Tuscany wine and culinary trip

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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.

Tuscany wine and culinary trip highlights

  • Private Chianti wine tasting: Sip renowned Chianti wines with a local sommelier in family-run cellars.
  • Hands-on Tuscan cooking class: Learn rustic recipes from nonna using seasonal market produce, then savor your creations.
  • Truffle foraging adventure: Join expert hunters and dogs in oak woods to unearth prized truffles.
  • Cellar-to-table vineyard dinner: Dine under the stars at a boutique estate with paired wines and farm-to-table dishes.
  • Customized cultural excursions: Explore hilltop villages, artisan workshops, and private museums.
DayMorningAfternoonEvening
Day 1Arrival in Tuscany; private scenic transferChianti Classico winery tour, tasting and lunchCheck-in and explore Colle Val d’Elsa
Day 2Vespa tour through Chianti Colli FiorentiniWine and olive oil tasting near San GimignanoRelaxed evening at your hotel
Day 3Private tour of Bolgheri estate with lunchBoutique winery tasting: Vermentino and SangioveseFree evening or dinner suggestion
Day 4Visit a Brunello winery with guided tastingOlive oil tasting at award-winning producerFinal Tuscan dinner or quiet night in
Day 5Farmhouse breakfast or vineyard walkPrivate transfer to the airportFarewell to Tuscany and flight home

Places you'll visit

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Colle di Val d'Elsa
Colle di Val d'ElsaColle di Val d'Elsa
Day01

Day 1: Arrival and Chianti Classico

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.

Chianti Region
Day02

Day 2: Vespa tour and San Gimignano

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.

Vespa in Tuscany
Day03

Day 3: Bolgheri wineries and Tuscan flavors

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.

Bolgheri
Day04

Day 4: Montalcino, Brunello and olive oil tasting

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.

Poggio Stenti
Day05

Day 5: Farewell to Tuscany

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.

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