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The Complete Tuscany Trip Itinerary

ByJulie and Andrew

What To See In 5, 7 or 10 Days

Even after more than a decade of exploring the region, we still get a thrill at discovering hilltop villages, exceptional eateries, and fantastic wineries of Tuscany. And now that we own our own little piece of Chianti, we get to be more spontaneous with our adventures, but it still requires some planning.

The key to an unforgettable holiday lies in a well thought-out itinerary. Using Florence as the central hub, we’ve designed 3 flexible itineraries to help you make the most of your time—whether you’re staying for 5, 7, or 10 days, or longer.

From iconic cities and landmarks to hidden gems, these itineraries and day trips from Florence, combine sightseeing, relaxation, and a taste of Tuscany’s rich history, culture, and cuisine. With our Tuscany trip itinerary, you’ll be perfectly placed to explore the region’s highlights, from rolling wheat fields and vineyards to cypress-lined white roads that lead to charming country villas.

Tuscany Trip Itinerary
⏭️ short on time? jump ahead.

8 Steps To Planning Your Tuscany Trip Itinerary

Planning ahead is the secret to fully enjoying Tuscany’s stunning landscapes and historic cities and towns. After a number of years of travelling, we use the following 8-steps to make the most of all of our trips to Italy.

Start by jotting down your ‘must-see’ destinations—those places that excite you most when you think of Tuscany.

In Florence, it might be the Uffizi Gallery or catching a sunset from Piazzale Michelangelo. Maybe Siena’s Piazza del Campo or the vineyards of Chianti are on your list. Don’t forget the rolling hills of the Val d’Orcia, with towns like Pienza, or the dramatic Crete Senesi with its striking landscapes.

Whether it’s iconic landmarks or hidden villages, this is your list—make it uniquely yours.

With your list in hand, start mapping out your journey. Aim to strike a balance between must-see landmarks and quieter, lesser-known spots to create a mix of excitement and relaxation. For example, after a day exploring the city of Florence, consider unwinding with wander through the streets of Lucca or travelling to the Chianti Classico region for a spot of wine tasting.

Be mindful of travel times—Tuscany’s winding roads are beautiful but can be slow, so plan stops that are geographically close to avoid long drives. Build in time to wander and enjoy unexpected discoveries, whether it’s a gelato or Aperol spritz in a village piazza or a spontaneous walk along a white road lined by cypress pines.

Most importantly, resist the urge to overpack your schedule—Tuscany is best enjoyed at a slower pace.

One of the first decisions to make for your Tuscany trip is how you’ll get around.

Will you rent a car to explore the scenic countryside and charming hilltop villages, or rely on public transport to travel between major cities like Florence or Siena? Will you join an organised tour or hire a car service for the day? Each option has its pros and cons.

A car provides flexibility and the chance to uncover hidden gems off the beaten path, but keep in mind parking can be challenging in city centres, and ZTL zones (restricted traffic areas) are strictly enforced.

Now that we stay in Italy for up to 3 months at a time, we lease a car for the duration of our stay. It’s really convenient and price wise, very economical for stays of 21 days or more.

On the other hand, trains and buses are budget-friendly and convenient for connecting larger towns, but schedules may limit your spontaneity.

Researching your options well in advance, will help you to avoid those last-minute scrambles and decide whether or not, you actually need a car. Consider your itinerary, travel style, and comfort level with driving in Italy.

Once your route is set, it’s time to think about accommodation.

Tuscany offers a wide variety of options to suit every traveller. From rustic farmhouses nestled amongst rolling vineyards to charming boutique B&Bs in historic towns, and even luxury hotels with breathtaking views, there’s something to match your needs.

Booking early is especially important during peak season, when popular areas such as Florence, Siena, and the Chianti region see high demand. By reserving ahead, you’ll have a better chance of securing your ideal spot and can enjoy peace of mind as your trip approaches.

Consider the location carefully to minimise travel time between stops, and don’t be afraid to mix it up—spend a few nights in the countryside and others in a lively town to experience the best of Tuscany.

Florence offers an incredible range of accommodation to suit every traveller’s style and budget. From cosy hostels to elegant boutique hotels and opulent 5-star luxury stays, there’s something for everyone. Whether you’re looking for a romantic hideaway, family-friendly comfort, or a spot close to the action, Florence has it all.

🏨 We recently spent two nights at the Hotel Palazzo Guadagni, a fabulous boutique hotel located in the Santo Spirito neighbourhood. With frescoed ceilings, antique furniture, and jaw-dropping views of the city, this hotel oozes history and charm. The rooms are spacious and full of character. It feels like you’ve stepped back in time—but with all the modern comforts.

