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Explore Tuscany: Florence & Siena


Experience idyllic destinations brimming with history and rolling vineyards that provide some of the world’s best wine in beautiful Tuscany.

You are viewing the 2023 itinerary. Select your departure year
8 days From $2,179 per person
Travel on your own following a well-planned itinerary

2023 Tour code: ST-FLSS-23

About the tour

Silvery olive groves and colorful vineyards sit upon a terrain filled with undulating hills and vistas so impressive that they have inspired centuries of art in Tuscany. This region in central Italy is beloved as the birthplace of the Italian Renaissance and has long been a destination celebrated for its gastronomy. This 8-day independent journey is your chance to immerse yourself in all its offerings. The itinerary follows a roundtrip course from Rome and includes visits to widely known cities and smaller towns alike. Spend several nights in Florence and Siena, and enjoy day trips to delightful destinations, the Chianti region, and Montalcino. Each day brings a new opportunity to delve into Italian culture through well-planned excursions either alongside a guide on your own or with an intimate travel group. Enjoy walking tours, guided excursions by foot or motorcoach, visits to cathedrals, tastings of regional offerings at vineyards and wine cellars, and, of course, plenty of time to sightsee independently. As you travel through the Tuscan landscape by high-speed train, note the vastness of the natural landscape and the breathtaking beauty that results from thousand-year-old architecture. All of this pairs with select private transfers and stays in luxurious hotels to create a journey that exceeds all expectations.


What’s included


Day 1 - Arrive in Rome

Set in the heart of Italy, Rome oozes history and exudes culture, making it the perfect place to begin your Italian exploration. As your flight arrives at Rome's international airport, a driver greets you to provide a private transfer to your four-star hotel. Take some time to settle into your room, and then begin to explore the area. Tonight, enjoy your first look at the city's incredible architecture and age-old sites on a small group tour. A local guide leads the way, offering fascinating insight at each stop. Overnight Rome.

Day 2 - Florence

A private driver takes you from your hotel to Rome's train station this morning, where on arrival, you board a high-speed train bound for Florence in northern Italy. There are approximately 160 scenic miles between these two beloved destinations; however, the journey takes less than 2 hours to complete. As you enter Tuscany, note the rolling hills, which give way to rich olive groves, vineyards, and lush orchards. In the backdrop, imposing mountains make for a picture-perfect scene. On arrival, a driver picks you up from Florence's train station and escorts you to your luxurious hotel. Revel in a private introduction to this Renaissance City on this afternoon's guided walking tour. Alongside a local, stroll between beloved buildings and famous sites throughout the city, with points of interest including the likes of the Duomo, Palazzo Vecchio, pretty piazzas, and Giotto's Bell Tower. You can upgrade this experience to a combination excursion that includes a walking tour through Florence and admission and touring at the Accademia, home to Michelangelo's famous statue, David.

Following your tour, take the rest of the day to immerse your senses in all of Tuscany's offerings. There are over 800 restaurants in Florence that cater to diverse palettes and utilize locally grown ingredients to create fantastic dishes, including the city's most notable offering, Bistecca alla Fiorentina. Overnight Florence.

  • Breakfast
Day 3 - Chianti Region Touring

Timeless scenes of rolling farmlands and lush vineyards welcome you to the Chiantigiana countryside in the heart of Tuscany. The Chianti region has a long-held tradition of producing delicious olive oil, wonderful wine, and flavorful meats and cheeses. Today, wrap yourself in these customs by embarking on a private tour through the region. An English-speaking driver greets you at your hotel this morning and escorts you through the serene landscape to Greve at the heart of Chianti. This medieval town is a hub for foodies and historians alike, as its timeless appearance sets an idyllic background while you meander between shops and get acquainted with the tastes of Tuscany. The excursion continues to a local farm, where the owners guide you through their grounds, showcasing their vineyards and olive groves as you walk. Learn about traditional harvesting and processing methods, and cap off your visit by tasting five varieties of wine, bruschetta prepared using freshly harvested produce, and cured meats processed locally.

Return to Florence with the remainder of the day at your leisure. You may wish to take a more in-depth look at some of the sights from yesterday's walking tour or start anew; after all, there is no lack of things to see in this incredible locale. From palaces and basilicas to the Mercato Centrale, an indoor market with nearly 150 years of history, there are adventures to be had, both big and small. Venture to the Piazza Michelangelo for sweeping views over the city or find your inner child on the carousel in Piazza della Repubblica, smack-dab in the historic heart of Florence. Overnight Florence.

  • Breakfast
Day 4 - Tuscany Your Way

Florence's setting makes it the ideal base to explore the diverse cities throughout Tuscany. Choose your adventure, and soak in the splendors that come with your new location.

Option 1: Pisa and Lucca
Spend a full day exploring two incredible cities, each brimming with fascinating sites and impeccable scenery: Pisa and Lucca. A private driver escorts you from your hotel and through the complex layers of the Florentine landscape to Pisa to begin your day. Find yourself left in awe as you explore the Piazza dei Miracoli, a UNESCO World Heritage Site that showcases the artwork, craftsmanship, and architecture of the Middle Ages. Visit the grand centerpiece of the square, the Cathedral of Santa Maria, where Galileo was inspired to invent the pendulum clock. Continue to the Baptistery, the monumental cemetery, and finally, to the building for which Pisa is best known, the 186-foot leaning marble tower. While it stands alone as an attraction, the Leaning Tower is actually Duomo's bell tower.

