Your first look at any one of the Hill Towns of Tuscany will take your breath away. You may have seen images of these stunning places in movies and books. But nothing can possibly prepare you for the real thing.
Once you experience this other-worldly countryside of abundance for yourself, you will understand perfectly why even the tiniest of these towns has been fought over continuously throughout history. Who wouldn’t want to own the top of one of these hills, looking out across brilliant landscapes, covered in vineyards that yield plentiful harvests for the finest wines? Who would not be inspired to paint or sculpt or roam the hills in search of gemstones to craft into exquisite jewelry?
If you have decided to travel to Tuscany, you have made an excellent choice. But there are three essential points you will need to understand before you set out on your travels.
Point #1: Give Each Destination At Least One Full Day or Three or Five
For a wonderful trip to Tuscany, plan to include five destinations, one large, one medium-sized, and three small. Florence, of course, is the absolute must as your large destination. Your trip to Tuscany would not be complete without including a visit to Florence. Few cities compare to Florence in terms of breathtaking beauty, as well as plentiful, awe-inspiring experiences. With its art and sculpture, gardens and architecture, history and culture, craftsmanship, wine and food, Florence will captivate you. Your time will race by. And likely you will decide that you simply must return another year.
Since Florence is the largest destination on your itinerary, plan to spend 5 days here. But then make day trips from Florence by train to two of your other destinations- the small but fascinating towns of Cortona and San Gimignano. Add five additional days to your trip, and split these between two remaining destinations, Montepulciano and Siena. So, your ideal trip will be 10 days total.
And what a trip it will be. You will have the time and latitude to truly soak in and enjoy this wonderful region. Sights to see. Art to peruse. Food and wine, relished at outdoor tables, overlooking the lively and spacious piazzas. Artisan shops. Local exuberance. Landscapes to inspire you. And the considerable fun of moving about amongst these towns and cities, with the journey as much a part of the delight as the arrival.
Speaking of having time and latitude… This brings us immediately to…
Point #2: Avoid Group Tours and Have a Better Experience on Your Own
This trip to Tuscany will be rich in experiences. And it may seem like it will be a complex trip to arrange and take on your own. So, you may be tempted to take the easy route of signing up for a bus tour. Yes, the descriptions for these tours always do sound appealing. And it seems like it would be so much easier just to turn over the controls for your trip, and let someone else be in charge.
If your thinking is leaning in this direction, think again. Your trip to Tuscany is overflowing with possibility, too much so to waste it trapped on a bus with 30 other people. You will want time to relish the experiences of each of these remarkable towns and cities.
A group tour will move too fast and try to pack in too much. It will be too constrained, including when you are sitting cramped up in the seats of that bus that was designed for a smaller breed of people than your towering American husband. It will be choreographed to someone else’s liking, with much precious time wasted waiting for your fellow chattering tourists to get back to the bus. And as you race through a city that the tour guide has already seen several hundred times, you will be traveling about in a noisy hoard, blasting past all those intriguing shops and appealing bistros.
This is not what you want for your own, long anticipated, trip to Tuscany. Instead, you will want to move about in freedom, walking about and pausing as you like, spending more time here and less time there as things do or do not capture you. Some of your most memorable moments will be your bistro stops, your visits to the shops that catch your eye, your pause to look out across a view of peaceful hills and valleys, your wandering into a restaurant on the piazza with a fabulous piano player.
You will want to be free to take your time to explore the leather market in Florence, and study the original oils and watercolors by the artists who are displaying their own original work in Piazza Michelangelo.
Sitting at an outdoor table at a restaurant behind the Duomo in Florence, or on the wall facing the Duomo in Siena, you may find yourself caught up in a photo orgy, taking shot after shot of the intricate marble work, starting with the full structure, then focusing in more and more closely for a sequence of photos that captures the inlays of green, pink and white marble or the gilded image above the door or the statues looming over you from the eaves.
A group tour, of course, does take care of your needs to get from place to place. But you will be able to handle this just as well, if not better, on your own. When you need a lift, catch one with an Uber or Taxi in town (keep your contact info readily at hand!), combined with trains to take you between towns and cities, and shuttle buses to carry you up the hills to the top. Making your way around, especially on the trains, is part of the fun, and adds to your experience as well as to your sense of accomplishment.
Speaking of needing a lift from time to time, we’ll move on to…
Point #3: There Will Be Lots of Hills Everywhere You Go
As you know from the term “Hill Towns,” there are very few places in Tuscany that are flat. You will be walking and riding up and down and up and down, everywhere you go, both within the towns and as you travel from one town to another.
For each Hill Town you visit, you will need to take a train to get to the bottom of the hill, then a shuttle bus to get to the top. This means that when you exit the train station, in Cortona or San Gimignano or Montepulciano, you will need to focus your attention on purchasing a shuttle bus ticket and catching a ride up to the top where the town awaits.
As a rule of thumb, when you are heading off somewhere in a city or town, plan to ride up, then walk down, every chance you get. In Florence, catch a taxi up to Piazza Michelangelo. Ask the driver to drop you off even higher up, in front of the charming Miniato Abbey, just above the piazza. From here, every direction you walk will take you down!
After you visit the Abbey, meander down to Piazza Michelangelo. While you are there, if the timing is right, try out the phenomenal lasagna at the restaurant just above the piazza, lunching at an outdoor table, with a view out over Florence.
Then walk a few steps down to explore the artwork and crafts for sale in the piazza. Pause frequently to look out over the wall to the rooftops of Florence, with the dome of the Duomo towering above its surroundings, and the Ponte Vecchio spanning the glistening thread of the Arno River. From here, wind your way down some more, until you arrive back at the level of the river.
So, are your ready for this? Grab yourself a guidebook, make your arrangements, and set off on a travel adventure that will become part of your life story.