The Loggia, a stunning rooftop terrace is a definite bonus. It’s the perfect spot to enjoy a morning coffee or unwind with an evening drink, with panoramic views over Florence and surrounding hills.

The hotel is a short stroll to Ponte Vecchio, Pitti Palace, and Boboli Gardens. Plus, you’re surrounded by artisan shops, as well as great local wine bars and eateries, including Il Santino Gastronomia, another one of our favourites, when we are in Florence.

If it’s BnB style accommodation you are looking for, try Antica Dimora De’ Benci. With its BIG rooms, comfy beds, ensuite bathroom, all the ‘mod cons’ and fabulous staff, we definitely recommend this one. They also serve a great buffet breakfast! Very well located within an easy walk to all of Florence’s major attractions.

Tuscany is alive with festivals, markets, and cultural events that showcase its rich traditions. From Siena’s iconic Palio horse race in July and August to the wine festivals scattered across Chianti, there’s always something to immerse you in local culture.

If you’re a food enthusiasts, you can enjoy the truffle festivals in San Miniato each autumn or explore the vibrant Sagre (food festivals) celebrating seasonal specialties in smaller towns. For art and music lovers, Florence’s Maggio Musicale Fiorentino, an annual opera and classical music festival, is a highlight.

To make the most of your visit, check local event calendars and plan around dates that interest you. These authentic celebrations add a special touch to your journey through Tuscany.

Tuscany’s official tourism website is also a great source of information.

Tuscany’s seasons will play a significant role in shaping your travel experience, so it’s essential to plan around the weather.

Spring (March to May): A delightful time to visit, with mild temperatures, blooming landscapes, and fewer crowds. Perfect for outdoor activities like hiking or exploring hilltop towns.

Summer (June to August): Long, sunny days make it ideal for relaxing on Tuscany’s beaches or dining al fresco. However, expect higher temperatures, especially inland, and busy crowds at popular spots.

Autumn (September to November): This season is perfect for enjoying harvest festivals and truffle hunting. The cooler weather makes it ideal for outdoor exploration, while the countryside’s changing colours provide stunning backdrops for your travels.

Winter (December to February): A quieter time of year with crisp, clear days and a festive atmosphere. Holiday markets and cultural attractions offer a more relaxed experience without the usual crowds.

When planning your Tuscan itinerary, less is often more. While it’s tempting to squeeze in as many sights and activities as possible, Tuscany is best enjoyed at a slower pace. The region’s charm lies in its relaxed rhythm, from sipping a glass of Chianti at a sun-drenched vineyard to wandering through the cobbled streets of a quiet village like Pienza or San Gimignano.

Allow yourself time to savour these moments without the pressure of rushing between destinations. Don’t forget to include some downtime—whether it’s a leisurely lunch at a family-run trattoria, a spontaneous stop for gelato, or a rejuvenating soak in one of Tuscany’s natural thermal spas.

By building in time to unwind and truly immerse yourself in the beauty of Tuscany, you’ll leave with memories that are as rich and relaxing as the region itself.

Creating a budget for your trip is an important step in planning a stress-free Tuscan getaway. Start by estimating costs for the essentials: transportation, accommodation, food, and activities. If you’re renting a car, factor in fuel, tolls, and parking fees, especially in cities with limited access. For accommodation, decide if you prefer charming agriturismos, boutique hotels, or luxury stays, as prices can vary widely.

Food costs can range from affordable trattorias to high-end dining, so allocate funds based on your preferences. And don’t forget activities like guided tours, museum tickets, or vineyard visits.

Be sure to include some wiggle room for spontaneous indulgences. Whether it’s a memorable dinner at a Michelin-starred restaurant, a private wine tour in Chianti, or a unique handcrafted souvenir, those splurges can make your trip extra special. Setting your budget upfront will help guide your choices and keep spending in check.

How To Get To Florence

Florence is very well-connected to both Rome and Milan, making it the perfect starting point for exploring wider Tuscany adventure.

Here’s a breakdown of your best options for getting to Florence:

  • By Rail: High-speed trains are the best way to reach Florence. Trains from Rome or Milan to Florence take about 1.5–3 hours and cost between €20–€70 depending on how early you book and the class of service. Trains are fast, reliable, and drop you directly at Santa Maria Novella, Florence’s central station, which is conveniently located in the city centre.

