Tuscany tours, walking and wine tasting in Italy

“A week long holiday in Tuscany, travelling in a small group with a local guide, at a beautifully relaxed pace. And plenty of beautiful wine too.”


Pisa | Florence | Tuscany wine tasting | Tuscany walking trails | Greve | Montefioralle | Fonterutoli | San Gimignano | Visit to Tuscan Wine School | Three wine tastings

Description of Tuscany tours, walking and wine tasting in Italy

Walking and wine tasting, Italy and its inimitable gastronomy, Tuscany with its enticing hills and hiking trails. It makes for a heady mix of beauty really on this week long holiday that takes in urban greats such as Siena and Florence. Mixed with more rural classics too, such as the medieval market town of Greve in Chianti, or the ancient stone village of Montefioralle, with views over Tuscan splendour all around, including cedar and olive groves that have just lined your morning’s walking trail.

Chianti is, of course, a recurring theme on this trip, with a visit to the Tuscan Wine School in Siena, or taking a walk around Fonterutoli where the castle estate is famous for its Chianti vineyards. Another day of walking up to the medieval, hilltop and walled town of San Gimignano is toasted with a wine tasting at nearby Villa Il Palagetto, most famous home to Vernaccia grapes.

The walking on this holiday is gentle and with few inclines. This is a Tuscany walking holiday that is all about savouring not only its picturesque landscapes but also their most famous produce. Staying in a converted stone farmhouse with stunning views, particularly from the swimming pool. Which deserves another toast.

Hello. If you'd like to chat about this holiday or need help finding one we're very happy to help. Rosy & team.

01273 823 700


Check dates, prices & availability

08 Oct 2016
£ 979
including UK flights
15 Oct 2016
£ 979
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22 Apr 2017
£ 949
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06 May 2017
£ 1019
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20 May 2017
£ 999
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10 Jun 2017
£ 1019
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24 Jun 2017
£ 1069
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15 Jul 2017
£ 1099
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19 Aug 2017
£ 1169
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02 Sep 2017
£ 1099
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09 Sep 2017
£ 1099
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16 Sep 2017
£ 1099
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30 Sep 2017
£ 999
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14 Oct 2017
£ 999
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Holiday type

Small group holiday

Small group travel is not large group travel scaled down. It is modelled on independent travel – but with the advantage of a group leader to take care of the itinerary, accommodation and tickets, and dealing with the language. It’s easy to tick off the big sights independently – but finding those one-off experiences, local festivals, travelling markets and secret viewpoints is almost impossible for someone without the insider knowledge gained from years in the field. If you’re heading off on a gap year your, perhaps – but for those with a two-week holiday, a small group tour will save valuable planning time.

The leaders are not guides – they’re not there to shepherd you around. Instead, they’ll let you know which local restaurant serves great value food – without running the risk of travellers’ tummy. They’ll allow you to avoid hour-long queues at train stations and attractions.

We like to think of small group travel as the Goldilocks option. It is independent travel without the fuss, worry and bunk beds – and organised travel without the coaches. And it’s cheaper than a tailor made tour. It’s sits somewhere in the middle – and we think it’s just about right.

What are the main benefits?
Big experiences
Have big, life-enriching experiences that would be impossible to organise without lots of time and insider knowledge.

Make the most of your holiday time by letting someone else do the hard work and boring logistics!

Peace of mind
Small group tours take care of the security aspects – and provide a safety net should anything unexpected happen.
Who is it ideal for?
Travellers who are short of time
If you don’t have three months to spend exploring, small groups trips let you cover more ground in less time. Your days are not spent queuing for tickets or finding hotels – so you can squeeze more into your holiday.

Solo travellers who’d like company
Likeminded travel companions plus peace of mind for those travelling alone. Single supplements are usually available – providing privacy if you want it.

Less confident travellers
Stray from the tourist trail without worrying about getting lost, and meet local people without dealing with the language barrier.
“I won’t get any privacy!”
Couples and friends have private rooms, and you can choose to eat alone or not. Single supplements give solo travellers their own room.

“There won’t be any free time”
Free mornings or afternoons let you explore on your own, or just relax.

“The accommodation will be basic”
Trips are as high or low end as you like. Though off the beaten track destinations won’t have luxury hotels, this is all part of the adventure.

