Chianti Wine & Medieval Tuscan Tours by Under The Tuscan Sun

Read the full experience

Stretching across central Tuscany’s rolling hills, the Chianti region is synonymous with legendary wines and landscapes etched by vineyards and centuries-old olive groves. Under The Tuscan Sun Tours offers an immersive full-day private shore excursion from La Spezia that unites wine tasting with the storied medieval atmospheres of San Gimignano and Volterra, delivering a blend of outdoor discovery and cultural depth rarely accessible in one seamless journey. Departing from the coastal port of La Spezia, this ten-hour experience ventures inland through a patchwork of cultivated hills and rustic farmsteads. The Chianti wine area itself is a defining highlight: guests sip renowned varietals direct from boutique wineries set against the backdrop of terraced vineyards that thrive on limestone-rich soils contributing to the grapes’ distinctive character. Olive trees, their branches silvery and wind-stirred, punctuate the landscape, adding a sensory richness to every stop. The excursion then moves east to San Gimignano, a medieval town famous for its skyline of surviving towers—once numbering 76, now thirteen stand proudly above narrow cobblestone streets. Here, visitors navigate historic piazzas and explore Romanesque architecture, absorbing layers of history embodied by structures like the Collegiata Cathedral and Piazza della Cisterna. Next is Volterra, a hilltop jewel perched on a rocky plateau. Known for Etruscan roots and preserved ramparts, Volterra invites a visit to the Piazza dei Priori and its acclaimed Etruscan Museum, revealing ancient art and frescoes that connect modern visitors with Tuscany’s deep, intertwining pasts. Under The Tuscan Sun Tours excels in delivering personalized attention, scaling groups to intimate sizes for focused, unhurried access. Their commitment to private, tailored transport from La Spezia via experienced local drivers and guides ensures logistics flow smoothly, optimizing time for wandering vineyards or absorbing historic streetscapes. This excursion stands out in the regional landscape for combining iconic Tuscan wine culture with immersive visits to two of Italy’s best-preserved medieval towns. It’s a gateway to Tuscany’s outdoors, history, and flavor, ideal for travelers seeking a day of layered discoveries beyond typical sightseeing.

Trip highlights

Difficulty

easy.

Duration

10 hours.

Fitness level

Suitable for most fitness levels; involves moderate walking on uneven cobblestone surfaces.

Frequently asked questions

Is the wine tasting included in the price?

Yes, the private shore excursion includes wine tasting sessions at selected Chianti wineries.

How many people are in a typical tour group?

Groups are kept small for a personalized experience, generally up to 16 guests.

Can dietary restrictions be accommodated during lunch or tastings?

Yes, Under The Tuscan Sun Tours can tailor food and wine pairings if informed in advance.

Is transportation provided from the port?

Yes, private pick-up and drop-off from La Spezia harbor are included, ensuring a smooth journey.

Are the towns accessible for those with limited mobility?

San Gimignano and Volterra have cobblestone streets and uneven surfaces; visitors with mobility concerns should discuss options with the operator.

What languages are the guided tours conducted in?

Tours are conducted in English by experienced local guides and drivers.

Local insights

Wildlife

Wild boar roaming Tuscan woodlands
Common buzzards circling over vineyards

History

Chianti’s defining vineyards evolved in the 13th century, while San Gimignano and Volterra preserve medieval and Etruscan legacies that shaped Tuscany’s cultural identity.

Conservation

Local wineries engage in sustainable farming practices, maintaining the landscape’s ecological health and supporting biodiversity among olive groves and vine rows.

About Under The Tuscan Sun Tours

Under The Tuscan Sun Tours is a Florence-based tour operator specializing in private and small-group experiences across Tuscany and nearby regions. Founded to connect visitors with the cultural, culinary and scenic highlights of central Italy, the company offers a wide range of day trips, shore excursions and immersive activities. Operating from Florence, Tuscany, the catalogue includes private VIP shore excursions from Livorno, La Spezia and Piombino to destinations such as Pisa, Lucca, Florence, Cinque Terre, San Gimignano and the Chianti wine region. Options span guided walking tours with reserved entries (Uffizi, Accademia), winery visits with tastings and meals, truffle hunting with trained dogs, cooking classes, Vespa tours and curated visits to Bolgheri for Supertuscan wine tastings. Services include private vehicles and professional drivers for full-day transfers, small shared tours for groups up to eight people, and tailored itineraries for families or wine enthusiasts. Specific shore excursions list included stops, tasting experiences and local activities, while other experiences emphasize cultural sites such as Michelangelo’s David, the Duomo, and Carrara marble quarries. Under The Tuscan Sun Tours works with licensed local guides and established wineries, restaurants and activity providers to deliver organized itineraries and reserved accesses. The business emphasizes clear pickup arrangements from ports (Livorno, Piombino, La Spezia) and from central Florence, offering a practical way to turn limited time into a full Tuscan experience.

Base locationLa Spezia, Tuscany

Tours offered161+

Specialtyothers

Adventure tips

Book Early for Private GroupsSmaller groups ensure personalized service and better time at wineries and towns, so reserve early especially in peak season.

Wear Comfortable ShoesCobblestone streets in San Gimignano and Volterra require sturdy footwear for easy walking and safety.

Stay HydratedTuscan summers can be warm—carry water to stay refreshed between wine tastings and walking tours.

Bring a Light JacketEvenings or early mornings may be cool during shoulder seasons; a light jacket adds comfort on the road and in towns.

Recommended gear

Comfortable walking shoes: Necessary for navigating cobblestones and vineyard terrain safely and comfortably.
Sun protection (hat, sunscreen): Protect yourself from prolonged sun exposure during outdoor tastings and walks.
Reusable water bottle: Stay hydrated throughout the day, especially while touring under the Tuscan sun.
Light jacket or layers: Provides warmth for early mornings, evenings, or cooler days in the Tuscan hills.