  • By Bus: A more budget-friendly option, but slower and less frequent. Buses take approximately 4–5 hours from both Rome and Milan, with ticket prices ranging from €15–€30. Keep in mind that bus stations are often located farther from the city centre, which may add time, effort and money to your journey.

  • By Car: Driving from Rome or Milan takes 3–4 hours, traffic depending. Car rentals start at €40–€80 daily, excluding fuel, tolls, and parking. Driving and parking in Florence is tricky and costly & parking near the city centre is scarce. There are pros and cons to having a car. Renting a car is certainly an advantage for exploring Tuscany’s countryside, but they can be more of a hinderance once you’ve reached Florence.

💡 TRAVEL TIP: If you are driving, avoid the stress of Florence’s city traffic and expensive parking by using the Villa Costanza Park & Ride. Located just off the A1 motorway, this secure car park costs just €7 per day and offers easy access to the city. From Villa Costanza, we hop on the T1 tram, which runs every 6–8 minutes. It drops us at Santa Maria Novella Station in about 20 minutes. It’s hassle-free, budget-friendly (€1,50 each way) and a perfect option for both day trips or longer stays.

  • By Air: Flying into Florence’s Amerigo Vespucci Airport is an option, particularly if you’re starting in Milan, but flights are often more expensive than rail or bus. From the airport, it’s a 20-minute taxi ride (€25 to €30 + €3 airport surcharge) or a 20-minute tram ride (€1.70 each way) to the city centre.

Rail travel is definitely the fastest, most comfortable, and eco-friendly way to reach Florence. With frequent departures, affordable pricing (especially with advance booking), and a hassle-free arrival at the city centre, it’s hard to beat the convenience of travelling by train.

Tuscany Trip Itinerary

Destinations For 5, 7, or 10 Day Itineraries

We’ve identified 10 destinations with activities and suggestions to mix and match based on your taste. To give you even more flexibility, we’ve included a couple of ‘swap out’ destinations if you have extra time or want to change things up. This way, you can tailor your itinerary to suit your interests and schedule.

Next, we’ve outlined our suggestions for 5, 7, and 10-day itineraries in Tuscany, each offering a balance of art and culture, scenic landscapes, and moments to relax. Whether you want to immerse yourself in Tuscany’s art and history, enjoy its renowned food and wine, or simply take in the stunning views, these itineraries are designed to help you craft a well-rounded Tuscan experience.

