Tuscany Road Trip For Couples (w/video)

2 Traveling Lovers

Driving through Tuscany has been one of those things I wanted to do my whole life, especially after seeing Under The Tuscan Sun many years ago. Not only did I love the movie, but it gave me a vision of what it would be like to live in a quaint Tuscan village which looked so appealing, especially during that time of my life.  We found the most scenic drive through the must-see towns, along with the less traveled quaint villages throughout Tuscany.  Here is what we learned during our “Tuscany Road Trip For Couples”.

Now years later, Joel and I were able to visit this area during our world travel journey, and we both absolutely fell in love with the Tuscany region. The rich beauty of Tuscany with its diverse countryside and colorful tapestries left us speechless at first glance. Everywhere we looked resembled a magnificent painting like nothing we’d witnessed before. It’s genuinely one of the most beautiful places on earth.

We spent a month in Italy during June of 2019, starting in southern Italy, visiting Sorrento, Amalfi coast, Pompeii, Rome, and then driving through and staying in Tuscany, before leaving for Cinque Terre in the Liguria region and finally ending in Venice.
This post will show you what you can expect when driving from Rome, through Tuscany while stopping along the way at wineries and to visit small towns. We will detail the towns we visited, along with the wineries, monuments, attractions, and give final recommendations so you will know if a road trip through Tuscany should be on your bucket list.


  • Should You Rent A Car In Rome?
  • Driving Through Pienza, Montalcino, Siena
  • What To Expect When Staying In Gambassi Terme
  • Day Trips From Gambassi Terme
  • Things Not To Miss In Volterra
  • San Gimignano & Wine Tour &Tasting
  • More Wine Tours & Tastings
  • Why Stay In Chiesina Uzzanese Province of Pistoia
  • The Montecarlo Wine Region

Should You Rent A Car In Rome?
First off, if you will be departing from Rome, make sure you rent the car after your stay in Rome. I wouldn’t wish driving around Rome on my worst enemy. I have never seen so many crazy drivers and stand still traffic for what seemed like hours (and I’m used to driving in Southern California). We suggest taking the bus or better yet the train system as your mode of transportation around Rome.

Also, try to stay in accommodations as close to the city center as you can afford, it will save on transportation costs (which add up quickly), and aggravation while sitting on buses trying to get around the city. We stayed in the northern end of Rome (still in the circle), and to be honest, it was too far from the main tourist sights.

For example, the day we toured the Vatican it took us 2 hours on the bus to go 12 km because of the traffic, much of the ride was a standstill. In hindsight, we should’ve taken the train, it’s roughly the same cost, and it’s faster or better, yet we should’ve stayed closer to the center. But this is what we’re here for right? To be honest about our mistakes, and to tell you through firsthand experience a better option. If you are staying in the city center, the best way to get around is on foot.


Pienza, Montalcino & Siena

Now, back on our topic, “Tuscany Road Trip For Couples”. Like I said if at all possible, avoid renting a car until the day you plan to leave Rome. We picked a rental car location at the northernmost point of Rome. It was very close to the freeway so we could get out of town without having to drive through any part of the downtown area. We are dividing our week-long accommodations between 2 regions of Tuscany, to maximize the number of towns we can visit during our stay.

Driving Through Pienza, Montalcino, Siena

Our first stop after leaving Rome was Pienza, although we stopped many times along the road because of the spectacular photo opportunities. Make sure you allow plenty of time for the drive to your Airbnb or hotel because you may not get a chance to drive back to these towns after you reach your final destination for the day. It was during this drive when I had my first feeling that we may not have allowed ourselves enough time to experience the initial trip to our first accommodation. It seemed as if each village we drove through had a story to tell, and we wanted to stay longer. There was the feeling of so much to see, yet so little time.

Pienza is a darling town with 15th-century medieval buildings and long narrow stone pathways. We walked through the main square, which leads to Piazza Pio II, and Duomo while enjoying the beautiful views of the countryside through the narrow streets. It’s a beautiful place to stop along the way for a bite to eat and a beer in the square. Many of the local shops have fresh cheese and local Italian wine for sale and to taste.

