Planning the perfect Tuscany itinerary can feel overwhelming with so many incredible places to choose from. My friend Cheryl and I discovered this firsthand when we visited Tuscany in August 2024.
Our trip was absolutely magical. We indulged in the most delicious food, from fresh pasta made by nonnas to gelato that melted perfectly on our tongues.
The beautiful art everywhere left us speechless. Especially the stunning frescoes that seemed to tell stories on every church and palace wall. I found myself staring up at those painted ceilings for way longer than Cheryl had patience for!
The medieval architecture transported us back in time. Stone towers reached toward the sky while ancient walls wrapped around hilltop towns like protective embraces.
We spent hours wandering through narrow cobblestone streets. We discovered hidden courtyards and tiny piazzas tucked into every nook and cranny of these ancient cities. Each turn revealed something new to marvel at.
And yes, the wine lived up to every expectation we had.
Whether you’re traveling with older kids, teens, or just adults who appreciate good food and incredible history, this guide will show you exactly how to spend an unforgettable 7 days in Tuscany.
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Best Time To Visit Tuscany
Wondering about the best time of year to visit Tuscany? The answer depends on what you prioritize: perfect weather, smaller crowds, or budget-friendly prices.
Peak Season
(June – August) Summer brings the warmest weather and longest days, making it ideal for outdoor exploration and extended sightseeing hours. However, this is also when Tuscany is at its busiest and most expensive.
Expect crowded trains, packed tourist sites, and higher accommodation prices. The intense heat can also make walking around medieval hilltop towns quite challenging, especially during midday hours.
Shoulder Season
(April – May & September – October) These months offer the best time to travel for most travelers. Spring brings blooming countryside and pleasant temperatures, while early fall delivers harvest season magic with comfortable weather.
Train schedules run frequently, attractions are open with reasonable crowds, and accommodation prices are more manageable.
The weather is perfect for walking tours and outdoor dining without the summer heat.
Off-Season
(November – March) Winter and early spring offer the most budget-friendly prices and smallest crowds, but come with trade-offs. Some smaller attractions may have reduced hours or close entirely. Train schedules to more remote destinations might be limited.
However, major cities like Florence, Siena, and Pisa remain vibrant year-round, and you’ll have famous sites largely to yourself.
I’d recommend shoulder season when public transportation runs at full capacity and you can enjoy comfortable weather for all the walking involved in exploring these beautiful medieval towns.
How Many Days Do You Need In Tuscany?
People always ask me how many days in Tuscany they should plan for. My answer is always the same: it depends! There’s honestly so much to see and do here that you could spend weeks exploring and still discover new treasures.
Being in Italy is all about slowing down. It’s about embracing that relaxed way of life where long lunches matter and conversations flow as freely as the wine. You’ll quickly realize that rushing from sight to sight misses the entire point of a Tuscan experience.
You will need to pick and choose what you do and where you go. Accept right now that you won’t be able to see it all. That’s actually a good thing because it gives you an excuse to return!
I chose 7 days in Tuscany for this itinerary because I believe it’s the perfect sweet spot. Seven days gives you enough time to see the absolute best sights while also allowing you to slow down and soak in all that authentic charm surrounding you.
You can linger over morning cappuccinos, take afternoon gelato breaks, and actually enjoy those magical golden hour moments that Tuscany is famous for.
Best Way To Get Around Tuscany
Much of Tuscany sits in rolling countryside where it can be more challenging to reach destinations with public transportation, but it’s definitely still possible. I personally don’t like driving in other countries. That’s my husband’s job! 😉
So when my friend and I traveled around Tuscany, we relied entirely on trains and buses. While public transportation isn’t connected to every single amazing hilltop town, it absolutely can get you to incredible places.
You can do everything on this 7-day Tuscany itinerary using public transportation without missing out on the magic.
The trains in Italy are reliable and comfortable. The buses fill in the gaps for smaller towns. Yes, you’ll need to plan around schedules.
If you want more freedom from schedules and dream of taking that classic Tuscany road trip through winding country roads, renting a car is definitely the way to go. You’ll have the flexibility to stop at vineyards on a whim and discover hidden gems off the beaten path.
Both options work beautifully. Choose what fits your travel style and comfort level.
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7-Day Tuscany Itinerary
Now let’s dive into the detailed Tuscany itinerary. It will take you through seven incredible days of art, food, and unforgettable experiences.
Day 1 – Tuscany Itinerary
Our Tuscany trip itinerary begins with iconic leaning towers, stunning marble architecture, and those classic tourist photos you’ve been dreaming of taking in Pisa.
Reservations – Day 1
These are quick links to the possible reservations needed on Day 1 of this Tuscany itinerary.
- Pisa Mover
- Pisa Food Tour
- Tower of Pisa Tickets or the Guided Tour of The Tower of Pisa and Cathedral
Fly Into Pisa
The airport is just a short distance from the city and incredibly easy to reach. Take the train shuttle called the Pisa Mover that connects the airport directly to Pisa Centrale train station.
