The Best Tour of Tuscany

best tour tuscany

the best tour of tuscany

For our 2015 honeymoon, which was by far the best vacation we have ever had, we went to the country that is the epitome of romance: Italy. For fourteen days, we immersed ourselves in the culture and created as many great Italian memories as possible. Zach’s favorite memory from Italy was driving a Ferrari around the Italian streets- surprise surprise. However, Steph’s favorite memory was wine tasting in Tuscany and exploring the beautiful Tuscan countryside.

Our day in Tuscany was spent with a tour guide from the company “Italy on a Budget” which turned out to be better than expected. It was the best tour of Tuscany!

 With the tour company, we chose their “Tuscany Experience” tour which visits four towns in one day: Siena, San Gimignano, Monteriggioni, and Chianti wine country. With it being only 60 euros a person, we had low expectations. However, since we try to make affordable decisions while traveling, we went with it.

We were also reassured when we learned this tour company caters to the younger population (18-39 year olds) because that meant we may have less down time and waiting around. A small, young, lively group of people could make the experience more enjoyable. So we were excited to go!

For more budget travel tips for Italy, checkout Visiting Italy on a Budget!

PS- Claire Imaginarium shares more of the most beautiful villages in Tuscany.

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At 8:45am we Uber'd to the tour company’s office in downtown Florence. We loaded into an 8 person tour van, met our guide, and we were off on our eight hour adventure through Tuscany. During the drive south from Florence to Tuscany, our tour guide was funny, educational, and friendly. All the tour guides for “Italy on a Budget” are local Italians who speak English, so it was nice to learn Italian history from someone who grew up in Florence and loved his country. [See Related: 2 Days in Florence: The Ultimate Itinerary]


Our first stop was Monteriggioni which was a super tiny town with just a few small shops. However it was cute, quaint, and oh so lovely. It is the town where part of the movie Gladiator was filmed and it’s also the most preserved medieval town in Tuscany. Being built in 1214 as a front line against war, the history here is apparent. Steph’s favorite part: each and every unique door!

best tour of tuscany
best tour of tuscany
best tour of tuscany

San Gimignano

The second stop was San Gimignano which was much larger than the last town and much more grand which is incredible since it was built in the third century BC. Known as the town with “fine towers” it also has beautiful views of Tuscany, and gelato that was to-die-for. In fact, the gelato here at Gelateria Dondoli is made by the world champion gelato maker, so you can’t miss out. We enjoyed wandering the streets, seeing the unique doors on all the little residences, and climbing up the hills for spectacular views.

best tour of tuscany
best tour of tuscany
best tour of tuscany
best tour of tuscany
best tour of tuscany


Next up was the more well-known town of Siena which was first settled in 900-400 BC. The Piazza del Campo plaza here hosts Palio horse races twice a year and it’s simply beautiful to sit here and admire the grandiose medieval buildings all around. We grabbed some coffee, pizza, and calzones before proceeding to do a little gift shopping for family. We couldn’t leave before checking out the gorgeous cathedral or Duomo here as well.

best tour of tuscany
best tour of tuscany
best tour of tuscany
best tour of tuscany

Chianti Winery

The last stop was into Chianti region which is picturesque. The photos you see of Tuscany with rolling hills, wineries, and cute brick homes are from this region. We stopped at the Tenuta Torciano winery here for authentic wine tasting. A member of the family that owns the winery gave us a lesson himself on how to properly hold a wine glass, how to swirl the wine, and how to taste it to its fullest. Maybe it’s just the wine speaking, but we had so much fun here! We learned a lot, the wine was incredible, and they even let us try some truffle oil which was OMG amazing. Everytime we hold wine glasses now, we joke about holding them correctly and we can appreciate the specific flavors in wine because of that experience. Just take a look at these Tuscany vineyards.

best tour of tuscany
best tour of tuscany

Follow our travels!

destination dorworth

Riding back from this day tour, I thought to myself “wow, I can’t believe we got all of that for just 60 euros!” I would have paid much more. It took away the stress of renting a car, driving in a foreign country where you don’t know the language, and it took us to places we wouldn’t have gone on our own. Our Tuscany experience was exceptional and filled our trip with memories we will never forget. No, “Italy on a Budget” is not paying us. We simply think credit is due to the company that contributed to our honeymoon being the best trip ever.

If you're planning a trip to Italy, definitely check them out for a tour of Tuscany. Italy is the heart of romance and we can’t wait to go back to those breath-taking Tuscany’s hills. 

destination dorworth

About the Author

Hello, we are Zach (@zachdorworth) and Steph (@stephdorworth). We are Mr & Mrs traveling the world one romantic city at a time while perfecting obsessively organized travel.

  • […] All in all, it was a fantastic trip, check the video for the full footage of these beautiful cities! Have you been to Tuscany before? How did you find it? Let me know in the comments below! This 4-day itinerary covers only the main cities and sights in Tuscany, however if you have longer I highly recommend doing a trip to smaller towns and the Tuscany countryside. […]

  • Great post! Loved all of the different places you got to cover in wine country! We were just up that way last week, and we have to say that it just may be one of our favorite areas out of all of Italy. Quiet, clean, gorgeous, and not to mention it’s affordable! Looking forward to more posts from the two of you 🙂

    • admin says:

      Jim & Steph, thanks so much! So cool that you were just there. It was hands down our favorite place we’ve ever been. So many people tell us Italy is their favorite. Now we know why.

  • Victoria says:

    Okay I have visited Florence before but that is it! The Italy On A Buget company sounds like something right up my alley! You went to some amazing places

  • Great to know that this tour is so good when the pricing is so reasonable, that’s a great find as many tours are much much more. Looks like it really gave you a good overview of the best of Tuscany too. I love historical small villages such as Monteriggioni, there’s something magical about exploring these and contrasting with the larger towns like San Gimignano — the square with the brick-built towers and tall buildings is just stunning. Your photographs of Siena are gorgeous, and show off the architecture of this wonderful town too. And no trip would be complete without the winery visit.

  • Dany says:

    We visit Tuscany at least once per year, and thus we’ve visited also the off the beaten path areas. San Gimignano is beautiful but it can be very, very touristy and crowded. Yet you’re right, gelateria Dondoli is awesome 🙂

  • Marissa says:

    I love little towns like Monteriggioni! I’d rather spend time there than a big city. I love those doors too.

  • I love guided tours and you certainly did a lot in a day. Glad to hear they have a faster tour for those who don’t need down time.

  • I love Tuscany, and your photos make me want to go back now! The scenery is so beautiful, and I could happily eat pizza and gelato every single day!

  • Izzy says:

    I studied abroad in Florence back in 2011 and dream about all the little weekend trips I would take. I miss it so much! Out of the Tuscany region, Siena was my favorite. The facade of the Duomo is beautiful but it was all about the tilework for me!

  • Megan Jerrard says:

    Tuscany is such an epic destination to spend a honeymoon – so cool guys! Italy on a Budget sounds like a really great company – with you on would have been apprehensive in only paying 60 Euros, but sounds like they really take care of you, cover some fab destinations, and it’s so great that the tour guides speak fluent English. It’s nice to have local tour guides too who have grown up in the area their whole life. Really makes the difference! Chianti region looks amazing, and exactly what I picture Tuscany to look like.

  • Jenna says:

    The Tuscany Experience sounds wonderful! We only had a day in Florence, so we just spent it wandering around the city, but this sounds like a great option for when we return! Love the architecture in San Gimignano. I would love to visit the Chianti Winery as well—can’t go wrong with an Italian winery!

  • […] For an affordable one-day tour of Tuscany, check out this article! […]

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