1 Week Tuscany Itinerary In A Beautiful Villa

Planning the perfect 1 week Tuscany itinerary can feel overwhelming with so many hilltop towns, vineyards, and unforgettable food experiences to choose from. This guide simplifies it all with a thoughtfully paced route based from a countryside villa, blending iconic highlights with slower, immersive moments.

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From wine tastings and truffle hunting to medieval towns like Siena and San Gimignano, this itinerary is designed for travelers who want to experience Tuscany deeply without rushing. Expect practical tips, scenic drives, and memorable local experiences woven into each day.

1 Week Tuscany Itinerary

When it comes to planning out a one-week Tuscany itinerary, there’s no shortage of hilltop towns, vineyard lunches, and postcard-perfect landscapes to fill your days—and then some.

Before we went on our trip, there seemed to be so many possibilities for how to see and, more importantly, enjoy the majesty of Tuscany.

How We Planned Our Trip

The genesis of this trip was, we were looking for somewhere to go to celebrate our 40th birthdays together. There were many ideas proposed but the one that stuck out the most was Tuscany, Italy.

What drew us in was the possibility of:

• Staying in one place the entire time.
• Great food and wine options.
• A slower and more laid back pace.
• Florentine steak.
• Exploring lesser-known places in Tuscany.

Key decisions we made that lead us to creating the itinerary we ended up with:

• Two of us had been to Florence before so it was easier to cut it out.
• Realizing that there were so many small towns to explore, we decided to make that our focus.
• Once we learned about the truffle hunting activity, we built around their times and availability.
• We absolutely loved the idea of staying in a rustic villa, especially the ones we found through Homes & Villas by Marriott Bonvoy.
• The cooking class in our own villa sounded amazing so that became a core part of the itinerary as well.
• Photographer side of me was drawn to so many of the famous locations so I snuck those in as well.

Who Is This Trip For?

In the end, we landed on a week that was not only great as a guys trip but could easily work for couples, a girls trip, families, and even a multi-generational group.

The key is the fact that booking a villa unlocks the ability to accommodate groups of all sizes. In addition, having your own kitchen allows you to buy all of the amazingly fresh ingredients to cook your own meals which is oh-so-Tuscan.

This itinerary is ideal for first-time visitors to Tuscany looking to hit the classics, as well as return travelers who want to slow things down and experience the region at a more relaxed, immersive pace.

As always, feel free to cherry-pick what speaks to you—whether that’s long afternoons by the pool, wine tastings in Chianti, or wandering cobblestone streets—and shape it into a trip that fits your travel style perfectly.

Day 1 – Journey To Tuscan Villa Life

Your first day will be dedicated to flying into Italy, picking up your rental car, and driving into the Chianti region of Tuscany which is where our particular villa was located.

After arriving in Rome in the morning (we took the red eye from Toronto), we picked up our rental car from the airport and set off on the scenic 3-hour drive into Tuscany.

If you’re not rushed for time, we recommend driving the coastal route instead of the main highway, which is only slightly faster. This way, you’ll have a nicer and toll-less view along the way.

While we could’ve driven all the way, we decided to make a quick pitstop in the town of Civitavecchia, which happened to be a big cruise ship port.

I know, this is a controversial decision, but when we stopped in town for a pitstop, the Smoky Gran Crispy McBacon at McDonald’s was something we could get onboard with. We made a quick order to-go and ate it in the beautiful waterfront next to the Michelangelo Fortress.

Sunrise over Montebuoni

That afternoon, we arrived in our villa L’Oliveta at Montebuoni. Turns out, this is your quintessential vineyard hamlet on one of the outstretched arms of the Montebuoni valley. It’s been converted to a cluster of villas, and our particular unit was called L’Oliveta.

To say that this villa is gorgeous is an understatement. While we could’ve easily booked a hotel in Siena or Florence, we wanted this to be a trip where we would have a cozy place to call home.