You can buy your tickets right before you get on for €6.50 one way. If you prefer to plan ahead, you can also purchase tickets online. The ride is quick and hassle-free, making it the perfect way to start your Tuscan adventure without any stress.
Where To Stay In Pisa – 2 nights
Since you’ll be spending two nights in Pisa to fully explore the city, here are my top recommendations for family-friendly accommodations.
- Prato dei Miracoli Residenza d’Epoca: If waking up to views of the Leaning Tower from your bedroom window is on your bucket list, this is your place. This exceptional property offers the rare chance to gaze at one of the world’s most famous landmarks from your room. Families will need two rooms. This increases the cost, but those unparalleled views and elegant comfort make it absolutely worth it for such a once-in-a-lifetime experience.
- Terzopiano: For families seeking budget-friendly comfort, Terzopiano delivers. It offers excellent value with its clean, spacious 3-bedroom layout for up to 6 guests. Located near Pisa Centrale train station, it’s perfectly positioned for exploring Pisa and venturing to other Tuscan destinations. It’s ideal for larger families who want to save money while still having plenty of room to spread out.
Alternatively Stay In Lucca
I really love staying in popular day trip destinations, as the evenings and mornings are usually quiet and relaxed. So you could stay in Lucca instead of Pisa and do a day trip to Pisa.
In this Tuscany itinerary, we are heading to Siena next. If you stay in Lucca, you will be traveling more on the train. However, if you flip the direction of this Tuscany itinerary to travel to Florence next, instead of Siena, then staying in Lucca would make sense.
Here are a few Lucca lodging options that would work great for families:
- Màrita Apartment: This beautifully updated 2-bedroom apartment sits in a stellar location within Lucca’s historic walled city. The thoughtfully decorated space gives families plenty of room to spread out. The exceptionally friendly host ensures a seamless stay. You’ll be steps away from cobblestone streets, charming piazzas, and the famous city walls.
- Casa Alice Lucca Centro: This charming centro apartment offers exceptional value for budget-conscious families. The setup is perfect with a queen bed for parents and twin beds for kids. What sets it apart is the impeccable cleanliness, prime central location for exploring on foot, and fantastic price point.
What To Do In Pisa For A Day
With your accommodation sorted, here’s exactly what to do in Pisa for a day to see all the highlights.
You can’t come to Pisa without taking those famous leaning tower photos! While most people go to the Piazza dei Miracoli first thing in the morning, I’d suggest visiting later in the afternoon and early evening when it’s less busy.
So let’s start somewhere completely different. This self-guided walking tour is roughly 30 minutes of walking with stops along the way.
Start At Tuttomondo Mural By Keith Haring
Begin your day at the colorful Tuttomondo mural by Keith Haring. It was painted in 1989 on the exterior wall of the Church of Sant’Antonio Abate. This massive 180-square-meter explosion of vibrant colors represents “All the World” and tells stories of harmony and peace in the world.
Palazzo Blu
After admiring the mural, head to Palazzo Blu to immerse yourself in some incredible art. This beautifully restored medieval palace houses an impressive collection.
It includes masterpieces by Benozzo Gozzoli, Orazio and Artemisia Gentileschi, and other renowned artists. Sometimes they will even have temporary exhibits from Picasso or Dalí.
If you are interested in art this would make a great addition to your Tuscany itinerary. You can easily spend an hour wandering through the elegant rooms and discovering both historical and contemporary pieces.
Chiesa Di Santa Maria Della Spina
After all that art, take a leisurely walk along the Arno River toward the Chiesa di Santa Maria della Spina. This tiny Gothic church sitting right on the riverbank is absolutely magnificent to see.
The intricate stone work and delicate spires make it look like something from a fairy tale. It’s small but perfectly formed.
Cross To Borgo Stretto
Cross the river and walk on the other side of the Arno toward Borgo Stretto. This pedestrian street is lined with beautiful shops, restaurants and elegant archways that are held up by massive columns.
It’s the perfect place to grab a gelato and soak it all in.
Piazza Dei Cavalieri And Palazzo Della Carovana
End this part of your walking tour at Piazza dei Cavalieri, the Knights’ Square.
Walk through the square to see the impressive façade decorated with the sgraffito technique on the Palazzo della Carovana.
The Square of the Knights is also a vibrant hub with charming cafes and shops.
The grand façades and historic atmosphere make it feel like you’ve stepped back in time.
Alternate Morning Activity
If you aren’t interested in a self-guided walking tour, another option would be to take a guided food tour.
This Pisa Food Tour, starts at 11:30am and guides you to 5 food stops in Pisa. You will enjoy traditional foods, avoid tourist traps and learn from a local food expert. A tasty way to visit Pisa and get to know it from a local’s perspective!
Lunch
My visit to Pisa was much shorter than I would have liked, and I didn’t have the chance to experience lunch here. I wish I had though! The options at the airport were absolutely terrible.
Along this walking tour route, I researched some highly rated restaurants that would be perfect to check out. Grab some tasty pizza or authentic Tuscan food whenever you start to get hungry.
