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Tuscany Wine & Hiking Tour

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  • Location: Italy
  • Duration: 7 days/6 nights
  • Departing from: The first night is in Florence on Sunday, Sept 24. Day 1
  • Tour finishes: Arezzo train station 10:00 a.m. on Day 7
  • Departures 2024: June 2 and Sept 22 and Private departures, contact us for details.
  • Price 2024: Euro €3,250 per person based on double occupancy and minimum group size of 4 pax. Single Supplement Euro €450. One guide accompanies departures of 2 - 8 people. Two guides accompany departures of 9 or more people.

Wine and hiking do mix!
Customwalks founder Brett Naisby has been living in the Chianti region of Tuscany since 1994, where he has been expanding his knowledge of the wines of Montalcino, Chianti, and Bolgheri, but also getting to know the owners and wine-makers from many of the region’s top producers, big and small. This makes all the difference when it comes to gaining access to special wineries, special wines, and the people behind them. Join us as we spend a week hiking from winery to winery, through Tuscany’s sublime wine country learning from local wine makers, agronomists, chefs and sommeliers about the area’s wine, cuisine, and culinary culture. This tour offers up the perfect combination of natural beauty, exercise, and learning, along with just the right amount of hedonistic wine and food consumption!

Tuscany Wine & Hiking Tour Includes

  • Accommodation: 6 nights accommodation (1 night in the 4-star Hotel Orto Dei Medici in Florence, 3 nights at the 4-star Relais Vignale in Radda in Chianti or Radda in Chianti, 2 nights at the 4-star Il Chiostro di Pienza in Pienza)
  • Meals: 6 breakfasts, 1 lunch, and 5 dinners
  • Luggage: Bags are transferred starting with pick-up from Florence and ending with the final transfer to Arezzo train station
  • Special events: Visit and tasting at three wineries, one in the Chianti Classico Panzano village classification, one in the Chianti Classico area Gaiole in Chianti village classification, the other in the Brunello di Montalcino area. Guided visits of the Castello di Brolio and Siena.
  • Transport: Private van transfers as indicated in the itinerary
  • Active days: 5 days of guided hiking and 1 day in Siena
  • Guides: At least 1 bilingual Customwalks guide accompanies departures of 2 - 8 people; 2 guides accompany departures of 9 or more
  • Max group size: Tours are capped at 14 people

Booking: Please e-mail us at info@customwalks.com to receive a booking contract or simply click on the BOOK NOW button or the 'Contact Us' tab. Thanks!

Tuscany Wine & Hiking Tour itinerary Request full itinerary

Day 1: Arrival Day

Independent arrival Florence and check into the four-star Hotel Dei Medici or similar. Dinner is on your own this evening. Overnight Florence. If you wish to arrive earlier, please let us know and we will book you the extra nights. We do not charge for this service. Hotel included.

Day 2

Pick up at the Hotel Orto Dei Medici and short transfer to the Villa Agape. A short hike to Abbazzia San Miniato al Monte for a visit of this exquisite basilica and monastery. One of Italy’s most beautiful medieval buildings. We will finish the morning with an urban hike (paved lanes, sidewalks, roads) through the historic Pian Di Giuliari district, a plateau that is dotted with Renaissance villas, and Galileo Galilei’s observatory and home. A 40-minute transfer brings us to la Cantinetta di Rignana, a classic trattoria set amongst the rolling hills not far from Panzano in Chianti. After lunch, a short transfer Fattoria Le Fonti, a beautiful small winery on the edge of Panzano in Chianti. Here we are welcomed by my friend Guido, who together with his wife Vicky own and run the winery. A brief visit of the winery is followed by a tasting of their Chianti Classico, Chianti Classico Riserva and “super Tuscan” wines. If it is a nice day, the tasting will include a magnificent view out over the vineyards onto the Villa Vignamaggio, where Da Vinci painted the Mona Lisa. Afterward, a twenty-minute drive brings us to Radda in Chianti where we check into the Relais Fattoria Vignale, an 118th-centurymanor house that is now a four-star hotel with magnificent views over the Chianti hills. A two-minute walk into the village for dinner t trattoria Da Giovannino. The Hike: Very easy hiking on gently rolling terrain and on paved surfaces. Morning distance: 5.5 kms. Hike time. 1.5 hours plus time for explanations of the history. Overnight Radda in Chianti at the four-star Relais Fattoria Vignale.  Transfer, winery visit and tasting and dinner included. Lunch not included.

