At a Glance

Satiate your echoing yearnings for a gourmet adventure on an exhilarating 8-day walking adventure in Tuscany and Chianti. From Tuscan villages, Siena and Florence, uncover Renaissance cities, mediaeval villages, enchanting vineyards, and spellbinding landscapes all while indulging in the best Chianti wine offerings and bespoke culinary incursions.
Start your awe-inspiring escapade at the idyllic Pancole in Chianti. Over the course of eight captivating days, you’ll traverse ancient cobblestone paths and unspoiled trails winding through Tuscany’s most picturesque locales. Discover the timeless allure of San Gimignano with its iconic towers, stroll through the vineyards of Chianti, and traverse through the historic core of Radda in Chianti, followed by an excursion to Siena, where the majestic cathedral and animated streets will spoil you with luxurious Italian fashion and artisanal offerings. Discover the birthplace ...
Trip Highlights
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What's Included
- All breakfasts, five dinners, three wine tastings
- 7 nights in a comfortable hotel on a twin-share basis
- 5 days of gentle walking and sightseeing
- All transport and listed activities as specified
- Tour leader throughout
Itinerary
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Begin your Tuscan escape at Hotel Le Renaie, a charming and enchanting family-run retreat nestled just 6.5km from the medieval jewel of San Gimignano. Upon arrival, you’ll be greeted by our tour leader for a warm welcome and an introduction to the unforgettable week ahead, brimming with culture, nature, and indulgence. Extend your adventure with an additional stay in the cultural treasures of Pisa or Florence. Speak with your sales representative to tailor the perfect beginning or end to your holiday. Dinner tonight will be the perfect introduction to the culinary delights of Chianti and the close to our first day. |
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Approx. 9 km (6 miles), 2-3 hours walking Today we immerse ourselves in history and natural beauty by walking a picturesque section of the Via Francigena. Once the road for pilgrims travelling from Canterbury to Rome, this iconic path leads us through rolling vineyards and silvery olive groves from Gambassi Terme to San Gimignano. A true feast for the senses. Later, we venture to Fattoria Le Caprine, a delightful farm estate renowned for its artisanal cheese. Indulge in a curated tasting experience featuring a trio of cheeses paired with three exquisite wines. Stroll through the estate grounds and breathe in the essence of Tuscany. The evening winds down with a relaxing dinner back at Hotel Le Renaie. Unwind with perhaps a game of billiards or a chilled glass of local wine on the terrace, embraced by serene garden views. |
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Approx. 8 km (5 miles), 2 hours walking Head to Radda in Chianti, where we’ll explore the lush and intimate beauty of the Chianti region. This morning's circular walk takes us deep into tranquil woodlands, revealing emerald valleys adorned with sprawling vineyards. The afternoon offers you time to soak in the sleepy charm of Radda. Perhaps enjoy an optional tasting of the renowned Chianti Classico at one of the region’s distinguished wineries—each glass a masterpiece of craftsmanship. |
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Approx. 8 km (5 miles), 2-3 hours walking Travel by train to the medieval city of Siena, where history whispers from every stone. Discover the city’s hidden treasures with a local guide on an exclusive tour that takes you beyond the tourist routes, including a visit to a private contrada museum—an experience few have the privilege of enjoying. Savour bites of local sweets from traditional botteghe (small, traditional shops), each treat revealing the flavours of Siena’s rich culinary traditions. For those seeking even more beauty, opt for a visit to Siena Cathedral, with its mesmerising gothic architecture and intricate interiors. Later, the Tuscan Wine School invites you for an enlightening one-hour session where you’ll learn the secrets behind Tuscany’s most celebrated wines—ideal for connoisseurs and curious tasters alike. |
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Today is yours to design. Indulge in a day of pure bliss basking by the tranquil poolside and granting your tired legs the sweet relief they truly deserve. Alternatively, for those who crave adventure, our expert tour guide will unveil the most unforgettable Chianti wine excursions and culinary classes this region has to offer. Prepare for a delectable culinary adventure! For the intrepid traveller, fret not, as our seasoned staff is always on hand to steer you in the right direction and give you unwavering support, even if you prefer to wander off on unguided trails or exciting day trips. You can choose to go to stunning Chianti towns such as Montefioralle where the Churches of Santo Stefano and San Cresci stand elegant and are worth a visit, the beautiful Panzano town; a historic hallmark of defense for Florence since the 12th century. |
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Approx. 4 km (2.5 miles), 2-3 hours walking Journey to Florence, the birthplace of the Italian Renaissance, by train. This city, once home to visionaries such as Leonardo da Vinci and Michelangelo, offers endless marvels to unveil. Join a local walking tour to discover Florence’s artistic and architectural wonders. For those with a love of fine art, a visit to the Uffizi Gallery is a must. Behold Botticelli’s majestic Birth of Venus and Caravaggio’s striking Medusa. To avoid queues, we recommend booking your ticket to www.uffizi.it/en/tickets in advance for the afternoon session if joining a morning tour. |
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Venture into the captivating town of San Gimignano, known for its medieval skyline of soaring towers. You’ll have the chance to explore its treasures, including the 13th-century Palazzo Comunale and the awe-inspiring Torre Grossa. Before our final dinner, we’ll visit the Cesani estate, a family-run winery celebrated for its exceptional vintages. Enjoy an authentic Tuscan experience with a guided wine tasting paired with bruschetta, extra-virgin olive oil, and a curated selection of Tuscan cheeses and charcuterie. A heartfelt meal together marks the perfect conclusion to your unforgettable Tuscan experience. |
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Reluctantly, we bid goodbye to Pancole and the inviting charm of Hotel Le Renaie. Cherish the memories you’ve created as you prepare for your departure or continue exploring Italy's endless wonders. Make your own arrangements for your onward travel or alternatively, airport transfers can be arranged at an additional cost, please contact us. NOTE: This itinerary is provided as an example only – prevailing conditions and local arrangements may cause variation. |
Dates & Prices
Please contact us for private departures and group bookings. Single Supplement is available on request.