Our next stop was Montalcino, a 15th-century beautiful village located on a hilltop just south of Siena. While walking around the town, we had the sense of being in a medieval castle within a stone fortress. Montalcino is famous for its wine and primarily known for its Brunello. We stopped at Enoteca di Piazza to sample the Brunello red wine. The town is within the Val d’Orcia National Park which offers picturesque scenery of rolling hills, olive groves, manicured vineyards, and ancient oak trees. The calmness and serenity in this town were palatable from the moment we arrived.

We loved Siena, and if we had it to do over again, we would have planned a more extended stay in this enchanting city, or probably spent a night or two. We thought it would be a crowded big city and it was more of a quaint medieval village (at least in the main square area) with narrow streets lined with homes and shops. We thought Siena was one of the most beautiful towns so far, with its gorgeous architecture, panoramic views of the countryside, beautiful churches, and monuments. We would definitely return to Siena for a more extended stay next time we visit Tuscany.

  • Piazza del Campo
    Our first stop in Siena was the main square Piazza del Campo, where you will find many cafes, shops, restaurants, and monuments such as the Palazzo Pubblico. The city center has been declared a UNESCO World Heritage Site. The city has many museums and galleries to visit, along with admiring the magnificent architecture of the Palazzo Pubblico and the Torre del Mangia. The Cathedral of Santa Maria Assunta with its magnificent interior and exterior designs is worth a visit.

TIP: We didn’t stay for dinner, but a restaurant was highly recommended by a local for an exquisite dinner, especially if you love truffles. It’s called Restorante Tar-Tufo (Siena), Via del Sole, 6a, 53100 Siena SI, Italy. If anyone tries it, let us know as we were sad to miss it after hearing the fantastic reviews.

Gambassi Terme

What To Expect When Staying In Gambassi Terme

Our final destination for the day was our Airbnb destination city, Gambassi Terme. We choose this town as the first of our two accommodation locations in Tuscany because of its proximity to many sights in the southern to mid-Tuscany region. I have to say this town took us by surprise. We loved the small-town, quaint vibe of this town. In the evenings, many of the locals and tourists would gather outside in the main square for drinks, chatter, antipasti, and Cicchetti (Italian tapas). It seems like such a friendly town where everyone knew everyone — such a different feeling for us.

Our Airbnb
Our Airbnb was in an ancient, yet renovated building on the second floor and although we loved it and our host was quite nice. Oh, we had a few issues at this one. We wanted to love it; the inside was nicely decorated, it had a functional kitchen, spacious living room a good-sized bedroom, even a washing machine and like I said we loved the town.

Unfortunately, the internet didn’t work at all, which is a huge inconvenience for us considering travel writing and video is our fulltime job, so that was a huge negative. The second issue was the water pressure was next to nil, to the point that you couldn’t even wash your hair. Oh, and did I mention there was no hot water or what little we had only lasted 30 seconds. Needless to say, I was unable to wash my hair during the time that we stayed at this location (luckily only 3 nights). I want to recommend it, and if it weren’t for those two issues, which are significant, I would recommend this place to stay. BTW he had great reviews, and he confirmed with me a week before that he had an excellent internet connection. He told us when we arrived, the internet was down and would be down for our entire stay. UGGG

*** Note – When Staying In Airbnb’s
At times, we have found it’s riskier choosing Airbnb’s over hotels. When using a hotel, they can typically move you to another room or transfer you to a different hotel. This situation can be a bit more complicated when staying in an Airbnb with problems. When something goes wrong at your Airbnb, you have a third party that you have to go through to try to rectify the situation, but it can take longer, and you never know which side the Airbnb company will side with. It’s not like a hotel relationship as in “the customer is always right” mentality. In regards to the Airbnb’s position, both the renter and host are their customer’s.

Sometimes finding a new Airbnb in your desired location may not always be possible. So if your host is unable to fix the problem while you’re there and Airbnb can’t find you comparable accommodations you might be out of luck. Luckily this was not one of our week or month long stays, and we could deal with three nights of no hot water and no internet. However, if you only had a week in Italy, it would be awful to have this happen and it would most likely ruin your vacation. If you are interested in checking out Airbnb prices. Click here. You will receive a $40 travel credit after your first booking.