Ristorante La Buca: This gem serves traditional Tuscan dishes made from fresh, local ingredients, and the staff is incredibly friendly. All the reviews rave about how delicious the food is! It’s conveniently located near the Tuttomondo Mural, so you can fuel up right after seeing Haring’s masterpiece.
Pizzeria il Borgo 21: Perfect for tasty pizza and pasta when you’re craving something more casual. It’s ideally positioned between Borgo Stretto and Palazzo della Carovana, making it an easy stop during your walking tour.
Both spots get consistently great reviews, so you really can’t go wrong with either choice!
Piazza Dei Miracoli – Square Of Miracles
The Piazza dei Miracoli, or Square of Miracles, is where you’ll spend the rest of your time in Pisa. It is a must-visit on any Tuscany itinerary.
Entry to the piazza itself is free, but you’ll need to book tickets in advance if you want to explore the insides of the buildings.
Important Things to Note
- Cathedral: Free with any other ticket purchase, no fixed time slot required
- Leaning Tower: Opens at 10am until 2 hours before closing
- Children & The Tower: Children under 8 cannot enter
- Tower timing: Timed entry only – if you’re late, you won’t be able to enter
- Tower climb: 251 steps, takes about 30 minutes to visit
- Other buildings: Baptistery, Camposanto, Sinopie Museum, and Opera del Duomo Museum have no timed entry
Ticket Options
- Single building + Cathedral: €8 (except Tower of Pisa: €20)
- All buildings except Tower of Pisa: €11
- All buildings including Tower of Pisa: €27
My Advice
Purchase a timed entrance ticket to the tower for afternoon or early evening when more slots are available and crowds are lighter.
The magic of Pisa truly lies in the Square of Miracles. If you’re going to climb the tower, I’d also buy tickets for the other buildings. It’s only €7 more and you’ll get the complete experience.
If you’d like to learn more about the history with a guided tour of the tower and cathedral, this would be a nice tour option: Leaning Tower of Pisa & Cathedral: Guided Tour
Buildings In The Square Of Miracles
To help you decide which buildings in the Piazza del Miracoli you’d like to explore, here are some short descriptions of each one.
Tower of Pisa: The iconic leaning tower is obviously the star attraction and the reason most people come to Pisa. Climbing to the top gives you incredible panoramic views of the city and countryside. Plus it’s a unique experience to be inside the world’s most famous architectural “mistake.”
Cathedral (Duomo): This stunning example of Pisan Romanesque architecture contains beautiful frescoes, intricate marble work, and impressive artwork that tells the story of Pisa’s wealthy maritime past. The ornate interior will take your breath away, especially the elaborate pulpit carved by Giovanni Pisano.
Baptistery: The largest baptistery in Italy boasts incredible acoustics that create an almost magical echo effect when voices or music fill the space. The mix of Romanesque and Gothic architecture, plus the stunning pulpit by Nicola Pisano, makes it a masterpiece worth experiencing.
Camposanto (Cemetery): This peaceful covered cemetery feels like walking through an open-air museum with its collection of ancient Roman sarcophagi and beautiful frescoes. It’s a serene contrast to the busy piazza and offers fascinating insights into medieval burial traditions and art.
Sinopie Museum: Here you can see the preparatory drawings (sinopie) that were discovered beneath frescoes during restoration work in the Camposanto. It’s like getting a behind-the-scenes look at how medieval artists created their masterpieces. Pretty cool!
Opera del Duomo Museum: This museum houses original sculptures and artifacts removed from the cathedral and other buildings for preservation. You’ll see works by Giovanni Pisano and other masters up close, plus learn about the construction and decoration of these incredible monuments.
Dinner
Time to treat yourself to a delicious dinner after all that walking and exploring. I researched highly-rated restaurants in Pisa to find these fantastic options for your evening meal.
Ristorante Tora Tora: Perfect for a delicious dinner on a small, beautiful piazza. Reviews consistently praise the great service, amazing food, and wonderful atmosphere that makes for a memorable evening.
Ristoro Pisano: This spot offers a homey, authentic vibe with big portions and flavorful food at a great price! It’s the kind of place where you’ll feel like you’re dining with locals rather than just passing through as a tourist.
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Day 2 – Tuscany Itinerary
Day 2 of this itinerary for Tuscany takes us on an enchanting day trip to Lucca. Here you’ll discover stunning churches and bike along the tree-lined walls that surround this medieval gem.
Reservations – Day 2
Day Trip To Lucca
To help you make the most of your time, here’s how to spend the perfect day trip to Lucca.
Getting To Lucca From Pisa
The easiest way to reach Lucca is by train from Pisa Centrale station. The trains run quite often and only takes about 30 minutes to arrive. The cost is around €4 per person.
Lucca’s train station is located just south of the walled city and easy to walk to and from.
You can purchase tickets at the train station or online. I like to purchase my train tickets online using Trainline. This way I can do it in advance and don’t have to wait in line.
If you do purchase your tickets at the station, be sure to validate them.
What To Do In Lucca, Italy In One Day
Lucca is famous for its perfectly preserved Renaissance walls that create a tree-lined promenade, its abundance of beautiful churches, and the iconic tower with trees growing on its roof.
