Italy Travel Ideas: Fall & Winter Vacation Packages

As the last of the bikinis and beach umbrellas are packed away and the verdant countryside takes on a fiery hue, Italian thoughts are turning to olive harvests, truffle hunting and the Dolomiti ski slopes. And for visitors, there are many reasons why a fall or winter vacation in Italy is the perfect destination. From tasty truffle pasta to warm Sicilian sightseeing, or from cheery Christmas markets to romance in Juliet’s hometown, there is plenty to occupy the traveler. So if you’re looking for some inspiration, check out our fall and winter vacation packages before you talk to our fabulous travel experts to customize your own perfect getaway, you won’t be disappointed!

Fall & Winter Vacation Packages in Italy

1) Off-Season Delight: Florence

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Florence’s Duomo is an enchanting sight to see during the holiday months

Italy has been attracting visitors and travelers for centuries. And one of the most popular stops is undoubtedly the city of Florence in Tuscany. It’s brimming with medieval architecture, bursting with Renaissance art and rightfully recognized as a world heritage site by UNESCO. And there’s no better place to explore the stunning sites than from the exceptional 4-star Hotel Brunelleschi as part of our off-season Florence vacation packages.

Perfectly located at the heart of the historic city, just a couple of paces from the breath-taking Duomo and with views over the city’s rooftops, the Brunelleschi makes an ideal base for your visit. The hotel itself is a unique amalgamation of the ancient and new, built around the semi-circular nucleus of the Byzantine Pagliazza Tower whose origins stretch back to the 6th century. Step outside and you have over 2000 years of history on your very doorstep.

Your vacation includes a tour of the city pointing out some of the most famous buildings in Italian history from Brunelleschi’s Duomo and Giotto’s beautiful bell tower to the medieval Ponte Vecchio and secretive Vasari corridor. Florence is great for a spot of shopping too, from designer labels to local artisans, so don’t miss the chance to visit the city’s perfume atelier to capture some sweet scents. And top off your vacation with a day of Tuscan truffle hunting with an experienced hunter and his loyal hound out in the hills around Siena.

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Italy, Florence. Wine shop selling local wines

And if you prefer a glass of wine to truffles, or have more time to explore further why not customize our vacation packages to match your personal tastes. So whether you add in a Florentine wine-tasting experience, a trip to the fascinating hilltop city of Siena or try your hand at making virgin olive oil, our friendly, helpful travel experts are on hand to design your perfect Italian escape.

2) Romantic Verona

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Juliet’s balcony, Verona

Alternatively if passion is your priority, there’s no better place to book than the 5-star Relais De Charme Il Sogno di Giulietta located in Juliet’s courtyard overlooking her famous balcony in the center of romantic Verona. The palazzo epitomizes love, or amore as the Italians would say, with four-poster beds, jacuzzis in every bedroom, sumptuous decor, charming views of the city and even private access to the courtyard after hours to soak up the most romantic place in the world together.

And if that’s not enough, you have some of the most historic locations all within a short distance of your love-nest. Our standard fall and winter vacation packages offer a guided stroll through over 2000 years of antiquity from the ancient gladiatorial amphitheater and Piazza delle Erbe that both date back to Roman times, to the nearby house of Romeo and Piazza dei Signori watched over by Dante’s imposing statue. So once you’ve oriented yourself, you can explore this beautiful city’s cobbled streets hand in hand creating your own romantic memories.

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Allegrini’s Villa della Torre

Time your visit well and Verona also offers a great traditional Christmas market, literally on the doorstep of your hotel. Or you can personalize your vacation with trips to nearby Mantua or Vicenza, or a private visit to the Allegrini Winery. Set in Valpolicella, literally meaning valley of many cellars, the Allegrini family has been at the heart of wine-making in the region for centuries passing the culture of wine-making from generation to generation. So lunch at their historic Villa della Torre together with a guided wine tasting of their wonderful vintages is the perfect romantic memory to take home. Cin cin!

