This one week in Tuscany, Italy Itinerary gives you a day-by-day guide to experiencing a magical getaway week in the countryside. This guide covers everything you need, from where to stay and how to get there to all the must-see towns including Pienza, Montepulciano, San Gimignano, and more! Tuscany is truly a dream! Picture rolling hills, vineyards stretching endlessly, and adorable villages that feel like they’re from a fairy tale. It’s the perfect getaway to savor mouthwatering Italian food, soak up stunning views, and dive into rich history.
This trip has been four years in the making for my family (I know, right)?!, all to celebrate my parents 40th wedding anniversary. We had the most unforgettable week exploring Tuscany, with everyone splitting off (25 of us total) for individual adventures before coming together for cozy dinners. After tons of research and planning, we’ve crafted the perfect itinerary to help you make your own Tuscan dreams come true!
7 Days in Tuscany, Italy Itinerary at a Glance:
*You can click each bullet to take you to the desired day itinerary in post!*
- Day 1: Arrivals, Hotel Dinner, Hot Springs
- Day 2: Pool, Pienza, Wine Tasting & Dinner Celebration at Hotel
- Day 3: Truffle Hunt, Siena, San Gimignano
- Day 4: Monteriggioni, Chianti, Pienza
- Day 5: San Quirico d’Orcia, Poggio Wine Tasting, Pici Pasta Making Class
- Day 6: Horseback Riding, Montepulciano, Communal Dinner
- Day 7: Tornesi Brunello Tasting, Castiglion del Bosco, Montalcino
- Day 8: Departures
Day 1: Arrivals, Hotel Dinner, Hot Springs
Arrive in Italy, and make your way to Tuscany! There is no airport in Tuscany itself, so you will have to fly into another city in Italy (we flew into Rome International Airport, another popular option is Florence) then get a rental car to drive into the countryside, took us about 2 and a half hours to our hotel.
I do not recommend visiting Tuscany without a rental car and you can book a rental car here. We chose Hertz after reading that it’s wise to be cautious with cheaper rental companies, as they often add numerous additional charges when returning the vehicle. The return process for the Hertz rental was smooth and easy.
Where to Stay in Tuscany
Stay at La Moscadella for the most enchanting stay in the perfect location in Tuscany. The Isabella Experience was a hidden gem tucked away in the Tuscan countryside close to Pienza. Isabella and the staff went above and beyond to help coordinate activities for our group and provide endless recommendations around the area. Breakfast was included each morning, there was a pool to lounge at, and the coursed dinners were intimate and delicious.
We stayed in the ‘La Vispa’ room which was spacious with the bedroom and living room area and you’re welcomed with snacks and wine set out for you upon arrival. The bathroom was perfection with all modern amenities.
After a long travel day, unwind at the hotel and enjoy dinner at La Moscadella with a delicious coursed meal and the most drool-worthy dessert. How cute are my parents below?! There was a large dining space with open windows to watch the sunset go down with an incredible mountain view.
Optional: Bathing under the stars at the Hotel Posta Marcucci Hot Springs Thermal Spa in Bagno Vignoni. Just a 30 minute drive away from La Moscadella, this is an exclusive bathing experience, held on Fridays and Saturday evenings only (for both guests and visitors) from 8:00 p.m. to 10:45 p.m. The healing thermal water of their two outdoor pools range from a temperature of 82°F to 100°F. You can reserve this experience here. We opted out as we were exhausted from the long travel day and wanted to spend the night catching up with all our extended family and friends!
Day 2: Pool, Pienza, Wine Tasting & Dinner Celebration at Hotel
Enjoy waking up in the Tuscan countryside to the sounds of nature instead of alarms. We loved how our room completely blocked out all the light—perfect for a good night’s sleep! Enjoy the breakfast spread at La Moscadella to fuel up for Day 2 in Tuscany.
La Moscadella Pool
Afterwards, head over to the pool for a morning of relaxation and taking in the sun. Our only complaint was that the pool water was very cold, so we instead laid out by the sun reading our books – rounded up some summer reads here.
Afternoon in Pienza
Drive over to one of our favorite Tuscan towns for the afternoon: Pienza. Stroll around the town and make sure you walk the perimeter of the town at the Punto Panoramico for breathtaking views of the landscape of Val D’Orcia. Pop in for a casual lunch on the terrace at Case Nuove followed by drool-worthy gelato from Buon Gusto Gelateria.
Celebration Dinner at La Moscadella
Head back to your hotel for dinner or explore one of the endless delicious restaurants in the area. As we were a group of 25, this was the one night we asked everyone to plan to dine at La Moscadella to celebrate my parent’s 40th anniversary with them.
