Siena
Luxury

Enter your dates to find available activities

Our most recommended Siena Luxury

From Florence: Siena, San Gimignano & Chianti Private Tour

1. From Florence: Siena, San Gimignano & Chianti Private Tour

Amongst the vineyards and olive groves of Chianti, lie medieval towns and UNESCO heritage sites. Explore them all on a private, 8-hour tour of the Chianti countryside, Siena and San Gimignano. A truly private tour, you will begin your day with complimentary pick-up at your Florence hotel by chauffeured private vehicle. Your English-speaking driver is at your disposal for a maximum of 8 hours. Your first stop will be in Siena, a medieval town. Here you will meet with your private tour guide, who is at your disposal for a maximum of 2 hours. Your guide will take you through the historic city center, where you may admire the splendid palaces and other points of interest. Your tour of Siena will conclude in the Piazza del Campo, one of the most beautiful piazzas in the world. Here, you will find the Palazzo del Comune and have some free time to enjoy lunch. The journey to your next stop, San Gimignano, will take you through Chianti territory. Along the road you will find panoramic vistas, as well as lush vineyards and olive groves. Along the way to San Gimignano you may wish to stop and admire the fortified hamlet of Monteriggioni. This hamlet is a small jewel built in the 13th-century and still embraced by ancient walls. San Gimignano you will find is a UNESCO designated world heritage site. Here you will be given free time to take in the historically interesting medieval town planning, as well as the numerous towers. You will soon find out why this place is called the “Manhattan of the Middle Ages”. Touring this extraordinary region of Italy is a wonderful experience and the fact that this tour is entirely private makes it even more special.

Florence: Experience Siena, San Gimignano, and Chianti

2. Florence: Experience Siena, San Gimignano, and Chianti

Explore the beauty of Tuscany in this tour from Florence to Siena, Castello di Monteriggioni, Chianti, and San Gimignano. Visit medieval towns and villages, and drive through idyllic vineyards, with the option to stop at an organic farm and winery for lunch. Meet your friendly guide at your accommodation and drive in an air-conditioned minivan to see the distinguished medieval architecture in Siena, like the seashell-shaped Piazza del Campo and Siena Cathedral before enjoying a scenic drive to Castello di Monteriggioni. Enjoy the small, fortified village and take a short stroll after lunch at one of the local restaurants. Travel along the Chianti wine road which is rich with castles and villages with a stop to admire a small medieval village surrounded by endless vineyards. Experience a unique dining setting while taking in an amazing Tuscan panorama with lunch at an organic farm in Castellina, with the lunch option. Journey to historic center of the picturesque medieval town of San Gimignano and see its ancient towers.

Exclusive Private Balloon Tour for 2 in Tuscany

3. Exclusive Private Balloon Tour for 2 in Tuscany

Experience the magical feeling of flying high above the cypress-studded hills and vineyards of Tuscany on a 1-hour private hot air balloon flight with just the love of your life or special friend. The exclusive adventure begins as soon as you arrive at the take-off field, which is dependent on weather conditions, and will be provided to you the day before your flight. Watch as the balloons are inflated and prepared before your eyes. Once the pilots have done their final checks and given you a briefing about flight safety, climb into the balloon basket - exlusive to you - and begin your float to altitudes of up to 2,000 feet (6,000 meters). Glide over valleys, vineyards, lakes and castles, enjoying breathtaking panoramic views of the rolling scenery below. Each flight offers a different experience, as the balloons are directed by the breeze. Upon landing, enjoy a glass of sparkling champagne before the transfer shuttle back to your take-off site.

