7 Day Tuscany Itinerary for an Unforgettable Trip
Tuscany is the kind of place that feels like a dream. Rolling hills bathed in golden light, charming medieval towns, and some of the best food and wine in the world. It’s one of those regions I keep finding myself drawn back to, and after two visits already, I can say with certainty there will be many more.
The first time we visited Tuscany, we did it wrong. What do I mean by that? We booked a packed day trip that rushed us through multiple towns in a single day. It was a great way to get a quick taste of the region, but it left us wanting more time, more flexibility, and more moments to simply slow down and enjoy where we were.
To help make your own trip as seamless as possible, I’ve put together this 7 day Tuscany itinerary highlighting some of our favorite experiences. With Tuscany being such a vast and varied region, it can be overwhelming to figure out where to go and how to get around. This guide is designed to simplify that process, offering a thoughtfully curated mix of iconic sights and countryside charm.
While there are countless ways to explore Tuscany, this itinerary focuses on two key experiences: the cultural heart of Florence and the picturesque beauty of the Tuscan countryside.
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Tuscany Trip Overview
Days 1-3: Florence
Day 4: Siena
Day 5: San Gimignano & Chianti
Day 6: Val d’Orcia, Pienza
Day 7: Montepulciano
Before You Go to Tuscany
Best Time to Visit Tuscany
Spring (April – May):
Rolling hills are lush and green, wildflowers are blooming, and the weather is pleasantly warm without the summer crowds.
Fall (September – October):
Harvest season for grapes and olives, golden light over vineyards, and still-warm temperatures.
I would personally avoid July and August as the temperatures get super hot, the crowds are at maximum, and some small towns close mid-August for summer holidays. Also, note that winter (November-February) has cheaper rates and fewer tourists, but many wineries and accommodations will close.
My top choice for this 7 day Tuscany itinerary would be May and September!
Rental Car vs No Car
Whether or not you need a rental car depends on how you plan to explore Tuscany.
If you’re spending most of your time in Florence and visiting a couple of nearby towns by train, you can get by without a car. Trains connect Florence to places like Pisa easily.
However, if you want to explore the Tuscan countryside, stay at agriturismos, visit small hilltop towns , or stop at scenic viewpoints along the way, renting a car is necessary. Many of Tuscany’s most beautiful spots are not easily accessible by public transportation, and having a car gives you the freedom to explore at your own pace.
Rental Cars: Book with Discover Cars for the best prices – I always choose a trusted company like Hertz, Enterprise, or Sixt within the search results.
Driving in Tuscany is generally straightforward, but there are a few things to keep in mind.
Many historic town centers have restricted traffic zones, known as ZTLs. Entering these areas without permission can result in hefty fines, so always park outside the historic center and walk in.
Roads in the countryside can be narrow and winding, especially between hill towns, so allow extra time for travel and take it slow.
Staying Connected and Covered
Having reliable data and travel coverage will make your trip much smoother, especially if you’re navigating countryside roads or relying on maps.
Using an eSIM allows you to stay connected as soon as you land without needing to find a local SIM card.
✦ ✦ ✦
Days 1-3: Florence (3 Days)
Begin your Tuscan adventure in Florence, the Renaissance capital of the world. Florence is the capital of Tuscany, and while it’s a compact city, it is full of treasures, from world-class museums to romantic viewpoints. It’ the perfect starting point for your dream Tuscany itinerary.
Fly into FLR (Florence Peretola Airport) which is a quick 20 minutes away from the city center.
Assuming that the first day you’ll spend some time flying in, getting settled and recovering from jet-lag, you’ll realistically have 2.5 days in Florence. This will be plenty of time to see the most important landmarks and highlights of the city. Florence is a very walkable city, and you’ll be on foot exploring this city so pack some comfy shoes!
Where to Stay in Florence
Stay in the city center of Florence, and since Florence is a compact, walkable city, you’ll be able to pretty much walk everywhere.