  • Highlights: Uffizi Gallery, Ponte Vecchio, and the Duomo. 
  • Why It’s a Must: Florence is the cultural heart of Tuscany, bursting with Renaissance art, architecture, and history. Explore the masterpieces of Michelangelo, Botticelli, and Da Vinci all in one day.
  • How To Get There: Florence is easily accessible by train, car, or plane. The Santa Maria Novella train station is a central hub for travellers. 
  • Travel Tip: Book museum tickets in advance to avoid long queues, especially at the Uffizi and Accademia. 
  • Optional Add-On: End your day with a sunset climb up Piazzale Michelangelo or one of Florence’s rooftop bars for panoramic views of the city.
  • Highlights: Piazza del Campo, Siena Cathedral, and San Domenico Church.
  • Why It’s a Must: Siena offers an authentic step back in time with its well-preserved medieval architecture and traditions like the Palio horse race. 
  • How To Get There: From Florence, Siena is about 1.5 hours by bus or car. The bus drops you close to the city centre, while cars need to park outside the historic zone.
  • Travel Tip: Use the San Francesco car park, which costs around €2/hour and is close to escalators leading to the centre. 
  • Optional Add-On: Visit the Museo Civico for a closer look at the city’s history and art.
  • Highlights: Wine tastings at local vineyards, charming villages like Radda, Castellina and Gaiole in Chianti.
  • Why It’s a Must: Chianti’s rolling hills and renowned wineries make it a paradise for wine enthusiasts and those seeking scenic beauty. Discover the legend of the Black Rooster and the history of the Chianti Classico region.
  • How To Get There: Drive from Florence or Siena; the region is best explored by car for flexibility.
  • Travel Tip: Book tastings in advance, especially during the high season.
  • Optional Add-On: Take a cooking class that pairs wine with Tuscan dishes.
  • Highlights: Gelato from Gelateria Dondoli, Torre Grossa climb, and artisan shops.
  • Why It’s a Must: San Gimignano’s medieval skyline, with its iconic towers, offers one of the most picturesque settings in Tuscany. 
  • How To Get There: It’s a 60 minute from Florence. but note that the parking outside the town can be limited. You can join a guided tour or catch a bus or train from Santa Maria Novella. The journey takes between 80min – 120min, and you will need to change to another bus at Poggibonsi.
  • Travel Tip: Arrive early to beat the crowds and enjoy quieter streets. 
  • Optional Add-On: Visit the Museo della Tortura for a quirky look at medieval history.
  • Highlights: Pienza, Montepulciano, Monticchiello, San Quirico d’Orcia, Bagno Vignoni and Montalcino.
  • Why It’s a Must: The Val d’Orcia’s rolling hills, dotted with cypress trees and charming villages, is quintessential Tuscany.
  • How To Get There: To see the best of this region, renting a car or joining a guided tour is the way to go. It’s a 1.5 hour drive from Florence via the motorway. The scenic SP146 road will take you longer, but you’ll be rewarded with amazing photo opportunities.
  • Travel Tip: Wear comfortable shoes—walking the cobbled streets of Pienza and Montepulciano, are best enjoyed without sore feet!
  • Optional Add-On: Enjoy a tasting of Brunello di Montalcino wine, coupled with locally made pecorino cheese.
  • Highlights: Leaning Tower of Pisa and Lucca’s city walls.
  • Why It’s a Must: Pisa is home to one of the world’s most famous landmarks, while Lucca offers a more relaxed vibe with its charming historic centre.
  • How To Get There: Both cities are easily accessible by train from Florence or by car (about 1 hour).
  • Travel Tip: Combine both cities in one day by visiting Pisa in the morning and Lucca in the afternoon.
  • Optional Add-On: Rent a bike and cycle along Lucca’s medieval walls.
  • Highlights: Arezzo Cathedral, the Piazza Grande, and speciality shopping.
  • Why It’s a Must: Arezzo is less crowded than other Tuscan cities and offers a mix of history, art, and local charm.
  • How To Get There: Take a train from Florence (about 1 hour) or drive.
  • Travel Tip: Plan your visit during the renowned Fiera Antiquaria, an antique market held on the first weekend of each month. It stretches through the streets and laneways of the historic centre, attracting vintage enthusiasts, collectors, and curious ‘window shoppers’ from all over Italy.
  • Optional Add-On: Visit the Basilica of San Francesco to see Piero della Francesca’s frescoes.
  • Food Recommendations: Bulli & Balene – Spritz e Cicchetti and Rabbit Rabbit Bistro.
  • Highlights: Piazza della Repubblica, Etruscan Museum, and hillside views.
  • Why It’s a Must: Cortona’s steep streets and gorgeous views over the Val di Chiana. The town was made famous by the book and film ‘Under the Tuscan Sun.’
  • How To Get There: Drive or take a train from Florence to Camucia-Cortona station (approximately 75min). From the station, it’s a 2.1km (1.3mile) walk to Cortona. There’s also the option of a bus (10min) or taxi (5min).
  • Travel Tip: Wear comfortable shoes for navigating Cortona’s hilly streets.
  • Optional Add-On: Stop at Lake Trasimeno for a relaxing lakeside break.
  • Highlights: Livorno’s historical architecture, including the Mercato Centrale and Terrazza Mascagni, a chequered walkway by the sea. Being a coastal port, there are plenty of seafood restaurants to choose from.
  • Why It’s a Must: Livorno offers a refreshing coastal escape and some of the best seafood in Tuscany.
  • How To Get There: Take a train from Florence (1.5 hours) or drive.
  • Travel Tip: Visit during lunchtime to enjoy fresh seafood at a local trattoria.
  • Optional Add-On: Spend the day at the beach in Castiglioncello, just south of Livorno. Known for its rocky coves and crystal-clear waters, it’s perfect for a relaxing day of swimming, sunbathing, or snorkelling. Take a regional train from Livorno Centrale to Castiglioncello Station (15-20min) or it’s a 20km drive (30 min). You’ll need to arrive early in summer to snag a spot. And a park!

Fiesole

  • Highlights: Roman Theatre, Etruscan ruins, and panoramic Florence views.
  • Why It’s a Must: Fiesole’s peaceful atmosphere and stunning vistas make it the perfect way to end your trip. Leonardo da Vinci reportedly tested his flying machines at Monte Ceceri, a 1 to 1.5 km ( (0.6 to 0.9 miles) from Fiesole, depending on the trail you take. Look for the signposts in Fiesole’s main square, the Piazza Mino.
  • How To Get There: Catch the ATAF Bus #7 from Santa Maria Novella to Fiesole (about 20 min) or it’s a 15-20min drive.
  • Travel Tip: Time your visit for late afternoon to enjoy a stunning sunset over Florence.
  • Optional Add-On: Have dinner at a hillside trattoria with views of the city.