Here is a list of some of the best things to do in Lucca to add to your Tuscany itinerary.
Biking The Walls
The highlight of any Lucca visit is cycling around the famous Renaissance walls on this scenic 3-mile loop. The path is wide and beautifully shaded by trees, making it comfortable even on warm days.
If you bike slowly, which you absolutely should to soak in the views and take photos, it takes about 25-30 minutes to complete the circuit.
There are multiple places to rent bikes both near the city walls and throughout downtown Lucca. Many of the bikes you’ll see look more like mini cycling cars than traditional bicycles, making it super easy and fun for the whole family to rent one and hop in together! No need to reserve in advance.
Climb Up The Guinigi Tower
I’ve climbed lots of towers throughout Europe, but this is the only one I have seen that has trees growing at the top! The Torre Guinigi is Lucca’s most iconic landmark and offers incredible panoramic views of the city and surrounding countryside.
The climb to the top is totally worth it for the unique experience of standing in a rooftop garden 130 feet above the medieval streets.
Regular admission is €8 for adults, with a reduced rate of €6.50 for families of 4 or more (2 adults plus 2 or more paying children), and children 7 years and under enter free.
This is a timed entrance attraction, so you must reserve your tickets in advance to guarantee your spot.
The combination of history, views, and those surprising oak trees makes this climb an unforgettable highlight of your Lucca visit.
Visit A Few Of The 100 Churches
Lucca truly lives up to its nickname as the “city of a hundred churches,” and you’ll spot beautiful bell towers and ornate facades around every corner.
While you could spend days church hopping, here are some of the most spectacular ones that are perfect for families to explore:
Basilica di San Michele in Foro – Free to enter, but the real magic is on the outside where the facade is absolutely unbelievable.
Basilica of San Frediano – Don’t miss the stunning golden mosaic on the facade that catches the light beautifully throughout the day.
Duomo di San Martino – Gorgeous both inside and out, especially the incredible frescoes covering the ceiling that will have you craning your neck in wonder. Tickets must be purchased at the door to enter.
Piazza Dell’Anfiteatro
Take in the beauty of Lucca’s most famous square, where the oval shape perfectly traces the footprint of an ancient Roman amphitheater. This unique piazza is absolutely magical with its ring of colorful medieval buildings creating an intimate, enclosed feeling.
It’s the perfect spot to sit down for a spritz and simply relax while soaking in the atmosphere. I wouldn’t recommend eating a full meal here since restaurants on squares tend to be tourist traps and not that good, but grabbing a glass of wine, mocktail, or beer is absolutely perfect for people watching.
You’ll love observing the mix of locals and visitors while admiring the incredible architecture that has stood here for centuries.
Wander Around Old Town
Simply getting lost in a Tuscan city is one of my favorite things to do, and Lucca is absolutely perfect for this kind of leisurely exploration.
The compact medieval center is made for wandering, with its pedestrian-friendly cobblestone streets and enchanting alleyways that seem to curve and wind in the most delightful ways.
You’ll discover cute side streets lined with artisan shops, stumble upon a stunning church tucked into an unexpected corner, or find a hidden piazza that feels like your own secret discovery. The beauty of Lucca is that there’s no wrong turn to take.
Grab a gelato from one of the many gelaterias and just soak it all in. Let your curiosity guide you rather than any map, and you’ll experience the authentic rhythm of daily life in this magical Tuscan gem.
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Day 3 – Tuscany Itinerary
Day 3 of this Tuscany travel itinerary whisks us away to beautiful Siena for a day filled with exploring cobblestone streets and enjoying exceptional wine tasting.
Reservations – Day 3
- Travel To Siena: Trains, Buses, Private Transfer, or Car Rental
- Winery Tour
Travel To Siena
Siena is about 2 hours from Pisa. There are a few different ways to get to Siena.
By Train
From Pisa, getting to Siena by public transportation is honestly when Italy’s train system doesn’t shine. You can definitely get around Tuscany by train and bus, but it isn’t always the most convenient option.
To travel from Pisa to Siena by train, you’d have to take a train to a bus to another train, which gets complicated quickly.
By Bus
You can also book a FlixBus, which offers a direct route from Pisa to Siena. This option is cheap and direct, which sounds perfect!
My friend and I used this bus, and while we loved that it was direct, it also showed up super late.
I guess the moral of the story is that public transportation is possible and inexpensive, but not always reliable.
By Private Transfer
Another option is to book a private transfer through services like GetTransfer.com for around €200-300 total. This gives you convenience and reliability without the stress of driving yourself.
By Car
Lastly, you can brave the roads and hire a rental car. Prices will vary depending on when you travel, but this gives you the most flexibility to explore at your own pace. Check out rental options below to see what works for your budget and comfort level.
Where To Stay In Siena – 3 Nights
Finding the right accommodation in Siena can make or break your experience, so I’ve gathered some excellent options based on different family sizes and budgets.
Siena UpTown – Sabrina’s Cozy Apartment: This charming hillside apartment is where we stayed during our Siena visit, and it was absolutely perfect for our needs. Sabrina is an incredibly friendly and helpful host, and the location is excellent. While it might feel a bit snug for a family of four, it’s ideal for three people or fewer who want an authentic Siena experience at an unbeatable price.
