- Hiking: 5-6 hour maximum on country paths
- Local specialties: Seafood, Pecorino, Olive Olive & Wine
- Siena: The City of the Palio
- Monteriggioni: 14 towered Citadel
- Monte Oliveto Maggiore and San Antimo Abbeys
- Montepulciano: The Pearl of the 1600
- Bagno Vignoni & San Quirico: Spas & Hot Springs
- Montalcino & Pienza
- Maremma: Towers Trek & Castiglione della Pescaia
The best way to experience the charm of Tuscany is on foot, at a pace slow enough to savor the rolling, green hills and to become familiar with the local people, cuisine and historical monuments of this area. Siena is a great place to start our tour and we’ve chosen this route because it is the heart and soul of central Tuscany. It includes a bit of everything wonderful about this region: artistic treasures, quaint villages, rolling footpaths and world-famous vineyards.
Starting from Siena we’ll visit its surrounding countryside and medieval villages, savoring the views that this land has to offer. We will then move south towards the seaside and Maremma Experienced guides will lead our group, walking between 8 and 10 miles daily, with our gear following us in vans as we go. There will be time to visit wine cellars, do a little shopping, and explore local art treasures. The van will take us to our starting points and transport us to our lodgings each evening. All is included from the time of your arrival in Tuscany. The groups are small, between 8 and 14 walkers; enough to create a sense of intimacy, but not too many for a small country inn or trattoria.
Day 1: Arrival in Siena – by 10.30 a.m. Walk tour with historic guide
Meeting in the hall of the Palazzo Ravizza, a charming hotel in a 15th century historical building in the center of Siena. After a rest and a welcome lunch we will start with a tour of Siena’s serpentine streets and splendid Piazza del Campo, then visit the Palazzo Pubblico, which houses several masterpieces of Italian frescos by Simone Martini and Ambrogio Lorenzetti. On the left hand side of the Palazzo Pubblico there is the famous 335 feet high bell tower, Torre del Mangia, which rises above all the other buildings of the city. We’ll also visit Siena’s massive black-and-white striped Duomo, home to works by Michelangelo, Donatello, and Pinturicchio. Dinner at “Nello La Taverna” in Siena. (B) / (L) / (D)
Day 2: Monteriggioni Ring Walk – 7 km
8.00 am – Fairly gentle, varied walk through woods, farmland and old settlements rich in history around the stunning Monteriggioni. This citadel is a picturesque village still completely contained within its unique 14 towered walls, which Dante, in his Divine Comedy, memorably compared to the giants who surround the deepest pit of Hell. We’ll tour the unique and well preserved town where you can still feel a lingering medieval presence in the little sleepy square. We’ll have a delightful picnic lunch at a local country farm. Afternoon in San Gimignano and Medieval dinner at the Gallo Nero restaurant in Siena. (B) / (L) / (D)
Day 3: Hiking through the Sienese Crete – 19 km
8.00 am - Shuttle to Monteroni d'Arbia and walk to Asciano. We'll cross through the famous Crete region, the clay landscape south of Siena, which consists of bare hillocks and ravines. We will then be transferred to visit the Monte Oliveto Maggiore Abbey, founded in 1313 by Bernardo Tolomei, and still functioning today and have lunch to the restaurant in the Abbey. The cloister walls are decorated with a cycle of frescos depicting the life of Saint Benedict by Luca Signorelli. After lunch we will walk the loop around the Abbey. Transfer to the Hotel Rutiliano in Pienza and dinner at the restaurant “Il Prato”. On way to the Hotel we will stop for a pecorino cheese tasting at country farm “Verdi Pascoli”. (B) / (L) / (D)
Day 4: Walk Pienza / Monticchiello – 5 km
10.30 am - Our five kilometers walk sets out immediately on quiet dirt roads with sweeping views. We traverse across the soft undulating hills of the lovely Orcia Valley, all the way to the enchanting hill town of Monticchiello. Almost no signs of the 20th century have made it past the walls of this medieval village. Here we will have a light lunch at the organic farm overlooking the valley. After lunch we will be shuttled to Montepulciano, Pearl of the 1600s and famous for its Vino Nobile. This six-mile stretch crosses vineyards, farmland and grazing pastures. Wine tasting at “La cantina del Redi”. Back to the Pienza for the night and dinner at the trattoria “La Buca delle Fate”. (B) / (L) / (D)
