As a travel journalist, people are constantly asking me what my favorite place is that I’ve travelled to. I would love to say that my answer is somewhere exotic and undiscovered, but I always say Italy. Why Italy? Well, it never gets old. I always enjoy every moment I have exploring the beautiful Italian culture, scenery, food, and language.
I have traveled to Italy at least 20 times now and I can honestly say that I love every corner of this country, but Tuscany definitely has my heart. I was only able to spend a long weekend here, but I already know that it is a place that I want to go back to time and time again!
I’ve put together this weekend getaway guide to show you the best of Tuscany in a short period of time and to give you a small taste of what this region has to offer.
WHAT TO DO
DAY 1
EXPLORE FLORENCE
Florence is the largest city in the Tuscany region and one of the most beautiful cities in Italy, let alone Europe. Arrive to Florence in the morning and spend the day exploring the major sites like the Duomo, Ponte Vecchio Piazzale Michelangelo and the Statue of David. Check out my guide to the 10 Most Instagrammable Spots in Florence to help guide your Florence itinerary!
P.S. Don’t forget to take a gelato snack break at Gelataria La Carraia
TRY A FLORENTINE STEAK
After you’re done sightseeing, refresh at the hotel and get ready for a nice steak dinner at Buca Lapi where you will eat the best Florentine steak – a specialty in Florence and the tuscan region! It is a massive t-bone steak, but it is ohhh so juicy and tender. I highly recommend sharing 1 steak between two people, unless you have a really big appetite!
DAY 2
If you’re into early mornings, wake up to see the Piazza del Duomo at sunrise and have the gorgeous views of the Cathedral to yourself. If you want to sleep in, take an easy morning and have a typical Italian breakfast with a cornetto (Italain croissant) and a cappucino or espresso.
ROADTRIP TO THE TUSCAN COUNTRYSIDE
Now it’s time for the best part! Rent a car or arrange a private driver to take you down to the Tuscan countryside. Tuscany is a rather large region in Italy that you could easily spend a week exploring. Since we only had a weekend here, we decided to head to the Chianti region of Tuscany, which is around an hour drive from Florence. As you are driving, you will see how the landscape beautifully transforms from cityscape to rolling hills filled with vineyards, olive groves and charming Tuscan towns.
VISIT THE CHIANTI WINERIES
Once you arrive from Florence, check into your accommodation and get ready for some serious wine tasting. Stretching from Florence to Sienna, Chianti is the most famous region in Tuscany. This area is a top spot not only because of its beauty, but also because it is the second largest producer of wine grapes in Italy.
Chianti wine has been an integral part of the region’s history for two centuries. Previously, Chianti wine had a reputation as being a poor-quality wine due to overproduction and dilution, but regulations for production have now been modernized and the Chianti varietals are a bright and medium-bodied red that can easily compliment any Italian meal.
Below, I’ve put together some of my recommendations for wineries in the Chianti region based on the quality of wine and the overall atmosphere:
- Castello di Verrazzano is a gorgeous castle located in Greve in Chianti, which has a long tradition of winemaking and an amazing farm-to-table restaurant.
- Dive into the long family history and tradition of the arts and academia at the ultra-modern Antinori nel Chianti Classico.
- Villa Mangiacane is an estate with a resort, restaurant and winery on-site. The property is also home to the Palazzo Machiavelli, which was designed by Michelangelo and has some of the most amazing views over the city of Florence in the distance.
- Visit the former monastery at the Badia a Coltibuono winery and take in the beautiful architecture while enjoying a wine and olive oil tasting.
- Castello Monterinaldi is an organic winery where you can also book fun activities like Tuscan cooking classes.
Travel Tip: I highly recommend booking a wine tour guide or private driver to take you from winery to winery unless you plan on having a designated driver in your group.
WATCH THE SUNSET OVER THE TUSCAN HILLS
After the tastings, drive to the charming town of Radda in Chianti perched atop the hillside and enjoy the sunset views over the rolling hills of vineyards and Tuscan countryside. After the sun sets, have dinner at nearby La Vin Osteria or Antica Trattoria La Torre.
DAY 3
RESET & RELAX
Start the morning with a breakfast al fresco to recover from all the wine-tastings. If you’re past your metabolic prime like me, you will need this morning to recover! Enjoy a long breakfast and take a dip in the pool or book an appointment at the spa if you’re in the need for a little pick-me-up.
ENJOY THE QUAINT TUSCAN TOWNS OR TAKE A DAY TRIP TO PISA
Depending on your stamina or your level of relaxation, take the rest of the day to drive around and explore some of the charming Tuscan towns in the Chianti Region like Greve in Chianti, Castellina in Chianti or Montefioralle, or you can take a short day trip to Pisa.
You all might know by now that I am an adventure seeker more so than a relaxer, so I chose to go to Pisa while I was in Tuscany. Pisa is around a 1.5 hour drive from the Chianti region on the western border of Tuscany. Pisa is definitely a touristic destination, but it is well worth a day trip or an overnight stay to explore the town and visit the Leaning Tower if you have never seen it before!
IF YOU CHOOSE TO EXTEND YOUR STAY
Tuscany covers a lot of land in Italy and does not need to be confined to a weekend getaway if you have the time in your schedule to explore more. I went here for a quick weekend with friends who were in town visiting from America, but I wish that I had stayed for the week. If you choose to extend your stay here, check out some of my recommendations:
- Visit the Terme di Saturnia hot springs and take a dip in the insta-famous turquoise pools at sunrise. If you prefer a luxe indoor atmosphere, visit the elaborate thermal baths in the spa town of Montecatini.
- Take a drive down to Asciano at sunrise or sunset to witness one of the most iconic views in Tuscany of the rolling hills and winding roads dotted with the iconic Tuscan cypress trees. If you’ve seen a photo from Tuscany, it’s probably from the drive here!
- Spend the day in Siena: a gorgeous medieval city full of history, beautiful architecture and amazing food, nestled between the Tuscan hills.
- Take a pasta-making class and master Tuscan cooking with a pro.
WHERE TO STAY
Finding accommodation in Florence, Pisa or Siena is relatively easy as there are many great hotel, airbnb and guest house options, but finding a place to stay in the Tuscan countryside can be a bit more difficult!
While in Tuscany, I stayed at the Hotel Villa Campomaggio located in Radda in Chianti. This hotel is on a stunning property surrounded by vineyards, rows of Tuscan Cypress trees and views of the hillside. They have a great little restaurant that serves breakfast and pasta during the daytime and a pool with an amazing view over the vineyards.
Not the place for you? Check out some of my other recommendations for hotels or guesthouses in the Chianti region that I would love to stay in next time:
WHERE TO EAT
Tuscany is full of amazing restaurants and you really can’t go wrong with anywhere you choose, but I’ve put together some of my top picks to help you with your decision:
FLORENCE
CHIANTI COUNTRYSIDE
PISA
Feeling inspired to travel under the Tuscan sun now? I hope this weekend getaway guide helps you plan your trip to my favorite part of Italy!
