Updated: February 11, 2024 | Has affiliate links

7 Charming Places on A Tuscany Itinerary for First Timers

7 Beautiful Places on a Tuscany Itinerary

Tuscany is Italy at its most iconic. Home to cities beaming with history, art, and culture; and charming hill towns combining scenic beauty, architecture, preserved archaeological ruins and fortifications, and their own rich histories; Tuscany is a top destination for travelers. Let’s explore together a one-week Tuscany itinerary that lets you explore the best of this beautiful region.

While it’s easy to spend much more time in Tuscany, it’s possible to see the best of Tuscany in one week. This Tuscany itinerary allows you to explore the churches, museums, and culture of Pisa, Florence, and Siena; the scenery and well-preserved fortifications of Monteriggoni, San Gimignano, Volterra, and Lucca; and the picture-perfect Cinque Terre.
You can easily extend this trip by adding day trips from and walking tours of the places featured on my Tuscany itinerary.

1. Pisa

Seeing the Leaning Tower of Pisa is a must on your Tuscany Itinerary
Seeing the Leaning Tower of Pisa is a must on your Tuscany Itinerary
See my photos from Pisa Tuscany

We begin our Tuscany itinerary in Pisa, a city filled with history, art, culture, and food. A 25-minute walk from the Pisa Centrale train station takes you to the Piazza dei Miracoli, a UNESCO World Heritage Site that’s home to Pisa’s most historic and significant buildings and landmarks.
At the Piazza dei Miracoli, you will find the iconic Leaning Tower of Pisa, the Romanesque Pisa Cathedral, the Gothic Baptistry of St. John, and the beautifully impressive Monumental Cemetery. Since there’s so much to see in one place, you quickly realize why Pisa is the starting point for the Tuscany itinerary.
Pisa Walking Tour

2. Florence

Panorama of Florence at night seen from Piazzale Michelangelo.
Panorama of Florence at night seen from Piazzale Michelangelo
See my photos from Florence Tuscany

Considered Tuscany’s most important city, Florence is the next destination on the Tuscany itinerary. Spend your first day visiting Florence’s churches, including the Duomo, the Basilica di Santa Croce, and the Medici Chapels. The churches are architectural wonders with impressive artworks. Across the Arno River, the Palazzo Pitti is home to five museums and the Boboli Gardens.
Devote your second day in Florence to visiting the Uffizi Galleries and the Accademia. The Uffizi Galleries feature works from Italian artists Sandro Botticelli, Caravaggio, Giotto, Michelangelo, and Leonardo da Vinci. The Accademia is home to Michelangelo’s David. Wrap up the Florence portion of the Tuscany itinerary by taking in a panoramic view of the city at sunset from the Piazzale Michelangelo, located on the Arno River’s west bank.

Plan Your Trip to Florence

Stay in Florence. We stayed outside of the city center since we had a rental car and needed free parking. Plus, dealing with Florence traffic and finding parking in the old city center is really, really difficult. So, we stayed at the very reasonable Novotel Florence North. This hotel has a free shuttle that takes you straight to the Florence train station where you can start exploring. You can also find other budget hotels in Florence.

Trains run 3-4 times hourly between Pisa’s Centrale Station and Florence’s Santa Maria Novella station. Travel times range between 55 minutes and an hour twenty-five minutes, depending on the train.
Florence Walking Tour

3. Siena

Another view of Piazza del Campo from Palazzo Publico
Piazza del Campo in Siena seen from Palazzo Publico
See my photos from Siena Tuscany

The next destination on the Tuscany itinerary is the medieval city of Siena. From Siena’s central train station, a 25-minute walk takes you to the beautiful Piazza del Campo, the heart of the city. The cobblestoned Piazza each year hosts the famous Palio de Siena horse races in July and August.
From the Piazza del Campo, a three-minute walk down Siena’s charmingly narrow streets takes you to the Duomo. A Tuscany itinerary highlight, the green and black striped cathedral features frescoes by Pinturicchio and artworks by Pisano, Donatello, and Michelangelo.

Plan Your Trip to Siena

Book a local tour. Enjoy a beautiful walking tour of Siena led by a local guide, who will take you to Siena’s attractions and give you a glimpse into its intricate history.