Hills of Florence

  • Highlights: The Piazzale Michelangelo, the Giardino delle Rose and the Basilica of San Miniato al Monte.
  • Why It’s A Must: Piazzale Michelangelo is one of Florence’s most iconic viewpoints, with panoramic views of the city, including the Duomo, Palazzo Vecchio, Arno River and Ponte Vecchio.
  • How To Get There: Return to Florence by ATAF Bus #7, getting off at Stazione Nazionale. Then walk to Piazzale Michelangelo. It’s just under 3km, whether you go via the centro storico or choose the route which takes you along the banks of the river.
  • Travel Tip: If you’ve achieved your step count for the day, you can catch a bus from Piazzale Michelangelo to Florence’s centro storico. The 2 options are:
    • ATAF Bus #12 runs a circular route and stops at key locations near the city centre, including Santa Maria Novella train station.
    • ATAF Bus #13 offers another scenic option, also connecting Piazzale Michelangelo with central Florence.
  • Optional Add-On: If you’re up for a little more exercise, continue climbing to the nearby Basilica of San Miniato al Monte, one of Florence’s oldest Romanesque churches. The peaceful atmosphere and even higher views of Florence make it worth the effort.

Vineyards at Brolio
Tuscany Trip Itinerary

Two Optional Swap Out Days (Without A Car)

If you would like to mix things up or add additional days to your Tuscany trip itinerary, here are a couple of ideas for the best day trips from Florence, without the need for a car.

Take a short train ride to Pistoia, a hidden gem packed with history and charm, or head to Prato to soak up its artistic vibe and fascinating past.

Both spots are easy to reach by public transport and offer a perfect mix of culture, history, and stunning scenery!

  • History and Highlights: Often overshadowed by Florence, this charming city has its own unique appeal and plenty of surprises. Known for its rich textile history, it was a medieval hub of fabric production and trade. Later, Prato flourished during the Renaissance, attracting artists like Donatello and Filippo Lippi, whose works can be admired here. Prato offers a mix of fascinating history, vibrant culture, and delicious culinary traditions, such as cantucci biscuits. From its well-preserved city walls to its impressive art and contemporary museums, this is a destination that deserves a spot on your Tuscany itinerary.
  • How to Get There: Take a train from Florence Santa Maria Novella to Prato Centrale. Trains run frequently, and the journey takes around 25 minutes, making this an easy trip.
  • Things To Do:
    • Prato Cathedral: Admire its elegant façade and step inside to view the stunning frescoes by Fra Filippo Lippi.
    • Emperor’s Castle (Castello dell’Imperatore): Wander the grounds of this 13th-century fortress built by Frederick II. The castle offers a glimpse into Prato’s medieval past.
    • Piazza del Comune: Stroll through this lively square, the heart of the city, where you can enjoy the local atmosphere.
    • Textile Museum (Museo del Tessuto): This fascinating museum, showcases Prato’s history as a textile production hub. Exhibits include historical garments, fabrics, and modern innovations in fashion.
    • Visit the Santa Maria delle Carceri Basilica, a beautiful Renaissance church, designed by Giuliano da Sangallo.
    • Walk the City Walls. Prato’s medieval walls are among the best-preserved in Tuscany. The leisurely walk along them provides unique views of the city and its surroundings.
    • If you’re a foodie (and let’s face it, we’ve all got to eat!):
      • Try the Mortadella di Prato, a local delicacy that’s unlike the mortadella you might know. Prato’s version is infused with spices and alchermes (a red Italian liqueur) for a distinctive flavour.
      • Take a coffee break at Piazza Mercatale, Prato’s historic square, which is one of the largest in Tuscany. It’s a great spot to enjoy a coffee or gelato and watch the world go by.
      • Visit the Biscottificio Mattei, Parato’s iconic bakery, founded in 1858, and try the city’s famous cantucci straight from the source.
  • Getting There: Take a direct train from Florence’s Santa Maria Novella station to Pistoia (about 40 minutes).
  • Highlights:
    • Piazza del Duomo: Visit Pistoia Cathedral with its stunning bell tower and Baptistery, a masterpiece of Gothic-Romanesque architecture.
    • Underground Pistoia: Explore the city’s hidden past through the subterranean passages of Ospedale del Ceppo.
    • Local Flavours: Wander the charming streets and enjoy authentic Tuscan cuisine at one of the many trattorias.
    • Market Vibes: On Wednesdays and Saturdays, browse the bustling markets for local produce and goods.

