Explore Tuscany by Rail: A Slow Journey Through Italy’s Hilltop Towns

There’s something romantic about train travel in Italy. The rhythm of the tracks, the rolling green hills, the sun-drenched vineyards and the effortless glide from one medieval town to the next. Tuscany, long loved for its rustic charm and cultural riches, is one of the best regions to explore by train. This is especially appealing for travellers keen to skip the hire car and embrace a slower, more sustainable pace.

Whether you’re a lover of art, history, fine wine or just a good plate of pici pasta, a Tuscan rail journey lets you soak in the magic of the region while avoiding the stress of driving its narrow, winding roads. With convenient rail passes, comfortable accommodation options and curated local experiences, Entire Travel Group makes it easy to uncover the best of Tuscany by train.

Why Travel Tuscany by Train?

Tuscany’s regional rail network is well-connected and scenic, with trains linking major towns and smaller villages across rolling countryside. Travelling by train is more environmentally friendly than driving and gives you the freedom to relax and enjoy the view. You’ll glide past vineyards, olive groves and sun-dappled fields, arriving right in the heart of each historic town.

With rail travel, there’s no need to navigate Italian road rules, stress over parking, or miss out on that second glass of Chianti. Everything is taken care of, and you can travel at your own pace. 

First Stop: Lucca – Walled Elegance and La Dolce Vita

Lucca is often overlooked in favour of its flashier neighbours, but those who visit this elegant town rarely forget it. Enclosed within Renaissance-era walls, Lucca feels like a secret garden of art, music and slow living.

Take the train from Florence or Pisa and arrive directly in the city centre. Settle into a boutique Tuscan hotel within walking distance of Lucca’s cobbled streets and piazzas. Spend your first afternoon renting a bike and circling the wide ramparts; locals love to cycle the tree-lined path that winds around the old town.

Explore the town’s Roman and Gothic heritage with visits to San Michele in Foro and the grand Lucca Cathedral. For music lovers, a stop at the Puccini Museum offers a look into the life of one of Italy’s most beloved composers, who was born here.

Dining in Lucca leans toward traditional Lucchese fare. Don’t miss:

• Tordelli Lucchese – handmade meat-filled pasta

• Buccellato – a sweet bread laced with aniseed

• Local wines from Montecarlo di Lucca

Stay for an evening opera performance or enjoy a slow sunset walk with gelato in hand. Lucca is Tuscany in miniature: refined, romantic and rich in character.

Next Stop: Siena – Gothic Grandeur and Medieval Magic

Siena is a striking contrast to Lucca’s quiet elegance. A medieval powerhouse, the city is best known for the Palio di Siena, a bareback horse race that roars through Piazza del Campo twice a year. But beyond the festivities, Siena reveals itself as a cultural treasure trove, layered with art, architecture and deep tradition.

The train journey from Lucca or Florence is a scenic one, bringing you to the outskirts of the city, where transfers can take you to your central accommodation. 

Wander through Siena’s steep alleys and be sure to explore:

• Siena Cathedral – one of Italy’s most striking Gothic churches, with intricate marble floors and a Piccolomini Library painted by Pinturicchio

• Piazza del Campo – the heart of the city, ideal for people-watching with a coffee or Aperol Spritz

• Museo Civico – housing frescoes that depict the civic pride of medieval Siena

Siena’s cuisine is rustic and comforting. Savour dishes like:

• Pici cacio e pepe – hand-rolled pasta with pecorino and pepper

• Cinta Senese pork – from a local heritage breed

• Panforte – a rich spiced fruitcake originating from the city

Add a local wine tasting experience to your visit. Entire Travel Group offers curated day trips from Siena into the nearby Chianti region, where you can taste some of the world’s best reds at family-run vineyards.

Final Stop: Montepulciano – Wine Country with a View

Perched high on a ridge overlooking the Val d’Orcia, Montepulciano is a quintessential Tuscan hill town famous for its noble wine, Vino Nobile di Montepulciano. The journey here involves a short transfer from the nearby train station at Chiusi-Chianciano, easily arranged as part of your Tuscany train holiday package.

Arrive in Montepulciano and feel like you’ve stepped into a Renaissance painting. Stone buildings, winding lanes and panoramic views await at every turn. It’s the perfect final stop for a relaxed and indulgent stay.

Must-dos in Montepulciano include:

• A tour of underground wine cellars carved into the town’s volcanic rock

• Sampling Vino Nobile di Montepulciano, one of Italy’s oldest classified wines

• Strolling the Corso and pausing for panoramic views of the Tuscan countryside

Stay at a charming agriturismo or vineyard estate, where hospitality is warm and the pace is leisurely. Enjoy seasonal dishes like:

• Crostini neri – toasted bread with chicken liver pâté

• Pappardelle al cinghiale – pasta with wild boar ragu

• Local pecorino paired with honey or truffle

For a romantic touch, consider a scenic countryside walk or a picnic among the vines arranged by your hosts. Montepulciano is also a great base for exploring neighbouring gems like Pienza or Bagno Vignoni, both accessible via short guided day tours.

Travel Tips for Rail Travel in Tuscany

Rail passes: Italy’s regional train network is reliable, scenic and cost-effective. Booking tickets or regional rail passes in advance can help avoid queues and secure the best fares.

Luggage: Pack light to make it easier when navigating cobbled lanes and station steps. Many boutique stays offer porter services or can assist with luggage transfers between towns.

Timing: Aim to travel in spring (April to June) or early autumn (September to October) for pleasant weather, fewer crowds and the added charm of the wine harvest season.

Language: A little Italian goes a long way. Simple greetings like buongiorno or grazie are always appreciated and can lead to warmer interactions with locals.

Sustainability: Train travel is a more eco-friendly way to experience Tuscany, reducing your carbon footprint while supporting local communities along the way.

Why Choose a Tuscany Rail Holiday with Entire Travel Group?

Entire Travel Group’s Tuscany rail holidays are thoughtfully designed for independent travellers who appreciate flexibility without the stress of planning everything themselves. Their self-guided packages offer:

• Pre-arranged accommodation in boutique hotels or villas

• Rail passes or point-to-point tickets based on your route

• Cultural and culinary experiences, including walking tours and tastings

• Optional transfers, luggage support and local guides

Whether it’s your first time in Italy or your fifth, a curated rail holiday lets you experience Tuscany at its most authentic. With no car keys to worry about, you’re free to enjoy every glass of wine, every scenic walk and every story told by a local guide.

Ready to explore Tuscany by rail? Let Entire Travel Group craft a tailor-made itinerary through Italy’s hilltop towns, combining culture, cuisine and countryside views in one unforgettable journey.