and contemporary villa
  • Delightful countryside views
  • Shaded balcony for al fresco dining
  • Bar/restaurant 15-minute walk
Reserve now for 2025 with a fully refundable deposit of £500

Use our Advanced Registration service to secure your 2025 holiday with a deposit of £500, fully refundable when prices are published

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La Perla del Mare

Puglia , Italy

Villa | Bedrooms 2 | Sleeps 4

  • Two-bedroom suite
  • Stunning sea views
  • Direct access to the sea
  • Private garden and terrace
Reserve now for 2025 with a fully refundable deposit of £500

Use our Advanced Registration service to secure your 2025 holiday with a deposit of £500, fully refundable when prices are published

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A brand you can trust

A brand you can trust

See what others say about us

See what others say about us
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

  • Award - Telegraph 2018
  • Award - Baby 2019
  • 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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Holiday ideas

  • Holidays in Corsica
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  • Holidays in France
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  • Holidays in Italy
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  • Holidays in Mallorca
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  • Villas in Turkey

Travel advice

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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