Over lunch at Yanni’s Gyros, friends mentioned their upcoming trip to Italy. With two weeks of vacation set-aside and plane tickets in hand, they were ready to decide where in Italy they would visit. We talked about the Grand Tour that so many take, visiting Rome, Florence and Venice. Anyone with a passion for art and history is sure to get their fill in those magnificent cities. Then we talked about, “seeing it all,” the approach that some love, starting down in Sicily and working their way up to the Alps in the north. With Italy being roughly the size of Arizona, that seems possible. “Seeing it all” is certainly a way to check a lot of Italy checklist boxes. A “see it all” trip might start with The Godfather sights of Sicily, move to the Instagram sights and pizza of the Amalfi coast, with a quick pop-in visit with the Pope and a stop at the Colosseum in Rome, then onto see the art of Michaelangelo in Florence, pasta in Bologna, a gondola ride in Venice, and then mountain hiking in the Alps. I am tired just typing it out.
Recently while eating pizza with my friend Roberto, he shared his perspective of the see-it-all-in-one-trip approach. As a native who lived in Florence for 30 years, he shared that when visiting the city he still discovers new treasures. That puts a 72-hour, top 10 visit to Florence into a new perspective. His other insight is to look up, not down while walking the city, any city in Italy. All too often I have been guilty of focusing on the map or the city guide. I have sadly spent more time looking down at my phone and the cobblestones than on the wonder and beauty above street level.
For me, a slow two weeks is a far better way to go. Let’s focus on spending two weeks in Northern Italy for now, and ponder two weeks in Southern Italy in a future blog post. Rather than seeing it all, trying to do it all, and ending exhausted, let’s talk about two weeks of experiencing Italy.
Arriving in Florence, let’s spend the first five days there.
Day 1: Day one is a bust due to jet lag.
Day 2: Day two is meant for recovery. Let’s make no plans, and just wander the magical city.
Day 3: On day three, a morning with a private guide is the best way to get the most out of our time, including a visit to the Uffizi museum for a viewing of Michelangelo’s masterpiece, the David sculpture.
Let’s pass the afternoon in the Duomo, and make the trip to the top of the dome, having purchased tickets in advance.
Day 4: The fourth day we might wander the streets, or take a car up to the village of Fiesole, where Michelangelo first learned to work with stone, chiseling the sidewalks.
Day 5: No trip to Florence would be complete without a visit to the jewelry shops on the old bridge, the Ponte Vecchio, with a few stops at the leather shops along the way.
With our stay in Florence at its end, let’s pick up the rental car.
For those who insist on squeezing in an extra stop into their Italy tour, you could spend a few days in Chianti country amidst vineyards and classic Tuscan villages.
One of my favorite places to stay amidst the vineyards is Hotel Villa Campomaggio. The apartments are spacious, but the best part is sharing a bottle of wine on the patio as the sunsets over the Chianti hills.
There are several restaurants nearby, and the town of Radda in Chianti is a short ten minute drive. The Monterinaldi winery is a stone’s throw from the hotel, offering a wonderful package that includes a winery tour with lunch in their villa.
The next leg of our journey takes us to southern Tuscany, Val D’Orcia, south of Sienna. This is the Tuscany of rolling hills and vineyards, photographed all so often.
Far from the hustle of city life, this is an area where the days are meant to be savored, great food and even better wine. Slow mornings spent with coffee, overlooking the clay hills and distant Mount Amiata, followed by long dinners with local wine are just what the doctor ordered.
Days 6-8: The small towns of Montepulciano and Montalcino each boast some of the best wine in Italy, the Nobile of the former and Brunello of the latter. The proprietors of the local vineyards, as well as the local enoteca (wine room) are more concerned that you enjoy the wine than that you buy a bottle. Five days in this area will give new meaning to vacation.
Day 9: The village of Pienza should not be missed, built by Pope Pius II to be a model renaissance town.
If you see an old man in an argyle sweater wandering the main street, please say hello to Renè for me and buy him some cigarettes. (I know, those things will kill you, but he is already over 90 and it is his only guilty pleasure.)
Day 10: If time allows, stop in Bagno Vignoni for the thermal baths, or at least for a coffee on the main piazza, a village center with a former thermal bath rather than the typical cobblestone piazza.
Saint Catherine of Sienna used to visit this village, as did Lorenzo the Magnificent (Medici), the Emperor Frederick Barbarosa and several popes. Maybe you should visit as well, but only if you are not rushed.
It is hard to go wrong with accommodations in this area, but I suggest staying at Relais Osteria dell’Orcia with our good friends Silvano, or Agriturismo La Selvella.
The final five days of our tour take us to Venice, with a stop along the way in either Bologna (best food city in Italy), Ravena (best mosaics), or Verona (home of Romeo and Juliet’s balcony and an amazing Roman amphitheater). Choose one of those stops at most along the way, not all three.
Day 11: Arriving at Venice, return your car after crossing the causeway at Piazzale Roma. From there spend the money, a small splurge, for a private water taxi. Arrive in style at your hotel.
Day 12: After a sound sleep in the serene island city, it is time to explore. Start early and walk, and walk, and get lost. The best cartographers get lost in Venice, and you should too.
Day 13: Piazza San Marco at sunrise is spectacular, as is the early morning arrival of the boats bringing new supplies to the stores and restaurants. Wander early, and simply relax after lunch.
The hard truth about Venice is that it is crowded from noon until 6:00 p.m. That is the time to read and nap, or explore a church well off the beaten path.
When dinner time rolls around, explore some more. Challenge yourself to navigate to a distant neighborhood, perhaps after a gondola ride at sunset.
Day 14: On the third day in Venice, take a vaporetto, the water bus. Wrap up the day with a private “cicchetti” tour, Venice’s answer to tapas.
Day 15: The final full day, take the waterbus further afield, perhaps to the islands of Burano and Murano, for the legendary glass and lace of Venice.
Comment with your favorite spots to visit in Venice, Florence, and Chianti!
Great advice. I’m wishing I could be there!
Us too!! Thanks for reading!
E bravo il mio Sergio e brava Molly
It was relaxing just reading this post and recalling those places. Thank you!