Day 3

After breakfast a private transfer to the Castello di Brolio. Our morning hike takes us under the massive walls of the castle, through their vineyards and olive groves to the castle itself, whose gray stone walls have stood for 900 years. Visit the park and gardens of the castle and the small but fascinating museum that is dedicated to Baron Benito Ricasoli, who was Italy’s first Prime Minister and who established the recipe for Chianti Classico wines. Lunch at a local trattoria followed by a visit of Ceramica Rampini’s workshop and store. Rampini produces hand-painted majolica ceramics using traditional techniques which feature Renaissance-era designs as well as contemporary motifs to decorate dinner sets, jugs, and vases. The Hike:  1 hour in the morning, relatively flat but sometimes rolling. Optional afternoon hike: 6 km (4 mi) loop over rolling, hilly terrain. Overnight Radda in Chianti.  Hotel, breakfast, and dinner included.

Day 4

Our morning hike starts directly from the hotel and leads up into the Chianti hills to the tiny hamlet of Bricciano, where we will meet Rory O’Kelly for a visit of his cantina. Yesterday we visited one of the largest producers in Chianti, today we visit one of the smallest! Rory’s South African father established this small boutique winery in the 1990s and Rory is continuing his father’s passion for the winery. He is intent on making world-class wine and the result is very persuasive. After the visit, we have a short hike to a private home where we have lunch. The afternoon hike takes us to the Castello di Meleto, a 13th century fortress that evolved over time into a Baroque summer residence. From here you have a short van transfer back to Radda. Dinner tonight is al fresco at Ristorante Le Panzanelle. The Hike:  1.5 hrs in the morning, 2.5 hrs in the afternoon through rolling terrain. Overnight Radda in Chianti.  Hotel, breakfast, lunch, dinner and tasting included.

Day 5

Today we have a scenic 40-minute van transfer to Siena, one of Italy’s most beautiful and historic cities. We have a guided visit with Rita, our favorite city guide. Only a native of this Gothic city can explain the furor and passion that surround the famous bareback Palio horserace, which is run around the city’s 12th century Piazza del Campo twice a year. You will have free time to explore the exquisite historic center and admire its Gothic architecture. Of course, you might get side-tracked by the shops and cafés along the Banchi di Sopra, Siena’s main pedestrian shopping street. Enjoy lunch in Siena and then meet up again before a scenic drive through the Crete Senese to Pienza. Our hotel for the next two nights is the lovely four-star Relais il Chiostro, a former Franciscan Convent dating back to the 13th century, located in an enviable position, in the center of the magnificent hamlet of Pienza, in the heart of the Val d’Orcia. The Hike:  Urban hiking in Siena. Overnight in Pienza.  Hotel, breakfast and dinner included. Lunch not included

Day 6

After breakfast we have a short transfer towards Montalcino to begin our hike to the 13th century Abbey of Sant’Antimo. The hike takes us through Brunello vineyards, verdant woods, and rustic farming villages before we arrive at the abbey. Sant’Antimo is one of the most important and famous examples of Romanesque architecture in Italy. After lunch at the trattoria in Castelnuovo dell’Abate we have a short drive to “Uccelliera,” one of Brunello’s premier small wineries, for a truly unique and insightful tasting in their cantina. We start in the cellar and taste directly from the barrels the still unblended Sangiovese wines from two different vineyards. Here we taste the difference that terroir makes to a wine, and also age and even the type of oak barrel that is used. We then move to the tasting room to taste a flight of their Brunellos. Return to Pienza for free time to explore the town’s shops, cafés, and wine bars. Tonight’s dinner is at our favourite trattoria in Pienza, which also happens to have a superb wine list with many old vintages cellared to perfection. The Hike:  2.5 hrs in the morning, through rolling terrain, mostly downhillOvernight Pienza. Breakfast, dinner, Brunello winery visit and tasting  and hotel included.