Palazzo Piccolomini: For families needing more space, this property offers generous family-friendly layouts with excellent sleeping arrangements for kids and breathtaking views from a quiet setting. Everything you’ll want to explore in Siena is easily walkable, making it perfect for families who want room to spread out without sacrificing convenience.
Residenza d’Epoca “Il Campo”: For an absolutely unbeatable location, imagine opening your window each morning to gaze directly onto Siena’s most famous square! This spacious, immaculately clean property puts you right on the Piazza del Campo with the iconic clock tower as your backdrop. While it comes at a higher price point, the premium is justified when you’re living on one of the most beautiful squares in all of Italy.
Vineyard Tour And Wine Tasting
After getting settled into your hotel in Siena, get ready to dive into the world of Chianti wine! This is exactly the kind of authentic experience that makes a week in Tuscany so unforgettable.
Hop in a taxi if you don’t have a car and head to La Lastra winery. You’ll definitely want to book your wine tasting tour in advance. This is the tour you want, especially if you don’t have a car. Even if you do have one, still book this tour!
Here’s the link to the wine tasting tour we went on.
The wine is absolutely delicious, the tour was both educational and incredibly fun, the meal was tasty, and the location is absolutely perfect.
You’ll feel like you’re nestled in the heart of the Tuscan countryside, surrounded by rolling vineyards and olive groves, when you’re really only a 10-minute drive from Siena.
It’s the perfect balance of accessibility and authentic rural charm that captures everything magical about Tuscany.
Evening In Siena
When you get back to Siena, you have a couple of wonderful options for spending your evening. If you’re interested in taking in the sunset from high above Siena, visit the Fortezza Medicea. Watch the sky transform into brilliant oranges and pinks while sipping another glass of wine or just enjoying some water from this historic fort.
It has a fun, relaxed outdoor vibe in the evening and feels like you’re hanging out with locals rather than just being another tourist.
The other option is to head down to the famous Piazza del Campo and wander through some of the enchanting medieval streets of Siena as the evening light creates magical shadows on the ancient stone buildings.
Both choices offer completely different but equally captivating ways to end your day in this stunning city.
Day 4 – Tuscany Itinerary
Day 4 of this Tuscany itinerary combines wandering through Siena’s historic streets with a visit to a charming, authentic Tuscan village that feels untouched by time.
Reservations – Day 4
Morning In Siena
Start your day by stopping into a cozy cafe to relax while sipping a perfect cappuccino and enjoying a delicious pastry before beginning your exploration of Siena.
A couple of great options are Torrefazione Fiorella, one of the top places in Siena for coffee and pastries, or Bar Sant’Agata Coffee Break, more of a local spot near the center but away from the busy tourist areas.
After fueling up, head straight to the Torre del Mangia (the famous clock tower) to buy your tickets for climbing the tower.
The ticket office opens at 10am, and you’ll want to go there first thing since tickets sell out quickly and can’t be purchased online in advance.
Ticket Options:
Only The Tower
- Single adult ticket: €10
- Family ticket (2 adults + children 11-18): €25
Combined Ticket
- Museo Civico + Torre del Mangia: €15
Civitas Senensium Ticket
- Museo Civico + Santa Maria della Scala + Torre del Mangia: €20
- Family ticket (2 adults + children 11-18): €40
My friend Cheryl and I purchased the Civitas Senensium Ticket, and it was absolutely worth it! Santa Maria della Scala was incredible and I’d highly recommend getting a combo ticket to experience it.
The Civic Museum was also beautiful to explore.
Tower tickets are for timed entry, but you can visit the Civic Museum and Santa Maria della Scala anytime during opening hours.
Siena Cathedral
Exploring the tower and the museums will most likely take all morning, but if you have any extra time, the Duomo di Siena is a stunning church to explore inside and out. Prices vary by season, but start at €5 and children up to 6 are free.
The Cathedral complex has other buildings that you can explore too. If you are interested in accessing the cathedral roofs and the other museums you can buy a combined ticket for €21 or €6 for children 7-11 years of age.
There is also the option to access the other museum buildings without the rooftop access for €14 or €3 for children 7-11 years old.
We didn’t get the chance to explore the inside of the Siena Cathedral and I wish we had. I am especially interested in the rooftop access option.
The Gate of Heaven, as they call it, are a series of rooms that aren’t normally open to the public and provide incredible views inside and outside of the cathedral. A unique experience.
Lunch In Siena At Il Ghibellino Osteria
Our absolute favorite restaurant in Siena was Il Ghibellino Osteria. The food was consistently delicious every time we went, but the best part that had us coming back again and again was their incredible bruschetta.
I’m not exaggerating when I say it was the best bruschetta we have ever eaten!
There’s something magical about the combination of perfectly toasted bread, fresh toppings, and that authentic Italian touch that made it completely irresistible. If you only eat at one place in Siena, make it this one.
