Tuscany Travel Guide: Things to Do, Wine Tours & Itineraries

You’ve been dreaming about this trip longer than you probably realize. The hills you’ve seen in a hundred photographs. The wine you’ve ordered at nice restaurants pretending you knew what you were doing. The life that somehow looks simpler and more beautiful from the window of a stone farmhouse.
Tuscany is the most visited region in Italy for a reason and not just by anyone. This is where people come for the trips that matter: honeymoons, anniversary celebrations, milestone birthdays, marriage proposals on a hilltop at sunset. It’s the place people choose when they want a Tuscany vacation to feel like a dream rather than a checklist. More Americans choose Tuscany for their honeymoon than any other destination in Europe, and those who come to visit wineries in Tuscany, join a Chianti wine tour from Florence, or spend a day trip from Florence into the Val d’Orcia tend to do the same thing: start planning the next trip to Tuscany before this one is over.
There is so much to do in Tuscany from Renaissance masterpieces in Florence to Chianti wine tour through the rolling hills of the Chianti countryside, from a 5 day Tuscany itinerary that hits the highlights to a slower 7 day Tuscany trip through hilltop towns and harvest-season vineyards. Knowing what to do in Tuscany, the best time to visit, how to get around without a car, and which wineries actually let you in without a booking that’s the kind of practical knowledge that separates a good Tuscany vacation from an extraordinary one. This Tuscany travel guide covers all of it.
Whether you’re a first-time visitor finally making “someday” happen, planning a Tuscany honeymoon, or simply chasing the best wine tour experience of your life this is everything you need to know before you go.

Getting Here: Rome or Florence?

Most flights from the US land in Rome. If yours does, don’t panic this is actually fine. The high-speed train from Rome to Florence takes 1 hour and 20 minutes, costs around €30–50, and runs constantly throughout the day. It’s one of the most pleasant train journeys in Europe: you board in a city, you step off in another one. No connection stress, no bags in overhead compartments on a bumpy road. Book on Trenitalia or Italo a few days in advance.
If you can fly directly into Florence (FLR) do it. It’s a tiny, easy airport, and you’re in the city centre in fifteen minutes. Budget airlines from other European cities use Pisa (PSA), which is an hour from Florence by regional train and equally painless.
The short version: fly into wherever is cheapest, and take the train to Florence. Tuscany begins the moment you step off.

Getting Around: The Thing Nobody Warns You About

Here is the honest truth that most travel sites dance around: Tuscany has almost no public transport worth speaking of outside the cities. The Chianti hills, the Val d’Orcia, Montalcino, Montepulciano, San Gimignano the places you came for are not on train lines. The buses that exist run on schedules that make sense only if you need to be in a specific village at 7:14am on a Tuesday.

So your options are:

Rent a car. The drives are genuinely spectacular, white gravel roads through vineyards, hairpin turns with views that make you pull over just to stand there. But, parking in historic centres is a nightmare, most medieval towns have ZTL zones (restricted traffic areas where cameras automatically fine tourists who drive in), and navigating narrow roads after wine tasting is, obviously, not ideal. If you rent, stay out of Florence and Siena with the car entirely.

Book a guided tour from Florence. This is what most people who’ve actually done it well will tell you they wish they’d done from the start. A good guide takes you to wineries that don’t receive walk-ins, knows which hilltop to be on at golden hour, and crucially does the driving while you taste. You’re not on a bus with forty strangers. You’re in a small group, with someone who grew up here, going places you genuinely couldn’t find on your own.

Our Tuscany day tours from Florence → keep groups small and the experience genuine. Worth looking at before you start piecing together an itinerary.

When to Go

Every season in Tuscany has a case to make. Here’s the honest breakdown:

April through June are close to perfect. Wildflowers everywhere, the hills are an almost aggressively beautiful green, temperatures are warm enough to eat outside but cool enough to walk. Crowds exist but haven’t reached their summer intensity. If you’re planning a honeymoon or special occasion trip and have flexibility, this is your window.

July and August full summer. Warm. But the long evenings are magical, the outdoor festivals are in full swing, and there’s an energy that cold months can’t replicate. Go early in the morning to any major site. Book everything weeks ahead.

September and October are arguably the most atmospheric months to be in wine country. The vendemmia the grape harvest is underway. You can smell it in the air around the wineries. The light goes golden and stays that way. Crowds thin. Prices drop slightly. This is the Tuscany of your imagination.

November through March: quiet, sometimes cold, occasionally extraordinary. Truffles are in season. You’ll have the Uffizi more or less to yourself. Some rural properties close, but the ones that stay open have a warmth and intimacy that summer can’t offer.

More detail in our Best Time to Visit Tuscany guide → including what’s actually open when, and how to read the weather.

