Vineyards in Montepulciano, Italy

Wine Connoisseur's Dream Tour of Tuscany

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Florence, Siena, Montalcino, Montepulciano...

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Suggested Duration

8 Days

Whether a lover of wine or a self-professed connoisseur, you will indulge in the variety of Tuscan vineyards with this personalized gourmet itinerary of Italy. Medieval towers crown the hilltops, cypress trees line the country roads, and vineyards blanket the verdant knolls. Sample the exceptional wines known as Super Tuscans or leisurely sip the excellent wines of Montepulciano. Savor the familiar flavors of a home-cooked Italian meal and wander the cobbled lanes of a charming, hidden medieval...

Customizable Itinerary

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Trip Highlights

  • Sample the distinctive flavors of Tuscany’s noble wines during a full-day tour of the wineries around the Montepulciano and Montalcino wine regions
  • Discover the subtle differences in the flavors, textures, and aromas of the variety of olive oils during a private tour of a historical orchard and mill
  • Enjoy exploring the Tuscan villages and hidden landscape that retain the majesty of authenticity around the region of Maremma
  • Savor the art of Siena with a private guided tour focused on the historic features that once rivaled the beauty and creation of Florence
  • Indulge in sampling boutique wines at family-owned vineyards around Maremma for remarkable flavors with distinctive character
  • Bask in the comfortable and familiar flavors of Tuscany with a home-cooked meal on a vineyard within the hamlet of San Miniato outside of Florence
  • Relish the delectable characteristics of Chianti Classico while on a private wine tour of the famous Italian wine region
  • Wander the lively streets of Florence with a guide to visit the delicious central market and iconic architecture and artistry of the Renaissance city

Detailed Description

Discover the flavors of Tuscany on an 8-day itinerary that celebrates the wines of Chianti, Montalcino, and Montepulciano. The cuisine accentuates the beauty and bouquet of the varietals you sample, while the landscape heightens the brilliance of each sip and every bite. This enchanting gourmet journey begins with your arrival at Florence-Peretola Airport. Your private transfer meets you at baggage claim and escorts you to a stunning hotel inside a remodeled palazzo at the heart of Florence. After taking a moment to settle into the comforts of your accommodation, you meet your guide in the lobby for a walking tour of the city of the Renaissance to discover the preserved history on display.  Find marvels hidden inside the various churches, palazzos, and museum alongside the contemporary culture of the central market.

The following day, your private transfer greets you after breakfast and leads you towards the Tuscan city of Siena. You stop at the center of the Chianti wine region to visit a selection of wineries and abbeys crafting the famous Tuscan wine. You continue to Siena for a guided, insider’s tour of the art around the medieval city walls and architecture. Embrace the luxuries of VIP treatment on a private wine tour of Montepulciano and Montalcino, and then stroll along the cobbled lanes of the small towns to view the surprising amount of wine bars opening to the narrow alleys and along the piazzas. Explore a selection of vineyards to learn about the cultivation of the wine that makes this place so special before a sample of the “Vino Nobile.”

Continuing on your journey, you travel to the region of Maremma, which boasts medieval towns and unique scenery maintaining the area’s authenticity. Enjoy the streets of the quiet, hidden towns for a cultural view of Tuscany before arriving at your villa. Discover boutique wineries and their unique flavors with a tour of the celebrated, smaller vineyards in the Maremma region before delighting in a traditional, elegant lunch. The next day, you will uncover the historic streets and soaring towers of San Gimignano before returning to Florence for the evening.

Immerse yourself in the robust flavors of dinner at a celebrated local restaurant in the evening. The following day you will visit the hamlets outside of Florence on a half-day tour of an olive mill in Ponte a Cappiano followed by a beautiful home-cooked meal in San Miniato. The remainder of the day is yours to enjoy the marvels of Florence, from the Uffizi Gallery to the Accademia, or to bask in the Boboli Gardens and wander the leather shops around San Lorenzo. On your final day, your private transfer escorts you to Florence-Peretola Airport for your flight home, or you could use one of our travel agents for Italy.

Starting Price

$2,859 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

Reviews of Zicasso's Referral Service

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