Tuscany's Cultural Cities by Rail
Italy
10 days / 9 nights
Rail
Guide Price £1,249 per person (based on 2 adults sharing)
Rail
Duration: 10 days/9 nights
Discover Tuscany’s charming cities on this wonderful rail holiday, encountering rich Renaissance heritage, medieval lanes, characterful piazzas and scenic vistas. From the world-famous cities of Florence and Pisa to the quaint, but equally enchanting Siena and Lucca, these historically layered cities offer a fascinating journey through time.
- Discover the enchanting lanes of medieval Siena
- Climb to the top of Florence's iconic Duomo
- Cycle along the ramparts of Lucca's historic walls
- Visit the world-famous Leaning Tower of Pisa
from £1,249
per person (based on 2 adults sharing)
Interested in this holiday? Call and speak to one of our travel experts.
Offers and News
Enjoy access to our latest offers, travel inspiration and news
Itinerary
Fly to Florence and take the train to the UNESCO World Heritage listed city of Siena. This medieval city is compact and pedestrian friendly so enjoy an afternoon strolling its charming lanes, making sure to visit the bustling central square, Piazza del Campo. From here, it is easy to visit the Museo Civico if you are interested in art history, as well as the Torre del Mangia, an imposing 88m tower that overlooks the square. Later, why not climb the 400 steps to the top for dramatic panoramas over the city. This evening, enjoy dining alfresco at one of the many inviting taverns.
Day 2 Siena
Explore the city’s most significant sites on your included guided tour. Begin by admiring the Basilica of San Domenico, a beautiful church made of red brick, before discovering the various ‘contrade’ (neighbourhoods), each with their own distinct character. Reach Piazza del Campo and learn about the Palio horse race before heading to the Siena Duomo, an impressive cathedral of black-and-white-striped facade. Spend more time exploring and less time queuing with your included Skip the Line ticket and let your guide lead you through the famed works of art held inside its Gothic interiors. The afternoon is free to explore at your own pace.
Day 3 Siena to Florence
Board your train to Florence and settle into your hotel. The birthplace of the Renaissance, Florence beckons with its beautifully intricate architecture, charming streets and museums filled with famed art pieces. Enjoy the rest of your day, soaking up the atmosphere, browsing the shops and finding a tasty bite to eat. For those seeking the perfect sunset view, why not head up to the Pizzale Michelangelo, a hilltop square boasting panoramic views over the city?
Day 4 Florence
This morning, make use of your included Duomo Skip the Line ticket. Defining Florence’s skyline, the iconic cathedral is not to be missed. With this ticket, skip the long queues and ascend the 463 steps to the top as you listen to your guide’s fascinating insight into the building’s creation over 700 years ago. After the steep climb, be rewarded with extraordinary views from the highest building in the city. The rest of the day is yours to explore at leisure, perhaps visit the Accademia Gallery to see Michelangelo’s David or explore the Uffizi Gallery, housing some of the world’s greatest art collections. Later, stroll down the famed 14th Century Ponte Vecchio bridge and browse in the jewellery shops built along it.
Day 5 Florence
Embark on your included wine and cheese tasting tour. Head off-road on a 4WD journey through the enchanting rolling hills to a Chianti winery and sample fine wines, olive oil and cheeses. Be guided through these historic local wineries with expert-led tastings and enjoy peaceful vineyard settings.
Day 6 Florence to Lucca
Take the train to the enchanting city of Lucca, renowned for its well-preserved walls that encircle its historic centre. After settling into your hotel, perhaps walk or cycle along the city ramparts which offer excellent views of the city and wander through the cobbled lanes of the old town.
Day 7 Lucca
This morning, opt to visit the Lucca Cathedral and admire its stunning mosaic facade before embarking on a challenging but rewarding climb to the top of the 15th Century Torre Guinigi. From here, see the famed seven oak trees perched on its roof as well panoramic city views. Enjoy a bite to eat in one of the main squares before perhaps visiting the Puccini Museum, once home to the famous composer. This evening, why not head to the central Piazza dell’Anfiteatro for dinner on your final night in Tuscany.
Day 8 Lucca to Pisa
Hop on board your train to Pisa, famed for its iconic 12th Century Leaning Tower. This afternoon, perhaps venture down the Borgo Stretto, a medieval street lined with characterful arcades, shops and cafés.
Day 9 Pisa
Immerse yourself in the city and opt to visit the UNESCO World Heritage Site, Piazza dei Miracoli. This beautiful, walled compound is home to intricate white marble monuments, including the famed Leaning Tower as well as a magnificent Duomo, Baptistery and cemetery. Why not climb the Leaning Tower for the most incredible views over the city. This afternoon, perhaps visit the quieter Piazza dei Cavalieri (Knights Square) or stroll through the Botanical Gardens before a scenic dinner near the Arno River.
Day 10 Pisa
Take the train from the city centre to Pisa airport for your flight home.
Additional Options: Extend Your Stay - The idyllic towns of Pienza and San Gimignano lie just a bus ride away from Siena. Why not extend your stay in Siena to pay a visit to these beautiful UNESCO World Heritage listed towns?
Price & Inclusions
- Flights
- 9 nights 4★ hotels
- Florence Duomo Skip the Line Tour
- Tuscan Wine and Cheese from Florence Tour
- Siena Duomo Skip the Line and City Tour
- Trains as detailed
- 9 meals
We negotiate new offers daily from discounted flights, tours and vehicle hire to free upgrades, added value and unique inclusions. Please call for our latest offers.
The tour itinerary, inclusions and departures are based on travel from 01/02/2026 to 15/12/2026. For holiday guide price terms and conditions, click here.
Work for Trailfinders
homeBook a Travel Centre Appointment
screen_shareBook a Virtual Appointment
Speak to a Travel Expert
We believe booking online is no substitute for one-on-one service. Between them our expert travel consultants have travelled to over 99% of the world's countries. As a result the service and advice they offer is second to none.
Your travel plans on the go
- View your up-to-date travel plans
- Book online & manage your account
- Flight details including baggage & seating
- Update your contact information
- Check visa & travel health requirements
- Access to E-Vouchers
- Trip Hub
Tales from the Trail
Top tips and travel inspiration from the Trailfinders team