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Explore Tuscany: Florence & Siena

You are viewing the 2024 itinerary. Select your departure year
8 days From $2,715 per person
4.5 stars(4 reviews)

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

Travel on your own following a well-planned itinerary

2024 Tour code: ST-FLSS-24

About the tour

Experience the birthplace of the Italian Renaissance and one of the world's most celebrated gastronomical regions in beautiful, artistic Tuscany. This central Italian expedition follows a roundtrip course from Rome and includes visits to widely known Tuscan cities and smaller towns alike. Spend several nights in Florence and Siena and your days exploring the intoxicating Cinque Terre, the beautiful Chianti region, and other delightful locales, such as Pisa and Lucca. Each day brings a new opportunity to delve into Italian culture and the rich historical essence of Tuscany. 

Unforgettable Experiences

Admire Rome’s ancient architecture
Admire Rome’s ancient architecture
From the Colosseum, where gladiators fought centuries ago, to great Roman buildings, piazzas, churches, and more, experience Rome’s best sights on an insightful small group tour.
Revel in a private introduction to Florence’s allures
Revel in a private introduction to Florence’s allures
Experience the Renaissance City in its purest form while walking through its age-old streets, looking upon points of interest like the Duomo, Palazzo Vecchio, and Giotto’s Bell Tower alongside a private guide.
Savor Chianti’s flavors and breathtaking scenery
Savor Chianti’s flavors and breathtaking scenery
Venture through the breathtaking Chianti region to see medieval castles and timeless churches and taste authentic Tuscan products, including cured meats, olive oil, and, of course, world-famous Chianti wine.
Step back in time in atmospheric Siena
Step back in time in atmospheric Siena
Home to well-preserved structures dating to the 12th century and winding, cobblestone pathways, Sienna is like a Tuscan time capsule, and exploring it on foot with a guide is truly memorable.
Explore Tuscany your way on optional excursions
Explore Tuscany your way on optional excursions
Customize your Italian adventure and experience beloved destinations in thought-provoking ways while joining optional excursions, such as hiking in the countryside, truffle hunting, or cooking classes.

What’s included


Day 1 - Arrive in the heart of the Holy Roman Empire: 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 4-Star hotel. Take some time to settle into your room, and then enjoy a chance to begin exploring. Rome is exceptionally walkable, putting many great attractions within reach of your hotel. Rather than walking around and getting a first look at the sites, you could instead grab a gelato and find a seat in one of the piazzas, getting your bearings while soaking in local life.

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 as the group meanders between sites dating to the ancient Romans, pretty buildings, and other quintessential Roman points of interest. Overnight Rome.

Day 2 - Into the rolling hills of Tuscany

A private driver takes you from your hotel to Rome's train station this morning, and on arrival, you board a high-speed train bound for Florence in northern Italy. As you enter Tuscany, note the rolling hills, which give way to silvery olive groves, prolific 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, with highlights including the Duomo, Palazzo Vecchio, 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 catering to diverse palettes and utilizing locally grown ingredients to create fantastic dishes, including the city's most notable offering, Bistecca alla Fiorentina. Overnight Florence.

  • Breakfast
Day 3 - Stacked villages and turquoise seas in the Cinque Terre

Wake early this morning with incredible scenery ahead in the remarkable Cinque Terre, one of the few remaining unspoiled stretches of the Italian Riviera. Your tour introduces the five old-world fishing villages that comprise this UNESCO World Heritage Site stretch of coastline: Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso.

Arriving in Manarola by coach, you have time to walk around before taking a lovely boat ride (weather permitting) to Monterosso. A short train journey then reveals Vernazza and Riomaggiore, where you enjoy a delicious lunch at a local restaurant before proceeding to La Spezia to rejoin the coach. With free time in each destination, you have plenty of time to experience the magic of the Cinque Terre.

Alternatively, staying in Florence brings the chance to explore the Florentine countryside on a half-day hiking excursion. A local guide leads the way, taking you through the Arno Valley from Bagno a Ripoli. Wander through serene olive groves and past old stone farmhouses, enchanting villas, and pristine country scenery. The 2 1/2-mile hike offers panoramic views of Florence's skyline and a lovely valley view as we sit down at a food shop for a typical Tuscan lunch. Overnight Florence.

  • Breakfast, Lunch
Day 4 - A free day among the history and gastronomy of Tuscany

Florence's setting makes it the ideal base to explore the diverse cities throughout Tuscany, and the day is yours to do just that. Staying in Florence brings the opportunity to discover classical art and stunning architecture. Perhaps pre-book tickets to the impressive Uffizi Gallery or wander through Piazza della Signoria to see its sculptures and gorgeous buildings.

This afternoon, you could join an optional group excursion to Pisa. Find yourself 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, then move on to the Baptistery and, finally, the 186-foot leaning marble tower. Your visit includes skip-the-line access to the Leaning Tower and a chance to climb its 294 steps for marvelous views over Pisa.

You can also upgrade your day to include a full-day tour of Pisa and Lucca. In Pisa, spend time in Piazza dei Miracoli, seeing all its renowned sites, including the world-famous Leaning Tower. Enjoy lunch at a local eatery upon arrival in Lucca and a chance to explore its captivating city center. Overnight Florence.