Are you interested in checking Hotel, Bed & Breakfast, or Villa accommodations prices in Tuscany?  Click here for our booking.com direct link.

Disclosure:  This post contains affiliate links where a small commission is received for the sale of products linked at no additional cost to you.  We only partner or promote brands and products that we believe in or have tried ourselves.  Thank you for your support. 🙂

Day Trips From Gambassi Terme
While staying in Gambassi Terme we took a few day trips, the first day was to the south, and then the second day we went to the north and eastern region of Tuscany. During this time, we visited several towns and wineries, and we documented our time in each place.

At many of the wineries, we were able to partake in a tour and tasting in addition to enjoying the grounds while getting fantastic drone footage. We think the drone footage videos we took during our time in Tuscany is some of the best that we’ve ever made. The scenery was so amazing that it didn’t take much to take fantastic pictures and video.

Many of the wineries are 4th and 5th generation wineries, and you could certainly tell the passion of the owners and workers at the wineries we chose as our top choices for Tuscan small town wineries. In most instances, it was evident they loved what they did and took great care in the product they were producing.

*** Coming soon: If you’re interested in reading specific details of each winery, we are working on the post, and we will add a link soon. In that article, we will give you a rundown of the wineries we considered our favorites during our time in Tuscany. Be sure to subscribe to 2travelinglovers.com so you won’t miss it. Subscribe here.

Things Not To Miss In Volterra

Volterra is a walled medieval town which is approximately 40 minutes southwest at Gambassi Terme. It’s known for its expansive views, medieval frescoes, and of course because of their Etruscan origins due to the numerous remains found in the area. In the 4th Century, BC the Romans built 7,300 meter long stone walls to protect the town from invaders. It was impressive to see and walk through the town. There are many Roman remains from which to visit that date back to the 1st Century, such as The Roman Theater.

The day we visited Volterra, “The Volterra Mistery, and Fantasy” event was in full swing. This year’s theme was the Gothic World and The Vampires. Many young people from the nearby towns dressed up and performed for the event. It was great fun to watch and get pictures and videos of the day. Their costumes were really impressive, and we had a great time sitting at one of the cafe patios while watching the portrayal of the Gothic World fantasy.

A few things not to miss in Volterra are:

1. Visit the Roman Theater
The Roman theater built in the first century AD, is located just outside the city walls. Its hours of operation are from March through November. If you are visiting during the winter, you can see it from the terrace within the walled city.

 2. Visit Piazza Dei Priori
Piazza Dei Priori built in the 13th century, and it’s the oldest Tower in Tuscany.

3. Visit the Duomo (Cathedral of Volterra)
The Duomo dates back to 1120, and the ceiling is spectacular and well worth a visit.

4. Visit Museo Etrusco Guarnacci

If you have an interest in history and enjoy tombs, this is an excellent museum for you to visit. There are many Etruscan artifacts on display, some of which include tombs, vases, coins, and ceramics with many dating back to the 4th century BC.

Tuscany Road Trip

Here is a video that shows our Tuscany Road Trip and the fun we had!

San Gimignano & Wine Tour &Tasting

Our first stop of the day was San Gimignano, a hilltop town approximately 30 minutes southeast of Gambassi Terme. It’s a small medieval town encircled by 13th-century walls. It’s known as the “Town of Fine Towers” or “The City Of Beautiful Towers,” and it’s famous for its magnificent skyline and medieval architecture. The historic center of San Gimignano is considered a “UNESCO World Heritage Site.”

San Gimignano was the first place we tried Vernaccia di San Gimignano wine, which is made from the variety of Vernaccia grapes grown on the hillsides in this area. It was great fun walking down these long narrow streets peeking in the boutiques and shops. We highly recommend stopping in this town even if just for a few hours.

A not-to-be-missed site in San Gimignano:

1. Duomo di San Gimignano
Duomo di San Gimignano is a 12th-century church in the historical city center of town, and it’s known for its frescoes which were completed by some of Tuscany’s most famous artists. As you walk through, you can’t help but be impressed and marvel at the beautiful architecture and displays of ancient art.