This location checked off all the boxes:

• Outdoor terrace with a direct view of the Chianti Valley and faces the direction of the sunset.
• Rustic villa space that had all of the amenities we were looking for, full kitchen, and plenty of lounge spaces.
• Idyllic surroundings that really made it feel like an escape.
• Pool access (although it was truthfully too cold in early April).

PRO TIP: Make sure to understand all of the inclusions of the villa. In our case, gas was not included with the rate. Since it was still cold, we were using gas mainly for heating and hot water. On our last day, they checked the meter and we ended up paying €68.

For dinner, we needed to find somewhere close by. Being in rural area of Chianti, not much was open that day but we lucked out in finding Ristorante La Grotta Della Rana just in the village below.

This was a great start to our trip with all of the classics we were salivating over when planning this trip.

Day 2 – Caverns, Picnics, And Cooking Class

Start the day with a light breakfast using the initial supplies provided by the B&B before heading out into the Tuscan countryside to the utterly charming hilltown of Montepulciano.

As your first town, you’ll take in the beauty of the mix of Renaissance and medieval architecture set amidst the picture-postcard Tuscan countryside. What Montepulciano is best known for is its surrounding vineyards and famed Vino Nobile di Montepulciano, which is why you’ll be starting your day with wine.

In Tuscany, wine-o-clock starts early and with the timing of the day, we booked the first Visit The Cathedral experience at De’Ricci Cantine Storiche for 10:30AM.

While there are a few wineries to choose from, this one stood out to us because we wanted to see the historic cellars that are built directly under the city. Dating back to 4th century BC, the De’Ricci family have always been caretakers of the caves and eventually wine cellar underground. This eventually lead to the creation of the Wine Cathedral which is quite impressive to see in person.

Something else you’ll experience and learn about is the equestrian staircase that was built to allow horses to pull the barrels up and down the cellar.

At the end of your tour, you’ll be able to try either 3 or 6 of their wines. In our case, we had their Il Vignone, Nobile di Montepulciano, and Soraldo di Montepulciano paired with cheese, cured meats, and bread.

From there, explore Montepulciano’s historic center, including Piazza Grande and the sweeping panoramic views from tumbling hillside as you wander through.

If you need a pick-me-up, in Piazza Grande is Bar Gelateria Duomo where you can grab some pastries, and espresso of course.

Before fully leaving the town, make sure to put Belvedere di Montepulciano on your GPS. It’s a quick roadside stop but it provides a superb view of where you were just roaming moments ago.

Timed perfectly for lunch, drive to Caseificio Cugusi & Silvana. They are one of the early pioneers of pecorino cheese in the area and is a must-try. Pecorino is something you’ll have quite a lot of on this trip and you’ll come to appreciate the hard Italian cheese made with sheep milk. The specific variety made here is the Pienza pecorino.

At the Cugusi shop, you’ll be able to purchase various award-winning pecorino aged to varying amounts for consumption later and you can also ask them to put together a picnic basket with a wide tasting selection of cheeses and local cured meats.

Technically you need to book the picnic online ahead of time but since it was still low-season in April, we were able to walk in and ask them to make one for us on the spot.

With the picnic basket of goodies that also include a cutting board, cutlery, glasses, napkins, and bread, you can pick one of the tables that have a prime view of the hills of Montepulciano.

For the afternoon, we hastily drove back to our villa because we arranged for a private chef to come over for a Tuscan cooking class with Chef At Home.

When we booked our L’Oliveta at Montebuoni villa, we didn’t want it to just be a place where we slept overnight but somewhere that we could have more as a home.

We ultimately selected Chef At Home and their Tipica Toscana cooking class. By using a mix of supplies available in the kitchen and mostly what they brought in by car, we made:

1. Zucchini fritters
2. Panzanella salad
3. Bruschetta with tomatoes and basil
4. Toast with blue cheese and sausage
5. Fresh egg pasta
6. Meat sauce Ragù
7. Chicken Hunter’s style with salad
8. Tiramisu

They also provided a bottle of Orvieto Classico red wine.

This was an exceptionally fun experience and would highly recommend it if you are renting a villa like we did. In addition to a delicious meal, we learned tangible skills such as making our own pasta from scratch, and how easy it is to make zucchini fritters and tiramisu.