Stay in Siena. If you have a rental car, stay at Castello Delle Quattro Torra in a beautiful location close to Siena. If you want to be very close to the old town, look at the beautiful Villa de STR which has great location and a great price. Or you can look for other budget hotels in Siena.

Get to Siena by train. From Florence’s Santa Maria Novella station, there is hourly train service to Siena’s central station. The journey takes an hour and a half.
Siena Walking Tour

3. Monteriggioni

The old walls at Monteriggioni date from the early 13th century
The old walls at Monteriggioni date from the early 13th century
See my photos from Monteriggioni

Perfect for a short stop along the Tuscany itinerary, you can visit the town of Monteriggioni enroute from Florence to either Siena. Originally a castle and overlooking the Siena hills, Monteriggioni lies within a well-preserved, fortified, towered wall. The Romanesque Gothic Church of Santa Maria Assunta is in the central Piazza di Roma.

Plan Your Trip to Monteriggioni

From Siena’s Via Tozzi bus stop, several buses make the 25-minute trip to Monteriggioni, with a more frequent service in the afternoon. From Florence’s Firenze Autostazione bus station, AT Bus #131 makes two daily afternoon trips to Monteriggioni, with a bus switch required in Poggibonsi. The total travel time is an hour fifteen minutes.

4. San Gimignano

Beautiful old stone arches and towers in San Gimignano
Beautiful old stone arches and towers in San Gimignano
See my photos from San Gimignano

San Gimignano is the definition of a Tuscan hill town, as you will see upon arriving from Monteriggoni. As you walk along the narrow streets from the Porta San Giovanni to the Piazza del Duomo and marvel at the well-preserved walled town and its 14 towers, you quickly realize why San Gimignano is part of the Tuscany itinerary.
The Piazza del Duomo is where you will find the Duomo di La Collegiata, San Gimignano’s main church. The Duomo has several beautifully painted frescoes. Before continuing with the Tuscany itinerary, take time to marvel at the Torre Rognosa, Torre Grossa, and Salvucci twin towers.

Plan Your Trip to San Gimignano

Stay in San Gimignano. Hotel Bel Soggiorno has amazing location, right inside the medieval walls, so within easy walking distance from anywhere. For more of a budget option but still close to Gate San Giovanni, try Il Feudo, which is also an excellent option. You can also find other budget hotels in San Gimignano.

From Monteriggioni, AT Bus #130 runs eight times daily from the Colonna di Monteriggioni bus stop to the Porta San Giovanni bus stop. The bus trip takes an hour, making nine stops along the way.

From Florence, take AT Bus #131 from the Firenze Autostazione to Poggiibonsi, then transfer to AT Bus #130 to the Porta San Giovanni bus stop. The travel time is between an hour forty minutes and two hours fifteen minutes.

Rent a car in Italy. San Gimignano is located in the Tuscany countryside and as such it is reached easiest by car. The drive from Florence to San Gimignano is gorgeous.
San Gimignano Walking Tour

5. Volterra

Steep narrow street Volterra leading to the ancient Porta all'Arco
Steep narrow street Volterra leading to the ancient Porta all’Arco
See my photos from Volterra Tuscany

Southwest of San Gimignano lies the walled hill town of Volterra, the next destination on the Tuscany itinerary. Entering Volterra from the sandstone Porta all’Arco gate, it is a five-minute walk to the Piazza dei Priori, where grand medieval houses and palaces, including the Palazzo Pretorio, line the square.
From the Piazza dei Priori, a four-minute walk takes you to the ruins of the Roman Theatre, one of Italy’s best-preserved theatres. As you walk through the city, take in scenic views of Volterra’s architecture, the Etruscan walls, and the Cecina Valley, a great way to remember this portion of the Tuscany itinerary.

Plan Your Trip to Volterra

There is no direct bus service between San Gimignano and Volterra. From San Gimignano, take AT Bus #130 to Colle di Val d’Elsa, then transfer to CTT Bus #770 to Volterra. The journey takes an hour fifty minutes, with buses running four times daily.

From Florence, take AT Bus #131 from the Firenze Autostazione to the Colle Val D’Elsa bus stop, where you will transfer to AT Bus #770 to Volterra. The journey between Florence and Volterra is five hours.