  • Breakfast
Day 5 - The fresh and distinctive flavors of Florence

In Florence, exquisite gastronomy is just as much a part of the culture as art, invention, and innovation. Experience the regional flavors firsthand today alongside a knowledgeable local guide. Meet a group of fellow foodies in Piazza S. Giovanni and embark on a walking tour that aligns your tastebuds with those of Florentines past.

Sip caffè, savor flaky pastries, and nibble on Tuscan schiacciata made with truffles. Sample locally grown produce, cheeses, cured meats, and Chianti wine from regional farms. Fried fish and creamy gelato round out the offerings and provide a comprehensive look at the diverse culinary offerings.

This afternoon, you can learn to make some Florentine specialties yourself on an optional cooking class at MaMa Florence. This cooking school brings traditional recipes to life through the instruction of experienced home cooks and professional chefs. Enjoy detailed demonstrations, farm-fresh ingredients, and dinner with wine.

For a day of Tuscan tastes in a different location, upgrade to a full-day tour featuring a cooking class at a family-run farm in San Gimignano. Enjoy a hands-on demonstration and lunch in an idyllic setting, then spend the afternoon in the UNESCO World Heritage historic center of San Gimignano. Overnight Florence.

  • Breakfast
Day 6 - Medieval sights and Italian delights in 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. Take some time to get acquainted with your new surroundings, then set out for a tour of the breathtaking Chianti region this afternoon.

Steeped in pictorial Tuscan scenery, this journey sees a small group through all the colors and textures of the rolling countryside, all the while focusing on its most famous product: wine. Centuries of cultivation have led Chianti to become a leading wine region. After driving past ancient villages and admiring medieval castles in the distance, the group arrives at a Chianti wine estate. Look upon wine in various stages of production in its cellars and taste the fruits of its labors while also sampling cured meats and bruschetta. From here, continue to Monteriggioni, a walled fortress dating to 1200, with time to explore its history before visiting another local winery and returning to Siena. Overnight Siena

  • Breakfast
Day 7 - Walking through Siena’s layered cityscape

Siena is a treasure trove of cultural riches and has an ancient footprint that is seemingly built layer upon layer, with each building somehow supporting the next. With so much to discover, the best way to see everything is on foot alongside a knowledgeable guide. This morning's excursion takes you through Siena's beating heart, Piazza del Campo, and to points of interest like Palazzo Comunale, the Cathedral, and the spectacular Basilica of San Domenico.

This afternoon, you can continue sightseeing independently or join a small group at a local shop to taste earthy Italian truffles. One of the most expensive and prized culinary delicacies, truffles can be eaten on their own with dishes or used as an infusing ingredient In various foods and sauces. Enjoy a chance to taste them in many forms alongside deli selections and wine or beer.

Should you wish to focus your entire day on truffles, you can join a private full-day tour with them as the centerpiece. Alongside an experienced truffle hunter, spend the morning hunting for the ingredients in Siena's woodlands, then venture back into the city for a tasting. Overnight Siena.


  • Breakfast
Day 8 - Tour conclusion

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. Here, your Tuscan expedition concludes, and you can return home, bringing fond memories of postcard-perfect Tuscany with you.

  • 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.




4.5 stars4.5 / 5 · 4 reviews

  1. 5 stars
  2. 4 stars
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  5. 1 star


4 stars

Submitted 17 Apr 2024

I think the tours were really well planned out and we were very happy with the private transfers. we had issues with our luggage fitting on the train (limited space for large bags). Like most European hotels, not all of them had A/C, so just something to keep in mind. We LOVED our hotel in Florence (spacious, more modern, and had A/C. only down fall was kind of noisy).

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5 stars

Submitted 19 Oct 2023

Had a great time exploring Italy and really enjoyed the walks and side trips planned for us by Vacations by Rail.

from Vacations By Rail
We are so glad to hear that you had a great time on your trip! We absolutely love these photos, and with you permission would love to share them on our social media.
Feel free to use them!

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4 stars

Submitted 08 Oct 2023

The hotel accommodations, transfers and rail tickets were great. Some of the included tours were great and others, not so great. The private walking tour and the food tour in Florence were terrific- knowledgeable guides all to ourselves but the two wine tours and the panoramic Rome by night had only drivers and no guides so the information we received from them was minimal. The two wine tours were late in arriving, then we were rushed at our stops. One wine tour was just 4 of us and there were generous wine and food samples and the other was two 8 passenger vans with skimpy taste with almost no food. Both tours had stops that the drivers could not tell us why we were there or what we were supposed to see. We stopped at a monastery that was closed at that time of day. The final Siena tour was late getting started and the guide kept allowing more people to join until there were 16 people, no headsets and was Italian and English speaking. It was so hard to hear and it seemed that more than half of the time the tour was in Italian. Very disappointing. The photo is the view from our hotel room- best hotel ever!

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5 stars

Submitted 08 Sep 2023

Loved the tours we had and any snafus were quickly resolved. Would use again.

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