Day 5: Bagno Vignoni / Ripa D’ Orcia Ring Walk – 11 km
9.00 am - Transfer to Bagno Vignoni, a tiny village that exists solely because of its thermal hot springs, famed since Roman times. The main town square is a thermal swimming pool!! You are no longer allowed to immerse yourself, but it’s a great photo opportunity. Walk to the Ripa D’Orcia, a site of a formidable 13th-century castle, well-known producer of extra-virgin olive oil and wine, whose owners have possessed it since 1484 and back to Bagno Vignoni. After a light lunch you can either take a swim in the 51-degree F waters of the bathing establishment, or just dip your feet in the natural hot water which emerges from the ground and flows down the hill. Afternoon in San Quirico d’Orcia, a pristine hill town whose nearly deserted streets are paved with terra cotta. We’ll pay a quick visit to the formal gardens called Horti Leonini. Visit to local ceramics factories. Transfer to the Hotel dei Capitani in Montalcino and dinner at “Re di Macchia” restaurant. (B) / (L) / (D)
Day 6: Sant Antimo Abbey / Ripa D’Orcia – 12 km
9.00 am - We will be shuttled for 4 miles from the wine capital, Montalcino, to the Romanesque abbey of Sant'Antimo, just down the hill. This is will be our starting point to start the 12 km trek to reach Ripa D'Orcia. This is a gorgeous and varied stretch of the country, the rolling contours of the Starcia valley giving away to the more dramatic scenery of the Val D’Orcia with its knolls and castles topped promontories. Pic nic lunch along the way. Dinner in local restaurant in Montalcino. (B) / (L) / (D)
Day 7: Maremma Natural Park & Castiglione della Pescaia – 7 km
Today we will travel to the seaside of southern Tuscany and explore the off-beaten tracks of the Wild Maremma. This area is a holiday heaven to Northern Europeans, but has remained undiscovered by international tourists. The uncontaminated nature and local culinary traditions, the noted wild boar is a mainstay of this part of Tuscany, are a strong magnet to this untouched paradise. We’ll be shuttled by van to the National Park of the Maremma to the start the most panoramic trek of the entire park called “Le Torri”. It is considered the most representative among the itineraries of the park because it touches all the environments of the protected area and has the advantage to offer beautiful views.
Check in to the hotel L’Approdo, in the ancient fishing village of Castiglione della Pescaia, for a seafood dinner. It will be at restaurant of the hotel where we will spend the night. A walk and visit to the preserved Medieval town of Castiglione della Pescaia by night is a must. The town is dominated by the fine Aragonese Fortress from where during the day you can savor breathtaking views of the coastline and the islands of the Tuscan archipelago among which are the famous Elba Island where Napoleon was banished and the Isle of Montecristo. (B) / (L) / (D)
Day 8: End of tour after breakfast**
** An extra day can be arranged for those that want to learn more about this area. We suggest kayaking in the marshes of the Diaccia Botrona Park in Castiglione della Pescaia, horseback riding on the beach (for expert riders only) and visit to Elba Island.
Season and Weather
The best period for hiking tours in Tuscany is definitely spring (May and June) or fall (September, October). May and June are usually in the 70’s, early 80’. The days are long and the temperature is perfect for dining al fresco after a walking day. Rolling green hills with red and yellow poppy and sunflower field sparkle the countryside. September and October bring the time the grape and olive harvest. The countryside gets busy. The temperatures are in the 70’s, with mild, but cooler days and earlier sunsets. It can rain, but it is still a fine time to be on foot. (B) / (L) / (D)
The sequence of walks or the walks themselves may be changed by the guide due to factors such as the weather.
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