From Pisa, venture to Lucca, whose layered history began with the Etruscans, saw the height of the Roman empire, and experienced further growth and influence during the medieval period. Impressive fortifications surround the city, and varied architecture speaks to the locale's long and winding tale. Lucca is a fantastic place to discover on foot. You may wish to look upon the 11th-century Lucca Cathedral, the Guinigi Tower that overlooks the city, or Lucca's beautiful piazzas, such as Piazza dell Anfiteatro and Piazza Napoleone, as you wander. Before departing, enjoy lunch with a glass of wine in one of Lucca's many restaurants.

Independent day trips to Pisa and Lucca are also available. Ask a rail specialist for details.

Option 2: Cinque Terre
The Italian Riviera is a postcard-perfect region brimming with awe-inspiring views and an easy, seaside ambiance. A mixture of resort towns and fishing villages dot the coastline and add further intrigue to the vistas. Of these, a group of five remote fishing villages known as the Cinque Terre fully embraces the unspoiled wonders of seaside Italy. Together, the quaint destinations - Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore - enjoy UNESCO World Heritage Site status and are a national park. Today, you will see why.

Arrive in the region aboard a deluxe motorcoach, with Manarola as your first stop. From here, cruise through the azure water to Monterosso and then board a train to Vernazza and Riomaggiore. There is plenty of time to stroll through each location and admire their similarities and differences before moving on to the next village. Savor fresh seafood and delectable local fare at a local restaurant in Riomaggiore, and find yourself enjoying the sea views just as much as the cuisine as you dine. Continue by train to La Spezia, where you meet your motorcoach once more and return to Florence.

Of course, if you are not up for an adventure, you are welcome to stay in Florence for the day to sightsee or relax to your heart's content. Overnight Florence.

  • Breakfast
Day 5 - Florence Food Tour

In Florence, exquisite gastronomy is just as much a part of the culture as art, invention, and innovation. A juxtaposition of typical peasant cuisine and royal fare fit for the aristocratic palates of the House of Medici collide to create a taste unlike anywhere else in the world. Experience the flavors of Florence firsthand today alongside a knowledgeable local guide. Meet a group of fellow foodies and your tour leader in Piazza S. Giovanni and embark on a walking tour that transports you through the centuries, aligning your tastebuds with those of Florentines throughout the ages. Sip caffè, savor flaky pastries, and nibble on Tuscan Schiacciata made with truffles. Sample locally grown fruits and vegetables, as well as cheeses, cured meats, and a Chianti wine from regional farms. Fried fish and creamy gelato round out the offerings and give you a comprehensive look at the vast and diverse culinary offerings here.

Alternatively, join an optional full-day tour that explores the Tuscan region. Options include:

● A full-day Tuscan wine and cheese tour, where you can savor fantastic views and even better cuisine while exploring Tuscany alongside an expert guide. Taste locally produced wines and cheese at several locations, each exemplifying the nuances of Tuscan gastronomy.

● A full-day cooking class with lunch and a visit to San Gimignano, where you learn how to prepare traditional Italian cuisine using fresh, delicious ingredients, then enjoy lunch and a visit to San Gimignano, a medieval town nestled in the hills of southwest Florence.

Overnight Florence.

  • Breakfast
Day 6 - Siena

Heading further south in Tuscany today, medieval Siena awaits at the end of your morning train journey. This city is surrounded by ancient walls and is filled with narrow stone streets that lead to sweeping piazzas and its UNESCO World Heritage city center. From afar, the city appears to be built layer upon layer, with each building somehow supporting the next. As you walk, the steep alleys and byways also hint at this fact. Make your way to the hotel for check-in on arrival, then join a guide in exploring your new destination.

Begin at the 13th-century Basilica of San Domenico, dedicated to St. Catherine of Siena. This Renaissance masterpiece sits as the crowning jewel of the city center, and its vaulted ceilings and beautiful altar speak to the love and detail that went into its construction. After visiting the cathedral, meander through the shell-shaped Piazza del Campo, looking upon the cafés, pubs, and historic buildings that line the cobbled streets as you approach the 12th-century Siena Cathedral. Step inside with your guide and take a look around at the magnificent interior. From its intricate statue and gorgeous pulpit to its striped stone walls, there is much to see in this historic structure.

Following the tour, you are free to spend your day in this atmospheric destination however you choose. Overnight Siena.

  • Breakfast
Day 7 - Montalcino Wine Tour

Ruby red wines and inspiring scenery lie ahead as you head out into the Tuscan countryside in pursuit of Montalcino. Your intimate travel group explores wineries and wine cellars alongside an expert guide on this excursion, learning about the love and care that goes into Montalcino wine. Savor samplings of wine, balsamic vinegar, and olive oil as you travel, as well as tastes of cured meats and salami. Take a deep dive into the local lore as you tour Montalcino and look upon its ancient fortress and historic buildings. This immersive experience is sure to leave you wanting for nothing.

Return to Siena following the tour with the rest of the day at leisure. The Publico Palace and Tower of Mangia are other sights to experience before the sun goes down. Overnight Siena. 

  • Breakfast
Day 8 - Siena to Rome

Relish the views of hillside Siena once more as you transfer by taxi to the train station this morning to join your high-speed train back to Rome. Reflect on the fabulous wine and unbelievable scenery of the last week as the three-hour route through Italy's interior unfolds. An English-speaking driver greets you as the train stations in Rome, and from here, you are taken to Rome's international airport, where your Tuscan expedition concludes.

  • Breakfast

Additional information

Departure times

Departure times vary based on selected rail vacation. This information will be provided in your final documents. For more information please speak with your rail specialist.

Mobility information

Due to the nature of our tours they are generally unsuitable for those with restricted mobility. If you’d like to discuss any particular vacation with us in this respect, then please don’t hesitate to call us.


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