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Short breaks in Italy & its islands

Short breaks in Italy
127  holidays found view
  • self-guided walking breaks in Italy
  • self-guided cycling breaks in Italy
  • festive breaks in Italy
  • city add-ons to combine with another holiday

 

Find a short break in Italy to suit you

Our short walking breaks in Italy cater for all levels, from a gentle discovery of the alluring landscapes just outside Florence, to mountain walking in the Apennines. If you are looking for a short cycling break in Italy, we recommend you head to Tuscany, an enchanting region that lends itself to discovery on two wheels.

Whether you choose walking or cycling – or, indeed, one of our New Year breaks – for your short break in Italy, you will enjoy a wonderful combination of cultural treasures, superb cuisine and genuine hospitality, leaving you feeling as though you’ve enjoyed a much longer holiday.

All our short breaks in Italy are meticulously researched, and you walk or cycle at your own pace guided by our detailed route notes. (We even provide notes for self-guided walking tours for the majority of the cities which we offer as add-ons or for New Year breaks.) To be sure of choosing the short break in Italy that is right for you, find out how our short walking breaks and short cycling breaks are graded.


To create your own selection of the holidays displayed below, use the search facility above.
1 - 10 of 26 Holidays
Page: 123
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Through the Mugello Hills to Florence
Short break in Italy
Archetypal Tuscany & spectacular Florence
This leisurely walk meanders through the vineyards and olive groves of the rolling Mugello Hills to historic Florence.
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23 Apr-30 Jun & 20 Aug-16 Oct 2016
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  • 4 nights
  • Grade: 1
  • Hotel-to-hotel walking
  • From £580pp
 
Strolling through Tuscany
Short break in Italy
Quintessential Tuscan landscapes
Visit the magnificent hill-top town of San Gimignano and the fortified hamlet of Monteriggioni before walking on to beautiful Siena.
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25 Mar-30 Jun & 20 Aug-31 Oct 2016
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  • 4 nights
  • Grade: 1-2
  • Hotel-to-hotel walking
  • From £435pp
 
Positano & the Punta Campanella
Short break in Italy
Picturesque coastal scenery
Get a flavour of the UNESCO-protected Amalfi Coast, enjoying far-reaching views as you walk from colourful Positano to Marina del Cantone.
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25 Mar-30 Jun & 30 Sep-31 Oct 2016
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  • 4 nights
  • Grade: 2
  • Hotel-to-hotel walking
  • From £720pp
 
The Cinque Terre
Short break in Italy
Liguria - the Cinque Terre & Portovenere
Visit all five of the Cinque Terre villages, as well as romantic Portovenere, and admire the drama of the green slopes rising from the sparkling waves.
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2 Apr-10 Jul & 20 Aug-23 Oct 2016
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  • 4 nights
  • Grade: 2
  • Hotel-to-hotel walking
  • From £498pp
 
Lake Iseo - Jewel of Lombardy
Short break in Italy
Italy's secret lake
The lakes of Lombardy make up one of the prettiest regions of northern Italy and Lake Iseo is indisputedly the jewel in the crown.
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15 Apr-31 May & 1 Sep-31 Oct 2016
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  • 4 nights
  • Grade: 2
  • Hotel-to-hotel walking
  • From £615pp
 
A Flavour of Tuscany
Short break in Italy
Tuscany - history & heritage
This delightful short break explores quintessential Tuscan scenery, and ends amid the Renaissance grandeur of magnificent Siena.
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22 Apr-30 Jun & 20 Aug-31 Oct 2016
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  • 4 nights
  • Moderate cycling
  • Grade: 2
  • Electric bikes available Hotel-to-hotel cycling
  • From £498pp
 
Quiet Mountains of the Apennines
Short break in Italy
Italy's little-known mountains
The rugged Apennines form Italy's spine and offer some of the country's best walking, as well as traditional hospitality at the friendly inns.
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14 May-16 Jul & 20 Aug-8 Oct 2016
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  • 4 nights
  • Grade: 2-3
  • Hotel-to-hotel walking
  • From £398pp
 
Rural Sardinia
Short break in Italy
The rich interior of Sardinia
Discover the very essence and unique character of this enchanting, little-known island, while staying in luxurious surroundings.
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26 Mar-30 Jun & 20 Aug-31 Oct 2016
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  • 3 nights
  • Flexible walk
  • Grades: 2 & 3
  • Centred walking
  • From £385pp
 
New Year Break - 'Brindisi' in Bologna
Short break in Italy
The heart of Emilia Romagna
Celebrate New Year in the handsome medieval centre of vibrant Bologna, famed for its rich heritage - and even richer gastronomy.
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29 December 2016-2 January 2017
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  • 3 nights
  • New Year breaks
  • From £325pp
 
New Year Break - The Delights of Lucca
Short break in Italy
Tuscany's walled jewel
Explore Italy's best preserved walled city, Lucca, and experience a festive break to remember.
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29 December 2016-2 January 2017
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  • 3 nights
  • New Year breaks
  • From £445pp
 
1 - 10 of 26 Holidays
Page: 123
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