Our 5 Day Tuscany Trip Itinerary

Our 5-Day itinerary reflects how we like to enjoy Tuscany—a mix of iconic landmarks and the quiet charm of the countryside. It’s designed to offer a bit of both: the energy of city life and the relaxed pace of rural escapes.

Over these 5 days, you’ll discover Tuscany’s variety, from its art and history to its wine and landscapes. With each destination just a short distance away, you’ll spend less time travelling and more time enjoying what Tuscany has to offer.

Day 1: Florence: Florence is Tuscany’s cultural heart. Explore iconic landmarks like the Duomo, Uffizi Gallery, and Ponte Vecchio. Start your trip with the Renaissance charm this city embodies.

Day 2: Siena and/or San Gimignano: Siena’s Piazza del Campo and medieval streets offer a unique contrast to Florence. San Gimignano’s towers and artisanal shops add a picturesque countryside vibe.

Tuscany Trip Itinerary

Day 3: Chianti Wine Country: Experience Tuscany’s quintessential rolling vineyards and indulge in wine tastings paired with local delicacies. Perfect for relaxation and immersion in rural beauty.

Day 4: Val d’Orcia (Pienza & Montepulciano): Known for its postcard-perfect landscapes, Val d’Orcia showcases Tuscany’s serene beauty. Pienza offers pecorino cheese and stunning views, while Montepulciano features excellent wines.

Day 5: Lucca and/or Pisa: Lucca’s well-preserved walls and charming streets provide a serene end to the trip, while Pisa’s iconic Leaning Tower is definitely worth seeing. Both cities are compact and easily explored in a day, as long as you make an early start from Florence.

Our 7-Day Tuscany Trip Itinerary

With extra time in Florence and the Val d’Orcia, you’ll have plenty of opportunities to soak up even more of the region’s rich art, history, and wine culture.

This itinerary brings together everything we love about Tuscany—stunning landscapes, incredible food, and a sense of timeless charm. The thoughtfully planned route keeps things simple, so you spend less time backtracking and more time enjoying each destination at your own pace.

Day 1-2: Florence

  • With extra time, explore Florence in more depth. Visit major landmarks like the Duomo, Uffizi, and Accademia Gallery, and enjoy a leisurely walk through Oltrarno for artisan workshops and authentic dining.

Day 3: Siena and San Gimignano

  • Siena’s Gothic charm and San Gimignano’s medieval skyline showcase Tuscany’s rich history and architecture. Both are close enough to fit into a day while still feeling unrushed.

Day 4: Chianti Wine Region

  • Dedicate a full day to wine tastings, vineyard tours, and soaking in the scenic countryside. Pair this with visits to quaint towns like Dedicate a full day to wine tastings, vineyard tours, and soaking in the scenic countryside. Pair this with visits to quaint towns like Panzano, Castellina or Radda in Chianti..
Tuscany Trip Itinerary - Chianti

Day 5: Val d’Orcia (Pienza, Montepulciano & Montalcino)

  • Val d’Orcia’s rolling hills, iconic cypress-lined roads, and culinary highlights make this a quintessential Tuscan experience. Pienza offers pecorino cheese, Montepulciano is famed for Vino Nobile, and Montalcino is home to Brunello.

Day 6: Lucca and Pisa

  • Explore Lucca’s bike-friendly walls and charming streets in the morning, followed by Pisa’s Leaning Tower and Piazza dei Miracoli in the afternoon. Both are compact, so you can see highlights without feeling rushed.

Day 7: Cortona or Arezzo

  • End the trip with a visit to a smaller, less-touristy town. Cortona offers hilltop views and an artistic vibe, while Arezzo is rich in art and antiques, giving you a taste of Tuscany’s quieter side.
Complete Tuscany Trip Itinerary - Antica Bottega Arezzo
Complete Tuscany Trip Itinerary - Arezzo Street at Christmas

Our 10-Day Tuscany Trip Itinerary

This well-paced 10-day itinerary lets you fully embrace the spirit of Tuscany without feeling rushed.

With two days in Florence and the Val d’Orcia, plus the flexibility to explore the Tuscan coast, it caters to a variety of interests. Ample time at each stop allows you to savour Tuscany’s highlights and immerse yourself in its unforgettable atmosphere.

Day 1-2: Florence

  • With more time, explore Florence’s key sites and hidden gems. Visit the Duomo, Uffizi Gallery, and Boboli Gardens. Take a day to enjoy quieter neighbourhoods like Oltrarno or a sunset at Piazzale Michelangelo.

