- Experience classic Tuscany on foot: rolling vineyards, Renaissance cities and medieval villages
- Sip chianti and other local wines on three separate tasting experiences
- See Siena through the eyes of local on a history and culture tour with a local guide
- Discover magnificent Florence on a walking tour with a local guide
- Feel like one of the family with a stay in the Tuscan hills at Hotel Le Renaie
Tuscany Walks & Chianti Wines
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- Tuscany Walks & Chianti Wines
Start
Finish
Availability
Land Only Trip Price
Optional Single Supplement
Saturday Saturday
11 Apr 2026 11 Apr 2026
Saturday Saturday
18 Apr 2026 18 Apr 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
18 Apr 2026 18 Apr 2026
Saturday Saturday
25 Apr 2026 25 Apr 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
02 May 2026 02 May 2026
Saturday Saturday
09 May 2026 09 May 2026
Availability
Guaranteed (Limited)
Land Only Trip Price CAD 4560
Optional Single Supplement +CAD 1197
Availability
This departure is guaranteed to go ahead but there are only 3 spaces left. Do not delay your booking!
View Trip NotesSaturday Saturday
09 May 2026 09 May 2026
Saturday Saturday
16 May 2026 16 May 2026
Availability
Guaranteed (Limited)
Land Only Trip Price CAD 4560
Optional Single Supplement
+CAD 1197
Available upon Request
Availability
This departure is guaranteed to go ahead but there are only 2 spaces left. Do not delay your booking!
View Trip NotesSaturday Saturday
23 May 2026 23 May 2026
Saturday Saturday
30 May 2026 30 May 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
13 Jun 2026 13 Jun 2026
Saturday Saturday
20 Jun 2026 20 Jun 2026
Availability
Available
Land Only Trip Price CAD 4560 Book with CAD 1140 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
29 Aug 2026 29 Aug 2026
Saturday Saturday
05 Sep 2026 05 Sep 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560 Book with CAD 1140 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
12 Sep 2026 12 Sep 2026
Saturday Saturday
19 Sep 2026 19 Sep 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560 Book with CAD 1140 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
19 Sep 2026 19 Sep 2026
Saturday Saturday
26 Sep 2026 26 Sep 2026
Availability
Available
Land Only Trip Price CAD 4560 Book with CAD 1140 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
26 Sep 2026 26 Sep 2026
Saturday Saturday
03 Oct 2026 03 Oct 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560 Book with CAD 1140 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
10 Oct 2026 10 Oct 2026
Saturday Saturday
17 Oct 2026 17 Oct 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560 Book with CAD 1140 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
17 Oct 2026 17 Oct 2026
Saturday Saturday
24 Oct 2026 24 Oct 2026
Availability
Guaranteed (Available)
Land Only Trip Price CAD 4560 Book with CAD 1140 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1197
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
10 Apr 2027 10 Apr 2027
Saturday Saturday
17 Apr 2027 17 Apr 2027
Availability
Guaranteed (Available)
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
17 Apr 2027 17 Apr 2027
Saturday Saturday
24 Apr 2027 24 Apr 2027
Availability
Available
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
01 May 2027 01 May 2027
Saturday Saturday
08 May 2027 08 May 2027
Availability
Guaranteed (Available)
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
08 May 2027 08 May 2027
Saturday Saturday
15 May 2027 15 May 2027
Availability
Available
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
22 May 2027 22 May 2027
Saturday Saturday
29 May 2027 29 May 2027
Availability
Guaranteed (Available)
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
29 May 2027 29 May 2027
Saturday Saturday
05 Jun 2027 05 Jun 2027
Availability
Available
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
12 Jun 2027 12 Jun 2027
Saturday Saturday
19 Jun 2027 19 Jun 2027
Availability
Guaranteed (Available)
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
28 Aug 2027 28 Aug 2027
Saturday Saturday
04 Sep 2027 04 Sep 2027
Availability
Available
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
11 Sep 2027 11 Sep 2027
Saturday Saturday
18 Sep 2027 18 Sep 2027
Availability
Guaranteed (Available)
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
18 Sep 2027 18 Sep 2027
Saturday Saturday
25 Sep 2027 25 Sep 2027
Availability
Available
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
25 Sep 2027 25 Sep 2027
Saturday Saturday
02 Oct 2027 02 Oct 2027
Availability
Guaranteed (Available)
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
09 Oct 2027 09 Oct 2027
Saturday Saturday
16 Oct 2027 16 Oct 2027
Availability
Guaranteed (Available)
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
16 Oct 2027 16 Oct 2027
Saturday Saturday
23 Oct 2027 23 Oct 2027
Availability
Available
Land Only Trip Price CAD 5510 Book with CAD 1377 deposit Book with CAD 500 deposit
Optional Single Supplement +CAD 1264
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesExtend Your Trip
Florence Hotels

Extend your love affair with Italy and discover Florence, the birthplace of the Italian Renaissance. Marvel at Michelangelo’s David, and climb the Duomo for sweeping views. With every cobbled corner tempting you to linger, and pit stops for carpaccio, ribollita or creamy gelato all but essential, it’s time to lean in and live your best dolce vita. Here are a few of our favourite hotels to inspire your stay:
Cellai Boutique Hotel: A charming boutique hotel set in a historic building near to Florence’s main sights. With individually styled rooms, cosy lounges and a welcoming atmosphere, it offers a warm base for exploring the city.
