This itinerary for an 'escorted segment' is designed to be included in a longer tour. Before and/or after the tour you can explore Italy in classic semi-independent JayWay style, but for a part of the tour where having an expert guide and driver gets you access to places beyond what's possible on your own or even on most commercial day trip, our expert Italy guide, Daniele, will be with you.
Take in the quintessentially Tuscan charm of the Chianti and Crete Senesi rolling hills over 4 days. staying in comfortable countryside lodgings in a hilltop villa or palazzo, and being expertly led to meet Daniele's friends, the winemakers, cheesemakers, and season and opportunity permitting, truffle hunters and their well-trained truffle hounds, as well as enjoying the UNESCO-listed highlights of Tuscany, such as San Gimignano, Pienza, Siena, or the Val d'Orcia landscape and wineries of Montalcino.
This sample itinerary starts and ends in Florence, but can be adjusted to your needs, from start and end locations, to whole days added or removed, and activities adjusted to your requirements. The first step on your journey of discovering the very best of Italy is to get in touch (click on Enquire) and Daniele will fine-tune the perfect itinerary for you.
Enquire About This Trip
Tell us the month of travel, how many travelers and what star level accommodation you'd like to stay in.
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What's Included
Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes.
Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.
Florence
Trequanda
Florence
package excludes:
- Flights from and to your home country.
- Tips for Tour Guides, Drivers and Local Reps.
- Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
- Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
- Travel Insurance. See the insurance link on our website
A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.
A Travel Advisor who speaks your language
We will make sure that all your requirements and interests are taken into account in preparing your itinerary.A totally tailored itinerary for your vacation
Your trip is customized for you by an experienced trip planner and an expert on the region.A choice of hand-picked hotels and excursions
We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.Detailed pre-trip preparation to make the most of every day
Your destination-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.On-trip Concierge Service to smooth out any bumps in the road
Your tour manager is at your service throughout your journey. We'll provide a local SIM so you can stay connected.Personalized Guest Page to make sure you're not missing out
Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.Day Stop in Florence
Day Stop in Florence



Day Stop in Florence
Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci's works are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.
Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci's works are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.
Day 1 - Day Stop in Florence
Day 1 - Day Stop in Florence
You will be met in the morning in Florence by Daniele, your guide for the next 4 days exploration of the delights of Tuscany.
3 Nights in Trequanda
3 Nights in Trequanda


3 Nights in Trequanda
Tucked away in a corner of Tuscany is an oft-overlooked area around the town of Trequanda where two of our favorite winemaker-agriturismos can be found. Idyllic places you'll never want to leave and decidedly remote so leaving is really only a possibility by car. This area is called the Colli Senesi, the Siena Hills, and it lies south-east of Siena. Here you'll find undulating terrain covered in vineyards, olive groves and wheat fields. This is great truffle-hunting country and an excursion with a truffle hunter and his dog is a must.
Tucked away in a corner of Tuscany is an oft-overlooked area around the town of Trequanda where two of our favorite winemaker-agriturismos can be found. Idyllic places you'll never want to leave and decidedly remote so leaving is really only a possibility by car. This area is called the Colli Senesi, the Siena Hills, and it lies south-east of Siena. Here you'll find undulating terrain covered in vineyards, olive groves and wheat fields. This is great truffle-hunting country and an excursion with a truffle hunter and his dog is a must.
Day 1
Day 1 - Arrival in Trequanda
The first attraction of your wonderful journey will be the famous hills of Chianti, around one hour drive from Florence.
Chianti, the red beating heart of Tuscany
Today you will enjoy the world-famous landscapes of Chianti wine region. Castellina in Chianti is an idyllic hilltop village nested among the picture-perfect rolling hills of Chianti. There you will dine on a sumptuous tasting lunch in the restaurant of a nobleman's palace, paired with the family's various wines. Later in the afternoon you will visit Monteriggioni, a medieval fortress which also sits atop a hill. If you're a gelato fan, then you'll be happy to find a gelateria conveniently inside the fortress. Included: private transfer, guided walking tours of Castellina in Chianti and Monteriggioni. The detailed content of the day and the timing can be modified and extended, according to your preferences.
Day 2
Day 2 - Your First Full Day in Trequanda
Montalcino and Montepulciano noble wines and Pienza's cheesemakers
You're going to be getting acquainted with the wines of Montalcino, the Rosso and Brunello by visiting a family run wine cellar. Then it's on to Pienza, one of Italy's centers of cheese excellence. As well as indulging in some exquisite pecorino you'll be swept away with the emption of a functioning 800 year old monastery with wonderful Renaissance frescoes. Your guide can also arrange the program to include a visit to medieval Montepulciano according to your preferences. Included: private transfer, guided walking tours, entrance to Montalcino castle, winery visit with tasting of Brunello di Montalcino or Nobile di Montepulciano. The detailed content of the day and the timing can be modified and extended, according to your preferences.
Day 3
Day 3 - Your Second Full Day in Trequanda
Signature sights of Tuscany : Siena and San Gimignano medieval wonders
Did you think skyscrapers were a modern invention? Medieval Italians were competing with each other to build the tallest tower in the town to show off their status. And nowhere did they go in for this with quite as much aplomb as San Gimignano, the 'medieval Manhattan'. Today you'll be visiting it and if you're feeling up to the climb, you can ascend the Torre Grossa and enjoy spectacular views of the countryside around the town. You'll then visit another Tuscan gem, Siena. Once a staunch rival to Florence, Siena is a more laid-back city, with a grand Duomo but its real highlight is the Piazza del Campo, a large square that hosts a traditional and world famous bareback horse race twice a year, in July and August. In between you will enjoy a lunch showcasing local delicatessen and wine. Included: private transfer, guided walking tours, entrance to San Gimignano Torre Grossa or Siena cathedral The detailed content of the day and the timing can be modified and extended, according to your preferences.
The 'Crete Senesi' Unesco heritage landscapes and Medieval villages
Today you will enjoy the landscapes of the rolling hills of the 'crete Senesi', the hills south of Siena. This is real 'Under a Tuscan Sun' territory. Your experienced local guide will stop in the most photogenic spots. According to your preferences and the detailed activities scheduled during the day, you will have the chance to visit the historic medieval villages of Asciano and Trequanda and the magnificent frescoed benedictine Monastery of Monte Oliveto maggiore, a truly unforgettable experience.
Day 4
Day 4 - Traveling to Florence
Your Tuscan adventure has come to an end. To facilitate your onward journey Daniele will take you to Florence in plenty of time for the train to your next destination, or the city center. If time allows, you could request a stop along the way at Florence's premier luxury fashion outlet.
Day Stop in Florence
Day Stop in Florence



Day Stop in Florence
Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci's works are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.
Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci's works are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.
Day 4 - Day Stop in Florence
Day 4 - Day Stop in Florence
Upon reaching Florence your driver will take you as close as possible to your accommodation, the railway station or the airport. As the city has several pedestrian only areas so you may need to walk a short way to your accommodation, depending on its location.
Glowing Reviews from Our Guests
Average of our Guest's Ratings of tour packages including these destinations

I had a fabulous experience due to JayWay Travel’s attention to detail and planning. You will not be disappointed as we had the perfect experience!
– Denise, Anita, Maureen, Mary, Jenny, Valerie & Rose, Virginia
Visited : Italy
Itinerary : Venice, Florence, Trequanda, Rome
Rating :