If you’d rather do a class off-site, we highly recommend this Tuscan cooking class in San Gimignano.

Day 3 – Siena’s Historic Streets & Timeless Tuscan Charm

Since we didn’t include Florence in our Tuscany itinerary, the city of Siena is as big as it gets. For day 3, the idea is to spend the full day here, soaking in what has to be one of the most charming medieval cities in Europe that isn’t pretentious and is easy to explore.

After the 45 minute drive (notice how far places are from each other even though they look close), you’ll arrive in Siena. Before you park, we suggest making a quick stop at a Supermercato Famila Ravacciano (Carrefour Market) while you still have your car.

PRO TIP: There are several parking lots we’ve marked on our interactive map. If you can, try to find a spot at Parcheggio Via Fruschelli. We’ve also provided two other options.

Once on foot, make your way to Bar Pasticceria Nannini Posta. This is a typical local cafe in Siena with tons of options for baked goods and espresso to kickstart your day.

Listed as a UNESCO World Heritage Site, Siena is a captivating Tuscan city that feels frozen in time, where Gothic architecture, winding medieval streets, and a rich cultural heritage come together to create an unforgettable travel experience.

The city certainly deserves a full day because every corner reveals layers of history and artistry, while its slower pace and authentic atmosphere offer a refreshing contrast to Italy’s busier destinations.

The morning was spent walking the historic cobblestone streets. What intrigued us first were all of the small shops, grocery stores such as Consorzio Agrario Siena, Torrefazione Fiorella, known for its espresso and cannoli, and Riproduzioni d’Arte Senese for their local artisan ceramics.

On a street lined with restaurants, Osteria Da Trombicche is an authentic Italian restaurant offering traditional homemade Tuscan cuisine.

With our bellies full, we transitioned to the bigger iconic sights in Siena starting with the shell-shaped Piazza del Campo and Palazzo Pubblico with its tower overlooking the city.

PRO TIP: If you enter Palazzo Pubblico, there’s an opening in its courtyard and if you look up, there are some great photography opportunities.

Continue exploring and maybe even having gelato along the way.

Centering on the Siena Cathedral, we made the most of our afternoon with the Opa Si Pass, which is the official admission ticket to get access to almost the entire monumental complex.

Also known as Duomo di Siena in Italian, this cathedral is easily one of the most well known of Gothic and Romanesque cathedrals in the country. Something that you can’t help being drawn to is the striking contrast of black and white.

Using the pass, you’ll be able to see the Siena Cathedral, Libreria Piccolomini, and the atmospheric Cripta beneath the cathedral, and Facciatone for panoramic city views.

Since we had a bit of extra time, we decided to drop off our things at the car since a few of us had purchased souvenirs, and then walk back into the city for dinner.

One of the top restaurants in the city is Taverna di San Giuseppe and when you walk in, you immediately notice its curved stone walls, Etruscan cellar, and numerous historic artifacts, oozing authenticity.

Never having had Bistecca alla Fiorentina before, we jumped head first into an order for the three of us which also included tableside carving. The perfect cut is well browned on the outside and rare inside.

Day 4 – Medieval Towns Of Monteriggioni And San Gimignano

Today will be a retreat into two contrasting medieval towns. One is a perfectly preserved walled city and another is known as “Town of Fine Towers” or “Medieval Manhattan” for its stone skyscrapers.

Being surrounded by so many vineyards in Chianti, you’ll start your day by first heading to one of the top estates in the area, Castello di Ama Winery which just so happens to be in the valley across from us.

When you get to the estate, you get a really good feel for the vastness of the vineyard with hectares of vines and olive groves. They also have an extensive contemporary art and sculpture collection around the property.

For us, we didn’t have time to book a guided tour, so instead we used it as an opportunity to walk into their shop, learn about what makes the terroir special, and sample a few wines.

With the Montebuoni vineyard in direct view of our villa, we had to buy a bottle of their special Montebuoni Chianti Classico Riserva.