Explore Monteriggioni Or Buonconvento
Next up, head to either Monteriggioni or Buonconvento for a peaceful afternoon escape. These two authentic small villages are easy to reach by public transportation and won’t take too much time to explore. Perfect for a relaxed half-day trip.
Wander their quaint cobblestone streets, climb up on the medieval walls of Monteriggioni for stunning countryside views, and grab an aperitif at a local spot where you’ll likely be surrounded by locals rather than tourists.
This is your chance to truly slow down, let your feet guide you through ancient alleyways, and experience the Italy that feels untouched by time.
There’s no agenda here except to soak in the authentic atmosphere and fall in love with Tuscany.
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Day 5 – Tuscany Itinerary
Day 5 of this Tuscany trip itinerary brings us to the enchanting hilltop village of San Gimignano, famous for its medieval towers and stunning panoramic views.
Reservations – Day 5
- None needed in advance
Day Trip To San Gimignano
To help you make the most of your time, here’s how to spend the perfect day trip to San Gimignano.
Getting To San Gimignano From Siena
Planning your San Gimignano day trip is straightforward, with good transportation options to suit different travel styles. Here’s how to get to San Gimignano from Siena.
By Car: Driving gives you maximum flexibility, though you’ll park outside the medieval walls since the historic center is closed to non-resident vehicles.
The best option is P1 Giubileo parking, which costs €1.50 per hour with a daily maximum of €6 and is both the largest and cheapest lot. Other options include P2 Montemaggio (€2/hour, max €20/day) and P3/P4 Bagnaia (€2/hour, max €15/day).
All lots are within easy walking distance of the town gates, with shuttle service available if needed.
Arrive early in the morning to secure good parking, especially during peak season!
By Public Transportation: This is the best way to get to San Gimignano for a day trip! The direct bus from Siena is easy and costs €6.20 one way (€8 if purchased onboard).
The journey takes about an 1 hour. It is exactly how Cheryl and I visited. Just be warned that the roads are quite windy, so if you get carsick, definitely take Dramamine beforehand.
Also, have cash ready just in case. The credit card machine on our bus wasn’t working, and we had to scramble to find cash for tickets!
By Tour: Tours from Siena to San Gimignano typically combine visits to other destinations like Volterra or the Chianti region and Montalcino.
While these combinations offer a great way to see more of Tuscany in one day, they definitely make for a very long day of sightseeing!
Here are some top-rated tour options departing from Siena:
- From Siena: Chianti and San Gimignano Sunset Tour
- Siena: San Gimignano, Chianti & Montalcino Small-Group Tour
- San Gimignano and Volterra: Day Tour from Siena
These tours are perfect if you want someone else to handle the logistics and don’t mind a packed itinerary. If you prefer a more relaxed pace to really soak in San Gimignano’s medieval charm, the direct bus might be your better bet.
Top Things To Do In San Gimignano
Wander All The Little Side Streets
Before shops and attractions officially open, spend time getting completely lost in San Gimignano’s enchanting maze of narrow cobblestone streets and medieval alleyways.
The early morning hours offer the most magical experience when you’ll have the ancient pathways almost entirely to yourself. Don’t miss the incredible panoramic viewpoints scattered around the town’s perimeter that offer breathtaking vistas of the Tuscan countryside.
For families with young kids, visit La Rocca Playground in Parco della Rocca. You will find swings, slides, and shade for an entertainment break.
Duomo Di San Gimignano
Around 10am when the Duomo opens, step inside this stunning Romanesque cathedral that’s an absolute must-see.
While the exterior looks relatively simple, the interior is breathtaking with incredible 14th-century frescoes covering every surface, telling biblical stories in vivid detail.
The artwork is so well-preserved. It feels like you are stepping into a medieval storybook. The kids will love spotting different animals and characters in the frescoes.
Climb One Of The Medieval Towers
You absolutely cannot visit San Gimignano without climbing Torre Grossa, the tallest of the 14 remaining medieval towers (there were once 72!). Head to Palazzo Comunale to purchase your San Gimignano pass for access to the Civic Museum, Pinacoteca, and the tower.
Spend just 4 euros more for the full pass that includes additional museums. It’s absolutely worth it for the small extra cost.
Find A Place For Lunch
By now, you will have worked up an appetite from all that tower climbing and wandering!
Great lunch options include Da I’ Mariani for casual focaccia sandwiches, RiccaPizza for affordable pizza by the slice (perfect for families), or Le Vecchie Mura for pasta with stunning views.
Don’t stress about finding the “perfect” restaurant. Sometimes the most memorable part is simply soaking in the magical medieval atmosphere.
Visit Quiet Museums In The Afternoon
When the afternoon sun is beating down and main piazzas are packed with tour groups, duck into the quieter museums included in your upgraded pass.
The Museo Archeologico, Spezieria di Santa Fina, and Galleria d’Arte Moderna offer a peaceful escape from crowds and heat, and you’ll virtually have these stunning spaces to yourself.
Walk A Section Of Via Francigena
Right outside San Gimignano’s walls, you can walk a section of the famous Via Francigena pilgrimage route that stretches from Canterbury to Rome.
