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Timeless Journeys
Through Italy’s Hidden Treasures
Experience the very best of Tuscany on an enchanting 8-day, 7-night tour combining world-famous art cities, medieval hilltop villages, rolling countryside, exceptional wines and authentic Tuscan flavors.
From the Renaissance treasures of Florence to the iconic Leaning Tower of Pisa, from the medieval streets of Siena to the picturesque landscapes of the Chianti wine region and the Val d’Orcia, this journey reveals the extraordinary beauty, history and cultural heritage of one of Italy’s most beloved regions.
Along the way, discover some of Tuscany’s most celebrated UNESCO World Heritage Sites, explore charming historic towns and enjoy wine tastings in renowned wine-producing areas. This itinerary combines guided cultural visits with opportunities to appreciate the landscapes, gastronomy and traditions that make Tuscany such a distinctive destination.
This carefully designed itinerary offers an excellent way to explore Tuscany’s most famous destinations while enjoying the convenience of 7 nights at the same hotel, without the need to change accommodation throughout the tour.
Discover Florence, the birthplace of the Renaissance, with its extraordinary artistic heritage and architectural masterpieces. Visit the monumental Piazza dei Miracoli in Pisa, home to the world-famous Leaning Tower, and explore Siena, a magnificent medieval city renowned for its Gothic architecture and beautiful Piazza del Campo.
Continue through the picturesque Tuscan countryside, where winding country roads, vineyards, olive groves and historic villages create some of the most iconic landscapes in Italy.
Discover the medieval charm of Monteriggioni and San Gimignano, explore the celebrated Chianti wine region, and travel through the breathtaking Val d’Orcia, a UNESCO-listed cultural landscape renowned for its rolling hills, cypress-lined roads and traditional rural scenery.
The journey also introduces you to Pienza, Montalcino and Montepulciano, three outstanding destinations where history, architecture and local gastronomy come together.
Taste authentic Pecorino cheese in Pienza and discover the celebrated wines of Tuscany, including Brunello di Montalcino and Vino Nobile di Montepulciano, with wine tastings included in the itinerary.
Tuscany is a destination to be experienced with all your senses.
Admire Renaissance masterpieces, discover medieval architecture, stroll through historic squares and enjoy the distinctive atmosphere of the region’s towns and villages. Between cultural visits, experience the traditions of Tuscan winemaking and savor the local flavors that have made this region famous around the world.
With guided visits, selected entrance tickets, wine tastings and comfortable accommodation included, this itinerary offers an appealing way to discover Tuscany’s cultural and gastronomic highlights in one well-organized journey.
And Florence deserves a little extra time: enjoy the opportunity to explore the city at your own pace, discover its artisan workshops and local markets, relax in elegant cafés and uncover hidden corners away from the busiest tourist routes.
Roads of Tuscany is an excellent choice for travelers who want to discover the region’s most famous destinations through a combination of art, history, scenic countryside and food and wine experiences.
TOUR DETAILS
Duration: 8 days / 7 nights
Destinations: Florence, Pisa, Siena, Monteriggioni, San Gimignano, the Chianti wine region, Val d’Orcia, Pienza, Montalcino and Montepulciano.
Accommodation: 7 nights at Dedo Boutique Hotel or a similar property.
Travel style: Organized guided tour with coach or minivan transportation and an expert multilingual tour leader.
AVAILABLE DEPARTURES – 2027
March 17–24, 2027
April 21–28, 2027
July 17–24, 2027
October 6–13, 2027
November 10–17, 2027
Other departure dates are available upon request.
PRICE PER PERSON
€2480 per person, based on accommodation in a standard double room.
Single room supplement: €486
Discover Tuscany through its unforgettable cities, spectacular landscapes, extraordinary art and world-renowned wines on this memorable journey through the heart of Italy.
Book your Roads of Tuscany experience and discover the art, flavors and landscapes that make this region truly unforgettable.
30 Minutes Before Event Time
Pick up, PRIVATE TRANSFER at “Amerigo Vespucci” Florence Airport (FLR),
So you won’t have to worry about anything, we’ll take you to your hotel where you’ll stay for 7 nights. Rest of the day at leisure and relax, you can familiarize with this enchanting city
Time arrival to be defined
Please note: in case of train delay over 20 min we cannot guarantee the private transfer service
Our Tip: Taste and Slow Italy Travel Agents Team will be glad to suggest how to spend your first day in Florence, nice hidden places to walk and where to find typical and authentic local food.
