Enjoy a tour of Tuscany’s villages and cities, as well as Tuscan wines and outstanding cuisine with our Tuscan food and wine tours. Explore Florence, Siena, Pienza, Montalcino vineyards and many more whilst soaking up all that this stunning region of Italy has to offer. After adventuring through the stunning countryside, stroll around historical sights, soak up the magnificent architecture and relax in luxury accommodations along the way. With experienced guides and knowledgeable hand-picked experts, uncover all that this region displays through private excursions and once-in-a-lifetime adventures. Our Premier tour with fine dining and mouth-watering cuisine in Tuscany allows guests to experience the very best of Italy.

Highlights of Tuscany

DAY 1

Arrive at Florence airport in the morning for a private group transfer. Travel through the rolling hills of the region, with breathtaking views of olive groves and vineyards. Enjoy a welcome lunch upon arrival at your villa, then observe as preparations are made for dinner, with an excellent selection of beautiful Tuscan wines to try. Enjoy the rest of the day at leisure.

DAY 2

Wake up to the stunning views of the Val d’Orcia countryside and venture into the city of Siena. The narrow, quaint streets, mediaeval towers, lovely piazzas and stunning architecture provide the ideal place to make the most of your time here. Wander around the Palio de Campo, where you will find bare-back horse racing in the main square, alongside some mouthwatering cafes and restaurants. Explore the renowned Palazzo Pubblico with its Gothic town halls, and breathtaking 14th-century tower. Travel behind the scenes into the neighbourhoods of Contradas to experience a beautiful church and fascinating museum. Enjoy the shopping opportunities on offer or grab a bite to eat in the afternoon.

DAY 3

Stroll among the vineyards in front of the beautiful Val d’Orcia landscape and visit an ancient cellar in Montalcino this morning. Taste the depth and richness of the superb, world-class Brunello wines produced with the Sangiovese grape. Meet a real Florentine shepherd who will open the doors to their family history and traditions. Visit the private dairy farm to learn about pecorino cheese making from this local expert and taste a mix of artisanal cheese at the farm. Enjoy time at leisure and explore the village of Pienza. Assist the Chef as much (or as little) as you wish for the evening Chef’s Dinner.

DAY 4

Depart for Cortona and visit an oil mill with a Sommelier to learn about the process of making Italian olive oil. Tour the olive grove and the machinery, including the Italian granite mill and modern equipment, and learn everything you need to know to select the best olive oil. Visit the well-known town of Cortona, made famous in the movie, “Under the Tuscan Sun,” for a guided walking tour. The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 metres (roughly 1968 feet) above sea level. Its dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. Enjoy a bit of history combined with a shopping excursion in the many wonderful art galleries and stores. Return to the villa to enjoy time at leisure before this evening’s dinner with a local culinary artisan.

DAY 5

After breakfast, travel to the medieval town of Montepulciano. This destination combines Tuscany’s superb countryside with some of the region’s finest wines. Make your way up the steep and winding walkways and arrive at the Piazza Grande, the heart of Montepulciano and the focus of the city. Stop in the middle of the square or near the lovely fountain and feel the unique atmosphere offered by the Plaza surrounded by the Duomo, the Palazzo Comunal, the Palazzo Tarugi and the Palazzo Contucci. Continue the tour with a wine tasting, including a light lunch. Enjoy an evening Chef’s dinner at the villa. 

DAY 6

For your last day in Tuscany, soak up the Tuscan sun poolside to rejuvenate. Appreciate a mid-afternoon wine tasting on the property with a Sommelier before dinner with wine pairings in the Tuscan countryside.

Highlights of Florence

DAY 7

Private Group Transfer to a hotel in Florence for two nights. On the way, stop in the beautiful town of San Gimignano, known as the Town of Fine Towers. San Gimignano is famous for its mediaeval architecture, unique in the preservation of about a dozen of its tower houses. Its hilltop setting and encircling walls, form an unforgettable skyline, which is why it comes as no surprise that the attraction is also a UNESCO World Heritage Site. There will also be time for shopping and exploring the sites, alongside a group lunch. Prepare for an evening at leisure in your hotel.

DAY 8

Embark on a guided walking tour of Florence’s Renaissance heart, including trips to the Duomo, the 14th century Ponte Vecchio, and San Lorenzo Market. Enjoy the afternoon at leisure to visit the Galleria dell’ Accademia to see works by many of the greatest artists of the 14th and 15th centuries, including Michelangelo’s famous sculpture of David. Alternatively, enjoy some last-minute shopping before reconnecting with the group for a Farewell Dinner.

DAY 9 Travel to Florence International Airport for flights home

Tour Departures

2026 Departures

March 22-30, 2026

Departing USA 03.21.26

April 19-27, 2026

Departing USA 04.18.26

May 17-25, 2026

Departing USA May 16, 2026

September 27-October 5, 2026

Departing USA 09.26.26

October 11-19, 2026

Departing USA 10.10.26

2027 Departures

March 21-29, 2027

Departing USA 03.20.27

April 18-26, 2027

Departing USA 04.17.27

May 16-24, 2027

Departing USA May 15, 2027

September 26-October 4, 2027

Departing USA 09.25.27

October 10-18, 2027

Departing USA 10.09.27