Day 7

Transfer to Arezzo train station for trains after 10:30 a.m. to Florence and Rome. Drive time is 1 hour. Transfer included.

Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.  

Activity rating: 1 out of 5= Easy
In general: 
A 1 out of 5 rated tour is a tour without any hiking. Hikes would be in towns, cities, and villages, and the countryside hikes would be on paved, or gravel/dirt roads, and occasionally on some packed earth trails. Elevation gain and loss would be negligible. This is a very easy tour for fit hikers, and is designed to be easy for anyone who can hike for 90 minutes on flat terrain without getting fatigued. This is our easiest "hiking" tour.
Actual hiking time: between 2 - 3 hours per day, mostly in the morning but sometimes also in the afternoon.
Distances: Usually between 4 - 6 km (2.5 - 4 m.). Max distance is 7 km (4.6 mi)
Terrain: Flat to gently rolling terrain with some rocky areas. We will be hiking on small paved roads, dirt roads, gravel roads, and gravel roads that will be rocky from rain erosion. We will hike on some trails that will be mostly gravel and/or packed earth with some tree roots.
Surfaces: Paved or gravel/dirt roads, and trails consisting mainly of compact earth and/or gravel.
Footing: Easy/good. Proper hiking shoes are always preferred, but sports sandals, running shoes, and tennis shoes are adequate
Hiking Poles: Not required
Compared to the Cinque Terre: This tour is significantly easier than the hikes in the Cinque Terre
Other: This tour is appropriate for first-time “hikers”.
Easy Tours: This is our only Level 1 out of 5 tour. However, all our boat-based tours could become level 1 out of 5 if you skip the hikes and hike around the villages, harbors, and towns that we visit. 
As a point of reference, what is a 1 out of 5 Activity rating? A 1 out of 5 rated tour is a tour without any hiking. Walks would be in towns, cities, and villages, and the countryside walks would be on paved, or gravel/dirt roads, and occasionally on some packed earth trails. Elevation gain and loss would be negligible.
As a point of reference, what is a 5 out of 5 Activity rating? A 5 out of 5 rated tour is a tour that would be physically challenging and technically difficult even for very fit and experienced hikers. The hikes would have steep ascents and descents on narrow, exposed trails with challenging footing, such as on scree fields, or through rock falls and boulders. Distances would be up to 25 km/16 miles per day and feature ascents of over 1,000 m/3,200 feet in a day. A 5 out of 5 tour would also mean that you would be carrying a heavier-than-normal pack. None of our tours are rated 5 out 5. Our most challenging tours are 4.5 out of 5, and they are the Dolomites Alta Via (because of some exposed trail that requires some technical expertise) and our Republic of Georgia tour which has some long hikes with over 1,000 meters of elevation gain.

Getting There: the trip starts in Florence. Florence is well connected by road, rail and air with the rest of Italy and Europe.

Air: Florence airport receives both domestic and international flights through European hubs such as London, Paris, Frankfurt, Amsterdam, Munich and Brussels. You can also fly into Pisa (about an hour away by train) on many low-cost airlines. For a complete list of Italian airports and a selection of low-cost airlines, see our "Transport Info" page.

Rail: The Eurostar and new Italo high-speed trains connect Florence with Milan (travel time about 2.5 hours), Bologna (travel time 35 mins) and Rome (travel time 1.5 hrs). See the Trenitalia website (in English) at this link. For alternative high-speed rail travel, see the Italo website. For complete information on using the Italian train system, see our blog post.

