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Activity Holidays in Italy

Kick back, fill up your glass, look out over some impossibly picturesque countryside, and feel the pace of life slow… right… down. Our wine holidays are about connecting you with a region properly, this means taking time to savour a culture and a landscape just as much as the quality wines that are produced there.

Whether it’s discovering a delicate Chianti in the rolling hills of Tuscany, seeking out little atmospheric wine bars on the softly lit streets of Rome, or sipping an earthy Aglianico in the shadow of Vesuvius, every wine holiday in Italy should be this immersive.

Most Popular experiences

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  • Chianti and Castle Tour from Siena

    5 Hours Italy

    Explore the beautiful Chianti wine region on this half-day scenic tour of the Tuscan countryside. Enjoy the stunning vie..

    Price from

    £79 pp
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  • Brunello di Montalcino Wine Tour

    5 Hours Italy

    On this half day tour to Montalcino, taste some locally made delicious wine as well as tasting some local delicacies and..

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    £93 pp
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  • Dinner in the Vineyards from Florence

    5 Hours Italy

    Enjoy this amazing and unique experience in the Tuscan wine region as you dine under the stars in a vineyard.

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    £121 pp
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  • Umbria Wine Lovers Experience

    6 Hours Italy

    Become an expert in Italian wine as you taste your way through a traditional Italian wineries. You will be led by a loca..

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    £158 pp
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  • Rome Off The Beaten Track

    3 Nights/4 Days Italy

    Discover Rome like a true Italian. Enjoy visiting the hidden gems of Rome and taste the local food and wine. You will al..

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    £764 pp
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  • The Great Chianti Classico Crossing

    9 Hours Italy

    Explore the enchanting rolling hills, gorgeous vineyards, delicious wines, famous castles and Tuscany all around on this..

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    £196 pp
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  • Best Places to Visit

    Tuscany

    With rolling hills & iconic cities, the only issue you'll have is deciding where to start in this id

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    Tuscany

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    Puglia

    The sunny, whitewashed heel of the boot, is home to an abundance of amazing beaches and hidden gems.

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    Puglia

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    Rome

    Rome needs no introduction. Charismatic, charming and captivating, from its history to vibrant stree

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    Rome

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    Verona

    Made famous by Romeo & Juliet, Verona itself is an open-air museum with many hidden paths.

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    Verona

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    Sorrento

    Nestled in the historic Bay of Naples, it’s the perfect base for exploring the picturesque Amalfi

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    Sorrento

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    Naples

    Naples is all about the raw & the spontaneous, it bubbles with volcanic drama and infectious energy.

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    Naples

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    Umbria

    A lush green paradise, landlocked Umbria is a magical region of truly authentic Italy.

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    Umbria

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    Lake Garda

    Enjoy its glistening waters, from quaint harbor towns in the south, to dramatic mountains in the nor

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    Lake Garda

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    Sicily

    One of Europe's most seductive destinations, Sicily sits at the heart of the Mediterranean and deliv

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    Sicily

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    Venice

    A truly unique, magical city, born out of a marble palace on a lagoon, and developing into a stunnin

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    Venice

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    Wine adventures in Italy

    The Italians view wine as absolutely central to a content way of life, and we agree. It’s something that brings people together, to bond a group of friends or family.

    And Italian wine is about so much more than Barolo, Montepulciano and Pinot Grigio, (though they are classics for a reason). A wine holiday in Italy will reveal to you the complexity of Italian grapes and the connection the wines have with the landscape – all whilst helping you understand Italian culture and how it is reflected in their wine.

    An Italian wine holiday helps you truly get in touch with an area’s heritage and culture, it’s landscape and physical conditions, and how they all come together to produce incredible, world-leading wines. It’s about exploring via bike, hike and tastebuds, about meeting the people who produce such a luxury that is craved all over the world.

    With local producers, fourth-generation artisans and family-run estates showing you the way around Italian wines, you’ll return with new skills and satisfied tastebuds.

    Where to experience wine holidays in Italy

    Explore one of the many diverse regions in Italy on a pure wine holiday, or combine your experience with another passion like cooking or cycling.

    Taste stunning Chianti’s in the soft breeze on the walls of a hilltop village in Tuscany, or experience a wine holiday of gliding through the stunning rolling hills of Umbria by bike, stopping at vineyards along the way.

    Head to the fiery Naples and relax in the shadow of Mount Vesuvius as you try earthy reds and gaze across a sweeping bay, or get to the beating urban heart of Rome or Verona as you wander the cobbled streets and narrow lanes on the search for amazing wine bars.

    Whatever your tastes, you can find a wine holiday in Italy to indulge your inner sommelier and a group of like-minded people to experience it with. Never settle for an ordinary Italian holiday again.

    Who are our Italian wine holiday guests?

    Fervent wine lovers, beginners who struggle to tell their Medoc’s from their Merlot’s – everyone is welcome on one of our Italian wine holidays.

    You’ll meet people of all ages and nationalities on cooking holidays in Italy, from solo travellers to couples to friends. Some love local, seasonal wines, others are simply looking for a getaway that blends relaxation with true indulgence.

    All that’s required is a passion for wine, a love of relaxation and a thirst for new adventures. Sound like you?

    Thousands of people have already discovered that our eclectic mix of wine holidays in Italy are as diverse as the people who go on them. Come and join them.

    Why choose Not In The Guidebooks?

    We’re passionate about helping people find the most amazing experiences on their travels, through meeting local people, exploring new places, and discovering alternative activities that make holidays special. We do this by carefully selecting partners in countries around the world who are experts in their local area, sourcing interesting people who can guide you through immersive experiences.

    We’ve got local partners all across Italy, from the Mediterranean coast to the rolling hills and quiet towns of Umbria. Choosing a Not In The Guidebooks holiday in Italy means you don’t have to choose between a beach holiday or an activity-filled break, you can get the best of both worlds with a unique trip.

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