Winding through the roads of Chianti, we didn’t plan it this way, but we ended up passing through Castellina in Chianti.

Feeling a tad hungry, we made a stop at Wine Bar La Sosta del Gallo Viandante where we ordered an espresso and a few breakfast cakes to tide us over.

Another 45 minute drive away is the perfectly preserved fortress of Monteriggioni. Perched atop a hill in the Tuscan countryside, the entire village is encircled with stone walls and watch towers like something out of Game of Thrones or Assassin’s Creed.

HOT TIP: There are two parking lots outside of the walls. The closest one requires you to drive all the way in. A heads up that these are paid lots.

When you go, we recommend that you allocate time to walk the city walls. They’ve built modern walkways to help preserve the stones. In addition to the views, it gives you an idea of what soldiers were seeing when trying to defend from sieges.

UPDATE: At the moment, the walkways on the walls are closed until further notice.

As we popped into various boutique shops and wandered the main square, this was another great excuse to have a gelato!

From one of the smallest towns, transition over to San Gimignano, which is really like the Manhattan of the Middle Ages. At one point there were 70 towers, a result of a rivalry between powerful families. Today, only 14 remain.

Coming here though, the towers loom around but you hardly notice them when you’re in the city itself and strolling through places such as Palazzo Comunale, Piazza della Cisterna, getting lost in the small alleyways, and the Parco della Rocca which is an oasis of serenity with its wisteria, breathtaking views, and historic charm.

No judgement for this next item on the itinerary. Make a stop at Gelateria Dondoli—famous for its award-winning gelato. Yes, more gelato. And no, we’re not ashamed.

End the day with a relaxed dinner at Riccapizza. Some reviews have claimed that they have the best pizza in Tuscany. We put it to the test by buying a whole pie to have at a nearby bench.

Piping hot and with the incredible view, the pizza was the perfect finish for the day.

Day 5 – Hunting For Truffles

You’re in for a real treat today. As we started delving into planning of this trip, we realized that there are only a few truffle tourism destinations in the world and Tuscany is one of them.

Start the day with a relaxed breakfast at the villa before heading out for a quick espresso stop at La Dispensa in the town of Fiano, which is just next to where we’re supposed to meet Mattia.

Mattia Nasi is the professional truffle hunter behind Oressea Truffle Hunting. After meeting us at the parking spot he suggested we parked, he drives us to their family’s private property.

Over the next 2 hours, we spent time with Mattia and his two truffle hunting dogs, Ardesia, a springer-spaniel, and Lily, a puppy in training. We started learning about how the business works, the cutthroat nature of it between other hunters, and his sustainable practices he’s using to maintain the land.

Once Mattia opened the gate, the dogs with their ears and tails erect, sprang into action, scampering into the forest. In a way, we were basically following the hunters closely and if they stopped to sniff the undergrowth, Mattia would dig further to uncover the truffle in the soil.

Being in April, white truffle season is over but there were still bianchetto (whiteish) truffles to be found. These don’t necessarily fetch as high of a price but still have intense garlic-forward flavor.

By the end of the experience, we had collected an entire bag full of truffles and to our surprise, Mattia gave the entire haul to us for us to use at the included lunch.

We opted to have lunch included with our truffle hunting and we didn’t have a lot of information about it. Turns out, right near where we parked is Ristorante C’era Una Volta.

Oressea Truffle Hunting partners with them for their experiences and will essentially take that bag of truffles you dug up and use them in a menu designed to allow truffles to take center stage.

With truffles emanating from your body, it’s time to hit the road again. Make your way to the picturesque hamlet of Badia a Passignano.

Surrounded by rolling hills and towering cypresses, there’s something magical about the fortified walls of the castle and corner towers.

The Passignano Abbey provides guided English tours throughout the day, but the timing didn’t quite line up so we ended up walking the San Michele Arcangelo church on our own.

From there, continue to Greve in Chianti, parking at Parcheggio Piazza Resistenza before exploring the town square.

