3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns

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(1 reviews)
Florence, Italy

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3 days (approximately)
Pickup offered
Offered in: English and 1 more

Escape the city and immerse yourself in the timeless beauty of Tuscany on a fully private, 3-day journey through rolling hills, historic villages, and unforgettable food and wine. Starting from Florence, your personal driver-guide will take you through the heart of Tuscany. You'll visit San Gimignano, Siena, Montepulciano, and the Chianti wine region. Enjoy exclusive tastings at family-owned wineries, admire Renaissance art, and relax each evening in hand-picked boutique countryside hotels.

This tour is curated for travelers who want to slow down, connect with authentic Italy, and enjoy VIP treatment from start to finish. Highlights:

Private driver-guide throughout the tour

Visits to San Gimignano, Siena, Montepulciano & more

Wine tastings in Chianti and Montalcino (Brunello!)

Time to explore, shop, and dine in historic piazzas

Option to include truffle hunting or cooking class

What's Included

Private transportation
Lunch (Optional[3])
Lunch
Air-conditioned vehicle
Private Guide

Meeting and pickup

Pickup points
You can choose a pickup location at checkout (multiple pickup locations are available).
Pickup details:

We pick up all the travelers. The guide will wait you at your hotel reception

Itinerary

Duration: 3 days (approximately)
    Day 1

    Val D'Orcia: Nature, Food & Wine, History Full Day Private Tour

    4 stops
  • 1
    Val D'Orcia

    Your guide will meet you in your hotel at 9:00 am and you will start amazing journey to Val D'Orcia - UNESCO heritage site since 2004. You will enjoy the magnificent landscape, among the Tuscan hills. It is the expression of wonderful natural features and also the result and testimony of the people who lived there. You can stop to make stunning photos.

    3 hours • Admission ticket included
  • 2
    Montepulciano

    You will visit Montepulciano - famous town stands on a hill 600 meters above sea level: from this height it is easy to get lost with your gaze among the green Tuscan hills, olive groves, vineyards and cypresses that pleasantly mark the whole landscape. Walking with your guide through the streets and main attractions of Montepulciano, you will also take a look at the picturesque corners that beckon you to turn off the main road and promise unforgettable views of the valley. Montepulciano has long been famous for its wine. It is mentioned in the documents of merchants as early as the 14th century. You will stop in a winery to taste local wine and typical food.

    1 hour • Admission ticket free
  • 3
    Montalcino

    The next stop is a charming medieval village, almost fairytale, surrounded by a mighty wall and dominated by an ancient castle of authentic architectural perfection. Montalcino is a beautiful historic town immersed in the beautiful landscape of the Val'orcia Natural Park and renowned throughout the world for the extraordinary production of the precious Brunello di Montalcino. The village has remained almost intact since the third century. Once you reach the top on which Montalcino stands, a real spectacle opens before your eyes: a continuous succession of winding hills dotted here and there with yellow and red flowers, ancient oaks, picturesque olive trees, scenic country roads that snake through harmonious vineyards and isolated cypresses here and there.

    1 hour • Admission ticket free
  • 4
    Pienza

    You will continue your guided journey to Pienza. Obtained the recognition of a Unesco site in 1996, it still communicates to the world the urban canons of the Renaissance for the rational organization of spaces and perspectives of sixteenth-century squares and palaces. After this private guided tour you will go back to your hotel enjoyng incredible views of Val D'Orcia.

    2 hours • Admission ticket free
    • Day 2

    Chianti Road, San Gimignano and Wine Tasting Half Day Private Tour

    2 stops
  • 5
    Strada Statale 222 Chiantigiana

    Your private guide will pick you up at 9 am at your hotel's reception and you will start your journey to Chianti region. The visiting card of this place is considered to be green hills, spread out under the endless blue sky, lush cypress trees piercing the clouds, unique architectural monuments and masterpieces of art and of course local food and wine.

    2 hours • Admission ticket included
  • 6
    San Gimignano

    Visit San Gimignano - UNESCO Heritage list since 1990, preserves with love the atmosphere of a fourteenth-century village and the appearance of one of the best examples of urban organization of the municipal age. You will visit Chianti vineyard, taste great Italian wines with local traditional food.

    3 hours • Admission ticket free
    • Day 3

    Pisa, Lucca & Cheese Farm with wine tasting Full Day Private Tour

    2 stops
  • 7
    Pisa

    Your private guide will pick you up at yur hotel and will bring you to Pisa .- a famous city rich in traditions, art and culture. Discover Piazza dei Miracoli, with its Leaning Tower, Baptistery and Cathedral.

    3 hours • Admission ticket free
  • 8
    Lucca

    Your next stop will be in Lucca - one of the most beautiful and beloved cities of art in Tuscany, it's a must visit in a classic itinerary to discover the region. After you will take a private guided tasting trip that includes a visit to a dairy that produces organic cheese. What is the origin of the name "pecorino"? Whence is it manufactured and how? Does Tuscany also manufacture ricotta? During your vacation in Italy, you will visit a stunning organic farm located on a hilltop. This farm will answer all of your questions about the region's cheese-making heritage. Taste different chesses types with local typical food & wines.

    5 hours • Admission ticket free

Additional info

  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels
Supplied by Events in Italy

Tags

Nature and Wildlife Tours
Multi-day Tours
Bus Tours
Private Sightseeing Tours
Likely to Sell Out
Car Tours
Food & Drink
Spring Break
New Product
Short term availability

Cancellation Policy

If you cancel at least 6 full day(s) before the scheduled departure time, you will receive a full refund.
If you cancel between 2 and 6 day(s) before the scheduled departure time, you will receive a 50% refund.
If you cancel within 2 day(s) of the scheduled departure, you will receive a 0% refund.

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