Florence: Give It More Time Than You Think

A lot of first-timers treat Florence as a one-night stopover on the way to the countryside. This is a mistake. Florence is one of the most extraordinary cities on earth the Uffizi, Michelangelo’s David, the Duomo, the Oltrarno neighbourhood where Florentines actually live. Give it at minimum two full days. More is better.
We’re putting together a dedicated Florence travel guide, coming soon, that goes deep on everything the city has to offer. For now: book the Uffizi and the Accademia in advance, cross the Ponte Vecchio into Oltrarno, and get to Piazzale Michelangelo at sunset with a bottle of something.

Where to Stay in Florence

For a first visit, staying in Florence and doing day trips into the countryside is almost always the right call. You have the best restaurants, the best transport connections, and you’re not dependent on a car.

Best neighbourhoods:

Oltrarno: Local, characterful, walkable. Slightly quieter than the historic centre at night.

Santa Croce: Lively, close to everything, good mix of restaurants and bars.

Around the Duomo: Maximum convenience, maximum tourists. Fine for a short stay, can feel relentless.

Where to stay in Florence, our complete guide.

If you want to sleep in the vineyard rather than commute to it, keep reading we cover agriturismo options in each zone below.

The Places You Actually Came For

Chianti

The hills between Florence and Siena are what most people picture when they picture Tuscany. They’re not wrong this is the landscape of the paintings, the calendars, the Instagram posts that made you book the flights. And it’s real. It looks exactly like that.

The wine zone is called Chianti, and it’s one of Italy’s great appellations. The grape is Sangiovese earthy, bright with cherry and dried herbs, firm boned, made for food. At its best, it’s the kind of wine that makes you recalibrate what you thought you knew about red wine.

The villages worth lingering in: Greve in Chianti (the main market town, good for stocking up on bottles), Panzano , Radda in Chianti (small, perfectly preserved, excellent views), and Castellina in Chianti.

Everything you need to know about Chianti wine

Montalcino and Brunello

South of Siena, in the hills above the Val d’Orcia, sits a small medieval town called Montalcino. From here comes Brunello di Montalcino one of the most celebrated wines in the world, aged for years before release, built to last decades in the bottle.

Tasting Brunello at the source, from a producer who can tell you about the vintage while you’re looking at the vineyard it came from, is one of those experiences that quietly changes you. It’s not about being fancy. It’s about understanding what wine can actually be.

The town itself is easy to fall in love with a fortress with a wine bar inside it (this is real), panoramic views, and a pace that makes city life feel vaguely absurd.

Our full guide to Brunello di Montalcino

Montepulciano

Don’t confuse it with the supermarket wine of a similar name (that’s from a different region entirely, Abruzzo). Vino Nobile di Montepulciano is a serious, underrated wine Sangiovese again, more approachable than Brunello, extraordinary value for the quality.

The town is visually dramatic in a way that even experienced Italy travellers find surprising: a long ridge with a sweeping Renaissance piazza at the very top, wine cellars tunnelled into the volcanic rock beneath the streets, views in every direction. Walking uphill to reach it earns you the first glass.

Our full guide to Vino Nobile di Montepulciano

San Gimignano

Medieval skyscrapers. That’s basically what San Gimignano is fourteen stone towers still standing from the dozens that powerful families built to show off their wealth in the 13th century. It’s touristy (understatement) and extraordinary in equal measure.

The trick: arrive before 9am, or stay until the day trippers leave after 5pm. The town transforms. The wine here is Vernaccia di San Gimignano Tuscany’s only white DOCG, crisp and mineral, best drunk cold in the shade of the piazza with a view of the towers. Not a bad afternoon.

Our full guide to San Gimignano

The Val d’Orcia

The one that stops you mid-scroll. The lone cypress trees on pale hills, the farmhouses in impossible positions, the roads that disappear into golden light. The Val d’Orcia is a UNESCO World Heritage landscape and it earns it there’s nowhere else quite like it.

Pienza is a tiny Renaissance town built as a utopian experiment by a 15th-century pope and is now one of the most perfect small towns in Italy. Bagno Vignoni has a Renaissance thermal pool at its centre instead of a piazza which tells you something about priorities. Castiglione d’Orcia is the hilltop you want to photograph from.

This area requires a car or a tour. There is no other way in.

The Wines of Tuscany: What to Actually Expect in the Glass

You don’t need to be a wine expert to get a lot out of Tuscany’s wine regions. But knowing a little about what you’re tasting and why it tastes that way makes the whole experience click into place.

The backbone of Tuscan wine is Sangiovese, the great red grape of central Italy. It’s not the easiest grape to love at first sip it’s leaner than a Californian Cabernet, more acidic, less obviously fruity. But that’s exactly what makes it extraordinary with food. It’s built for the table.

