My first Italian teacher, Joe Bonefest, had two maxims for his visits to Italy. First, stay in each place for a minimum of four days. Second, the driving distance on day trips cannot exceed one hour each way. Too many times I have not adhered to those rules, yet every time I plan a trip “according to Joe” I have been thrilled.
Why Tuscany? Isn’t it too touristy?
Tuscany’s fame as a destination cannot be disputed, but has it become a caricature of itself? Are there hordes of tourists that make the place unbearable?
In my view, it is an emphatic no. Yes, there are busloads of people around the Duomo of Florence and in line to see Michaelangelo’s sculpture of David at the Uffizi, but Tuscany has so much more to offer and some things are worth the line.
With a bit of effort to spend the majority of your trip away from the obvious tourists sites, you just might stumble upon the real magic of Tuscany and a way of life that has much to teach us.
Day 1: Arrive at Florence Airport, and stay in Lucca. There are plenty of places to stay in Lucca, but my preference is an agriturismo a short drive from town. An agriturismo is not a farm stay as we would think of it in America, it is more like staying at the country home of distant relatives. For example, try Agriturismo La Conte. Stay here for a few days and gain your sea legs while overcoming the jet lag. You might have the hosts prepare a traditional Tuscan dinner for you, but make sure that you are hungry.
Day 2: Explore Lucca…See the wooden sculpture of Christ with its rich history. Visit the many shops, and rent a bike atop the old city wall. Have a drink in the oval shaped piazza. Take part in the late afternoon passegiata, as the locals walk the city center streets to meet and greet their friends. Relax, relax, relax.
Day 3: Take the train from Lucca to Florence. Of course, you could drive, but should you? Traffic in the center of Florence is restricted, and it is easy to miss the signs noting the beginning of the pedestrian only zone. Take it from me, the police will ensure that tickets for traffic violations make their way to you back home.
Arrange for a private guide to show you the sites in Florence, as this will save time and energy. With guides you can jump the lines, and you are sure to have a much deeper experience. One of our favorite guides introduced Liz and her friends to an ancient silversmith, hidden in a closet off a back alley. Turns out that he is world renowned, but we would have never known about him on our own.
Day 4: Wander the nearby countryside. Many visitors want to see the famous leaning tower in Pisa. Yes, that is fascinating and the Duomo is spectacular, but I prefer wandering up the Garfagna valley to visit the villages along the Sechio river, with a coffee stop on the Devil’s Bridge.
Day 5: Time to decamp and visit Chianti. Get ready for some Chianti Classico wine. If you only drink white, fear not. You will find it.
On your way from Lucca, you might stop in San Gimignano, the city with dozens of medieval towers. The town is often crowded, so I suggest a quick stop. They claim to have the best gelato in Italy, but I am a skeptic on that. Still, you should do your own research, as who minds a bit of gelato while traveling.
Stay that night in Radda in Chianti as the Relais Vignale, and have a Tuscan dinner at La Loggia restaurant overlooking vineyards. (Another great place to stay is Hotel Villa Campomaggio, just 10 minutes from town, yet amazing.).
Day 6: A day of Chianti wine… Tour the Castello Albola winery, and enjoy lunch with wine pairings. End the day in Radda with dinner at Cafe Dante.
Day 7: A short road trip to Pranzano, with a visit to the world famous butcher for picnic supplies. Don’t miss lunch at Il Vecovino.
Day 8: After a morning hike through the vineyards on the Radda ring route, jump in your car and visit Greve and Castalina in Chianti. Both are charming towns. Seek out a small winery along with way for some wine tasting, and be sure to ship a case home as a momento of the trip.
Day 9: Roadtrip to Forti di Marmi or Viareggio, trendy beach resort towns that offer the best in dining as you wrap up your trip. An afternoon at a private beach club is a sure way to ensure that you have completely relaxed on vacation. Best of all, both towns are close to the Florence airport.
Day 10: Fly home… or add another week onto your trip and explore Umbria.
Should I be heading home? You make me want to!!!! I would just suggest to pass by Pisa in the way back from Viareggio/ Forte dei marmi and instead spend time in Siena. When in San Gimignano, if you are a white wine passionatos then drink the Vernaccia and then instead of heading back home ( US) I would stay for 5 more months 🥲🙏
A trip to Italy is always a good idea! That is a great add – thank you for sharing!
You bring these cities to life with such great detail. Super helpful.
Thank you! We love thinking back on the memories and pretending we’re there