SatoVacations Logo Mobile

Away from the Crowds in Tuscany

By Claudia Viani

Tuscany is a must see bucket list destination. Year after year crowds of visitors peacefully invade Italy to see major Tuscan cities such as Florence, Siena and Pisa. Most want to see famous artistic and historic treasures from the Medieval and Renaissance era, go shopping, and savour Tuscan cuisine and extraordinary wines. Others dream of visiting a charming small town surrounded by friendly locals or the peacefulness of hilltop views and serene countryside vistas. With some strategic planning, you can experience the best that Tuscany has to offer through a local lens. We recently achieved this balance on the CWT Vacations’ Escape to Tuscany hosted group tour.

The Val D’Orcia Region

The 14-day small-group tour started in the town of Pienza, located in the heart of the Val D’Orcia region between Montalcino and Montepulciano, just south of Siena. Our base for five nights was at a lovely property just outside the city walls. Known as the Ideal Town from the Renaissance era, Pienza provides a very relaxed atmosphere featuring beautiful piazzas, local artisan shops, family-owned food emporiums featuring locally produced pecorino cheese, and a variety of quaint restaurants.

Pienza has stunning views of Val D’Orcia, and our tour included sunrise and sunset photography sessions in the countryside areas of this Unesco World Heritage region. Only accessible with small vehicles, our local guide ensured we were provided with views of picturesque valleys and cypress-lined rolling hills. This was our ultimate “away from the crowds” experience, shared only with a handful of other visitors.

The nearby medieval hilltop towns of Montalcino and Montepulciano are surrounded by vineyards produce two of Italy’s best-known wines, Brunello di Montalcino and Vino Nobile. Whether you are a wine lover or not, you soon become acclimatized! One of the highlights of the visit was a privately-guided tour and wine tasting at Azienda Agricola Ercolani in Montepulciano. This historic wine cellar includes a museum of medieval artifacts and underground caves that cross the streets of Montepulciano.

A unique local experience was a private sunset farm tour and dinner at Podere Il Casale, a 65-hectare organic farm offering a jaw-dropping view of the same. Dinner was served in the 600-year-old farmhouse where the owners live, cook and service their property.

Historic Masterpieces and Medieval Villages

Siena did not disappoint. Upon arrival, we visited their Gothic Cathedral dedicated to the Assumption of Mary. Stunning inside and out, it features the jaw-dropping work of Italy’s finest artists including Michelangelo. We were also fortunate to view the cathedral’s unique 56-panel mosaic marble floor, uncovered only during the month of July and from late August through to late October.

Next, we visited the stone towns of Volterra and San Gimignano. Boasting 14 of their 72 medieval original towers, San Gimignano was once a thriving stop for pilgrims traveling enroute to Rome. Today, the town’s easy accessibility from Italy’s major highway, continue to make it very popular with tourists. An early afternoon visit allowed our group to disperse and enjoy free time without the masses. Volterra is another walled, mountain-top town with rich history dating back to the eighth century BC. Known for its unique Etruscan and Roman architecture, and the production of Alabaster products, it has attracted a more artistic type of local. To our delight, we found it to be much less touristy or crowded.

The latter part of our tour brought us to the town of Lucca. Arriving at our beautiful villa at dusk was a welcome respite after a busy day. Originally built as a hunting lodge, today it is a charming 15-room boutique hotel nestled in the countryside surrounded by olive groves. Best of all, this was our home for the next eight nights.

A walking tour of Lucca with a very passionate historian and guide, took us back to the fifteenth century. Very much lived-in, the historic center is enclosed by large walls, known as ramparts, where you will find locals and visitors alike enjoying a stroll or bicycle ride. After our walking tour, we set off to the nearby hills and wine region of Montecarlo where we enjoyed a private wine tasting and Italian feast at a local winery. The beautiful weather allowed us to enjoy a leisurely lunch al fresco under a pergola and walkabout the estate and vineyard.

We chose Lucca as our base for its close proximity to many of Tuscany’s popular towns and sites such as Pisa, Florence, Seaside and Cinque Terre. We went to Pisa in late afternoon to skip the crowds. The cathedral is a must, and Baptistery a gem, especially every 30 minutes when the attendant breaks into song to give visitors a demonstration of the amazing acoustics.

Our day in Florence to see Michelangelo’s David was truly spectacular. If you really want a local experience, visit the Mercato Centrale. A famous outdoor and indoor food emporium accessible from the San Lorenzo leather market area. Peaceful moments can be experienced at the Boboli gardens, often described as an open air museum and easily accessible in the Oltrano area of Florence. Of course, one cannot miss the Ponte Vecchio, Piazza della Signoria/Uffizzi Gallery and the Duomo. Our day ended with a trip to nearby Piazzale Michelangelo, a popular lookout providing a fantastic sunset panoramic view of Florence.

We travelled from La Spezia by boat to Cinque Terre to ensure the best views of these iconic multi-colour villages clinging to the rugged coastline. We travelled from village to village by train and all were unique in their own individual way.

Our tour ended with the satisfaction of knowing that we, as a group of like-minded individuals, were able to visit the authentic towns and popular attractions of Tuscany. We were fortunate to share the experience of visiting so many local venues and places that over the centuries have inspired famous artists and poets, and yet were still tucked away from the crowds and carefully preserved for our enjoyment and respect.

CWT Blog Index


Add Some Sunshine to Your Inbox

Sign up for our emails to get extra perks and savings, amazing travel packages, and inspirational content to start your next travel experience.