The Flavours of Florence, Tuscany & Umbria

8 days

Combine a trip to two of Italy’s most beautiful wine regions, Tuscany and Umbria, with a stay in the Renaissance city of Florence. From Michelin-starred eateries and simple slow food in hilltop towns to tours and tastings in acclaimed vineyards, this tour celebrates the flavours of Tuscany and Umbria, and highlights the beauty of these romantic regions.

Trip Highlights

  • Return flights to Pisa or Florence with private airport transfers

  • Two-night stay in a luxurious hotel in Florence, plus a half-day historical city tour

  • Visit to a famous Antinori vineyard, including a Michelin-starred lunch paired with wines from the estate

  • Five nights’ stay in two sumptuous hotels in the heart of Italian wine country: Hotel Le Fontanelle in Tuscany and Castello di Reschio in Umbria

  • Sample some of Tuscany and Umbria’s acclaimed wines with private chauffeured tours and tastings in some of the regions’ finest wineries

  • Visit the medieval hill town of Montalcino and sample the region’s famed Brunello wines

  • Discover the slow food of Tuscany and Umbria with a series of unforgettable meals celebrating the best local produce, including dinner with wine pairings in Siena

  • Option to include an exclusive wine tour and lunch in Tuscany via helicopter

from $7,554 per person



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Trip details

Day 1

Upon arrival at Florence or Pisa International Airport, you’ll be met by your private driver and transferred to your five-star hotel in the heart of Florence. The afternoon is yours to relax, unwind and start exploring this magical city.

In the evening we can provide recommendations and reservations for dinner to get your trip off to the perfect start.

Day 2

After breakfast it’s time for a taste of Florence, centre of the Italian Renaissance and home to gourmet Tuscan food and wine. Get your bearings with a private half-day tour of the main historical sites and a look at some of the masterpieces in the Uffizi Gallery. En route back to your hotel, perhaps our guide can tempt you with an aperitif or two in some of the city’s acclaimed bars.

Day 3

Today you’ll leave the city behind and head into the rolling hills of Tuscany. Lunch is at one of the region’s most revered dining destinations – savour traditional Tuscan cuisine with a modern twist at the Michelin-starred restaurant of a famous Antinori wine estate, paired with wines from the vineyard.

In the afternoon, sample some of the region’s famous Chianti Classico at a family-run, organic winery high in the Tuscan hills, before checking into Hotel Le Fontanelle for the next three nights, a luxurious boutique hotel and spa surrounded by the hills, vineyards and olive groves of Chianti.

Day 4

From your base in the heart of the Tuscan countryside, you can enjoy a day as relaxed or extravagant as you wish. Hike through the undulating hills and vineyards, explore the local area by bike, lounge around the pool admiring the view, or enjoy a picnic amongst the vines.

If you fancy an extra-special treat, we can arrange for an exclusive wine tour and lunch by helicopter. Marvel at the bucolic countryside from above, enjoy a private guided tour of the vineyards and winery, then savour a meal of Tuscan delights complemented by wines from the estate.

After a chilled day making the most of your time at the hotel, we’ll whisk you to the enchanting city of Siena. The historical centre is a UNESCO World Heritage Site, and you’ll have time to wander the winding streets, admiring the Renaissance art and architecture – and perhaps enjoying an artisan gelato from one of the city’s many gelaterias.

In the evening you’ll savour more of the exquisite slow food the region is famed for, sampling traditional Tuscan cuisine paired with local wines.

Day 5

Today you’ll swap the Tuscan hills for the green heart of Italy, the unspoiled and pristine region of Umbria. But there are more Tuscan treats in store on the way.

Your private wine guide will take you to Montalcino, a medieval hill town near Siena, home to one of Italy’s best-known wines. Meet a truly innovative winemaker producing outstanding Brunello wines, before a delicious lunch of local specialities paired with wine. Then continue to Montepulciano to learn about biodynamic viticulture and enjoy a magical tasting.

Your accommodation for the next three nights is a thousand-year-old castle renovated into an exquisite hotel, set on a hilltop amid Umbria’s verdant rolling hills.

Day 6

Today you’ll discover why Umbria is so beloved by gourmands. Often overshadowed by its more popular neighbour, Tuscany, this region boasts an array of medieval hilltop villages, sumptuous regional cuisine, and delightfully undervalued wines that are now making waves in the world of wine.

Your private wine guide will collect you after breakfast for a day of wine tours and tastings. You’ll explore two of Umbria’s finest wineries, sample a selection of local wines, and taste some regional specialities at lunch. Depending on the time of year, you may be able to go truffle hunting with an expert troubadour and truffle dog.

Day 7

And relax! Today is yours to enjoy as you wish. Spend the day enjoying the delights of the hotel – activities include horse riding, biking, cookery lessons, wildlife watching, fishing, or chilling in the Bathhouse, ancient wine cellars renovated into a deluxe spa.

Alternatively we can arrange for more wine tastings, a trip to the sublime medieval town of Perugia, or an excursion to spend the day relaxing waterside in the Umbrian Lakes.

Day 8

After a final night into your sumptuous castle bedroom, it’s time to bid farewell to your tour of Florence, Tuscany and Umbria. You may have time for a final wander of the grounds or dip in the pool before beginning your onward journey, your taste buds delighted by the flavours of Tuscany and Umbria.

All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do.

Enquire Now +44 (0) 20 8877 4940
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We came to Bordeaux for part of our honeymoon and took the First Growth Bordeaux tour. SmoothRed worked with us to curate a trip based on our desires. The 8 Chateaux we visited, the 3 delicious lunches, and the hotel were wonderful, but what set the trip apart was our…

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