It was such a special night for our family! My sisters and I created a photo book (shown below) for everyone to sign, featuring a selection of pictures from every year over the past four decades. We made the photo book through Mixbook, which made it incredibly easy to transfer photos from our phones—the perfect gift for anyone who has it all! We also printed out additional photos from throughout the years to display. While everyone enjoyed the Lutteraia Wine Tasting through La Moscadella before dinner (couldn’t stop raving about it after), my sister, John, and I were busy setting up the surprise display!
Day 3: Truffle Hunt, Siena, San Gimignano
Truffle Hunt
11 AM – 1 PM: Start your morning with a truffle hunt with Nico in another nearby town: Montisi. This was a group tour for 17 of us coordinated through Isabella at La Moscadella and this was easily a highlight of the trip for us. Nico is a professional truffle hunter and it was fascinating hearing him share his family history tracing back 3 generations of truffle hunting, the ruthless competition growing and many people trying to trespass on their land, and the process of training the dogs for hunting.
Truffle Hunting Outfit details here 💙
The experience was definitely more informative vs hunting around as we had anticipated. However we were so captivated learning about Nico’s history and the current state of truffle hunting that it was well worth doing. After hiking through his land for a while, we were able to watch his two dogs go sniff out some truffles! Afterwards, we walked to a table and bench setup for him to serve us homemade wine, homemade truffle spread, AND homemade olive oil. The dream!
If staying at a different hotel, rounding up some alternative options below!
Siena
3 – 4:30 PM: Freshen up at your hotel after the hunt before making the drive into Siena for the late afternoon. Siena is a medieval town famous for their famous Polio race between the ten participating neighborhoods. The city is nestled high on a hill, but there are escalators at the bottom you can take all the way up. Once at the top, it is very walkable. We did find Siena to be the busiest town we explored in Tuscany with it being so close to Florence. Note, John and I split up from the group to have a date afternoon/evening for the two of us!
Our one regret was not getting a tour of the city as there is fascinating history to learn in the city that we did not get to appreciate while wandering around. I would recommend booking this walking tour if you want to do a tour as the timing is perfect – starts at 3PM! This gives you enough time to freshen up after truffle hunting and ensure you arrive in Siena in time for the tour.
If you do not take a tour, make sure to stop by the Piazza del Duomo (explore the gorgeous Siena Cathedral most similar to the famous Duomo in Florence), Piazza del Campo, and the Fontebranda when walking around. There are also a lot of shops you can explore while in Siena! If you do decide to have dinner in Siena, La Taverna di San Giuseppe or Osteria da Divo both look incredible!
San Gimignano
5:30-9:30 PM: Continue to drive north towards another charming medieval town: San Gimignano. The drive is about 50 minutes to get there from Siena. Pop into DiVineria for a refreshing charcuterie board and aperol spritz. This hit the spot and was perfect outdoor seating!
Then make your way to the Terrazza of Rocca of Montestaffoli for some stunning panoramic views of the countryside. This is the most picturesque area we were in awe of the views and couldn’t stop taking photos!
San Gimignano outfit details 🧡
Make your way to Gelateria Dondoli for some of the best gelato in the world. They’ve received the world champion award many times and are known for a unique spin on flavors such as Saffron, Rosemary, and Pine Nut gelato. Note there was a line when we first walked by, but we were able to try later upon return when the line died down! It was delicious but please don’t waste an afternoon waiting an hour in line for gelato – there are so many other delicious places to try if they are packed.
Make your way to the perfect restaurant to end the night Le Vecchie Mura. This restaurant is all outdoors with panoramic views of the countryside. We did not make a reservation so put our name in while waiting on the benches with a spritz in hand. The wait wasn’t too bad and we enjoyed a spritz in hand watching the sunset while we waited for a table to open. This was the most perfect, romantic way to end Day 3 in Tuscany!
The drive home was our longest at an hour and a half, so please drink responsibly to ensure you arrive home safely!
Day 4: Monteriggioni, Chianti, Pienza
11:30-3 PM: Begin Day 4 in Tuscany by exploring the small, medieval town of Monteriggioni, about an hour drive from La Moscadella. Monteriggioni is famous for its well-preserved walls and picturesque towers that date back to the 13th century. It’s an extremely small town with only a few restaurants and shops total, so you can explore it pretty quickly.
We stopped into a cute restaurant with a garden patio called Ristorante da Remo. The menu featured a variety of homemade pastas, and we couldn’t resist ordering more Aperol spritzes to enjoy with lunch.