This ancient trail offers incredibly quiet, peaceful views of rolling Tuscan hills and a chance to literally follow in medieval pilgrims’ footsteps.
It is perfect for stretching your legs away from the stone streets and crowds.
Eat The World’s Best Gelato
No San Gimignano visit is complete without gelato from world-famous Gelateria Dondoli, known for original flavors like pink grapefruit and sparkling wine.
They’ve won numerous international awards, though be prepared for massive lines!
Drive To A Viewpoint
If you have a car, cap off your day by driving to a panoramic viewpoint to see San Gimignano’s iconic towers rising from the countryside.
Type “viewpoint panorama” into Google Maps to find four different locations that offer perfect postcard shots and give you a whole new appreciation for this special medieval town.
Visit A Winery
For those with cars, explore the local wine scene famous for crisp white Vernaccia di San Gimignano.
Pietraserena Winery is perfect for families with farm animals and a playground, while Tenuta Torciano offers the magical experience of sipping wine while admiring San Gimignano’s towers in the distance.
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Day 6 – Tuscany Itinerary
Day 6 of this Tuscany travel itinerary brings us to the most famous city in Tuscany, Florence, where Renaissance art and architecture await around every corner.
Reservations – Day 6
- Train to Florence
- Tickets to the Galleria Dell’Accademia or Skip-The-Line Guided tour of the Accademia Gallery
- Tour of the Duomo or Bell Tower
- Divina Terrazza reservations
- Pasta and Gelato Making Class
- Sunset boat tour on the Arno River
Travel To Florence
It’s fairly easy to get to Florence from Siena by train. You can grab your train tickets through Trainline, which is exactly how Cheryl and I visited. The journey is straightforward and comfortable, making it a great option for families too.
Taking a bus is actually a little shorter than the train since it follows a more direct route. However, I’m more comfortable traveling by train than bus, so we decided the train was our best bet for this leg of the journey.
Driving is also an easy option if you have a rental car, taking only about an hour between the two cities. This gives you the most flexibility for timing and luggage, though you’ll need to factor in parking once you reach Florence.
All three options work well depending on your comfort level and travel style!
Where To Stay In Florence – 2 nights
Finding the perfect place to stay in Florence can make your visit so much more enjoyable, especially when traveling with family.
Condotta 16 Apartments: These stunning 2-bedroom apartments in the heart of Florence offer private balconies or terraces that make all the difference. What I love about these apartments is how bright, airy, and spacious they feel, combined with impeccable cleanliness. While they’re on the pricier side by my standards, the rates are actually mid-range for Florence.
Boutique Santa Croce: For families seeking a budget-friendly option without sacrificing location, this property delivers excellent value in Florence’s historic center. While the accommodations are more compact, they remain comfortable and thoughtfully designed, proving you don’t need to spend a fortune for a fantastic location.
Granduomo Charming Accomodation: Perfectly positioned just steps from Florence’s magnificent Duomo, this welcoming property combines an unbeatable location with exceptional hospitality. The super friendly staff goes above and beyond, including stocking the kitchen with complimentary snacks and drinks. A thoughtful touch that’s especially appreciated when traveling with kids.
What To Do In Florence
There’s so much to do and see in Florence. You can easily spend 2 days exploring and not see it all. Here are the best things to do in Florence.
Grab Some Breakfast At Forno Ghibellina
Start your day at this beloved neighborhood bakery just blocks from Mercato di Sant’Ambrogio, where locals line up daily for their famous stuffed brioche with sweet or savory fillings.
This cozy spot serves excellent Italian coffee, fresh sandwiches, and authentic pastries that offer a genuine taste of local Florence far from the tourist traps surrounding major attractions.
Galleria Dell’Accademia: Meet Michelangelo’s David
This is the moment you’ve been waiting for. Standing face to face with Michelangelo’s original David at the Accademia Gallery.
Book tickets well in advance as they sell out quickly, and aim for the earliest time slot to avoid crowds.
If you can’t get tickets, there’s a free replica of David in Piazza della Signoria that still gives you a sense of the sculpture’s impressive scale and detail.
Book Your Duomo Experience: Climb the Dome Or Bell Tower
Go to the impressive Duomo complex to climb either Brunelleschi’s iconic dome (463 steps) or Giotto’s Bell Tower (414 steps) for breathtaking panoramic views over Florence.
The dome climb takes you through stunning interior frescoes, while the bell tower offers a different perspective and better photo opportunities of the cathedral itself.
Both climbs are strenuous with narrow staircases, but the 360-degree views make every step worthwhile.
Lunch – Sandwich At Pino’s Sandwiches
After all that climbing, refuel at Pino’s Sandwiches for delicious, authentic Italian sandwiches at incredibly reasonable prices.
This beloved local spot serves generous portions with plenty of vegetarian options alongside famous meat selections. You might even meet Pino himself behind the counter for a personal touch to your dining experience.
Wander The Streets And Get Gloriously Lost
Step away from main tourist routes and duck down side streets where crowds thin out just one block away from popular areas. These quieter streets reveal Florence’s authentic character with local residents, charming cafes, and beautiful Renaissance architecture.
