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Chianti Hills Sunset tours

Our most recommended Chianti Hills, Tuscany Sunset tours

From Florence: Chianti Wine Tasting at Sunset Day Trip

1. From Florence: Chianti Wine Tasting at Sunset Day Trip

Experience for yourself what makes Tuscany so beautiful as you explore the stunning landscapes of the Chianti Hills, a mountainous area of Tuscany in the provinces of Florence, Siena and Arezzo. Travel from Florence aboard a comfortable and climate-controlled vehicle.  Choose Enjoy an afternoon tour in a comfortable car or minivan, traveling through the region's. Be captivated by views of vineyards, cypress trees and hilltop villages, with a glorious view around every bend.  Explore a wine estate and visit the cantine (cellars). Indulge in a tasting experience of delicious local wines and enjoy a typical Italian appetizer (cheese with jam and bruschetta).  Enhance your experience by selecting the option that includes dinner at an open-air restaurant in the countryside to taste some Tuscan specialties and drink good Chianti wine. Return to your meeting point in Florence at the end of your tour. 

Sunset in Siena & Dinner in Chianti Tour from Florence

2. Sunset in Siena & Dinner in Chianti Tour from Florence

On this afternoon and evening tour, you will depart Florence in the early afternoon for the 1-hour drive to Siena. Enjoy the scenic Chianti countryside of delightful hills and vineyards en route. You will have free time in Siena to take in the medieval atmosphere as you wander through its narrow streets. Admire the artistic heritage of this city, exemplified by the Gothic cathedral and the impressive Torre del Mangia in the stunning, world-famous Piazza del Campo. Before leaving Siena, you will have a chance to experience the sunset from a panoramic viewpoint. Then you will continue on to a typical wine estate in the heart of the Chianti region. Nestled between the Tuscan hills and amid vineyards you will be served a delicious dinner that includes typical Tuscan products such as salami, bruschetta, and other unique delicacies. Dinner is accompanied by top-quality local wines personally selected by the owners of the winery. Enjoy this perfect way to end your afternoon in Chianti!

From Siena: Chianti and San Gimignano Sunset Tour

3. From Siena: Chianti and San Gimignano Sunset Tour

Explore the Chianti wine region and the hilltop town of San Gimignano on a sightseeing and wine-tasting tour from Siena. Travel in a small group and enjoy comfortable transfers by air-conditioned vehicle. Depart Siena in the early afternoon, and drive past the vineyards of the Chianti wine lands: neat rows of vineyards, and landscapes shaped into works of art by the combined forces of nature and mankind. Head to a Chianti wine estate to tour the grounds and wine cellars. Learn the winemaking process before sitting down to a tasting of local Chianti wines and olive oil. Explore the medieval fortress of Monteriggioni and marvel at its intact ring of walls and turrets. Travel to the village of San Gimignano to enjoy the charming streets and laneways as the sun begins to set and daytime crowds have departed. Admire the medieval towers at a leisurely pace, and explore the many streets and squares. Visit the boutique stores of local crafts and products. Enjoy a typical Tuscan dinner at a local farm in the countryside. Taste the white wine of San Gimignano, the Vernaccia, or have some local Chianti red wine. Weather permitting, dinner will be served outdoors. Return to Siena after dinner.

From Siena: Dinner in the Chianti Vineyards

4. From Siena: Dinner in the Chianti Vineyards

Discover the history, landscapes, wines, and culinary traditions of Chianti on this day trip from Siena. Travel in a comfortable and climate-controlled vehicle to a quaint farm in the hills. Engage your senses as you try a range of wines and savor a gourmet dinner.  Enjoy the convenience of being picked up from a centrally-located meeting point in Siena. Admire the Tuscan countryside as you travel to a farm tucked away in between rows of vineyards where grapes ripen in the Italian sun.  Pick up a wine glass to carry with you on your visit to the farm's winery. Sample a variety of delicious wines as you walk along a charming wine route. Visit the estate’s historic chapel before finally heading to your candle-lit dinner under the stars.  Listen to harmonious background music and lookout at the vineyards as you indulge in a farm-fresh gastronomic experience made from traditional recipes. Taste pappa al pomodoro or ribollita ( both are variations of Tuscan bread soup) and barbecued meat served with seasonal vegetables.  Let yourself get carried away by the warmth and fragrances of the barbecue and the perfumes of the grapevines, which enhance the dining experience. After dinner be escorted back to Siena where the tour will finish.

From Florence: Sunset Wine Tasting Tour in Vintage Car

5. From Florence: Sunset Wine Tasting Tour in Vintage Car

You have dreamed of a romantic Italian getaway, get ready to make that dream a reality with our vintage Fiat 500 Sunset Drive and unique Wine Tasting experience. Your adventure is shaped from the start with the fantastic and compelling narrative of the Fiat 500 history, its relevance in Italian history. After you have become familiarized with your car and understand its personality, our guide will lead the convoy on the adventure of a lifetime. The gentle hum of the engine, the feel of the meandering roads opens us to the breathtaking view of the tuscan hills and as we drive into the past, we are exposed to the historicTuscan Villas, cypress lined roads endless vineyards and captivating olive groves. At our stop you will enjoy a Spritz cocktail followed by a wine tasting and sampling of the best local Tuscan cheeses and meats. This adventure will warm your heart with memories that will last a lifetime.

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Other Sightseeing Options in Chianti Hills

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What people are saying about Chianti Hills

Overall rating

4.3 / 5

based on 77 reviews

Guillermo was outstanding! Fun, knowledgeable and wonderful company.( and an excellent driver!) This tour covered so much of what you want to see and experience of the Tuscany country. The group size of 6 was perfect. The winery visit and farmhouse dinner were “bravissimo!” A highlight of our 2 week trip covering Rome, Siena and Florence.

Excellent guide Francesco, and excellent group of people along with us on the tour. Small group of 8 people total is perfect size for wine tour. Skip the large tour bus and pay more for this, well worth it.

Excellent homemade food, rich wines, a Great driver and knowledgeable tour guide led to a wonderful afternoon/evening.

Ambre made the tour very fun as well as educational. Would highly recommend!

Luigi was a wonderful and very knowledgeable guide