More Info
- The departure and finish point is Castellina in Chianti
- The nearest major international airport is Florence Airport, Peretola which has international and domestic flights from Florence and is about 38 km from the center of Castellina in Chianti. Another major airport is Pisa International Airport which has international and domestic flights from Pisa and is 76 km from Castellina.
- Airport transfers are only included with scheduled group transfers from Pisa Airport. Alternatively, joining location starts in your accommodation in Castellina making your own arrangements there. The journey takes approximately 1.5 hours by drive and so we recommend joining the scheduled group transfer. If not, airport transfers can be arranged at an additional cost, please contact us.
April and May departures can expect warm days and although rain is possible, it seldom lasts long. Nights may be cool. We strongly recommend a fleece-lined jacket or warm sweater in these months. June sees the start of summer and July and August can become quite hot by mid-afternoon, so this time is kept free for lunch. Although rain is unusual, torrential cloudbursts are not unknown. September and October are cooler and wetter, yet visibility is often better. Swimming is usually still possible at this time.
The walking level on this trip is rated Level 2 Leisurely/Moderate.
Level 1 Leisurely: Experience is not necessary; anyone fit and healthy enough to complete a weekend walk will thrive. Walks are often optional. Trails are seldom flat, so expect a reasonable number of ascents and descents. You normally walk for two to five hours per day; daily ascents will likely be around 985ft to 1,640ft (300m to 500m), perhaps with the odd day around 1,970ft (600m).
Level 3 Moderate: Expect easy, medium-length walks or harder, shorter walks. Some experience is useful, but not essential. Good health and reasonable fitness are important. There will be walks at higher altitudes and some longer, harder days. Generally, though, the underfoot conditions will be fair. A walking day is normally five to seven hours; daily ascents will likely be around 1,640ft to 2,625ft (500m to 800m), perhaps with the odd day around 2,955ft to 3,280ft (900m to 1,000m).
Level 5 Challenging: Fitness is vital with extended walking in mountainous terrain. You might also experience high altitude, challenging climates and remote locations. Trekking experience is desirable, but not vital if you are confident in your physical condition. Walking days are usually between six and eight hours, although they may be longer for passes or peaks. Daily ascents can be around 2,955ft to 3,280ft (900m to 1,000m), perhaps with the odd day around 3,610ft to 3,940ft (1,100m to 1,200m).
Level 7 Tough: Trekking experience is essential and preferably at altitude. You need complete confidence in your ability to trek for many days over difficult terrain. You may encounter extreme altitude and weather conditions and may need to use ice axes and crampons. Stamina is essential as walking days last six to nine hours (sometimes more on occasions). Daily ascents will likely be around 2,955ft to 3,280ft (900m to 1,000m), perhaps with the odd day around 3,610ft to 3,940ft (1,100m to 1,200m).
Split and optional grades: Where a trip falls between two grades, an intermediate or ‘split’ grade is used. For example, Level 2 (Leisurely/Moderate). Occasionally there are optional ascents available; in this case, the grade will be highlighted.
This trip offers a good mix of city and countryside walks. During the walks, the terrain and path type include paved tracks, forest trails and gravel. The walks are not technically difficult, although there are some ascents and descents, so a reasonable amount of fitness is required. Please be aware, the Radda walk on Day 3 can be challenging due to the length and hilliness of the walk. The area is quite hilly and most drives, although short, follow twisty mountain roads through wooden areas.
Tuscany can be very hot in summer, especially from June to August but heatwaves can also happen in April and May. Temperatures can reach the high 30Cs (around 100F). We try to start our walks earlier to avoid the hottest hours of the day but temperatures and humidity will be high. You should feel comfortable and be used to walking in the heat. Agriturismo accommodations are not normally equipped with air conditioning, therefore rooms can be quite warm at times. The number of mosquitos may increase (significantly) in summer, so we recommend bringing repellent.
Single supplement from AUD 522
A private minibus is used for airport transfers and most excursions plus the local train/bus services on certain days. Transfers are no longer than 45 minutes and road conditions are good.











