Day 1: Arrival in Florence
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 and begin your Italian adventure.
In the evening we can provide recommendations and reservations for dinner to get your trip off to the perfect start.
Day 2: Begin your Florence Tour at the Uffizi Gallery
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 aperitivo or two in some of the city’s acclaimed bars.
Day 3: First Wine Tour in Tuscany
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 you’ll stay in a luxurious boutique hotel and spa surrounded by the hills, vineyards and olive groves of Chianti.
Day 4: Wander the Streets of Siena
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: From Tuscany to Umbria
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: Wine Tours and Tastings in Umbria
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: Relax in your Umbrian Hotel
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: Final Day in Italy
After a final night into your sumptuous castle bedroom, it’s time to bid farewell to your tour of 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.
Where You Could Stay in Italy
Hotel Lungarno, Florence
Located in the historic heart of Florence on the southern banks of the River Arno, Hotel Lungarno is an exquisite boutique hotel with iconic views over the river and Ponte Vecchio.
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The Place Firenze
A luxury hotel in Florence located in the heart of historic centre, in the magical setting of the stunning Santa maria Novella Square
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Hotel Le Fontanelle
Surrounded by vineyards and olive groves and set against a backdrop of rolling Chianti hills, Le Fontanelle is a quintessentially Tuscan hotel.
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Castello di Reschio
Set within the rolling hills of Umbria, Castello di Reschio is a restored 10th-century castle, complete with its own Roman-inspired thermal baths.
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Borgo dei Conti
Borgo dei Conti Resort is a 13th century castle in the enchanting Umbrian countryside that seamlessly blends historical grandeur with contemporary luxury.
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We craft each itinerary just for you. Contact our Travel Designers to plan a gourmet wine tour through Tuscany and Umbria.
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