Best hotels in Florence
$$$
Hotel Calimala (My personal favorite boutique hotel)
Hotel La Gemma
Brunelleschi Hotel
Hotel Milu Florence
Soprarno Suites
While in Florence, you can’t miss the Duomo, or the Cathedral of Santa Maria del Fiore. I still remember seeing this church for the first time in person, and I couldn’t believe how beautiful it was. It literally feels like you are stepping into a painting.
Climb the dome of the duomo or alternatively climb Giotto Tower, the bell tower of the Duomo for panoramic views of the city. I chose to go up the bell tower to see the Duomo’s dome (which you can’t see if you’re standing on it).
Walk through Piazza della Repubblica, Piazza della Signoria, and see Palazzo Vecchio.
Grab a sandwich from the famous All’antico Vinaio for lunch, book a spot for the Uffizi Gallery and in the evening stroll by the Ponte Vecchio, an ancient medieval bridge that spans across Arno River.
Don’t forget to try Bistecca Alla Fiorentina or the Florentine steak, and grab some gelato from Gelateria dei Neri or Gelateria La Carraia.
Book tickets to the Accademia to see Michelangelo’s David, check out the Basilica of Santa Maria Novella and Officina Profumo Farmaceutica di Santa Maria Novella, the world’s oldest pharmacy that now has become a perfumery brand.
Grab lunch from Mercato Centrale and walk through its outdoor leather markets.
Head to the Pitti Palace and its Boboli Gardens for a peaceful afternoon, and finish the day with another great Tuscan meal.
One of my favorite memories from Florence is watching the sunset from Piazzale Michelangelo, so if you have time, I recommend grabbing a bottle of wine to go from a local store and heading here for one of the most beautiful sunset scenes.
This covers the main attractions in Florence.
Click Here’s my full travel guide on Florence with locations on a Google Map.
Day 4: Siena (1 Day)
Pick up Rental Car
In Florence you were better off without a car, but this all changes once you leave this city. Although the next few cities (Siena and San Gimignano) are connected by buses, I would highly recommend having a car once you leave Florence for the rest of this Tuscany itinerary.
I recommend using Discovercars to search for the best rental car deals.
Driving allows you to stop at picturesque spots to admire the beauty of Tuscany, and some of the smaller towns that don’t have public transportation. Most of the Tuscany towns will have ZTL, or restricted traffic zones so you won’t be able to drive inside the city walls. However they do have parking lots on the edges of town, so you can easily park and walk into the city or town to explore.
Let’s start the Tuscany road trip. On the morning of your 4th day, pick up a rental car from Santa Maria Novella Train Station, and head to Siena, the medieval city known for its shell-shaped piazza and the Palio horse race.
The drive is about 1 hour, and it’s an easy drive. To find parking in this city, I would simply search “Siena Parking” in Google Maps and look for one of the red P signs.
Siena makes a great base for the next 2 days of this itinerary.
Best Hotels in and Near Siena
Inside the city center:
Residenza d’Epoca Campo Regio Relais
Palazzo Lenzi
Casa Ciseri
Villa del Sole Siena
Grand Hotel Continental Siena
Luxury Tuscan Countryside Hotels near Siena:
Borgo San Felice – located in the Chianti countryside, this luxurious 5 star hotel has elements that are exactly quintessential Tuscany and produces its own wine.
Hotel Le Fontanelle – this dreamy hotel has rooms with beamed ceilings and terracotta floors, and views of rolling hills of Chianti vineyards and valleys.
Borgo Santo Pietro – the ultimate Tuscan dream in a 13th century villa. This is a bucket list hotel for me.
Spend the day in medieval Siena. Grab a cappuccino or lunch by the Piazza del Campo, visit the Palazzo Pubblico which houses the Civic Museum, and maybe even climb the Torre del Mangia tower for some incredible views.
You’ll definitely want to visit the Siena Cathedral and marvel at the intricate facade as well as the interiors of the beautiful cathedral.
Twice a year, the city’s legendary horse race Palio di Siena takes place on July 2 and August 16.
I also have a guide on Siena with more recommendations here.
Day 5: San Gimignano + Chianti (1 day)
On the 5th morning of this 7-day Tuscany itinerary, take your car and drive to San Gimignano, about 45 minutes away. This hilltop town is known for its medieval towers, and is recognized as a UNESCO World Heritage Site.