From Florence: San Gimignano & Siena Tour

4. From Florence: San Gimignano & Siena Tour

Discover the historic cities of San Gimignano and Siena on this tour that takes off from Florence. Lose yourself in San Gimignano, between high towers and artisan shops, and taste the best gelato in the world. Then, admire the famous Piazza del Campo and cathedral in Siena. The journey begins in San Gimignano, the village built between the hills of Chianti and Val d'Orcia. It is recognizable in the distance for the high towers that dominate the landscape of vineyards, from which the famous wine Vernaccia is produced. The driver will leave you at the door that opens between San Gimignano's thirteenth-century walls so you are able to explore the village on your own. Enter San Gimignano’s lively historic center characterized by narrow streets, picturesque squares, tower houses, palaces, churches, and ancient convents. The village is populated by numerous artisan shops, art galleries, and shops selling typical products including the famous saffron. Stop at a small wine bar and taste a glass of Vernaccia, a fragrant local white wine, or visit the most famous ice cream shop of the village and savor their gelato. Enjoy the freedom to choose how you spend your time here. Less than an hour away, a guided walking tour of Siena awaits. The city, built on three hills, features characteristic streets bordered by ancient palaces. Admire the folkloric multicolored flags, the oldest bank in the world, and Piazza del Campo, the very heart of the city, with its fountain, Fonte Gaia. See the baptistery of the 14th century and the unforgettable Romanesque-Gothic cathedral, one of the most beautiful in Italy.

Chianti: Private Tour & Wine Tasting at Castle-Wineries

5. Chianti: Private Tour & Wine Tasting at Castle-Wineries

Explore three of the most ancient and emblematic castles in the heart of Chianti Classico, which also serve as wineries. Visit beautiful estates erected centuries ago and taste a wide variety of prestigious wines. Feast on a gourmet lunch fit for a king as part of this tasting adventure. Enjoy an experience of traveling back in time to three Tuscan castles. Visit one of the best-known and most admired wineries in the region and worldwide. You'll also experience a winery which operates inside the walls of a medieval fortified village, as well as a third picturesque vineyard and castle.

From Florence: Siena & San Gimignano Day Trip with Lunch

6. From Florence: Siena & San Gimignano Day Trip with Lunch

Meet your driver and tour leader in your hotel lobby to embark on a full-day trip to Siena and San Gimignano. Hop aboard a private vehicle for a scenic drive through the rolling hills of the Chianti region, covered with vineyards and olive groves. First up, make your way to the town of Siena, stopping at the Basilica of San Domenico. Inside the church are the relics of Saint Catherine, the patron saint of Siena. Take a stroll to the Piazza del Campo to see the political center of town where the famous horse race Il Palio is held twice a year. From there, meander towards the Gothic Cathedral, which boasts an impressive collection of artworks by Michelangelo, Donatello and Bernini. Along the way, pass by a delicatessen that sells wild boar salami. If you fancy it, you can step inside for a tasting. Then, it’s onward to lunch at a boutique winery surrounded by the Chianti hills and vineyards. Taste the wine and the famous extra virgin olive oil with seasonal produce. Make your second stop at the walled town of San Gimignano, a UNESCO World Heritage site. See the 13 towers that dominate the skyline as you drive towards it. Learn how San Gimignano gained importance during the Middle Ages as a stop on the pilgrim route between Italy and France, known as Via Francigena (the road to France). The townsfolk produced silk and cultivated saffron that still grows around its foothills. Another industry that still exists here is that of Vernaccia di San Gimginano, a white wine. Learn about the region's history and where to find the best artisanal stores, coffee shops and gelato spots from your guide. Check out a selection of artisan stores selling locally made products. Stroll the winding streets, admiring spectacular views of the valley beyond. Afterward, meet your chauffeur for the transfer back to your accommodation in Florence. On the way, stop for one last magnificent panorama at Piazzale Michelangelo, and gaze upon views of the city. Before you leave, don’t forget to ask your local guide for tips on what else to see, do and eat during your stay in Florence.

Frequently asked questions about Siena Luxury

What are other things to do than Luxury that are worth visiting in Siena?

Other Sightseeing Options in Siena

Want to discover all there is to do in Siena? Click here for a full list.

What people are saying about Siena

Overall rating

5.0 / 5

based on 1 reviews

Fantastic experience !! Alessandro provided solid communication before, during & after our tour. He was on time, provided great information during the different visits and was very attentive to all our questions. As someone that has completed many tours like this, I particularly appreciated the patience with the family (when you have kids!!!) as well as the good driving. Highly recommended !!!