Places you'll visit


Turn your wish for authentic Italian flavor into a tailor-made reality with this Tuscany wine and culinary trip. Curate each day with a local specialist to match your tastes, pace, and interests, create private encounters with artisan producers, and savor rustic dishes in handpicked settings.
Book a personalized trip to Italy now to craft unforgettable food and wine memories designed just for you and return home with stories that linger.
| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| Day 1 | Arrival in Tuscany; private scenic transfer | Chianti Classico winery tour, tasting and lunch | Check-in and explore Colle Val d’Elsa |
| Day 2 | Vespa tour through Chianti Colli Fiorentini | Wine and olive oil tasting near San Gimignano | Relaxed evening at your hotel |
| Day 3 | Private tour of Bolgheri estate with lunch | Boutique winery tasting: Vermentino and Sangiovese | Free evening or dinner suggestion |
| Day 4 | Visit a Brunello winery with guided tasting | Olive oil tasting at award-winning producer | Final Tuscan dinner or quiet night in |
| Day 5 | Farmhouse breakfast or vineyard walk | Private transfer to the airport | Farewell to Tuscany and flight home |


Arrive at the airport and meet your private driver for a scenic drive through Tuscany. Meet your sommelier guide at a modern Chianti Classico estate for a private tour, light lunch, and guided wine tasting. Visit a family-owned boutique winery celebrated for organic viticulture and handcrafted wines.
Check in at a charming hotel near Colle Val d'Elsa to unwind and explore the medieval town, artisan shops, and panoramic views. This authentic, tailor-made opening sets the tone for your Tuscany wine and culinary trip and defines your Italy travel experience.

Your hotel pickup kicks off a tailor-made Vespa tour through the rolling hills of Chianti Colli Fiorentini. Stop for scenic photos, meet your local guide, and enjoy a hands-on ride that ends with a traditional Tuscan lunch paired with local wine and olive oil.
In the afternoon, visit a family-run vineyard near San Gimignano for a guided tasting of Vernaccia wines and stories straight from the source.

After hotel pickup, meet your sommelier guide for a private tour of a renowned Bolgheri estate. Walk through the vineyards, learn about local varietals, and enjoy a tasting of signature wines paired with a farm-to-table lunch featuring seasonal produce and classic Tuscan dishes.
In the afternoon, visit a boutique winery for guided tastings of Vermentino and Sangiovese. Hear the stories behind the wines and enjoy a relaxed, personalized experience before your return to the hotel.

Meet your sommelier guide for a tailored visit to a renowned Montalcino winery. Learn about Brunello’s aging process and terroir, and taste cellar-aged vintages paired with artisan-cured meats and local wines over a relaxed lunch.
In the afternoon, visit an award-winning olive oil producer for a tasting of premium oils and a behind-the-scenes look at traditional pressing methods. Return to your hotel with a deeper taste of Tuscany’s craft and culture.

Enjoy one last leisurely morning in the fascinating Tuscan countryside, with options like a farmhouse breakfast, a stroll through vineyards, or a relaxed coffee overlooking rolling hills.
It’s one last chance to soak up the flavors and feel of the region on your bespoke Italy trip. At the scheduled time, your private driver will transfer you to the airport for your flight home.