There were once about 72 towers in the city representing wealthy and powerful families, but currently there are 14 towers including the Torre Grossa, the tallest tower.
I loved walking through the narrow streets and checking out local shops along the streets. Also, you can’t leave San Gimignano without having a gelato at the Gelateria Dondoli that won a world championship. You’ll probably find a long line out the door of the gelato shop, but don’t worry it moves quite quickly. On our first visit to San Gimignano it rained, and even rain couldn’t stop the cravings for gelato!
After spending some time strolling around San Gimignano, head into the heart of the Chianti region. With over 300 wineries dotted across the Chianti Classico area, you’ll be spoiled for choice. This is, after all, the land where the very name Chianti instantly brings up images of rolling vineyards and bold reds.
Visiting a winery is one of the best things to do in Chianti. We visited a winery that served hearty pasta with a wine tasting.
You could research and book wine tours yourself, or you can join one of these tours as a group.
Come back to your base near Siena and spend the night.
After visiting Siena, San Gimignano and the Chianti wine region, you’ll head south into the Val d’Orcia for the next part of your Tuscany itinerary. Val d’Orcia is the iconic rolling hills dotted with cypress trees, olive groves and beautiful scenery everywhere you look.
I recommend finding an agriturismo, or a farm stay type of accommodation in this region. This is truly an experience in itself. See below for some hotel options for the next 2 nights of your Tuscany 7 day itinerary.
Beautiful Hotels in Tuscany
There are TONS of charming agriturismos (farm stays) in Tuscany. Here are a few that I found attractive. Unlike large hotels, these hotels usually have just a few rooms so they tend to book up very quickly in high season.
For this itinerary, we will spend the next two days near Montepulciano, so it would be best to select your home base around here. This is where your ideal Tuscany dreams unfold to life! Olive groves, cypress trees, dreamy pools… these hotels are photographs turned into life and absolutely bucket list worthy.
Villa Poggiano – a family run, beautifully-decorated place that makes you feel right at home.
Precise Tale Poggio Alla Sala – on classically gorgeous Tuscan countryside grounds (cypresses, vines, olive trees…) with a spa and homemade pastas and pizzas.
Relais Villa Grazianella – a 17th century villa with a pool overlooking the olive groves and vineyards of Tuscany.
Poggio Piglia – charming Tuscan style rooms with wood-beamed ceilings, natural stone walls and hardwood floors.
Borgo San Vincenzo – hotel with all the Tuscan charms and also modern touches.
Rosewood Castiglion del Bosco – ultimately lavish rustic-chic, located on a sprawling Tuscan estate with a Brunello di Montalcino winery and an 18-hole golf course.
Lupaia – located on a hilltop overlooking Montepulciano, this hotel is in a converted stone farmhouse that you’d never want to leave.
Day 6: Pienza + Val d’orcia (1 day)
On day 6 of this 7 day Tuscany itinerary, depart Siena and drive towards Pienza. The drive is just over an hour, and incredibly scenic as you approach Pienza. You are now in Val d’Orcia, a UNESCO World Heritage Site and truly the postcard Tuscany.
SP146 is a scenic road that gives you panoramic views. Feel free to stop at any point to admire the rolling hills of Tuscany.
When you arrive in Pienza, park at one of the parking lot on the edge of the city. Pienza is a small village, but incredible charming. It’s a fairytale town that captures the essence of Renaissance beauty and rural tranquility. While its neighboring towns are more known for their prestigious wines, Pienza is famous for its Pecorino cheese, a hard cheese made of sheep’s milk. Make sure to sample some at a local store! It doesn’t take more than a couple hours to see this village.
Walk around Piazza Pio II, the central square of Pienza surrounded by historic buildings, cafe and shops with a picturesque fountain in the center. You can tour the Cathedral of Santa Maria Assent or visit Palazzo Piccolomini, a Renaissance palace built by Pope Pius II, with elegant architecture and a serene courtyard with panoramic views of Tuscany.
Visit local cheese shops and sample the famous pecorino cheese in various flavors and ages. You could even book a dairy farm tour.
