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Short breaks in Italy & its islands

Short breaks in Italy
131  holidays found view
  • self-guided walking breaks in Italy
  • self-guided cycling 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, you can take your pick of Tuscany, South Tyrol and Basilicata, three enchanting regions that lend themselves to discovery on two wheels.

Whether you choose walking or cycling 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.) 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.
Through the Mugello Hills to Florence
31 Mar-14 Jul & 25 Aug-31 Oct 2018
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Short break in ItalyThrough the Mugello Hills to Florence
This leisurely walk meanders through the vineyards and olive groves of the rolling Mugello Hills to historic Florence.
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4 nights, from £560pp
(excluding flights)
31 Mar-14 Jul &
25 Aug-31 Oct 2018
Grade: 1
Hotel-to-hotel walking
Strolling through Tuscany
31 Mar-30 Jun & 25 Aug-31 Oct 2018
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Short break in ItalyStrolling through Tuscany
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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4 nights, from £540pp
(excluding flights)
31 Mar-30 Jun &
25 Aug-31 Oct 2018
Grade: 1-2
Hotel-to-hotel walking
Apples & Vines
14 Apr-31 Jul & 18 Aug-27 Oct 2018
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Short break in ItalyApples & Vines
Staying in the historic towns of Bolzano and Trento, cycle through the vineyards and orchards coating the valley floors beneath high peaks.
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4 nights, from £715pp
(excluding flights)
14 Apr-31 Jul &
18 Aug-27 Oct 2018
Grade: 1-2
Electric bikes available
Hotel-to-hotel cycling
Positano & the Punta Campanella
31 Mar-30 Jun & 1 Sep-31 Oct 2018
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Short break in ItalyPositano & the Punta Campanella
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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4 nights, from £850pp
(excluding flights)
31 Mar-30 Jun &
1 Sep-31 Oct 2018
Grade: 2
Hotel-to-hotel walking
Genova & the Portofino Peninsula
31 Mar-30 Jun & 25 Aug-31 Oct 2018
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Short break in ItalyGenova & the Portofino Peninsula
This is a discovery of the historic port of Genova and the timeless landscapes of the Portofino Peninsula on the Ligurian Riviera.
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4 nights, from £395pp
(excluding flights)
31 Mar-30 Jun &
25 Aug-31 Oct 2018
Grade: 2
Centred walking
Lake Iseo - Jewel of Lombardy
13 Apr-30 Jun & 1 Sep-15 Oct 2018
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Short break in ItalyLake Iseo - Jewel of Lombardy
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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4 nights, from £715pp
(excluding flights)
13 Apr-30 Jun &
1 Sep-15 Oct 2018
Grade: 2
Hotel-to-hotel walking
The Cinque Terre
1 Apr-14 Jul & 25 Aug-20 Oct 2018
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Short break in ItalyThe Cinque Terre
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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4 nights, from £595pp
(excluding flights)
1 Apr-14 Jul &
25 Aug-20 Oct 2018
Grade: 2
Hotel-to-hotel walking
A Flavour of Tuscany
19 Apr-30 Jun & 25 Aug-31 Oct 2018
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Short break in ItalyA Flavour of Tuscany
This delightful short break explores quintessential Tuscan scenery, and ends amid the Renaissance grandeur of magnificent Siena.
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4 nights, from £578pp
(excluding flights)
19 Apr-30 Jun &
25 Aug-31 Oct 2018
Grade: 2
Electric bikes available
Hotel-to-hotel cycling
Sassi & Trulli
1 Apr-30 Jun & 25 Aug-31 Oct 2018
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Short break in ItalySassi & Trulli
Staying in truly remarkable accommodation, discover the unique cave dwellings, rock churches and conical stone houses of this corner of southern Italy.
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4 nights, from £665pp
(excluding flights)
1 Apr-30 Jun &
25 Aug-31 Oct 2018
Grade: 2
Electric bikes available
Hotel-to-hotel cycling
Quiet Mountains of the Apennines
12 May-21 Jul & 25 Aug-6 Oct 2018
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Short break in ItalyQuiet Mountains of the Apennines
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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4 nights, from £480pp
(excluding flights)
12 May-21 Jul &
25 Aug-6 Oct 2018
Grade: 2-3
Hotel-to-hotel walking
Lecce City Add-On
1 March-30 November 2018
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Short break in ItalyLecce City Add-On
Discover the most complete Baroque town in southern Europe, famed for its sumptuous architecture lavishly adorned with characteristic putti.