6. Lucca

The beautiful Amphitheater Square in Lucca was built on the ruins of the old Roman Amphitheatre
The beautiful Amphitheater Square in Lucca was built on the ruins of the old Roman Amphitheatre
See my photos from Lucca Tuscany

Lucca, a fortress city, shows it belongs on the Tuscany itinerary by greeting you with the intact Renaissance Wall that forms a ring around the city and its six entry gates. Besides the Renaissance Wall, the oval-shaped Piazza Anfiteatro serves as a reminder of Lucca’s history, as it was originally an amphitheater where gladiator games were held. Cafes and restaurants surround the Piazza, making it ideal for people watching.
The childhood home of opera composer Giacomo Puccini, at the Piazza Cittadella, is a museum devoted to his life and works. Finish up your time in this stop on the Tuscany Itinerary by walking seven minutes to the impressive Duomo di San Martino, where frescoed arches and Renaissance paintings adorn the Gothic cathedral.

Plan Your Trip to Lucca

From Florence’s Santa Maria Novella station, 1-3 trains each hour take the one hour twenty-minute to one hour fifty-minute trip to Lucca’s train station. The closest entry gate is Porta San Pietro, west of the train station. Alternatively, AT Bus #DD runs sixteen times daily between Florence’s Leopolda bus station and either the Lucca train station or Piazzale Verdi. Travel time via bus is an hour fifteen minutes.
Lucca Walking Tour

7. Cinque Terre

Beautiful Vernazza harbor in Cinque Terre
Beautiful Vernazza harbor in Cinque Terre
See my photos from Vernazza

The Cinque Terre is a beautiful, rugged, traffic-free, popular group of charming mountainside villages on the Ligurian Sea that’s also a national park. While the Cinque Terre is in Liguria, you can easily add it to the Tuscany itinerary, as it is an hour forty-five minutes from Lucca via train.
Get an early start and take the train to each of the Cinque Terre’s villages, Riomaggiore, Manarola, Comiglia, Vernazza, and Monterosso al Mare. Visit Comiglia last, as a steep zig-zag footpath with 385 steps connects the train station to the mountaintop village.
Spend 1-2 hours in each village admiring the churches, castles, and architecture; hiking the local trails; enjoying the beaches; or tasting wines made with mountainside-grown grapes. The scenic and popular Sentiero Azzurro, a series of coastal paths, attracts hikers, especially the Via dell’Amore path between Riomaggiore and Manarola. You may say at the end of the day that the Cinque Terre was the best destination on the Tuscany itinerary.
June 2023 Update: Parts of the Via dell’Amore hiking path is closed until mid-2024 due to a landslide. Check the official Cinque Terre website for current status of the trail.

Plan Your Trip to Cinque Terre

From Lucca, trains travel hourly or twice-hourly to the La Spezia Centrale station, with a transfer required at Viareggio. The trip takes an hour forty minutes.
Once at the La Spezia Centrale Station, express trains stop at each Cinque Terre village. From 8 AM to 8 PM (0800-2000 hours), trains operate every 10-30 minutes. It takes nine minutes to travel between La Spezia and Riomaggiore, and 25 minutes to travel to Monterosso al Mare. At the La Spezia Centrale Station, purchase a money-saving Cinque Terre Treno MS one-day card that covers both unlimited train travel and use of the hiking trails.
Returning to Pisa from the Cinque Terre, trains run up to four times an hour between La Spezia Centrale Station and the Pisa Centrale station. Travel times vary from 40 minutes on a super-fast Frecce train to an hour twenty-five minutes on a regional train.

Can You See Tuscany in One Week?

You can see Tuscany and the Cinque Terre in one week. By following the Tuscany itinerary, you’ll explore the culture, history, and art of Pisa, Florence, and Siena; see iconic sites like the Leaning Tower of Pisa and renown works like Michelangelo’s David, take in the beauty, architecture, and archaeological past of Tuscany’s hill towns; and soak in the gorgeous views from the Cinque Terre’s villages, hiking trails, and beaches.

  1. Charming Tuscan Itinerary
  2. Charming Things to Do in Pisa
  3. Charming Walking Tour of Florence
  4. Amazing Churches of Florence
  5. Best Things to Do in Siena
  6. Best of San Gimignano
  7. Charming Volterra
  8. Best Things to Do in Lucca
  9. Is Cinque Terre Overrated?

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