Day 3: Fiesole and Florence Hills

  • Just outside Florence, Fiesole offers ancient Roman ruins, hilltop views, and a peaceful escape. It’s a relaxed way to enjoy Florence’s surrounding countryside.

Day 4: Siena and San Gimignano

  • Siena’s Gothic architecture and San Gimignano’s medieval towers are must-see cultural icons, perfect for a day trip without feeling rushed.

Day 5: Chianti Wine Region

  • Spend the day visiting wineries and indulging in wine tastings, surrounded by picturesque rolling hills. Combine this with visits to charming towns like Radda, Castellina or Gaiole in Chianti.

Day 6-7: Val d’Orcia (Pienza, Montepulciano & Montalcino)

  • Dedicate two days to fully experience Val d’Orcia’s beauty. Explore Pienza’s streets and pecorino cheese shops, Montepulciano’s wine cellars, and Montalcino’s Brunello wines while enjoying leisurely drives through iconic landscapes.

Day 8: Lucca and Pisa

  • Spend the morning cycling or walking Lucca’s walls, then visit Pisa for the Leaning Tower and Piazza dei Miracoli. With extra time, explore Pisa’s less touristy areas to get a view of the more authentic Tuscan life.
Complete Tuscany Trip Itinerary - Leaning Tower of Pisa
Complete Tuscany Trip Itinerary - Piazza dei Miracoli:

Day 9: Cortona or Arezzo

  • Explore one of these charming towns for a quieter, more authentic Tuscan experience. Cortona offers breathtaking views and artistic flair, while Arezzo features stunning churches and a vibrant antique market (if timed right).

Day 10: Livorno

  • For a unique finish, visit Livorno for fresh seafood and views along the Mediterranean.

Frequently Asked Questions

From the best times to visit, ideal trip lengths to transportation options and must-see destinations, we answer some of the most common questions to help you make the most of your Tuscan getaway.

For a complete experience, we recommend that you devote at least 10 days to your stay in Tuscany, if you can. This will give you ample time to visit multiple cities, explore the countryside, and discover hidden gems. It also allows you to travel at a more relaxed pace, where we can truly enjoy the beauty and culture of the region.

We find spring (April to June) and autumn (September to October) are the best times to visit. The weather is pleasant, and the crowds are smaller. During these seasons, the landscapes are especially beautiful, and you can enjoy local festivals and events with less hustle and bustle.

For first-timers, the city of Florence for its iconic art and architecture and Siena for its historic centre are definite must sees. Be sure to spend a day in the Tuscan countryside, with a day in Chianti hills and vineyards. Even if you aren’t a lover of wine, the region of Chianti is spectacular! We are definitely a little bit biased.

Tuscany has something for every type of traveller, whether you’re drawn to its art and history, culinary delights, or natural beauty. Here are some of the highlights:
Florence: Explore the Uffizi Gallery, admire Michelangelo’s David at the Accademia, and take in city views from Piazzale Michelangelo.
Siena: Walk through the stunning Piazza del Campo, climb the Torre del Mangia, and visit the Duomo with its intricate façade.
Pisa: Stroll through the Piazza dei Miracoli and see the iconic Leaning Tower and nearby cathedral.
Medieval Towns: Explore San Gimignano, known for its towers, and Volterra, rich in Etruscan history.
Wine Tasting: Visit vineyards and enjoy tastings of Chianti Classico wines paired with local cuisine.
Truffle Hunting: Join a guided truffle hunt in areas like San Miniato or the Crete Senesi during autumn.
Tuscan Cuisine: Enjoy ribollita, bistecca alla fiorentina, and freshly made pasta dishes.
Hike or Cycle: Drive or bike through the rolling hills, visiting towns like Pienza, Montepulciano, Montalcino, the Apennine Mountains or Florence’s hills.
Relax on the Coast: Visit the beaches of the Maremma or the island of Elba for stunning seaside views.
Local Festivals: Witness the Palio horse race in Siena or enjoy harvest and wine festivals across the region.
Visit Thermal Spas: Soak in the natural hot springs of Bagno Vignoni or Saturnia.

Getting to the Cinque Terre from Florence is relatively straightforward, however be prepared for a long day.

The options are by car (90min), train (2.5hrs), hire a driver or join a guided tour. The best choice depends on your budget, how comfortable you are with driving in Italy, and what you plan to do once you arrive.

A tip: In summer, the port of La Spezia’s can see up to 3 cruise ships docking in a single day, each unleashing thousands of sightseers. Plan accordingly to dodge the crowds!

