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Short breaks in Italy & its islands

Short breaks in Italy
130  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.
  • Strolling through Tuscany
    31 Mar-30 Jun & 25 Aug-31 Oct 2018
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    Short break in Italy

    Strolling through Tuscany

    Visit the magnificent hill-top town of San Gimignano and the fortified hamlet of Monteriggioni before walking on to beautiful Siena.
    Read more >
    4 nights, from £540pp
    (excluding flights)
    31 Mar-30 Jun &
    25 Aug-31 Oct 2018
    Grade: 1-2
    Hotel-to-hotel walking
  • Through the Mugello Hills to Florence
    31 Mar-14 Jul & 25 Aug-31 Oct 2018
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    This leisurely walk meanders through the vineyards and olive groves of the rolling Mugello Hills to historic Florence.
    Read more >
    4 nights, from £560pp
    (excluding flights)
    31 Mar-14 Jul &
    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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    Apples & Vines

    Staying in the historic towns of Bolzano and Trento, cycle through the vineyards and orchards coating the valley floors beneath high peaks.
    Read more >
    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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    Get a flavour of the UNESCO-protected Amalfi Coast, enjoying far-reaching views as you walk from colourful Positano to Marina del Cantone.
    Read more >
    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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    This is a discovery of the historic port of Genova and the timeless landscapes of the Portofino Peninsula on the Ligurian Riviera.
    Read more >
    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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    Lake 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 Italy

    The 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.
    Read more >
    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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    A 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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    Sassi & Trulli

    Staying in truly remarkable accommodation, discover the unique cave dwellings, rock churches and conical stone houses of this corner of southern Italy.
    Read more >
    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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    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.
    Read more >
    4 nights, from £480pp
    (excluding flights)
    12 May-21 Jul &
    25 Aug-6 Oct 2018
    Grade: 2-3
    Hotel-to-hotel walking
  • Venice City Add-On
    17 February-22 December 2018
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    Short break in Italy

    Venice City Add-On

    Famed for its canals, gondolas, piazzas and bridges – there’s nowhere quite like the floating city of Venice.
    Read more >
    2 nights, from £152pp
    (excluding flights)
    17 February-22 December 2018
  • Siena City Add-On
    1 March-30 November 2018
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    Siena 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.
    Read more >
    2 nights, from £80pp
    (excluding flights)
    1 March-30 November 2018
  • Florence City Add-On
    1 March-30 November 2018
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    Short break in Italy

    Florence 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.
    Read more >
    2 nights, from £128pp
    (excluding flights)
    1 March-30 November 2018
  • Bologna City Add-On
    1 March-31 October 2018
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    Bologna City Add-On

    Explore historic buildings and famous art galleries in this lively city famed for an astonishing richness of trattorie and restaurants.
    Read more >
    2 nights, from £136pp
    (excluding flights)
    1 March-31 October 2018
  • Rome City Add-On
    17 February-22 December 2018
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    Rome 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.
    Read more >
    2 nights, from £140pp
    (excluding flights)
    17 February-22 December 2018
  • Pisa City Add-On
    1 March-15 November 2018
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    Pisa City Add-On

    Set amid classic Tuscan countryside yet near the sea, this atmospheric city boasts world-famous architecture and unknown gems.
    Read more >
    2 nights, from £104pp
    (excluding flights)
    1 March-15 November 2018
  • Palermo City Add-On
    1 March-15 November 2018
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    Palermo City Add-On

    Discover the noisy, colourful streets of this historic and captivating city, where myriad invaders have left their mark.
    Read more >
    2 nights, from £84pp
    (excluding flights)
    1 March-15 November 2018
  • Catania City Add-On
    1 March-30 November 2018
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    Catania 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.
    Read more >
    2 nights, from £154pp
    (excluding flights)
    1 March-30 November 2018
  • Lucca City Add-On
    2 January-30 November 2018
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    Lucca City Add-On

    Walk round the most intact medieval walls in Italy to discover a charming Renaissance city bursting with art and history.
    Read more >
    2 nights, from £90pp
    (excluding flights)
    2 January-30 November 2018
  • Verona City Add-On
    1 February-22 December 2018
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    Verona City Add-On

    Enjoy a few days exploring magical Verona, made famous by the romantic story of Romeo and Juliet.
    Read more >
    2 nights, from £124pp
    (excluding flights)
    1 February-22 December 2018
  • Turin City Add-On
    6 January-9 December 2018
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    Turin City Add-On

    Explore the rich historic legacy, religious icons and incredible art collections of this elegant city famed for its Slow gastronomy.
    Read more >
    2 nights, from £164pp
    (excluding flights)
    6 January-9 December 2018
  • Genova City Add-On
    4 January-31 October 2018
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    Short break in Italy

    Genova City Add-On

    Discover the rich historical legacy that led to Genova, birth place of Christopher Columbus, being named la Superba, the proud one’.
    Read more >
    2 nights, from £120pp
    (excluding flights)
    4 January-31 October 2018
  • Naples City Add-On
    8 January-21 December 2018
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    Short break in Italy

    Naples 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.
    Read more >
    2 nights, from £170pp
    (excluding flights)
    8 January-21 December 2018
  • Lecce City Add-On
    1 March-30 November 2018
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    Short break in Italy

    Lecce City Add-On

    Discover the most complete Baroque town in southern Europe, famed for its sumptuous architecture lavishly adorned with characteristic putti.
    Read more >
    2 nights, from £116pp
    (excluding flights)
    1 March-30 November 2018