3) Christmas Markets in Trentino-Alto Adige

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Piazza Duomo, Trento

But Verona is not the only Italian city to stage festive fun with the Christmas markets in Trento and Bolzano also offering the perfect white Christmas getaway. Surrounded by spectacular mountains, your base is the elegant 4-star Grand Hotel Trento in the picturesque 16th century city of Trento. From here it’s just a short walk to the celebrated seasonal market where you’ll find everything festive from handmade decorations to artisanal gifts to the traditional presepe nativity scenes adored by Italians. And don’t miss the typical regional food and drink on offer, it’s the perfect way to refuel after your shopping spree!

From Trento explore the mountain city of Bolzano-Bozen, capital of the South Tyrol province and ranked as having the best quality Italian life in 2014. The city has a distinctly Alpine feel and you’ll probably hear more German spoken than Italian due to its old Austrian roots. You can even meet one of its old neighbors as Otzi the iceman, the world’s most famous glacial mummy, has his home in the city’s South Tyrol Museum of Archaeology; he’s well worth a visit! Bolzano is also renowned for its festive Christmas market and, like Trento, promotes local artisanal producers selling local crafts, hand-carved wooden decorations, pottery and the all-important Christmas sweets. It’s a fabulous place to shop for presents.

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Christmas market in Piazza Walter, Bolzano

And finally, round your trip off raising a toast to Christmas at one of Italy’s best sparkling wine producers, the Cantine Ferrari. The legend began with Giulio Ferrari who dreamt of creating a wine that could compete with the best French Champagnes. And as you’ll discover, he succeeded in spectacular fashion with Ferrari sparkling wines becoming the market leader and the Italians’ celebratory wine of choice. Your guided winery visit and gourmet lunch is a great way to celebrate together.

4) Catania: The Sicilian Soul

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The bay of Giardini-Naxos with the snowy Mount Etna in the background. Winter view from Taormina

If, on the other hand, you prefer winter warmth to snowy Christmas scenes then our tailored vacation packages in Catania, Sicily are what you need. The island is a popular late escape as the sunshine lingers on well into the autumn and winter with blue skies, temperate climes and fragrant almond blossom even when the mainland thermometers are registering single figures. And Sicily offers a unique insight to Italy too, with its fusion of Arab, Greek, Norman and even Germanic influences trickling down through centuries of occupation to produce a blended cuisine and architecture unseen anywhere else.

Based at the luxurious Relais Monaci delle Terre Nere, an elegant eco-boutique bolthole set in 40 acres of olive groves, vines and fruit trees, you might be hard pressed to leave this little piece of paradise. But explore a little further and you’ll find a lot to keep you entertained. From the stunning Mediterranean views to Catania’s Baroque splendor, or from vibrant open-air markets to the towering pinnacle of Mount Etna, Europe’s highest active volcano, this really is a wonderful east-coast spot for a relaxing retreat.

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The Ancient theatre of Taormina

Book now and our vacation packages include a walking tour of nearby Syracuse and Ortigia, two ancient Sicilian gems just an hour outside Catania. Or why not have a chat with our friendly travel experts who can help you to design your perfect personalized escape. You could upgrade to a suite for a sumptuous stay. Or add a trip up the coast to Taormina’s ancient, hilltop theater built 2000 years ago by the Romans. Or tickle your taste buds with a trip to a chocolatier in Modica. The choices are almost endless and so too are the memories you’ll create in Sicily in the fall.

Customizing the perfect Italian vacation packages

Italy is a beautiful country all year round and perfect for a fall getaway or winter retreat. And whether you pick a city base or a scenic paradise there are plenty of ways to customize your vacation to suit your tastes. Leave us a comment with your favorite spots for a low-season holiday and give our travel experts a call for some more inspiration. Buon viaggio tutti, happy travels everyone!


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