Chianti Classico is your entry point and a great one. Expect flavours of sour cherry, dried herbs, a hint of leather, and firm tannins. Drink it with pasta, grilled meat, anything with tomato. The Gran Selezione tier is where it gets serious: single-vineyard wines aged longer, more concentrated, closer to Brunello territory. Price range at source: €15–25 for a good standard Chianti Classico, €40–80 for Gran Selezione.

Brunello di Montalcino is the heavyweight. More structured, more tannic, built to age for decades. A young Brunello (say, 5–8 years old) can feel a little austere grippy, tight, not immediately giving. An older one, properly cellared, is something else entirely: dried roses, tobacco, dark fruit, forest floor. If you’re tasting at a winery in Montalcino, ask if they have any older vintages open. Worth every cent. Price at source: €35–80 for a standard Brunello, €60–150+ for Riserva.

Vino Nobile di Montepulciano sits between the two, more approachable than Brunello, more serious than everyday Chianti. Excellent value. If you’re watching your budget but don’t want to compromise on quality, this is your wine. Price at source: €18–35.

Vernaccia di San Gimignano is the white crisp, dry, faintly almond on the finish. Refreshing on a hot day in a way that red wine simply isn’t. Drink it young and cold.

And then there are the Super Tuscans wines like Sassicaia and Ornellaia from the Bolgheri coast, made from Cabernet Sauvignon and Merlot rather than Sangiovese. They broke the Italian wine rulebook in the 1970s and 80s and are now among the most celebrated (and expensive) wines in the world. Not traditional Tuscany, but worth knowing about.

One practical note: rosso versions exist for both Brunello and Montepulciano , Rosso di Montalcino and Rosso di Montepulciano. Same grapes, same producers, shorter aging, lower price. A fantastic way to taste the terroir without the Brunello price tag.

Tuscany Itinerary: 5 Days or 7 Days?

5 Days in Tuscany

The right amount of time to get a genuine feel for Florence and hit two or three highlights in the countryside.

Day 1–2: Florence. Arrive, settle in, walk the city. Uffizi on day two book ahead.

Day 3: Chianti region. A full day in the wine hills.

Day 4: San Gimignano and Volterra. The towers in the morning before the crowds. Volterra an older, quieter, less visited Etruscan hilltop town in the afternoon. Completely different atmosphere.

Day 5: Val d’Orcia. Pienza for the morning (try the Pecorino cheese , it’s made here), then drive or tour through the cypress lined landscape to Montalcino for a Brunello tasting before heading back.

7 Days in Tuscany

With a week, you can breathe. Less rushing, more sitting somewhere beautiful with a glass of something good.

Day 1–2: Florence. Two proper days. Museums, Oltrarno, Piazzale Michelangelo at sunset.

Day 3: Chianti. Full immersion.

Day 4: Siena. One of the most beautiful medieval cities in Europe and criminally underrated. The Piazza del Campo, the Duomo, the narrow streets. Half day is possible; a full day is better.

Day 5: Montalcino and the Val d’Orcia. Brunello tasting in the morning, Pienza and the landscape in the afternoon. This is the day that ends with everyone quiet in the car on the way back, in the best possible way.

Day 6: Montepulciano. The dramatic ridge town, wine cellars under the streets, lunch with a view. Pair it with a stop in Cortona (yes, the Under the Tuscan Sun town) if you have time.

Day 7: Florence, slower. The neighbourhood you didn’t get to, a long lunch in Oltrarno. Leave at a human pace.

What Does a Tuscany Trip Actually Cost?

Tuscany has a reputation for being expensive, and it can be but it doesn’t have to be. Here’s an honest breakdown.

Getting around: Day tours from Florence typically run €160–280 per person for a full day including transport, guide, and wineries visit. Car rental starts around €60–80/day for a small car, plus fuel and parking (budget €10–20/day for parking).

Winery visits: A standard tasting is usually €25–40 per person. A cellar tour plus tasting is €45–55. A full wine and food pairing lunch at a winery, the experience worth splurging on runs €60–120 per person depending on the producer and the wines poured.

Restaurants: A proper trattoria lunch (two courses, wine, water) runs €25–40 per person. Dinner at a good restaurant in Florence, €50–80 per person with wine. A quick lunch panino, glass of local wine at a bar is €10–15 and often just as satisfying.

Museums: Uffizi tickets are €20–25 depending on the season. Accademia is €12–20. The Duomo complex in Florence is €20 for the combined ticket. Most smaller churches and municipal museums in Tuscany are €5–10 or free.

Coffee: Espresso at the bar is €1–1.50 almost everywhere. The moment you sit down at a table, the price doubles or triples. Stand at the bar like the locals do.

