Destinations / Europe / Italy / Tailor-Made Italy: Tuscany & Cinque Terre

Tailor-Made Italy: Tuscany & Cinque Terre

9 days, 5-star from $14,995

One of the most alluring regions in Italy, Tuscany, offers a journey for the senses to any traveller ready to savour its great offerings. This private, tailored itinerary takes you through beautiful historic towns like Siena, San Gimignano, Pienza, Lucca, and Montepulciano. See the leaning tower of Pisa, and marvel at the coastal gems of Cinque Terre. Discover Tuscany’s flavours and culinary traditions by visiting wine and olive estates in Chianti, enjoying some of the best local cheeses in their places of origin, and going truffle hunting. A comprehensive journey to this sun-kissed land awaits!

Italy at a Glance

For the most part, Italy is welcoming towards the LGBT community. You can enjoy a hassle-free vacation and express yourself rather freely yet respectfully if you visit the most popular destinations. While generally safe, you’ll want to stay alert around the most popular tourist destinations, as pickpocketing is still quite common in Italy. Tuscany has not only some of the most beautiful cities in Italy but also more than a few stunning mediaeval hilltop towns dotted around the rolling hill and cypress tree landscape. Famous landmarks, a vibrant local culture, and particularly delectable cuisine are only some of the charms on offer. The best time to visit is between March and October. Summer months are peak travel season, June in particular, with plenty of celebrations taking place. July and August are the hottest months. The best way to get around Tuscany is by a rental car or rail – the rail connections are particularly good!

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Euro (EUR)

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Not needed for travellers from the US, Canada and Europe

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Best Time To Visit

May – October

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Central European Standard Time (GMT+1)

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Homosexual Activity


Photo: Karl Muscat

Photo: Jack Ward

9-day travel itinerary


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Arrive in Florence, Pisa or Rome

Fly to Florence, Pisa or Rome, and transfer to your hotel, where you can leisurely unpack and enjoy the rest of the day at your own pace while enjoying the surroundings.


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Chianti | Wine & Olive Oil

Get to know two of Tuscany’s major exports – wine and olive oil. Visit a winery in Chianti for a private tour and wine tasting. Afterwards, you’ll learn about olive oil varieties and production in Tuscany at a local producer’s estate. Enjoy the charming hilltop town of Montefioralle, one of the region’s secret treasures, and dine at the nearby Benedictine abbey’s Michelin-starred restaurant.


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Siena | Truffle Hunting

Visit one of Italy’s loveliest mediaeval towns, Siena, for a walking tour and marvel at the famous Piazza del Campo and the Gothic cathedral, the Duomo. Enjoy lunch at one of the town’s osterias before an adventurous evening that will take you truffle hunting – tonight’s dinner will, of course, incorporate this treasured gastronomic gem.


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Montepulciano & Pienza | The Art of Cheesemaking

There’s no lack of charming towns in Tuscany, and today you are visiting two of them – Montepulciano and Pienza, both offering commanding views of the surrounding Tuscan landscape, and remarkable historic architecture. After visiting Pienza, head to the countryside to visit a local cheese farm, where you will not only get a peek inside the cheesemaking tradition but will also sample some of the best local produce.


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San Gimignano & Pisa | Renaissance Treasures

Today journey on to Pisa. The route takes you past yet another mediaeval hilltop town, San Gimignano, famous for its town walls and well-preserved towers. While there, walk the quaint streets and make sure to stop at the Collegiata, Palazzo del Popolo, and the Church of Sant'Agostino. After lunch, continue to Pisa. An experienced local guide will take you on a walking tour to famous sites like the Leaning Tower and Piazza dei Miracoli. Along the way, you’ll learn about the fascinating history of the buildings and will be able to take memorable photos.


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Lucca | Fortified Medieval City

Enjoy a relaxed morning at your hotel’s thermal baths and set yourself up for the day that will take you to Lucca, another wonderfully-preserved town with beautiful mediaeval architecture. Walk the cobbled streets or go for a different vantage point altogether by cycling around the city’s well-preserved Renaissance walls. Before heading back to your hotel, enjoy a lovely meal at one of the town’s many restaurants and osterias serving authentic Tuscan dishes.


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The Cinque Terre | Five Charming Villages

At the epicentre, today is the famous Cinque Terre – five picturesque villages, strewn on Liguria’s seaside cliffs on the Italian Riviera. Steeped in tradition, the villages of Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso are guaranteed to charm you upon first sight. The combination of terraced vineyards, fishing town customs, colourful houses, and stunning views of the azure blue sea make Cinque Terre a place unlike any other.


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Pisa | A Tuscan Cooking Lesson

Today you will visit the private home of a local chef, who will reveal time-honoured secrets to Italian home cooking. With a guiding hand, you’ll help prepare pasta from scratch, as well as meat and vegetable dishes, and a dessert in a traditional manner that you’ll later enjoy – lunch has never tasted better! Later in the day, visit The Charterhouse Monastery of Pisa and the National History Museum which showcases the admirable world of Carthusian monks and the contemplative lives they used to lead in the monastery. Then in the natural history part of the museum, marvel at exceptional treasures from the annals of history.


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Depart Florence, Pisa or Rome

After breakfast, travel to your departure airport for a flight home.

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Additional recommended experiences

Make your trip even more memorable by choosing from a variety of optional activities. For example, learn how to cook traditional Tuscan dishes in a private class hosted in a local family's home. After a trip to the food market with your host, you'll be welcomed into their kitchen to prepare a delicious meal. And if you're interested in sightseeing, consider taking a guided tour of Pisa's Piazza dei Miracoli and Leaning Tower, followed by a bike ride along Lucca's city walls. As you take in the beautiful views of the historic city centre and picturesque gardens, make sure to stop at a café for refreshments while enjoying the view of the San Martino Cathedral.

Let Us Book Your Luxury Italy Vacation

Get in touch if you would like us to arrange your Italy trip. Did you have a different Italy itinerary in mind? No problem. We tailor every trip to your individual travel style and budget so just let us know what you’re looking for.


A private itinerary designed for you


Hand-selected luxury accommodation


Exclusive insider-access opportunities and inspiring sightseeing


English-speaking local guides


Airport meet and greet with private transfers

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