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Dreamy Tuscany Weekend

Always dreamed of a romantic weekend in the beautiful countryside of Italy? Well, it’s time to make those dreams come true with this perfect weekend itinerary for Tuscany, specifically Chianti!

Recommended Itinerary:

Day 1:

  • Drive from Florence to Castellina in Chianti
  • Check into accommodations – I recommend Borgo di Pietrafitta Relais
  • Enjoy Chianti

Day 2:

  • Biking and wine tasting
  • Romantic Italian Dinner

Day 3:

  • Wine tasting and lunch
  • Head back to Florence

Day 1:

Drive from Florence to Castellina in Chianti

The first thing you’ll need to do is figure out how to get to Tuscany:

  1. Rent a car – although driving in Italy might be intimidating, renting a car is the most convenient way to get from Florence to Tuscany. Out of all of Italy, this was the most chill drive because once you’re on the outskirts of Florence, it’s mostly country roads. You will have to go on the autostrada (freeway) for a bit, but the rules are very similar to the US.
  2. Hire a car – If you’re not up for driving, you can always hire a car. You can do this through taxi services, car services, or your hotel. The issue with this is it will limit your flexibility once you’re away from the city.
  3. Book a Tour – If the driving situation is too much altogether, there are many tour options that will take you around the region. Check out Airbnb, Get Your Guide, or Viator.

Check in to Accommodations 

Where we stayed: Borgo Di Pietrafitta Relais – this beautiful hill top borgo is made up of multiple villas, a main hotel area, a chapel, open lawns, an infinity pool, and more. This place has a historic charm that felt right out of a fairytale. We enjoyed staying there in the summer, but disclaimer, there is no A/C in most of the rooms, including the villas.

The infinity pool onsite was such an added bonus. We were able to make an afternoon spritz and go lounge by the pool overlooking the rolling Tuscan hills. This was truly an incredible experience.

Borgo di Pietrafitta Chianti
Borgo di Pietrafitta Tuscany Chianti Infinity Pool

Enjoy a spritz by the pool

Go out for Dinner

We didn’t really eat out in Tuscany except for our wine tastings, but there were so many cute restaurants right in the main square of Castellina in Chianti. Rosticceria Il Re Gallo was recommended to us, as well as a Michelin Star restaurant – if you’re feeling bougie – Tavola di Guido. 

If you’re just hungry and aren’t looking for a dining experience, go by one of the local shops and get a porchetta sandwich. These are insanely delicious and will satisfy your hunger.

Spritz by the pool Chinati
Local market Chianti

Day 2:

E-Bike Cruising

I really wanted to explore Chianti by bicycle, so to cover the most ground, I booked E-bikes. For 40 Euros per day, I booked E-bikes from Noleggio Chianti 500. The owner taught us how to use the bikes and recommended some routes for us.

He said that when you’re in Chianti, you want to ride on the “white roads.” This means the white gravel paths that go through the hills and vineyards. This was absolutely stunning but I only recommend this for good bikers. Some people in our group we’re inexperienced and struggled on the gravel, we even had one person crash.

That being said – it was absolutely beautiful! You can also stay on the main roads since they aren’t very busy.

Wine Tasting

We rode our E-bikes to a wine tasting at Rocca delle Macie. This 20 Euro tour took us through the history of Chianti Classico, showed us the wine making process, and included a full wine tasting. We were all pretty exhausted and sweaty by the time we got here – so if you want to look cute and be refreshed, maybe don’t go on such a long bike ride before.

Relax at the Borgo

As much as we loved going out, one of our favorite memories in Chianti was picking up some fresh pasta and veggies from the local store, and cooking back in our villa. The borgo where we stayed has tons of outdoor seating, so we cooked up a nice meal, opened a bottle of wine from the day’s wine tasting, and enjoyed the sunset from the property.

e-bikes chianti
Roca della Macie

Day 3:

Slow Morning and Checkout

One of my favorite parts of being in Chianti was just slowing down. After running around from museum to museum in the bustling cities of Rome and Florence, it was so nice to just enjoy my cappuccino with an incredible view and not be rushed to go anywhere. Leave yourself time to enjoy this component of the country. After your slow morning, checkout and get on the road.

Tenuta Casanova Wine Tasting and Lunch

DON’T MISS OUT on this experience. It was easily my favorite experience in Chianti and probably the best wine tasting I’ve ever done. Make sure you call ahead for a reservation because this is a small vineyard and they can’t accommodate tons of people or walk-ins. I highly recommend the wine pairing with lunch. The owner is so passionate and leads most of the tours himself. While the estate makes incredible wines, the owner’s real passion is balsamic vinegar. They will teach you about the history, flavor profiles, and current process for making wines, oils, and vinegar.

The lunch is a whole other experience, with food homemade by the owner and paired beautifully with their wines. Everything is local and made from scratch – they even accommodated gluten free beautifully with homemade gluten free lasagna and more!

I can’t recommend this experience enough and I would definitely go back!

Cappuccino Chianti
Tenuta Casanova

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