Road: The A1 Autostrada connects Florence with the rest of Italy. Travel time from Milan is about 5 hours, from Bologna 1.5 hours, and from Rome about 3 hours.

Getting Away at the End of the Trip: The trip ends with a van transfer to the Arezzo train station after breakfast on day 7. We arrive around 10:00 a.m. to make 10:30 connections to Florence, Rome, or other destinations.

If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.

5/5
RatingRatingRatingRatingRating  
5 out of 5
Ratings based on 4 Verified Reviews



Average ratings
5.0
Guides
5.0
Quality of itinerary
5.0
Food quality & variety
4.8
Value for money
4.8
Right amount of activity
5.0
Overall satisfaction

Reviews
5
by Mary E.
Posted Jan 23, 2024

What’s not to love about walking in picture-perfect Italian villages and wine-growing regions and feasting on amazing Tuscan wine and food. Francesca was a perfect guide, always flexible and accommodating to our group’s preferences and energy levels, plus she’s such a fun person to be with. Customwalks has great relationships with local businesses in the region that we wouldn’t have found on our own, and we always felt like an “insider” enjoying all the amazing meals and tastings featured in our itinerary. Other tour highlights included a visit to a ceramics workshop and store (wonderful souvenirs!), a superior guided tour of Siena, and a master class with a noted winemaker. Our only regret is that we didn’t buy more wine to enjoy later!

4.8
by Cathy S.
Posted May 30, 2022

This is my third Customwalks tour. As usual, I was thrilled with the attention to detail, the food, the wine and the people. Brett managed everything so well and made everyone feel welcome. Tuscany is lovely in May, the temperature was just right. We ate so well and in so many beautiful settings. It's hard to say which was my favorite. The villa we stayed in was perfect. Can't wait to do it again!

5
by N. Fisher
Posted Oct 05, 2015

Four of my friends and I decided to take this tour back in March. We worked with Brett, the owner, to set up a private tour...We are sooooo happy we did that. The experience was truly a unique and special one! This was a fantastic trip! Spending time with great friends, eating delicious food, drinking some fantastic wine and seeing a beautiful part of Italy! What more could one ask for!! One thing that made this trip so unique and wonderful was our guide, Marco. His love for his country and culture was palpable and it wonderfully oozed into every part of our trip and made it a one of a kind experience. Brett and his Custom Walks Team (Marco and Manu) are fantastic and we felt they truly \customized\ the tour just for us. Thank you for a wonderful vacation!!!

4.8
by MSL
Posted Jan 31, 2015

We did this walk in 2007. It was our first walk with CW staff. It and Puglia were the easiest walking trips we have done. We particularly liked the food on this tour, probably our favorite, but all have been very good.



If you have any questions or specific requests about any of our tours, we’re here to help. You can fill in the form below, send us an email, or call us and we’ll get back to you as soon as possible.

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Italian operations office

What’s not to love about walking in picture-perfect Italian villages and wine-growing regions and feasting on amazing Tuscan wine and food. Francesca was a perfect guide, always flexible and accommodating to our group’s preferences and energy levels, plus she’s such a fun person to be with. Customwalks has great relationships with local businesses in the region that we wouldn’t have found on our own, and we always felt like an “insider” enjoying all the amazing meals and tastings featured in our itinerary. Other tour highlights included a visit to a ceramics workshop and store (wonderful souvenirs!), a superior guided tour of Siena, and a master class with a noted winemaker. Our only regret is that we didn’t buy more wine to enjoy later!
by Mary E.


This is my third Customwalks tour. As usual, I was thrilled with the attention to detail, the food, the wine and the people. Brett managed everything so well and made everyone feel welcome. Tuscany is lovely in May, the temperature was just right. We ate so well and in so many beautiful settings. It's hard to say which was my favorite. The villa we stayed in was perfect. Can't wait to do it again!
by Cathy S.


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