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
£2075To£2195including UK flights
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8 Days
Small group
More info
From £1595 - £1795 excluding flights.
Optional single supplement from £255 - £270.
Make enquiry

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.


Price information

£2075To£2195including UK flights
Convert currency:
From £1595 - £1795 excluding flights.
Optional single supplement from £255 - £270.
Make enquiry

Check dates, prices & availability

Travel guides

Italy walking
Passionate, food loving, fiery, elegant, religious and beautiful. These clichιs about Italians pretty much fit the picture of walking holidays in Ital...

Holiday information

Small group tours:
Small group travel is not large group travel scaled down. It is modeled 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. Those with a two-week holiday, a small group tour will save valuable planning time.
Dietary requirements:
We can cater for vegetarian and vegan diets.


11 Reviews of Tuscany tours, walking and wine tasting in Italy

4 out of 5 stars

Reviewed on 11 Jun 2023 by

Most memorable were the beautiful walks out of Bomerano, guided by the most delightful, knowledgeable and professional walk leader you could wish for. Read full review

Reviewed on 23 Apr 2023 by

One of our most memorable trips! Read full review

Reviewed on 25 May 2023 by

Benefited locals by our custom Read full review

Reviewed on 26 Jun 2022 by

The whole holiday was lovely. The scenery/accommodation/fellow travellers Read full review

Reviewed on 12 Oct 2022 by

Average. Dreadful accommodation if you are unlucky! Some had good rooms. Some did not (i.e. me). Had to pay another E200 for a decent room for last 4 nights! Read full review

Reviewed on 20 Oct 2019 by

Very good! Fantastic scenery, Lovely walks, Wine tasting and Great food. Read full review

Reviewed on 12 Sep 2019 by

Tuscany tour not that memorable. Read full review

Reviewed on 08 Oct 2018 by

Very good Read full review

Reviewed on 22 Oct 2018 by

Well organised and lovely accommodation Read full review

Reviewed on 27 Sep 2017 by

The stunning views of the coastline during the walks. Read full review

Reviewed on 01 May 2016 by

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. Read full review

Responsible Travel

As the pioneers of responsible tourism, we've screened this (and every) holiday so that you can travel knowing it will help support the places and people that you visit, and the planet. Read how below.


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.

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