Lunch and dinner at leisure
Breakfast at your hotel then… It will be an art day!!! Among museums, squares and many monuments, we’ll take you to discover some of the most important artistic treasures of Florence.
in the morning Immerse yourself into the two thousand year old history in the “Cradle of the Renaissance,” through the eyes of an expert, local guide, who will take you on an unforgettable journey to discover the most beautiful squares and monuments of Florence.
Florence is literally dotted with ARCHITECTURAL WONDERS and WORKS OF ART. On our group tour, you will admire firsthand the sites and monuments that have made Florence one of the most visited destinations in the world.
To start your tour, you will head to REPUBBLICA SQUARE, one of the most elegant and historically important “piazzas” in Florence, overflowing with refined cafés and luxury shopping. Follow your guide through the characteristic streets and picturesque alleys until you reach LOGGIA DEL MERCATO NUOVO, where your guide will demonstrate a symbol of good luck by caressing the nose of the famous PORCELLINO (wild boar) BRONZE STATUE. On this tour, you will learn all sorts of local legends, fascinating stories, and unexpected facts about Florence.
Right around the corner, your guide will lead you to the intriguing PONTE VECCHIO – a true icon of the city. This bridge is famous for its exclusive jewelry stores, unique structure, and for being the only bridge spared during the bombings during the Second World War.
Then, follow your guide to ACCADEMIA DEI GEORGOFILI and UFFIZI SQUARE, where you will discover the heart of Florence – SIGNORIA SQUARE. This true open-air museum is dominated by the imposing PALAZZO VECCHIO and the magnificent LOGGIA DEI LANZI, home to fascinating statues such as PERSEUS by Cellini and the RAPE OF THE SABINE WOMEN by Giambologna.
Your journey through Florence will lead to SAN GIOVANNI SQUARE, home of the wonderful FLORENCE CATHEDRAL and BRUNELLESCHI’S DOME, as well as the Baptistery and Giotto’s Bell Tower. Continue your tour by visiting the INTERIORS OF THE CATHEDRAL OF SANTA MARIA DEL FIORE, saving your time by SKIPPING THE LONG QUEUES at the entrance and taking advantage of your expert guide, who will reveal all the secrets of this immense wealth of art and architecture.
Lunch at leisure
Our tips if you prefer street food: In Italy there is a thin line between junk food and excellence food… we will advice you where to find the most hidden and authentic street food kiosks.
Evening at leisure
I suggest to reserve a dinner to the Trattoria Da Sabatino the most authentic place to eat where the locals eat!
Breakfast at your hotel. Today we have to get up early otherwise we’ll miss the scheduled group tour of the day !!!
In the early hours of the morning you will depart from Florence with destination Pisa. You will be able to fully appreciate the architectural magnificence of the city. In fact, once you arrive in Pisa you will be welcomed by our guide who will show you the marvellous Piazza dei Miracoli: during the guided tour you will be able to admire the Baptistery and the famous Leaning Tower, culminating inside the imposing Cathedral. Before leaving for Lucca, you will then have some free time for a little shopping or a cappuccino.
Lunch at leisure
You will then continue on to Lucca, famous for its ancient walls still intact and interrupted by imposing gateways. A local guide will take you to the heart of the town’s historical centre, walking along the walls themselves, from which you will enjoy a breathtaking view over the rooftops of the houses.
Together with our guide, you will admire Lucca’s most interesting monuments and churches, including Piazza dell’Anfiteatro, the Guinigi Tower, the Cathedral of San Martino and a relaxing stroll through the picturesque alleyways and antique shops.
Our tour ends with a pleasant stop at a pastry shop located in the heart of Lucca’s walls, where we can taste the famous buccellato, the city’s traditional cake.
Dinner at leisure
A Journey Through Art: Your Exclusive Uffizi Experience
Wake up to a delightful breakfast at your hotel, then get ready for an unforgettable artistic adventure in the heart of Florence!
Join our expert local guide, a true art enthusiast, for a fascinating deep dive into the treasures of the Uffizi Gallery—a must-see for first-time visitors and seasoned art lovers alike.
As you walk through the magnificently adorned halls, your guide will lead you on an engaging journey through the masterpieces of the Renaissance, bringing to life the stories behind the works and the vision of the artists who shaped art history.
Your tour begins with the revolutionary talents of Giotto and Masaccio, the pioneers of Italian painting, and follows the evolution of art across the centuries. Prepare to be mesmerized by Botticelli’s ethereal “Birth of Venus”, Leonardo da Vinci’s delicate “Annunciation”, and Michelangelo’s powerful “Tondo Doni”, among many other timeless masterpieces.
But the experience doesn’t stop there! As you explore the vast halls and sunlit corridors of the Uffizi, you’ll be treated to breathtaking panoramic views of Florence through the museum’s iconic windows—a picture-perfect moment to capture!