After lunch, pay to climb up the tower walls of Monteriggioni, you can’t miss the kiosk to purchase tickets. The views were amazing at the top and worth the trek up.
Chianti
3-5:30 PM: Make your way to another highlight of our week in Tuscany Castello La Leccia. This is located in the gorgeous northern Chianti region famous for their Chianti wine. The grounds and garden were stunning, and this is absolutely a hotel I would want to return to as a guest. You can book a 3 PM tour and wine tasting in advance here or take your chances at getting a spot walking in.
We walked in with no reservation and could’ve done the tasting, but opted out since we had a long drive home. Instead, we ordered a bottle and sat in the garden admiring the views, easily some of the best we had seen yet.
5:30-7:30 PM: Head back to the hotel to freshen up for dinner in Pienza!
Pienza
7:30-9:30 PM: Walk around Pienza admiring the gorgeous views again before headed to dinner. We were recommended to try Ristorante Il Rossellino, however we weren’t blown away by the meal and would not recommend ourselves to try. An alternative option that we wished we had tried instead was right across the street and looked incredible: Sette di Vino! Your hotel can assist in making reservations too.
Two piece set is from boutique in NYC: Mure + Grand 💙
10-11:30 PM: Finish the night with drinks at the coziest cocktail bar: Idyllium. We loved this spot and was gorgeous to watch the stars and moon at nightime over the stunning Val D’Orcia.
Day 5: San Quirico d’Orcia, Poggio Al Vento Wine Tasting, Pici Pasta Class
12-1 PM: Start Day 5 in Tuscany by venturing to the charming village of San Quirico d’Orcia. Nestled in the heart of Val d’Orcia, this picturesque town has a variety of cute shops and inviting streets to explore.
Paula’s red dress ❤️ (top left photo)
Our favorite shop of the entire trip, Corinne di Braconi was here and you have to check it out! We had a blast trying on the cutest dresses and bought some sandals and dresses from here. John also got a gelato from Golosi di Gelato while we shopped and said it was the best he’s ever had!
Poggio al Vento
Continue on to a wine tasting at Farmhouse Poggio al Vento coordinated through La Moscadella. Enjoy a wine tasting at a family owned establishment committed to sustainable and organic practices with breathtaking views of Tuscany behind you. We loved learning about the history of the establishment and how they generate the wine every year. The tasting include light snacks including cheese and bread.
Pici Pasta Class
End the night with a Pici Pasta class at La Moscadella. Isabella’s son, Niccolò, led our group through the art of making “Pici”. He grew up learning how to make the pasta with both his grandmother and mom. It was such a fun and cool experience learning a family passed down recipe and art of making Pici.
Not only was the class one of our favorite experiences, the Tuscan meal following was our favorite meal we had at La Moscadella. The antipasti buffet laid out to start was heavenly and we had a blast getting to try the pici we made afterwards! The tiramisu to end was *chef’s kiss*.
I can’t recommend this Pici Pasta Class and Tuscan Dinner experience enough, but if for some reason you aren’t able to do this, linking some alternative options below!
Day 6: Horseback Riding, Montepulciano, Communal Dinner
10:30-1 PM: Start your morning with a guided horseback ride via Scuola Cantero along the Tuscan trail. La Moscadella also helped coordinate this for us, but you can also try inquiring here. John and I broke off for this to be our date activity and we had a blast. If you are a beginner horseback rider, do not fret, as John and I did not have much experience riding horses and had no issues going through the trails!
Upon arrival, they strap you in and give you some practice laps first teaching you the commands before hitting the trails. John’s horse was giving us a good laugh since it couldn’t stop eating along the trail. 😆
Our tour was located in the Sinalunga region, just northeast of La Moscadella. Make sure you confirm directions before leaving with hotel! We got super lost as we lost service when getting close. We found it eventually but would have saved time had we confirmed before.
If exploring a different Tuscan region, linking some alternative options below or this Horseback Riding Tour with Picnic Tour in Val d’Orcia.
Montepulciano
1-2 PM: Drive over to spend the remainder of the day in Montepulciano. The drive is about 20 minutes from Scuola Cantero. Montepulciano is a charming medieval hilltop town, known for its stunning views and rich history. Wander through its picturesque streets, lined with boutique shops and inviting cafes. Make sure to try the famous Vino Nobile di Montepulciano, a high-quality red wine made primarily from Sangiovese grapes!