Stop for, you guessed it, a gelato at Gelateria Mordicrema and pick up any essentials at the local COOP for a relaxed evening back at the villa.

For this day, we made it a point to make it back to our villa before sunset. That way, we could enjoy sips of the copious amounts of wine we bought, and enjoy the peaceful Tuscan countryside setting.

With all of the extra truffles from the hunt, it only made sense for us to cook our own dinner. It doesn’t get better than fresh pasta and truffles in Tuscany.

Day 6 – Carne Diem

One of the world’s most famous butchers is located in the unassuming hilltop town of Panzano of Chianti and we made it our mission to incorporate it into our villa-based itinerary.

Skipping breakfast, we made our way to Castello di Brolio, a Middle Ages castle that is now part of the Ricasoli, one of the iconic wineries that we wanted to visit.

The challenge we had was that there were only so many winery tours we could do on our trip and you quickly learn that you have to cluster activities in the same region. This being in Chianti, this was the best way to fit it in. However, none of the tour timings worked for pre or post lunch so we figured we’d try to fit this in from 10-11AM.

In a very Italian way, the front gate didn’t open at 10AM as it was supposed to. We hung around until 10:30AM and decided the timing would be too tight.

In the end, we went back down to the bottom of the hill where you’ll find the Ricasoli wine shop. We ended up picking up some wine, honey, and olive oil.

We first heard about Dario Cecchini from Netflix’s Chef’s Table where he was featured in season 6. Coined “the world’s most famous butcher”, this might be one of the wildest and most memorable meals you’ll have in Tuscany.

With his philosophy of deep respect of animals and putting together menus that use every part of the animal, you can feel the intense reverence when he shouts “Carne Diem!” from the top of his lungs.

Located in his hometown of Panzano in Chianti, his Antica Macelleria Cecchini is a true dedication to meat. To properly experience it, you need to do the Officina Cecchini where a succession of different cuts of grilled beef keeps coming in this communal-style meal.

Meat sweats not withstanding, we came out incredibly full, and incredibly grateful for being able to see this first-hand.

In the afternoon, you’ll be driving through Castellina in Chianti once again. We stopped here to go for a bit of a stroll to walk off some of that feed. On our way out, we couldn’t say no to gelato at Gelateria di Castellina before continuing on toward the Val d’Orcia region.

While a bit out of the way, I really didn’t have a good grasp of where was the best place to photograph Podere Belvedere which is something we had planned for the next day. As a result, I carved some time to detour down to San Quirico d’Orcia so we could scout the area.

Across the street is also Maximus’ house from the movie, “Gladiator” so we snapped a few photos here from behind the gate.

We recommend that you come to get comfortable with where to park, how far to walk along the road to get to the opening that has the best view of the villa. We also tried looking for other viewpoints but ultimately the one you see in the photos was the best in terms of angle and the least amount of obstruction.

The exact location is on our interactive map below.

While it seemed like a long way south from Chianti, we made it worth it by ending the day in Pienza because there is another iconic spot that is also brilliant at sunrise or sunset.

The above is Podere Terrapille, another location used in “Gladiator” where Maximus glides his hands over the tall golden grass.

With the sun dipping to the right, the colors were absolutely incredible. I couldn’t believe my eyes with how perfect this scene was.

Before we left Pienza, we picked up a few more supplies at the Coop for another home-cooked dinner thanks to our abundance of truffles.

Day 7 – Iconic Sunrise

This time of year, sunrise is at 6:37AM so this meant a super early wake-up call since it takes 1 hour and 16-minute drive to get to the Podere Belvedere photography spot.

We left the villa just after 5AM and got to the parking spot at 6:20AM. When we arrived, there were already 8 other photographers all lined up.

We found some empty spots in between and set up to photograph the landscape change with the lighting of the sun.

There is something truly special the way the fog, rolling hills, background of cypress-lined roads, and dancing golden light comes together with the famed villa perched on the hill.

Chapel Vitaleta

Agriturismo Baccoleno

Continue the morning with a series of photo stops. There’s of course the same Maximus’ House across the street if you wanted to see what this looked like in the morning.

