Overview
Discover Montalcino: Private Tours, Experiences & Custom Travel
Montalcino is a town which is situated in one of the most enchanting natural landscapes of the world. The long lines of vines have assigned Montalcino a prestigious position amongst Italian wine producers. The fabulous Brunello and Rosso di Montalcino are exported throughout the world and considered to be amongst the very best Italian wines.
Montalcino represents a wealth of history with its unchanged Medieval appearance: the Castle of Artigiano, the Castle Poggio alle Mura, the Romitorio Fortress and the Church of St Resituita, not to mention the Nearby Abbey of St Antimo. Culture and art are present in the United Museums which combine the Civic Museum and Diocesan Museumwhere one finds a host of frescos from the Siennese school of the XII and XIV centuries.
Visitors can also experience the popular festivals which represent historical traditions, such as the tournament for the opening of the hunting season, or the Festival of the Thrush, a spectacular event with processions, period costume and local gastronomy.
Montalcino in pictures
Gallery
A few frames from our own trips. The rest are in the gallery below.
Map
Get your bearings before you go
Multi-Day Holidays Tours
Whole journeys, planned end to end
Private & Small Group Tours in Montalcino
Days out with people who know the way
Private Wine Tour of the Orcia Valley
The Orcia Velley in south-eastern Tuscany is one of the most beautiful regions in Tuscany and a world renowned UNESCO World Heritage site. Known for the golf-course-like hills of green and gold (depending on what season you visit), this area is fam...
Montalcino Cooking Experience
Join us in the heart of the Brunello di Montalcino region for a refined culinary immersion on a historic vineyard estate. Beginning with a guided tour of the cellar and vineyards, you will then don your apron to create classic Tuscan dishes — working...
Pienza, Montepulciano and Tuscany's Beautiful Orcia Valley
The Orcia Valle or Val D`Orcia located in South Eastern Tuscany is an area of Tuscany very infrequently visited by tourists, although it is one of Italy`s most beautiful landscapes to behold and we highly recommend if you have the time that you disco...
Music and Wine in the Val D'Orcia
If you want to experience the genuine beauty of the Tuscan countryside, taste the great wines produced there and learn how they are made, try out the traditional dishes and learn how to cook them, enjoy a wellness session with your loved one, or simp...
Hotels
Rooms we would happily sleep in again
Photo Gallery
Explore Towns and Cities in Tuscany
Every town here has its own personality. We know them by name.
Arrezzo
Bagno Vignoni
Barga
Carrara
Castiglion Fiorentino
Chianciano Terme
Chianti
Cortona
Elba Island
Fiesole
Florence
Livorno
Lucca
Maremma
Montalcino
Montecatini
Montepulciano
Monteriggioni
Monticchiello
Pienza
Pietrasanta
Pisa
Porto Santo Stefano
San Gimignano
San Miniato
Saturnia
Siena
Terme di San Filippo - San Filippo Natura Hot Springs, Tuscany
Val D'Orcia
Viareggio
Volterra
Our Featured Properties
Stays we picked one by one
Popular Transfer Routes in Montalcino
The rides our guests ask for most, with a driver who knows the way.
Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Montalcino and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.
Every journey is different. Tell us where you need to go.
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Tell us about your dream trip and we'll craft the perfect itinerary for you.
In their words
Stories That Stay With You
Here's what our guests share about their unforgettable journeys
From the journal
IVS Magazine
Latest
8 June 2026
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