2-3:30 PM: As you’re wandering around, pick out a fun spot for lunch, they are so many options! We stumbled upon Osteria del Borgo which had outdoor seating with a beautiful view. As you can see below, it was a bit of an overcast day, so photos don’t do the view justice!
An alternative option to explore is Amoremio which a friend recommended after visiting Tuscany, which also looks incredible! Said to try the cheese and truffle toast 🙂 This is a family owned business which is a great spot to try if looking for a more personalized and authentic experience.
I would also recommend looking into a De’Ricci cellar tour which you can book here. You can
choose your route : 3 or 6 wines 20/25€ upon your arrival at the historic cellar. We were unable to walk in as they were fully booked up when we arrived.
3:30-6 PM: After lunch, enjoy walking through town and make your way over to Enoliteca Consorzio Vino Nobile. They had a large selection of wines for sampling, along with a prepaid card system that allowed us to pour and charge per glass, making it a fun, choose-your-own-adventure experience. While the service wasn’t as personalized as you might find elsewhere, the outdoor patio with a gorgeous view made for a beautiful setting. We truly enjoyed lounging outside with wine in hand and soaking in the good vibes!
Additional Tour Options in Montepulciano
Podere Spedalone
7:30 PM-Midnight: Freshen up at the hotel before driving over to our favorite dinner spot of the entire trip: La Pecora Bianca restaurant at Podere Spedalone. This was an unforgettable night and this is a must do during your week in Tuscany itinerary! We planned for all the kids to do dinner here together, there were 12 of us total. This was a communal dinner so there was a full other side of the table full of other groups.
The experience started with aperitivo on the lawn watching the sunset go down. We were greeted with champagne and they had a full table of appetizers to start the meal. After about an hour and a half, you will be seated at the dinner table for the next courses.
The pasta bolognese was INCREDIBLE. I don’t even eat red meat but knew if I was going to try red meat, it would be at this farm to table restaurant. No regrets, I devoured every bite! They also served the most beautiful desserts pictured bottom right to finish the meal.
We can’t recommend this experience enough, this was easily a top highlight of our week in Tuscany! We also met some really fun groups that were also dining here that night.
Day 7: Tornesi Tasting, Montalcino
11-2 PM: Start your day with a wine tasting and lunch at Azienda Tornesi. This winery specializes in the famous Brunello red wine of Montalcino. The tasting was a full tour and history of the grounds along with apps and a light lunch. The lunch was OK, the wine was easily the highlight of this experience along with the gorgeous views.
Note the sky was not as clear due to Saharan dust that blew in the last couple days leading to an overcast, yellow tinted sky which was a bummer, but the views were still gorgeous nonetheless.
Montalcino
2:30-4 PM: Drive over to explore the nearby town of Montalcino. Montalcino is another charming hilltop town famous for their Brunello wine of the region.
Castiglion del Bosco
4-5:30 PM: We strolled around Montalcino for an hour or so before making a detour to explore the Rosewood Castiglion del Bosco (~25 minute drive). This was our one and only travel fail of our week in Tuscany. 😅 This location was high on my bucket list to explore, however when we arrived, we were unlucky that they closed down the wine tastings early due to a supply issue with a broken gate. Therefore, we turned ourselves right back around. If we were to do this again, we would’ve booked a cheese and wine pairing (details on their site to book) followed by dinner at Ristorante Campo del Drago.
The one thing we did learn from this detour is I have mixed feelings about recommending to stay here. The location was at least 10 minutes driving on a straight gravely dirt road. This was extremely tucked away, so only really worth it if you want to stay here without many detours as was a pain to get out. It felt much more industrialized vs the more charming locations we explored in Tuscany before. The grounds were definitely stunning though!
Montalcino
5:30-7 PM: Head back to Montalcino for dinner. We stumbled upon the coziest restaurant Enoteca Grotta del Brunello. This was a cave like restaurant with an extensive wine selection. I was a bit wined out at this point in the trip (can’t believe it but true!) so opted for a spritz instead! It was a cute spot, nothing mind blowing with the food, but we had a great time.
7-11 PM: Afterwards, we headed back to La Moscadella to enjoy the last night of our unforgettable week in Tuscany to hangout with the family and play games together!
Day 8: Departures
Departures home or onto next chapter of your trip! For me, following our week in Tuscany I went on to spend 5 days in Florence with Paula and our parents followed by a sisters getaway to 4 days in Sardinia. John was a gem and drove our rental car back to Rome airport with another family member for departures home!
Hope this one week in Tuscany, Italy recap helps you plan your magical week away, and I’m always a DM or email away if you have any questions in planning your trip!
xx,