If you’re looking to escape the crowds and experience Tuscany’s quieter side, here are some less-traveled spots that offer charm and tranquility:
Monticchiello – A tiny medieval village in the Val d’Orcia with stunning views, cobblestone streets, and a peaceful atmosphere.
Casole d’Elsa – A charming village which combines history, art, and countryside views without the usual tourist buzz.
Castiglione della Pescaia – A picturesque coastal town with pristine beaches, a historic centre, and a quieter vibe than busier coastal destinations.
Montecarlo – A charming, small wine town near Lucca known for its excellent yet under-the-radar white wines.
Bolgheri – Famous for its Super Tuscan wines, this picturesque area is quieter than Chianti but equally breathtaking.
Lunigiana – A remote and lush region in northern Tuscany filled with castles, hiking trails, and unspoiled nature.
Garfagnana – Nestled in the Apuan Alps, this area offers stunning landscapes, ancient villages, and excellent opportunities for hiking and outdoor activities.
Pieve di Santo Stefano – A quiet town in the Casentino Valley with a strong connection to art and literature, surrounded by peaceful forests.
San Giovanni d’Asso – Known for its truffles, this village offers a tranquil escape in the Crete Senesi region.
Pitigliano
Often called “Little Jerusalem,” this ancient town perched on a tuff rock offers incredible views and a rich history without large crowds.

Tuscany is easy to explore by car, and it’s one of the best ways to fully enjoy the region’s beauty and charm. While there are some challenges, such as narrow roads and city parking, its freedom and flexibility make it well worth it. Just make sure to plan accordingly, especially when navigating cities or remote areas.

Exploring Tuscany without a car is definitely possible, though it may require a bit more planning. The region has a good public transport network connecting major cities and towns, and some rural areas are accessible by bus or train. However, reaching more remote villages or hidden gems can be challenging without a car. While public transport is reliable, it’s less frequent in rural areas, so flexibility is limited. If you’re based in a city or major town, you’ll have plenty to see and do, but for a more in-depth experience, a car may be more convenient.

The Tuscan countryside offers a wide variety of accommodations, from charming farm stays to luxury villas. Whether you prefer the wine-filled hills of Chianti, the stunning vistas of the Val d’Orcia, or the serene atmosphere of Maremma, there’s a perfect spot for everyone to enjoy the peaceful side of Tuscany.

Absolutely! Just over an hour away by train, Lucca is a charming destination with well-preserved medieval streets, historic city walls, great food and a peaceful atmosphere that invites exploration. A day trip from Florence to Lucca offers the perfect escape from the city’s lively pace.

Tips For A Stress-Free Trip To Tuscany

  • Getting Around: Renting a car can be the most convenient way to explore Tuscany beyond Florence. However, if you prefer not to drive, consider booking a driver or a guided tour for your day trips to ensure hassle-free travel.
  • Timing: Start your days early to make the most of each destination, especially during peak tourist seasons when popular spots can get crowded.
  • Packing: Bring comfortable shoes for navigating cobblestone streets and pack layers to adapt to the changing weather, particularly in spring or autumn.
  • Reservations: Book accommodation, popular restaurants, and key attractions in advance, especially during high season, to avoid disappointment.
  • Local Insights: Learn a few basic Italian phrases—it’s a small effort that goes a long way in connecting with locals and enriching your experience.
  • Pace Yourself: Tuscany is best enjoyed at a leisurely pace. Avoid cramming too many activities into one day so you can fully savour the region’s beauty and charm.

Whether you’re drawn to Florence’s Renaissance treasures, the beauty of the Val d’Orcia, or the sun-drenched Tuscan coast, this guide gives you the flexibility to mix and match stops to suit your travel style. These itineraries aren’t rigid schedules—they’re a foundation to help you craft your perfect Tuscan adventure.

Take your time wandering through medieval hill towns, sipping wine in a Chianti vineyard, or catching a golden sunset over the cypress-lined countryside. We’ve included plenty of options and suggestions to inspire your journey.

With the freedom to tailor your trip, you can create an experience that reflects your interests—whether it’s packed with exciting activities or designed for leisurely enjoyment.

So, what are you waiting for? Start planning your journey today and get ready to fall in love with Tuscany!

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A day trip from Florence to Lucca offers the perfect escape from the city’s lively pace. Just over an hour away by train, Lucca is a charming destination with well-preserved medieval streets, historic city walls, great food and a peaceful atmosphere that invites exploration. What sets Lucca apart is its blend of history, culture, and…