As with many of these attractions, be sure and check the hours before going because many have limited hours or may be closed during the winter months. All in all, San Gimignano is a busier town than some of the other Tuscan towns we have visited, there’re lots of shops, and there’s plenty of parking on the outskirts of town.

More Wine Tours & Tastings

1. Azienda Agricola San Quirico

Azienda Agricola San Quirico is a 10-minute drive northwest of San Gimignano. We didn’t have a reservation; however, they were kind enough to include us in an upcoming tour for us to collaborate with them by sharing our experience at their winery with our readers.

We went on a fantastic tour of their facilities, explaining every aspect of the winemaking process. Following the tour, we were able to taste their wines, and we have to say not only was the tour fantastic, but the wines were excellent too. The video in this post shows the tour, along with others during our time in the Tuscany region.

2. Villa Pillo
Villa Pillo is 10 minutes north of Gambassi Terme. Villa Pillo is a traditional Tuscan farm winery founded in medieval times. It’s located in the heart of the Chianti area not far from Pisa, Florence, and Siena. One of the reasons we love this winery was the time Megan, the employee spent with us. She spent a great deal of time explaining the region, the winery and even took us down to the wine cellar from the mid-1700s.

3. Valvirginio
Valvirginio Is a short 2-minute drive north of Villa Pillo. It’s a cooperative Tuscan Winery with its production center in the valley by the river Virgininio in the municipality of Montespertoli. Today after 40 years, more than 850 companies mainly located in the areas of production of Chianti DOCG, Chianti Classico, Tuscany IGT, Tuscany IGP oil, give their crops to the production sites of the co-operative. This winery is not your typical winery, as they weren’t prepared for tastings; however, we were about to taste a few, and they were quite good.

4. Agricola Tamburini

Agricola Tamburini wines go back to the 19th century. Today the farm covers 50 hectares of land between the historic Chianti region in the prestigious Montalcino production area, where they make a small selection of Brunello di Montalcino DOCG. In addition to the vines, the farm also has around 1,000 olive trees which produce organic extra virgin olive oil. Tamburini wines and olive oil products are sold in Italy and abroad.

This winery in a gorgeous area of Tuscany with beautiful views of the countryside from every direction you look. It would be a perfect place for a party or get-together as the outside has many tables and areas from which to sit, relax, and drink wine overlooking the vineyard. One Chianti we especially liked is called “The Boss,” which is named after the family matriarch and owner. It is a 10-minute drive southeast of Valvirginio.

5. Corbucci

When you first arrived at Corbucci, you may feel as if you’ve arrived at someone’s home. It has the appearance of a typical house until you go to the rear of the property, where you will find unbelievable expansive views of their vineyard and the beautiful countryside. They are located in the heart of Tuscany, and they produce different types of wine such as the famous Chianti DOCG, the San Gimignano DOCG white, and Francesco Paolo Corbucci, along with other exclusive wines. We enjoyed all of our tastings, and we would highly recommend this winery, for both the fantastic views, the excellent attention paid by the staff, and of course the wine.

6. Soc. Agr. Santa Lucia Vini

Santa Lucia is located in Gambassi Terme on the Valdelsa hills. It is important to note that this winery should be visited by appointment only. They were kind enough to show us around although an appointment is highly recommended. They are well-known for their red wine called Domino. It’s an elegant and full-bodied wine which is aged in small oak barrels.

Why Stay In Chiesina Uzzanese Province of Pistoia

Today we moved on to our second location in Tuscany to a town called Chiesina Uzzanese, an hour north of Gambassi Terme. We chose this location because it is in Northern Tuscany, it is a 45-minute train ride away from Florence, and it is proximate to Pisa. We decided not to stay in Florence this trip because we wanted to stay in the smaller towns within the Tuscany region.

To be honest, Chiesina Uzzanes was nothing special, other than it was proximate to some of the other cities we wanted to visit during our time in Tuscany. We stayed in an Airbnb, and this time we didn’t have any issues, and it happened to be one of the least expensive places we stayed while visiting Italy. Go Figure. Lol

If you decide to stay in Chiesina Uzzanese, and you want to take a day trip to Florence, your best bet would be to take the train to Florence because it’s expensive to park there and quite frankly after going I wouldn’t want to drive around the city streets of downtown Florence. Many train stops run right through Chiesina Uzzanese so hopping on a train is easy and economical.