“I won’t like the other travellers!”
Tour operators try to create groups with a similar demographic – age, families, activity levels... Chances are, you’ll even make new friends.

“Will we be following an umbrella?”
Valerie Parkinson
Meet a group Leader
Name: Valerie Parkinson

Story: The first British woman to climb Manaslu, Valerie climbed Everest for her 50th birthday. She’s spent fourteen Christmas Days trekking to Everest Base Camp, and is involved insetting up Responsible Tourism initiatives in the Himalayas.
Roshan Fernando
Meet a local guide
Name: Roshan Fernando

Story: Roshan has led over 130 trips – he adores showing travellers around Sri Lanka. He won the company Leader Award in 2010, but his career highlight was working on their Tsunami Project – which earned him a responsible tourism award.

Responsible tourism

Responsible tourism: Tuscany tours, walking and wine tasting in Italy


Few holidays have as little detrimental impact on the environment and local residents as a walking trip. Erosion on and adjacent to popular paths is a growing problem in certain places and therefore our trip leaders encourage clients to stick to advised routes in order to minimise this. We do believe in leaving no more than footprints, although this tour does encourage clients to have a positive effect by engaging with locals, using cafes and restaurants, and investing in traditional gifts and local produce. By visiting a number of places of interest and offering additional optional excursions, we support those who run these trips and the upkeep of historically important sites.

UK Office:
It all starts at home so we have first worked at reducing our carbon footprint in our UK Offices. Through energy conservation measures and recycling policies, we are proud to be actively reducing the waste produced and our impact on the environment. We support various projects all over the world to try and give something back to the places we visit.


Accommodation and Meals:
We will spend seven nights at Villa Casalta- a charming renovated farmhouse in the heart of Chianti. The villa is family-run and staff members are local to the region, meaning we have a more positive impact on local economy: local employment opportunities are created and income generated is reinvested in the area. Surrounded by incredible vineyards and woodland, the farmhouse has access to some very fresh, local ingredients, including renowned Chianti wines, olives and olive oil. Many meals are provided and will include a number of regional specialties including locally cured meats on crostini, Tuscan bean soup, fish stew, homemade pasta and Florentine steak. The owners are environmentally conscious and try to minimise negative effects on their natural surroundings by paying attention to recycling and energy conservation.

Local Craft and Culture:
We arrange for three wine tastings over the course of the trip, where we learn about local wines and how they are made. This includes a session in the farmhouse, one in Villa Il Palagetto, where excellent Vernaccia wines are produced, and a short course at the Tuscan Wine School. These are great opportunities to support local suppliers and to encourage the traditional methods of local wine production. We also engage with local culture by visiting many places of interest- for example, Siena, with its many galleries and impressive gothic cathedral, and small mediaeval villages such as Greve in Chianti and nearby Montefioralle, where prized Chianti wines are grown.

Group Size:
This small group tour has a maximum of 16 participants, meaning that we have a low impact on the environments and communities we visit and are able to ensure that we do not disrupt or lead to the displacement of local people. The small number also allows us to stay in unique, family-run hotels that cannot benefit from coach tours and other mass tourism due to their limited sizes.

Reviews of Tuscany tours, walking and wine tasting in Italy

You can trust Responsible Travel reviews because, unlike many other schemes, reviews can ONLY be written by people who we have verified have been on the holidays.

I am reborn! Simply the best holiday I have ever been on
Some great stories to tell the grandchildren. Would recommend to a friend
Very enjoyable
It was OK
A bit disappointing really

Reviewed on 01 May 2016 by

1. What was the most memorable or exciting part of your holiday?

Viewing the city of Florence from the Viewpoint of Piazza Michaelangelo

2. What tips would you give other travellers booking this holiday?

Come prepared for any kind of weather. We had wind, rain, thick cloud and hot sunshine.

3. Did you feel that your holiday benefited local people, reduced environmental impacts or supported conservation?

Very much so. We stayed in a very lovely converted farmhouse, ate in local restaurants, shopped in small towns and villages, and tasted the local Chianti Classico in several wineries.

4. Finally, how would you rate your holiday overall?

A wonderful mixture of fabulous walks through forests and vineyards, local history, culture in Siena and Florence, a fabulous cookery course in a nearby restaurant, and several most enjoyable and informative wine tastings.

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