Tuscany Wine and Fly Tour


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    Aegean Outdoors on TripAdvisor

    5 days / 4 nights
    Period of Operation : April to November
    Min Participants : 4
    Max People : 7
    Tour Description

    Wine lovers around the world know that Tuscany needs no introductions and for a long time we have been looking for a special place where we can welcome our guests. We found it in a picturesque convent of the eleventh century, where from its balconies you can admire the vineyards, with the thousand color shades they take on both in spring and autumn, dotted with soaring cypresses and ancient olive trees.
    We invite you to explore the lush flower and vegetable gardens, visit the vineyards and discover a rare wine cellar, where you will savoir various wine samples from the region along with traditional Italian delicacies!

    During our Panoramic Helicopter Tour, you will enjoy the best views of the Chianti region, with its vineyards and colorful medieval towns like San Gimignano and Florence gazing upon the former homes of Leonardo da Vinci and Michelangelo!

    Trip Highlights
    • Wine tasting in one of the oldest wineries of Tuscany
    • Panoramic Helicopter Tour
    • Visit Florence and surrounding villages
    • Immerse yourself in Italian cuisine
    • Italian Truffle Hunting

    Level of difficulty

    Easy. Participants should feel comfortable in a helicopter and do not suffer from fear of heights.


    Day 1Tenuta Torciano Winery - Welcome dinner

    Your journey in this amazing region starts with a private transfer from the airport to your accommodation in the area of San Gimignano, a medieval village situated in the heart of Tuscany, between Florence and Siena. In the evening, your own private driver will take you to Tenuta Torciano, a 300 years old winery, where you will enjoy a welcome drink followed by a typical Tuscan dinner with an exclusive Wine Tasting experience! Welcome to Tuscany!
    Overnight in San Gimignano (D)

    Day 2Siena, Truffle Hunting and Cooking Class

    Mighty Italian breakfast and private transfer to Siena, the city of Palio. Here your private guide will be waiting for you for a walking tour to discover this important city of Tuscany.
    Our tour of Siena starts from the famous “Duomo” a.k.a. Cathedral of the Assumption, a masterpiece of Gothic architecture containing famous works of Michelangelo, Donatello and Bernini. Then we’ll follow the path of “Via Francigena”, an essential communication road in the city’s history and a road along which you can admire the most important buildings and monuments, eg. Monte dei Paschi – the oldest bank in Europe and the Palazzo Tolomei – one of the most beautiful Italian Gothic palaces, once belonged to the family of Pia de’ Tolomei, whose tragic story was mentioned by Dante Alighieri in the Divine Comedy, Palazzo Chigi Saracini and the venue of the Chigiana Music Academy.
    We’ll finish our Siena tour in the monumental Piazza del Campo, the beating heart of Siena’s culture and extraordinary architectural setting, where twice a year, the famous Palio di Siena takes place.
    After the walking tour you will have some free time to explore the city on your own (shopping time!).
    Next destination is the small medieval village of Monteriggioni, for some free time to enjoy this pearl of Tuscany before we head to Tenuta Torciano, where an expert guide with his dogs will be ready to take you into the word of an Italian treasure: truffle!
    In our own private truffle wood, we will enjoy one hour of truffle hunting and you’ll be taught how to identify various species of trees and the ideal habitat for truffle growth. At the end of the experience, you will relax and enjoy a delicious truffle-based dinner in the vineyard or inside the cellar! Overnight in San Gimignano (B, D)

    Day 3Helicopter Panoramic Tour

    After a delicious Italian breakfast, we will board our helicopter in Tenuta Torciano private helipad for an unforgettable helicopter ride above Tuscany!
    Flying over the surrounding hills, we’ll have a 360° view of the beautiful vineyards of Chianti and its medieval villages such as San Gimignano, Certaldo, Monteriggioni up to Siena.
    After we land and enjoy our lunch, we will visit the marvelous city of San Gimignano, the “Medieval Manhattan”!
    Its medieval charm and beauty make it a small but precious jewel of Tuscany, known all over the world. Preserved so well, the town has managed to retain its character, you’ll feel as if you’ve taken a stroll back in time!
    Your private guide will immerse you in this Middle Ages Tuscan gem city through its history, art and local flavors. Aside from the gorgeousness, you will also find some of the best views in all of Tuscany from its many towers, in fact San Gimignano is also called “Town of Fine Towers”. The town itself is very small, making walking the best way to get around, discovering also the small cafes and boutiques.
    Next stop, Castellina in Chianti, right in the heart of Tuscany. Walking through the narrow streets of the medieval village you will be able to see churches, fortifications and archaeological sites dating back to 2000 years ago. Between medieval castles and elegant buildings, you will feel once again catapulted back in time!
    What better way to finish this glorious day with a great dinner along with delicious wine from the region.
    Overnight in San Gimignano (B,L,D)

    Day 4 A day in Florence

    Your trip in Tuscany can’t miss a visit of Florence. An unforgettable experience on the streets of this extravagant city, cradle of the Renaissance and home to unparalleled artists. Your private guide will show you the most emblematic monuments of the city such as the incredible Cathedral, overlaid by the masterpiece of the Dome – designed by Filippo Brunelleschi, the fascinating Ponte Vecchio, the Church of Santa Croce and the imposing Palazzo Pitti.
    Florence will also captivate you with its boutiques and the elegance of some historic streets, chosen as a showcase by the most important designers in the world, such as the beautiful Via Tornabuoni, along which, all the big fashion brands offer their products. After the tour you will have some free time to explore the city on your own.
    In the afternoon your driver will take you to Tenuta Torciano Winery for an amazing dinner along with wine tasting. Tonight we will try the famous Fiorentina steak!
    Overnight in San Gimignano (B,D)

    Day 8Departure day

    Breakfast is at your leisure at the hotel. Private transfer to the airport. (B)

    ** On this final day we can transfer you to any other point of Italy or extend your program any way you wish us to.


    Price is based on a minimum attendance of 4 people (Please contact us for less or more participants)

    Price Includes

    • All accommodations based on double occupancy
    • All transportation during the trip
    • Private trip leader/guide throughout the tour
    • All activities mentioned in the program
    • Professional tourist guide
    • All meals mentioned in the program
    • Helicopter Tour

    Price Excludes

    • Flights to/from Italy
    • Hotel taxes (payable locally)
    • Personal insurance
    • Any meals not mentioned in the program
    • Personal expenses
    • Gratuities
    Recommended Gear

    Please consider taking along the following items on your trip. This is not a fixed list, but more of a guideline, so feel free to add and remove items as you see fit.

    What to bring

    • Day pack to carry camera, water and snacks
    • Outerwear
    • Casual clothing made of light-weight fabrics
    • Long-sleeve shirt
    • Sun hat or baseball cap
    • Sunscreen and lip protection
    • Sunglasses and retainer strap

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