Driving along the road, there’s a fantastic view of Chapel Vitaleta from across the valley which we’ve also marked on our map.

Since Pienza is not far away, this makes for a great breakfast stop. In the medieval town, there isn’t much open this early in the morning, but Bar II Casello is great for pastries and coffee.

The photography spot that’s a bit out of the way is the striking cypress-lined driveway at Agriturismo Baccoleno. It’s another one of those famous locations and we managed to squeeze it in before our next activity.

One of the highly rated activities in the area is Podere iI Casale, a family-run organic farm that produces a variety of goods including fruits, vegetables, olive oil, wine, grains, honey, and Pecorino cheese.

One of the experiences they offer is Tasting Tour which includes a tour of the farm, their cheesemaking process, a visit to their goats and sheep, and ends with a cheese and wine tasting.

We particularly enjoyed the sample of deli meats, Pecoronio cheeses of different ages, and amazing wine of course. All of this is with the backdrop of Val d’Orcia behind.

In the afternoon, our photography adventures continued with a stop at the famous Cipressi di San Quirico. It’s a breathtaking view of clusters of cypress trees, isolated in the rolling hills of San Quirico d’Orcia which is why photographers flock here.

We had grand plans to explore another medieval town, Montalcino, but time became an issue after how long it took for us to find parking here. As a result, we took a quick espresso break at Bar Le Terrazze.

The grand finale of the trip is a visit to Podere Le Ripi on the hills near Montalcino, offering a deeper dive into another famous Tuscan wine, the Brunello.

Booking the Wine Tour Terroir for 4PM, we spent the late afternoon learning about their relatively young and fresh take on winemaking in this area, getting a behind-the-scenes look at their vineyard,and architecturally stunning cellar with cathedral as its base and spiral ramp surrounding it.

To end off the tour, you get to taste 5 different wines, which had a distinct difference from others we’ve had so far. We got to try:

• Cappuccetto Rosa – Toscana Rosato IGT
• Attenti al Lupo – Toscana Rosso IGT
• Sogni do Folia – Rosso di Montalcino DOC
• Amore & Magia – Brunello di Montalcino DOCG
• Cielo d’Ulisse – Brunello di Montalcino DOCG

We loved the whimsical art on many of their wine labels!

End the evening with dinner at Vineria Aperta Montalcino, the perfect final night in Tuscany.

Technically there’s an 8th day but it’s largely uneventful, checking out of the villa early in the morning and driving back to Rome before flying back home.

Map Of Tuscany Itinerary

We put together a simple visual guide to help you follow along with this 7-day Tuscany itinerary, from your villa base in Chianti to hilltop towns, wineries, iconic photography viewpoints, and locations to park.

Use this map to plan driving routes, group nearby stops and get a clearer sense of how each day connects across the region.

Where To Stay In Tuscany

Choosing where to stay in Tuscany can shape your entire experience, whether you’re looking for a countryside escape, a charming hilltop town, or easy access to multiple regions.

What Region Should You Choose?

Tuscany covers a massive area and is quite spread out. At its heart is Siena but there’s Val d’Orcia to the southeast, Chianti north of it, and San Gimignano to the northwest.

Learning from our trip, I believe this largely depends on your interests of where you want to focus on. However, if you’re like us and want to see a bit of everything, it ultimately comes down to finding a villa that you love.

The other deciding factor could be whether you’re a photographer or not. One learning we had was that the drive from Chianti to San Quirico d’Orcia for Podere Belvedere is over an hour to catch sunrise so that isn’t as ideal.