At the end of your guided tour, you are free to continue exploring at your own pace. Revisit your favorite artworks, soak in the grandeur of the gallery, or simply unwind at the Uffizi café, sipping on a cappuccino or spritz while enjoying a spectacular view of the Florentine skyline.
Renaissance art, stunning cityscapes, and an unforgettable experience—this is Florence at its finest!
Highlights
Breakfast then a great group tour experience in Tuscany countryside.
Discover the untouched charm of Tuscany—a day of unforgettable experiences awaits amidst ancient towns, rolling vineyards, and exquisite wines!
Your journey begins with a comfortable morning bus ride from Florence toward the enchanting Chianti region. As you traverse lush green hills, you’ll arrive at Monteriggioni, a true hidden gem nestled in the Tuscan landscape. This quaint medieval town, with its perfectly preserved walls and inviting piazza, offers you a unique opportunity to step back in time and savor its timeless ambiance.
From Monteriggioni, our adventure leads you to the heart of medieval splendor in Siena. Stroll through the legendary Piazza del Campo—famed for its historic Palio and stunning Gothic architecture. Admire the imposing Palazzo Pubblico and its iconic Torre del Mangia before continuing your guided exploration toward the majestic Duomo, one of Italy’s most celebrated Gothic masterpieces. And if you’ve chosen the complete tour, you’ll have additional free time to wander Siena’s historic center at your own pace.
Next, prepare to be mesmerized by the postcard-perfect landscapes of the Chianti region. Enjoy a wine tasting in a charming cellar where you’ll sample the region’s best Chianti, paired with delicious homemade snacks and an in-depth tasting of local wines and extra virgin olive oils.
Finally, our journey culminates in San Gimignano—an evocative medieval town recognized as a UNESCO World Heritage Site. Famous for its crisp Vernaccia white wine and its iconic towers that soar like ancient skyscrapers, San Gimignano invites you to lose yourself in its narrow alleys and breathtaking vistas.
Experience Tuscany in its purest form—a harmonious blend of history, culture, and natural beauty that promises memories to last a lifetime. This tour will offer you a complete immersion in the spectacular Chianti hills, ensuring an unforgettable experience.
Breakfast at your hotel and departure to Val d’Orcia.
Leave Florence and immerse yourself in the authentic heart of Tuscany with a visit to the enchanting Val d’Orcia, a UNESCO World Heritage Site. Discover the charming towns of Montalcino, Pienza, and Montepulciano, and enjoy two exclusive wine tastings paired with the famous fresh Pecorino cheese!
Your journey begins in Montalcino, the land of renowned wine Brunello, where a delightful wine cellar welcomes you for an unforgettable tasting experience. Stroll through the picturesque streets to the hilltop, where a breathtaking panorama unfolds before your eyes: sun-drenched rolling hills, ancient oak trees, evocative olive groves, winding country roads through pristine vineyards, and solitary cypress trees. Make sure to have your camera ready!
Next, continue on to Pienza, the “ideal city” envisioned in the 15th century by the celebrated architect Bernardo Rossellino at the behest of Pope Pius II. Here, admire authentic architectural gems such as the Duomo and Palazzo Piccolomini—filming locations for scenes in Zeffirelli’s famous Romeo and Juliet—and revel in one of the most evocative panoramic views of the Val d’Orcia.
Your final stop is Montepulciano, home to the renowned Vino Nobile and, more recently, a filming location for the movie “New Moon.” Delight your palate with a combined wine and Pecorino tasting in a captivating historical setting: a genuine underground cellar where wine was traditionally stored beneath ancient walls, before heading back to Florence.
This exclusive experience offers a complete immersion into the timeless flavors, scents, and landscapes of Tuscany, leaving you with unforgettable memories of art, nature, and tradition.
Highlights
The group tour Includes
Breakfast and all day at leisure!
You can spend the entire day relaxing or in case you feel energetic enough you can take the day to explore Florence your own way, do some shopping, visit other world-famous museums and galleries, or just stroll around… it’s up to you!!!
Our Tip: Ask Taste and Slow Italy Travel Agents Team, we will suggest you how to spend your last day in Florence, best and most authentic place to do shopping. We warmly suggest you to visit Ferragamo museum and Gucci garden area. Two places absolutely amusing. Then the renaissance gardens scattered everywhere around Florence. Or the hidden and enchanting area of Fiesole…
Breakfast at the hotel.
Today the trip concludes and it’s time to say your goodbye.
A private transfer will take you from your hotel to the airport whenever it’s convenient for you. In case you have an afternoon or late evening flight you could have more of Florence sights, do some last minute shopping or gallery and museum hopping.