Spadai: Located just 100m from the Duomo, this contemporary hotel combines sleek design with excellent comfort and service. Its central location, modern rooms and thoughtful touches make it ideal for travellers wanting to be right in the heart of Florence.
Balestri: Overlooking the Arno River near Ponte Vecchio, Hotel Balestri blends classic Florentine style with modern amenities. With river views, refined rooms and easy access to the historic centre, it’s a relaxing and well-placed option for extending your stay.
This is just a glimpse of what’s possible. Speak to your sales representative, who can guide you through the options and arrange everything for you.
Reviews
Add your own reviewBeautiful Tuscan countryside, good wine, delicious food, and history
I thoroughly enjoyed this trip. It was a great blend of walking through the beautiful Tuscan countryside, tasting organic wines, sampling delicious local foods, and getting a bit of Renaissance and medieval history with visits to Sienna, Florence, and San Girmignano.
Most Inspirational Moment
Witnessing the passion of the younger generation who have chosen to continue the legacy of small family run wine and olive farms. This is very heartening in an over commercialized world.
Thoughts on Group Leader
I can’t say enough about Roberta. She has a wonderful, positive energy and sincere passion for the area. She is extremely caring and has a natural ability to make everyone feel included without it feeling forced at all.
Advice for Potential Travellers
Bring your appetite,
Tuscany Walks & Chianti Wines
A wonderful trip with a great group leader who went above and beyond to make sure we were all comfortable and well taken care of.
Most Inspirational Moment
Not really one moment for me. I loved the walks in beautiful Tuscany. The suppers we had together were really nice.
Thoughts on Group Leader
Jordan was amazing. He really went above and beyond to make sure we all had an amazing trip, which we did.
Advice for Potential Travellers
The number of kilometres each day was not a lot, but be ready to do up and down of hills - Tuscany is a beautiful mountainous region.
It's Not Just About the Wine
The whole week was fantastic! The walks were beautiful, the group was lovely and gelled well, the wine and food were delicious, the hotel staff was gracious and accommodating, and Jordan (our guide) made the whole experience work!
Most Inspirational Moment
Sitting around during down times or at meal times hearing other people's stories. It was great getting to know the other travelers, laughing and sharing experiences.
Thoughts on Group Leader
Jordan was brilliant! He set the tone for the whole week, making it fun and safe. He provided great routes to walk, all sorts of fascinating knowledge, and kept an eye out for the needs of each individual. His passion was evident in his respect and care for the group and the locals.
Advice for Potential Travellers
Be willing to be open and engage with the other travelers. It makes a huge difference in the whole experience, even if you are doing this solo.
A fabulous week in Tuscany
The week was full of many different experiences. Despite a smaller group than usual, the walking was excellent, even though it was very hot. The wine-tastings were very different, and all informative, some with some nice nibbles included. The hotel is lovely with an excellent (ask for a room with a view) with a swimming pool and home made pizzas to die for. City-wise, we visited St Gimignano, Siena (brilliant guided tour included) and Florence. Our guide, Jordan, did a great job keeping us under control.
Most Inspirational Moment
Meeting El Magnifico in his bakery in Siena
Thoughts on Group Leader
Brilliant
Advice for Potential Travellers
Make sure you get a room with a view Take lots of water on the walks!
Tuscany Kevin
An excellent tour with sensible walks, great food and marvellous sightseeing.
Most Inspirational Moment
Revisiting Siena
Thoughts on Group Leader
Outstanding
Advice for Potential Travellers
Enjoy!
A wonderful trip from beginning to end!
I had a brilliant experience walking and wine tasting in Tuscany, led by our fantastic guide, Jordan. This trip has a good balance of picturesque walks, wine tasting and city days and offers a great introduction to one of Italy’s most beautiful and historic regions. Our itinerary ran seamlessly and there was never a moment where I felt it was too full-on, as we were given plenty of free time between activities. I would do this trip again in a heartbeat!
Most Inspirational Moment
Visiting Florence - a city steeped in history and culture!
Thoughts on Group Leader
Fantastic - Jordan went above and beyond to ensure we enjoyed our holiday.
Advice for Potential Travellers
Plan ahead for the free day. There are activities you can book through the hotel but availability can be limited.
Tuscany Walks & Chianti Wines is set in a beautiful rural location.
A very relaxed but full itinerary walking holiday. Challenging walks at times with lots to do but well balanced with down time to enjoy the surroundings and wine.
Most Inspirational Moment
It's hard to pick one moment as the scenery is beautiful. We were inspired by the views every day, the countryside, the villages, Siena and Florence. Not to mention the local wines!
Thoughts on Group Leader
Liz was amazing, it was all about the groups needs and keeping us safe, doing her utmost to ensure we had the best possible experiences. Liz's knowledge of the region was impeccable. Liz was friendly and a great part of the group.
Advice for Potential Travellers
The hotel is quite rural, be prepared for the lack of a convenient shop!
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