The honest overall picture: A well-planned week in Tuscany for two people Florence hotel, day tours, good restaurants, a few winery visits, museums runs roughly $4,000–6,000 all-in excluding flights. You can do it for less with more careful choices; you can easily spend more if you lean into the luxury end. The sweet spot is spending on experiences (the winery lunch, the guided tour) and being more relaxed about everything else.

Visiting Wineries: You Have to Book in Advance

This surprises almost everyone: you cannot simply show up at a Tuscan winery and expect to taste. Most of estates require advance bookings sometimes weeks ahead in high season. This isn’t pretension. These are working farms, often family-run, with limited space and staff. A booking tells them you’re serious. What they give you in return is often extraordinary: a walk through the cellar with the winemaker, barrel samples, wines not yet released, the kind of access you can’t buy in a wine shop.
Most visits offer:

Tasting only: Three to five wines, often with local cheese and charcuterie

Cellar tour + tasting: The full behind-the-scenes experience, worth it

Wine and food pairing: A seated lunch or dinner with matched wines frequently the best value and the most memorable meal of the trip

Book directly through the winery’s website, or through a tour operator who has existing relationships with producers who don’t accept individual walk-in bookings.

Where to Stay: Make Florence Your Base

For a first visit, Florence is almost always the right answer. Every major destination in Tuscany is reachable as a day trip, you’re surrounded by great restaurants and wine bars in the evening, and you don’t need a car for any of it.

If you’ve been before and want full immersion in the countryside, agriturismo stays on working wine estates are magical, but they require a car and a different kind of trip. For most first timers, Florence by night and Tuscany by day is the formula that works.

What to Wear (Seriously, Read This)

Churches are everywhere in Tuscany, and they all require covered shoulders and knees. This applies to you regardless of gender, regardless of how hot it is, regardless of how casual the church looks from outside. A lightweight scarf or a layer in your bag solves this completely. Don’t be the person turned away at the door of a 13th-century chapel because of a sleeveless top.

Your shoes matter more than your outfit. Every Tuscan historic centre is cobblestone. Every agriturismo involves some uneven ground. Hills are involved everywhere. Stylish flat shoes or quality sneakers: yes. Flip flops by midday: you will regret this. High heels: only if you’re dining somewhere and not moving much.

Layer everything in spring and autumn. Morning in the hills can be cold even when the afternoon is warm. A light jacket takes up almost no space and saves the day regularly.

For dinners at nicer restaurants: smart casual. You don’t need a jacket. But visibly beach casual tank tops, athletic shorts is out of place in the evening. Italians dress for dinner. It’s worth meeting them halfway.

Shipping Wine Home

Yes, you can bring wine back. Here’s how to actually do it.

The easiest option: check a bag specifically for wine. Purpose-made wine travel bags (available at most enotece and wine shops in Florence) cushion bottles properly. Three bottles per checked bag is a reasonable maximum. Wrap each one in clothes for extra padding.

Shipping from Italy: Most larger wine shops and enoteche in tourist areas offer international shipping, and many wineries ship directly. This is the right call for valuable bottles or larger quantities.

US customs: You get four litres duty free per person ( 5 bottle) to put in the luggage. Anything beyond that is technically dutiable, though amounts for personal use are rarely scrutinised. Each US state also has its own laws on receiving wine shipments some states freely accept direct to consumer international shipping, others don’t. Worth checking your state’s rules before having a winery ship to your home address.

For the UK, Australia, and Canada: Generally more straightforward, though import duties apply above your personal allowance. A reputable Florentine wine merchant can handle the paperwork.

The wine you taste at a small estate in Chianti probably isn’t exported. Which is either an excellent reason to ship a case home, or an excellent reason to come back.

Tracing Your Italian Roots

If your family has Italian roots, Tuscany might hold more than just beautiful landscapes. Italy has some of the best-preserved parish records in the world baptisms, marriages, deaths going back to the 16th century. The Antenati portal has millions of records digitised and free to search. We’ve had clients find their great great grandparent’s baptismal record in a church a few kilometres from where they were standing. It changes the trip.

A Few Last Things

Tipping: Not mandatory in Italy the way it is in the US, but leaving a few euros after a good meal is appreciated. In bars, leaving small change is normal. For an exceptional tour guide, a tip is a genuinely warm gesture.

Afternoon closings: Many smaller businesses and museums close from roughly 1pm to 3:30pm. Build this into your plans rather than fighting it, it’s an excellent excuse for a long lunch.

The coffee: Order at the bar standing up. Espresso, macchiato, or cappuccino (only at breakfast ordering cappuccino after a meal is the one thing that will make an Italian look at you with genuine pity). The ritual matters.

Say buongiorno. Every time you enter a shop, a restaurant, a winery. Every single time. It costs nothing and changes everything about how you’re received.