Tour Details

Small-Group Day Trip to Castellina and Greve in Chianti from Siena

From: £108.63

Duration: 8 hours

Category: Sightseeing

This small-group tour from Siena takes you to Tuscany’s northern Chianti region, known as the Florentine Chianti, where you’ll visit the pretty villages of Castellina and Greve (officially known as Castellina in Chianti and Greve in Chianti). During this full-day trip, see breathtaking landscapes, enjoy a traditional lunch and visit two wineries with your expert guide. Meet the area's famously welcoming inhabitants and get a taste for life in the Florentine Chianti!

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

Leave Siena early in a luxury minivan with your guide, and set off to the Chianti hills, enjoying views of beautiful forests, rows of vineyards and pretty medieval hamlets. Your first stop is the walled village of Castellina in Chianti, where you'll explore the town and its covered medieval walkway with your guide. See the fascinating Castle of Castellina, which dates to the 15th century and was built by the order of Lorenzo il Manifico, a popular Florentine statesman in medieval times.

Next, head to the beautiful town of Greve in Chianti, famous for its triangular-shaped piazza and for being the home of famous sailor Verrazzano. Have leisure time here to sample wines (additional cost) or visit the local boutiques and market stalls.

From Greve, you'll take a short drive over to Montefioralle, a village that claims to be the birthplace of Amerigo Verpucci, the famous cartographer who gave his name to the Americas. Enjoy a walk along Montefioralle’s cobbled streets and take in the breathtaking views.

Just outside of this beautiful village is a family-run winery, where you'll enjoy a delicious Tuscan lunch, consisting of cured meats, home-grown vegetables and cheeses, and enjoy a wine tasting of the famous Black Rooster Chianti Classico. While you eat and drink, learn from your friendly guide about the region’s customs and traditions. Then visit another, larger winery, where you’ll be guided through the process of wine production and visit the wine cellars. Hear more about Chianti’s famous red wines, including how they are made and the differences in flavor of the various blends and grapes.

Your last stop before returning to Siena is the beautiful Abbey of Passignano, where you’ll admire the glorious landscapes of the surrounding countryside. The abbey, whose existence has been documented from the beginning of the 11th century, was once one of the most powerful castles of the Val di Pesa.

Nearby tours

  • tours

Small-Group Montepulciano and Pienza Day Trip from Siena

Duration: 8 hours
Category: Sightseeing
From: £108.63

Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO-listed ...

read more

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Duration: 8 hours
Category: Sightseeing
From: £108.63

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover the cellars where these incredible wines age, mee...

read more

Small-Group San Gimignano and Volterra Day Trip from Siena

Duration: 8 hours
Categories: Culture & History, Sightseeing
From: £108.63

Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round the Fortress of Monteriggioni, explore the UNESCO World Heritage-li...

read more

Small-Group Chianti and San Gimignano Sunset Trip from Siena

Duration: 8 hours 30 minutes
Category: Sightseeing
From: £116.68

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...

read more

Small-Group Chianti Wine-Tasting and Castles Trip from Siena

Duration: 8 hours
From: £97.77

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the re...

read more

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