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2 nights, from £116pp
(excluding flights)
1 March-30 November 2018
Naples City Add-On
8 January-21 December 2018
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Short break in ItalyNaples City Add-On
Explore the energetic and ancient city of Naples, set on the wonderful arc of the Bay of Naples, beneath the familiar face of Mount Vesuvius.
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2 nights, from £170pp
(excluding flights)
8 January-21 December 2018
Genova City Add-On
4 January-31 October 2018
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Short break in ItalyGenova City Add-On
Discover the rich historical legacy that led to Genova, birth place of Christopher Columbus, being named la Superba, the proud one’.
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2 nights, from £120pp
(excluding flights)
4 January-31 October 2018
Turin City Add-On
6 January-9 December 2018
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Short break in ItalyTurin City Add-On
Explore the rich historic legacy, religious icons and incredible art collections of this elegant city famed for its Slow gastronomy.
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2 nights, from £164pp
(excluding flights)
6 January-9 December 2018
Verona City Add-On
1 February-22 December 2018
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Short break in ItalyVerona City Add-On
Enjoy a few days exploring magical Verona, made famous by the romantic story of Romeo and Juliet.
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2 nights, from £124pp
(excluding flights)
1 February-22 December 2018
Lucca City Add-On
2 January-30 November 2018
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Short break in ItalyLucca City Add-On
Walk round the most intact medieval walls in Italy to discover a charming Renaissance city bursting with art and history.
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2 nights, from £90pp
(excluding flights)
2 January-30 November 2018
Catania City Add-On
1 March-30 November 2018
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Short break in ItalyCatania City Add-On
Discover the rich history of Sicily's second city, dominated by nature and the countless civilisations that have left their mark - including an unusual elephant.
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2 nights, from £154pp
(excluding flights)
1 March-30 November 2018
Palermo City Add-On
1 March-15 November 2018
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Short break in ItalyPalermo City Add-On
Discover the noisy, colourful streets of this historic and captivating city, where myriad invaders have left their mark.
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2 nights, from £84pp
(excluding flights)
1 March-15 November 2018
Pisa City Add-On
1 March-15 November 2018
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Short break in ItalyPisa City Add-On
Set amid classic Tuscan countryside yet near the sea, this atmospheric city boasts world-famous architecture and unknown gems.
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2 nights, from £104pp
(excluding flights)
1 March-15 November 2018
Rome City Add-On
17 February-22 December 2018
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Short break in ItalyRome City Add-On
Rome’s status as a city of culture, civilisation, history, gastronomy and learning is without equal. It is arguably the greatest city on earth.
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2 nights, from £140pp
(excluding flights)
17 February-22 December 2018
Bologna City Add-On
1 March-31 October 2018
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Short break in ItalyBologna City Add-On
Explore historic buildings and famous art galleries in this lively city famed for an astonishing richness of trattorie and restaurants.
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2 nights, from £136pp
(excluding flights)
1 March-31 October 2018
Florence City Add-On
1 March-30 November 2018
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Short break in ItalyFlorence City Add-On
Marvel at Renaissance masterpieces, or head into the nearby hills for a walk that rewards you with fine views of Florence’s graceful cityscape.
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2 nights, from £128pp
(excluding flights)
1 March-30 November 2018
Siena City Add-On
1 March-30 November 2018
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Short break in ItalySiena City Add-On
Surrounded by olive groves and vineyards, this beautiful Gothic city is an art lover’s paradise, and easy to explore on foot.
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2 nights, from £80pp
(excluding flights)
1 March-30 November 2018
Venice City Add-On
17 February-22 December 2018
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Short break in ItalyVenice City Add-On
Famed for its canals, gondolas, piazzas and bridges – there’s nowhere quite like the floating city of Venice.
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2 nights, from £152pp
(excluding flights)
17 February-22 December 2018