The Villa We Chose

Other Villas We Considered

What To Pack For Tuscany

Packing for a week in Tuscany is all about balancing comfort, practicality, and a bit of style for those countryside dinners and hilltop towns. Between cobblestone streets, vineyard walks, early sunrise shoots, and relaxed villa days, you’ll want a mix of versatile pieces that work across different settings without overpacking. Here’s a simple breakdown of what to bring to make the most of your time in Tuscany:

• Comfortable walking shoes – Essential for cobblestone streets, uneven vineyard paths, and long days exploring hilltop towns.
• Light layers (jackets, sweaters, scarves) – Mornings and evenings can be cool, even in warmer months, so layering is key.
• Smart casual outfits – Perfect for winery visits, cooking classes, and dinners out where you’ll want to look a little more put-together.
• Swimwear – Ideal for relaxing at your villa pool or enjoying downtime between day trips.
• Day backpack – Handy for carrying water, snacks, camera gear, and essentials while exploring.
• Reusable water bottle – Great for staying hydrated during long sightseeing days and reducing plastic use.
• Sunscreen & sunglasses – Tuscany sun can be strong, especially when you’re out in open countryside and vineyards.
• Camera or smartphone with good storage – You’ll want plenty of space for landscapes, sunsets, and hilltop views.
• Portable charger – Long driving days and photo-heavy outings can drain your battery quickly.
• Small crossbody bag – Useful for keeping essentials secure while wandering busy towns like Siena or San Gimignano. For the photographers out there, the Peak Design 7L Outdoor Sling with the XS camera cube is perfect for this kind of trip where you don’t want to carry a heavy backpack around.

7 Must-Know Travel Tips In Tuscany

Here are a collection of tips that we made note of during our time in Tuscany that we wish we knew before we went.

1. Speed Cameras – While it isn’t as aggressive as in the UK, there were plenty of pop ups on our app while navigating indicating speed cameras. That said, we are convinced that a lot of them are fake as we couldn’t find them half the time. That said, a good idea to use Google Maps to know when they’re coming.
2. Fuel Up Frequently – This is something we’ve learned over the years but it’s always a good idea to fill up frequently so you never run into a situation where you run out, especially in more rural areas of Tuscany. Detours just to get to a gas station can end up wasting a lot of time.
3. Tipping – Similar to the rest of Europe, we suggest the round-up strategy. This means for most meals, you’re tipping 1 to 2 Euros. For something like the truffle hunting experience, we tipped 5 Euros per person.
4. Coperti – Europe is infamous for their sneaky bread fees. In Italy, you’ll sometimes encounter something called coperti. This is a cover charge which includes not only bread but also table service, linens, tableware, and bread. This isn’t a tip but is a mandatory fee. Unlike in other countries where you can reject the bread to avoid getting charged, that isn’t the case here so you might as well enjoy it.
5. Parking – In larger towns and villages, you’ll notice that there are painted lines on the ground indicating parking spaces. What you need to know is that white lines are free, blue lines are paid, and yellow lines are accessible spots. Another quick tip to find parking on Google Maps is to use the word “parcheggio”.
6. Cash vs. Card – While Italy is a very card-friendly country, there are still many situations where you’ll need cash. For one, many of the experiences we did (i.e. cooking class and truffle hunting) only took cash. Also, while many parking machines accept card, there were random ones that didn’t. Also, if you hope to tip, the credit card machines don’t prompt a tip line which means you have to leave cash on the table.
7. Lots of Driving – The big thing we learned about Tuscany is how spread out everything else. There is also really only the one highway that cuts through. Everything else are windy one-lane roads that twist through the valleys. This is why you really need to plan out your locations each day because the driving will take you longer than you think. The best way to mitigate this is by clustering sights to specific regions or towns instead of constantly going back and forth.

Arrivederci, Tuscany!

Ever since coming back from this trip, I’ve been raving about Tuscany to everyone that will hear it. It may have been under the influence of gelato but I stand by this being an incredible trip, especially as a group or as a couple.

Our villa, L’Oliveta was a dream and being able to do our cooking class from our villa, cook with all of the truffles we got, and hanging out with friends with all the space we had was simply perfection.

The real magic of Tuscany is in slowing down, soaking it all in, drinking lots of wine, and letting the landscape set the pace. I hope you get to experience it as well!

Frequently Asked Questions

This article was sponsored by Homes & Villas By Marriott Bonvoy but all opinions are our own. This was a trip that we personally did before the sponsorship.