Don’t miss exploring Florence’s legendary leather shops during your wandering. You’ll practically trip over the world-renowned craftsmanship throughout the city.
Admire The Free ARt In Piazza Della Signoria
Visit this magnificent square that serves as an open-air sculpture gallery with Renaissance masterpieces completely free of charge.
Here you’ll find the replica of David, Cellini’s Perseus with the Head of Medusa, and the Loggia dei Lanzi with additional treasures you can admire up close without paying a euro.
Ponte Vecchio: Florence’s Most Interesting Bridge
See the iconic medieval bridge with its unique shops built directly into the structure, but be prepared for serious crowds.
The smart approach is walking along the Arno River on both sides for spectacular views from different angles, then doing a quick walk across to experience it firsthand before escaping the tourist traffic.
The Famous Florence Wine Windows
Discover the historic “buchette del vino” dating back to the 17th century, where noble families sold wine through small openings in their palazzos.
Visit places like Buchetta del Vino di Babae for the magical experience of ordering through a tiny window. It feels like stepping back in time and makes for a delightful treasure hunt for wine lovers.
Dinner At Osteria Vecchio Vicolo: Pasta Perfection
End your day at this cozy osteria serving some of the most incredible pasta in Italy, with perfect al dente texture and rich, authentic flavors.
The intimate atmosphere and generous portions create the perfect ending to your Florence adventure after hours of walking and exploring.
Watch The Sunset: The Perfect Florence Finale
Choose between two fantastic sunset options: the 25-minute uphill walk to Piazzale Michelangelo for spectacular panoramic views of the entire city, or reserve a table at a rooftop bar like The Divina Terrazza for cocktails with Duomo views.
Both offer magical ways to end your Florence adventure with unforgettable memories.
Kid-friendly Options In Florence
- Keep kids happy with authentic gelato from La Gelatiera or Sbrino. It’s a cultural requirement!
- Try vintage photo booth fun at Foto Automatica locations for silly family memories.
- Book a hands-on cooking class for pasta and gelato that teaches authentic techniques.
- Take rides on the vintage carousel in Piazza della Repubblica for pure joy.
- Explore the peaceful Bardini Gardens when kids need space to run.
- End with enchanting sunset boat rides along the Arno River that offer a unique perspective of the city’s landmarks.
Day 7 – Tuscany Itinerary
Day 7 of this 7-day Tuscany itinerary gives you the perfect choice: continue exploring Florence’s endless treasures or take a delightful day trip to the charming city of Arezzo.
Reservations – Day 7
- Train to Arezzo
- Florence links in Day 6 reservation list
Option 1: Day Trip To Arezzo
If you’d like to experience another small town in Tuscany, Arezzo makes a fantastic day trip from Florence. It’s only about an hour away by train or car, making it perfectly accessible for a relaxed day of exploration.
This charming city showcases everything magical about Tuscany without the overwhelming crowds of Florence.
Arezzo seamlessly weaves together stunning Renaissance masterpieces, perfectly preserved medieval architecture, and that authentic local culture you’ve been craving.
Unlike Florence’s tourist-heavy atmosphere, Arezzo lets you experience genuine Tuscan town life at a comfortable pace while still treating you to world-class art and fascinating historical treasures.
You’ll love wandering streets where locals actually live and work, creating that authentic Italian experience many travelers dream about.
Top Things to Do in Arezzo:
- Basilica de San Francesco – Marvel at Piero della Francesca’s world-famous frescoes
- Piazza Grande – Explore this stunning sloped medieval square with unique architecture
- Monthly Antique Market – Browse treasures on the first weekend of each month
- Fortezza Medicea – Climb up for breathtaking panoramic countryside views
- Historic Center – Stroll through enchanting medieval streets at your own pace
- Clock Tower – Ascend to the top for spectacular views over Arezzo’s rooftops
Option 2: Continue Exploring Florence
Since there’s so much to see and do in Florence, sticking around and continuing your exploration of the places you missed the previous day is also a fantastic option.
You could revisit favorite spots, dive deeper into museums you rushed through, discover new neighborhoods, or simply enjoy a more leisurely pace without the pressure of covering major attractions.
Choose what suits your travel style best and make the most of your last day in Tuscany.
Whether you’re drawn to the authentic charm of Arezzo or want to savor more time in Renaissance Florence, both choices will create beautiful memories to cap off your incredible week in one of Italy’s most magical regions.
Conclusion
This 7-day Tuscany itinerary takes you through the very best of what this incredible region has to offer, from iconic leaning towers and medieval hilltop villages to world-class art and unforgettable wine tastings. You’ll have experienced the perfect blend of must-see attractions and authentic local culture that makes Tuscany so special.
Whether you’re cycling ancient walls in Lucca, climbing towers in San Gimignano, or getting lost in Florence’s Renaissance streets, each day brings new discoveries and magical moments. The beauty of this Tuscany itinerary is that it gives you a taste of everything while still allowing time to slow down and savor that relaxed Italian pace of life.
Tuscany has a way of capturing hearts, and I have no doubt you’ll already be planning your return visit before you even leave. Buon viaggio!
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