*** Restaurant recommendation for Chiesina Uzzanese – Restorante La Favola Mia

Are you interested in checking Hotel, Bed & Breakfast, or Villa accommodations prices in Tuscany click here for booking.com direct link.

Disclosure:  This post contains affiliate links where a small commission is received for the sale of products linked at no additional cost to you.  We only partner or promote brands and products that we believe in or have tried ourselves.  Thank you for your support. 🙂

The Montecarlo Wine Region

Our plan for today was to visit a few wineries in the Montecarlo area within the Lucca region, which is a 10-minute drive from Chiesina Uzzanese. The Montecarlo region has one of the earliest DOC’s, it’s known for robust wine production, and extensive rolling vineyards. The Montecarlo region started to produce wine before Napoleon during Medieval Times. The Montecarlo region consists of 10 wineries. We found this region to be one of the best places to visit wineries.

Montecarlo is a small village which was built in two years from 1333 to 1335, and it still retains its medieval structure. There is a beautiful fortress with ancient walls, a crypt, a medieval church, and an 18th Century Theater. Montecarlo wines are unusual for the region, as they’re typically made from Semillon, Sauvignon Blanc, and Pinot Blanco grape varieties. The Montecarlo region differs from the other Tuscany regions because of the mild climate and its location near the sea.

1. Fattoria del Teso

Fattoria del Teso winery dates back to the Roman times. They offer several options which include a tasting of 5 wines, with the choice of appetizers, a light lunch, or a full lunch. We didn’t have an appointment, yet they went out of their way to make room for us, taking us around their grounds, and providing us with wine tasting. Their service was exemplary, and the wine was distinctive and quite tasty. We suggest making a reservation to be sure they can accommodate your needs. You can make a reservation on their website at Fattoria del Teso.

Our next stop was Buonamico winery, a 5-minute drive northwest of Fattoria del Teso.

2. Buonamico

We named this winery the “Instagram winery” because everything looked so perfect. As we walked through the tasting and sitting rooms, it was as if each area was set up for the perfect Instagram photo. There is a sitting area off the wine tasting room that has the appearance of an upscale library except instead of books; there was wine. It would be a perfect place to relax with a glass of wine and a good book.

It’s perched on a hilltop surrounded by picturesque rolling vineyards and olive trees. The resort includes a hotel which consists of 11 luxury suites, a wellness center, an on-site restaurant called Syrah, wine shop, and of course the winery. Buonamico was a beautiful winery with upscale offerings.

If you want to make reservations or you’re interested in more information, click here for booking.com.


Chiesina Uzzanese to Pisa

Chiesina Uzzanesa is only a 45-minute drive to Pisa. We went to Pisa on our way out of Tuscany towards Cinque Terre; however, if your plan isn’t to continue north, this would be a great day trip. One of the reasons we choose Chiesina Uzzanesa as a home base was because of its proximity to Pisa, Tuscany, and Florence. The town itself wasn’t anything spectacular, but that made it an affordable option while staying in northern Tuscany.

Closing Words

I hope you found our article “Tuscany Road Trip For Couples” to be useful and you are excited to visit the Tuscany area.  If you have any questions feel free to contact us through our website we would be happy to help or hear about your trip through Tuscany.  

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The drone we use is the DJ Spark with Remote Control Combo.  We like this drone because it’s compact, it’s effortless to take on trips, it’s easy to fly, and it shoots 1080p.  All of our drone footage on our blog posts and youtube videos are taken with this drone. We highly recommend it. If you are interested in checking it out here is the Amazon link:  Click here.             

Another item we use daily is our Primocean Backpack with an insulated cooler bag.  We use this as Christie’s carry on bag on the plane and as our cooler at our final destination.  We used to use a different backpack and we switched to this one because it’s better made of durable material with quality zippers.  We love this backpack!!  The cooler section is smaller; however, all the compartments and the quality of the backpack make it a much better choice for basically the same cost.  We wish we would have thought of this item a long time ago. If you are interested in checking it out here is the Amazon link: Click Here.  

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