Tour Details

Small-Group Chianti and San Gimignano Sunset Trip from Siena

From: £116.68

Duration: 8 hours 30 minutes

Category: Sightseeing

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine cellars. Then head to the UNESCO World Heritage-listed town of San Gimignano after the day’s crowds have dispersed. During the sunset, dine in a beautiful farmhouse overlooking the San Gimignano towers and the rolling, vine-covered hills.

Numbers are limited to eight people on this small-group tour, ensuring you'll enjoy personalized attention from your guide.

Your small-group tour begins in the afternoon with a comfortable drive in a luxury minivan from Siena to Chianti -- a region of Italy famous for its beautiful vineyards and landscapes shaped into works of art by the combined actions of nature and man. Arrive first in the village of Castellina in Chianti, and enjoy a gelato (own expense) as you walk through its medieval alleyways and town center with your guide.

From here, enjoy the drive to a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the winemaking process. Sit down and savor a tasting of Black Rooster Chianti Classico wine and olive oil (included).

Then head to Monteriggioni, a perfectly preserved medieval town with a complete ring of walls and turrets built in the 13th century. It was Siena’s main bastion of defense against the armies of Florence during the Middle Ages, and today it is a quiet hamlet. Enjoy leisure time here to explore the charming city on your own.

In the late afternoon, arrive in San Gimignano and explore this romantic town of towers. You'll have free time to enter its impressive church, the Collegiata di San Gimignano, or explore the Civic Museum (entrance fees at own expense). Alternatively, shop in the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars; or discover the town’s many hidden beauties.

After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner, accompanied by tastings of Vernaccia (the famous white wine of San Gimignano) and red Chianti wine. Your Tuscan dinner, consisting of cured meats, home-grown vegetables and cheeses, will be served on a terrace overlooking the cultivated fields and the ‘skyline’ of San Gimignano’s towers during sunset. As your tour comes to an end, meet your guide back at the minivan for the relaxing return journey to Siena.

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Culture Shock Rating

We have a wide range of tours designed to give you an insight into the destination you're travelling in and there is something for everybody. The culture shock ratings considers the destination visited, transport used, activities undertaken and that "Wow, I'm really not at home now!" factor. While generalisations are always tricky, a summary of our gradings is as follows…

20%

This is the least confronting of our tour range. Transport used on the trip is either private or a very comfortable public option, the activities included are usually iconic sites and locations that are not all too confronting.

40%

The tour can include a mix of private and public transport providing a level of comfort that is slightly below what you would experience at home. Sites visited are usually iconic sites, tours can also include market visits, visits to communities etc that provide the traveller with a fantastic insight into destination.

60%

Expect to rough it for parts of this tour, whether it's a packed public bus where you are forced to stand, a visit to a local market, a local community, you are sure to have an experience that is very different from what you're used to at home.

80%

The comforts of your home town and the environment you are used to are more of a rarity. Expect some challenging transport options, visits to local sites and areas that don't resemble anything at home.

100%

You're out there in the global community! You are likely to be exposed to the elements, travel in whatever means of transport is available and basically take it as it comes, whatever comes! It can be tough.

Physical Rating

Our physical rating gives you an idea of how much huffing and puffing you can expect on the tour. While generalisations are always tricky, a summary of our gradings is as follows…

20%

These tours have very limited physical activity. Usually climbing in and out of the transport provided, walking through sites, markets etc included in the itinerary.

40%

These tours have a bit of physical activity but nothing that should challenge you too much. This could be climbing on and off public transport through to a walk through the destination you're travelling in, they can include walking only tours or a combination of walking and transport.

60%

These tours involve a bit of physical activity from walking up and down hills in the destination you're travelling in or the surrounding areas. Climbing on and off local transport or riding a bike up to 30 kms along predominantly flat terrain or jumping in a kayak for a gentle paddle on flat water.

80%

These Tours will provide you with some solid physical activity. Whether its bike riding, walking, trekking, kayaking or riding on public transport you will need to have a good level of fitness to enjoy this tour.

100%

Be prepared for some serious physical activity. These tours are our most challenging and involve some serious walking, hiking or bike riding. Can involve step climbs by foot or pedal and some challenging public transport options in the destination you are travelling.

Luxury Rating

Some trips are like a stroll on the beach, while others have you trekking alpine passes. Some of you thrive on camping out on the savannah, while others may prefer a hot shower and a comfortable bed in a lodge. Follow the grading systems below to find the right trip for you.

To help you choose the trip that's right for you, we've broken all of our trips down into four service levels. Measuring the comfort level of the accommodation and transport. So whether you're travelling on a budget and want to save money by using public transport, or prefer upgraded accommodation and are happy to pay a little more, then we have a level for you.

25%

This is grassroots travel at its most interesting

50%

Authentic experiences with some of the comforts of home

75%

For those who like to travel in comfort

100%

All the unique experiences wrapped up with a gold ribbon