Take it slow, have lunch at a local trattoria, and head to the edge of town and walk along the town walls that gives you breathtaking views of Val d’Orcia countryside.
After touring Pienza, drive to your dreamy countryside hotel, villa, or agriturismo and check in. This was part of the trip I had looked forward to so much, so we decided to stay in and simply enjoy the hotel and relax at the pool. We chose to dine at the hotel with the sun setting over Tuscan rolling hills, and this was one of the most memorable dinners of our trip.
Day 7: Montepulciano (1 day)
On the last day of the trip, you’ll be visiting the legendary wine town of Montepulciano, known for Vino Nobile. The other famous town for wines is Montalcino (home of Brunello) and while you can try to squeeze these two in one day, Montepulciano is a larger town, so you could easily spend the entire day here.
Taste the rich reds, explore the cobblestone streets, and soak in those last golden Tuscan hills as your trip comes to an end.
Stroll around Piazza Grande, located at the highest point in town and surrounded by Renaissance buildings, shops and cafes. Check out the Cathedral of Santa Maria Assunta which is on the souther side of the piazza, and the Palazzo Comunale or the Town Hall where you can climb it for panoramic views. However, Montepulciano is on a hill and you can get breathtaking views of Tuscany even without climbing if you head to the walls.
There are tons of places to sample wine in Montepulciano. Make sure to research ahead of time to find one that suits your preferences, and book a tasting in advance as it can get busy.
Cantina de’ Ricci: Located in Palazzo Ricci, a Renaissance palace with an impressive underground wine cellar.
Cantina Contucci: One of the oldest wineries in Montepulciano, established in the 16th century.
Azienda Agricola Ercolani: Features informative tours and generous tastings.
On our last evening we again admired the beautiful views of Tuscany from our hotel. After your journey through the Tuscan countryside, you can drive 2 hours to Rome and drop off the car rental, and head back home. We did stay a few days in Rome to see the Trevi Fountain and the Colosseum, but that will be in a separate post as this is a 7 day Tuscany itinerary that focuses on Tuscany.
Final Thoughts
There you have it. You just spent an incredible one week in Tuscany, experiencing the Renaissance charm of Florence, the medieval magic of Siena and San Gimignano, and the rolling hills and wine country of Val d’Orcia, Pienza, and Montepulciano.
I hope this 7 day Tuscany itinerary is helpful for planning your trip to Tuscany, a region I hold dear in my heart and one I truly believe everyone should experience at least once. As always, feel free to adjust the itinerary to match your pace and preferences.
If you have more time, consider adding a few days in Cinque Terre (easily reachable by train from Florence) or wrapping up your journey with 3–4 days in Rome.
Check out my other Italy Travel Guides for more inspiration and planning tips!
USE MY CHECKLIST TO PLAN YOUR TRIP!
- Flights
- Search for the best flights on Skyscanner to get to your destination
- Search for the best flights on Skyscanner to get to your destination
- Hotels
- I use Booking.com for most accommodations
- For Asia, I prefer Agoda as they have the most competitive prices. I also compare prices on Klook (you can use my code MINYWANDER for a discount so see if that’s a better deal)
- For vacation rentals, especially for larger families, consider VRBO
- Transportation
- Trains & Ferries – book on Omio
- Rental Cars – I usually book on DiscoverCars
- For reliable airport pickups, use Welcome Pickups
- For Asia I use Klook (code MINYWANDER for a discount) – Japan trains for example
- Activities & Tours
- GetYourGuide and Viator are my go to’s.
- For Asia, I prefer Klook as there are more options – use code MINYWANDER
- E-sim
- Stay connected with Airalo E-sims.
Check out my other Italy posts!
-
One Day in Venice Itinerary You’ll Want to Steal
-
7 Day Tuscany Itinerary for an Unforgettable Trip
-
Siena, Italy: Perfect Mini Travel Guide
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Ultimate Florence Travel Guide: Best Things to Do, Where to Stay and Day Trips (2025)
-
The Ultimate Cinque Terre Guide
-
Ultimate Venice Travel Guide: 13 Best Things to do in Venice and Where to Stay
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