Tours of Tuscany

Your questions about Tuscany tours, answered

Planning a trip always brings up questions – that’s why we’re here. Read on for answers to the ones we hear most often. Or check out our Italy travel guide for more practical advice.

Here’s some peace of mind upfront: when you choose us, you can Book With Confidence, knowing your payments are protected. Curious about the details? You’ll find them in our booking terms and FAQs.

1. Which cities and regions are covered in the tours?

On these Tuscany tours, you won’t just get to experience the country’s most famous wine region. For instance, you could combine Tuscany with not-to-be-missed cities like Rome and Venice.

During the Tuscan leg of your trip, you’ll stay in Florence and smaller towns in Tuscany or Umbria. Here are some of the places you can explore within Tuscany on these tours:

• Florence
• Pisa
• Siena
• Lucca
• Val d’Orcia
• Chianti
• Montepulciano
• Pienza
• Montalcino

Each tour page includes a detailed itinerary – check this out for inspiration or call one of our Italy experts to talk things through.

2. What do these Tuscany tours include?

It depends on the tour. But all of our Italy packages include carefully selected accommodation with breakfast, a personalised itinerary, and a detailed travel guide with insider tips. You’ll also get 24/7 support during your trip and insights from your travel expert in Rome.

If you opt for a self-drive tour, you’ll get a rental car from trusted partners with unlimited mileage, CDW insurance, and a second driver included. Some road trips also come with cooking classes, wine tastings and private airport transfers.

Or if you choose a small group tour, your package includes a professional English-speaking guide and transport in a minibus with your fellow guests. Groups are capped at 16 guests, and departures are guaranteed. Small group tours also come with experiences like pizza and gelato-making classes, wine tastings, and guided city tours.

See the “What’s included” tab on individual trips for a full list of inclusions.

3. What’s the difference between self-drive and guided tours?

On a self-drive tour, we hand you the keys. We plan the route, book the hotels, and prepare your insider guides – then you explore Italy at your own pace, stopping where you like, lingering as long as you want.

A guided small group tour is a different rhythm. You travel with a group of like-minded people (capped at 16), led by an experienced local guide who brings the history and culture to life. It’s ideal if you’d rather sit back and take it all in than focus on road signs.

You’ll get the same quality of accommodation and benefit from our Italy-based team. It’s really about how you’d prefer to experience Italy.

4. How many days do I need for a Tuscany tour?

You can visit Tuscany on Italy tours that range from 7 to 14 days. A week is enough to cover Tuscany, Umbria and Rome properly, including a stay in Florence. But if you want to add other destinations like Venice, we recommend our 10, 12 and 14-day options.

We can also extend your tour at key overnight stops. Just add extra nights when you book online, or mention it to your travel consultant.

5. When is the best time to visit Tuscany?

Our Tuscany tours run from April through October, with May, June and September being particularly good months to visit.

Spring brings wildflowers across Val d’Orcia and milder temperatures perfect for walking and city sightseeing. September means harvests in the vineyards – a brilliant time to travel if wine is your thing. Summer is the warmest and busiest time, so it pays to book ahead for popular restaurants and galleries.

Read our weather and climate guide and blog on the best time to visit Italy to learn more.

6. What Italian food should I try – and where?

This list could be endless, but here are a few recommendations to get you started:

• Rome: Cacio e pepe, carbonara, supplì (fried rice balls), and real gelato – not the stuff piled high in the touristy places
• Tuscany: Pici (hand-rolled pasta), bistecca Fiorentina (the steak), pecorino from Pienza, Brunello di Montalcino
• Florence: Lampredotto (tripe sandwich from a street stall – trust us), ribollita, and a Negroni in the Oltrarno district
• Orvieto and Umbria: Wild boar, dove, pigeon – unusual meats, yes, but genuinely worth trying

Check out our guide to Italian food to find out how to make culturally sustainable choices and get a more local, immersive experience.

7. Are cooking classes and wine tours included, or are they extra?

It depends on the itinerary you go for. Some of our tours include food and wine experiences, such as a pizza-and-gelato-making class in Rome, a pasta-making class in Florence, and a Chianti wine-and-food tour. Check the “What’s included” tab of the trip you’re interested in to see whether it comes with food and wine tasting experiences.

You can also add wine tastings, food-making classes, and other activities to your trip as optional extras.

8. Can I customise my itinerary?

Yes. In fact, we recommend it. Every tour can be adapted with extra nights and additional experiences. Take your pick from optional extras like a guided Colosseum tour, a visit to the Vatican Museums, and a wine tasting at the Casisano estate in Montalcino.

Want an extra night in Rome to visit the Vatican at your own pace? Done. Prefer more time in the Tuscan countryside rather than pushing straight to Florence? We can make that work. Just let us know when you’re booking, and your Rome-based travel expert will sort it out.

9. What should I pack for a trip to Italy?

If in doubt about what to wear in Italy, smart-casual is generally a good default. Particularly in the evenings, you’ll notice the locals often make an effort to dress smartly for their passeggiata (evening stroll). And it’s good to know that when visiting churches, you’ll often be required to cover your shoulders and knees.

For exploring the Tuscan countryside in spring or autumn, bring a light layer for evenings. Summer is warm and dry, so breathable fabrics and sunscreen are your best friends. Meanwhile, comfortable walking shoes are essential year-round – the cobbled streets of Siena and Florence are beautiful but unforgiving.

Check out our Italy packing guide for a detailed packing list and more advice on what to bring.