Tuscan Traveler

14 DAYS IN TUSCANY

Summer-Fall 2020

With Covid-19 still fresh in our collective consciousness, when will we start looking for ways to recover from these months of social distancing?  The characters in the 1991 English film Enchanted April found their panacea to a dreary winter of isolation in Italy. But what about the Italy of 2020, after the ravages of this tenacious pandemic?  Did Covid-19 deal Italian tourism a body blow?  I know that some will never travel to Italy this year and maybe for years to come and I understand that.  Fear, like pain, is intensely personal. Cautious travelers and not just the elderly and infirm will likely avoid the crowded cities this year.  

But if you are willing to travel internationally and are perhaps still a bit wary, you should consider Tuscany.  The jewel like Renaissance villages and small towns have survived through centuries of hardship but this year they need the world to visit them.  Be assured that Italians will do their part to hang on.  Most small businesses are family owned and few have the burden of fixed costs borne by American companies.  Italians can flex on everything for a few months–including rent, food and labor–by relying again on simple Tuscan home cooking and support from ‘la famiglia’.  Landlords and banks are similarly indulgent because litigation is expensive and far slower than in the US, buying most of the fabulous restaurants, small markets and village stores just enough time to make it to the high season.  If the high season ever comes.

But will Tuscany be completely safe?  It is said that life begins at the end of our comfort zone. The Tuscan hill country has miles of open space and its villages are uncrowded and its citizens respectful and shy.  This itinerary seeks out those hidden places where you can experience the real Italy at the edges of your comfort zone.  

As Aldous Huxley once wrote, “to travel is to discover that everyone is wrong about other countries.”  The small towns and villages of Italy have still not completely recovered from the last recession and they cannot survive this high season if fear keeps us home.  Without travelers, Tuscany will wither away into more empty buildings and fallowed fields while its people fade into the anonymous existence of city dwellers.  Is June too soon? Maybe September? Let’s just hit the road again this year.

Trequanda, Tuscany– 7 nights

The writer Beth Elon in her classic, A Culinary Traveler in Tuscany, writes lovingly about the Crete Sinese region of Tuscany. “Lying to the east and south of Siena are landscapes of almost unsullied beauty.  The hilly pastures meld into the voluptuous, rounded, crater etched hills of the Crete Sinese.  Few factories and modern housing schemes disturb the rolling pastures and intermittent woods, the contrast of cypress and red earth.  Ancient towns dot the olive and vineyard laden hills.” For the perfect Tuscan experience, begin your stay at off-the-grid Trequanda, the oldest of these ancient towns.  

Trequanda is one of the five Cinque Sorrelle, surrounded by its sister medieval villages of Montisi, Castelmuzio, Petroio and San Giovanni d’Asso.  With its central hilltop location and fabulous restaurants, Trequanda is the perfect place to come back to for an evening cocktail and dinner. You will fall asleep to the stillness of the night and be woken only by the birdcalls and sunlight streaming through your open window.  Clustered around its 14th century village church is an old castle, a pharmacy, bank, museum, butcher and deli, and market, all within a light evening stroll through the wind washed countryside.  There is no problem here with hordes of tourists. 

For lodging, Trequanda has several quaint places serving a range of budgets. For a moderately priced 3-bedroom option, check out our place in the center of town on a cobblestone street, Casa Trequanda, https://www.vrbo.com/440247. The handful of individual rooms at the Conte Matto (the Mad Count!) is the only way to get momma Loriana’s breakfast (included in the room charge) at their fabulous restaurant.  

The luxurious La Casa dei Fiordalisi is perfect for a larger group willing to pay more for their great service, elegant rooms and pool.  If you are looking for isolation, the winery Fattoria Del Colle a couple of miles outside of town has great rooms, a pool and a nice restaurant framed by unbroken vistas of vineyards and forest.  There is something for everyone who chooses Trequanda as their base. 

Day 1.   If you get in early, do a light lunch at the 100% vegan Osteria Ciriera in the piazza, which makes some of the best pici pasta in Tuscany.  Pici is a Tuscan classic, thick spaghetti type noodles rolled by hand and served in many sauces.  Although Pici with wild boar (con cinghiale) is my favorite, with it’s thin red layer of fat at the bottom of a picked cleaned bowl, the vegan pastas at Ciriera are wonderful.  After your siesta, go to the Bar Caffé La Torre in the square and enjoy an aperativo or caffé coretto (coffee with booze) with the friendly locals. For dinner, wander over to Il Conte Matto or for late arrivals, do the evening walk to Paradiso for a great pizza and gelato. 

Day 2.  Sleep in and enjoy the tranquil morning.  Do a walk before coffee and get to know the village.  Listen to the birds, feel the breezes flowing through the town as you dig into your book at Ciriera with your iPad and enjoy the free wifi, a great cappuccino and a pastry.  Amble over to the local grocery store on Corso Matteoti on your way back and pick up some basic supplies for your stay.  The local bakery, Il Vecchio Forno, has Italian sandwiches, pastries and bread, if you get there early.   In the late morning, set your GPS to Pienza, a small town less than 20 minutes away that you can stroll through in an hour. 

Winding through the verdant vineyards and stately olive groves, you arrive at Pienza quickly, the first planned city in Italy built by Pope Pio II in the 12th Century.  There are several good lunch spots after you are done with the sights, but you can also buy some bread, the famed aged pecorino, a bottle or two of vino and olio and antipasti for a picnic on the church steps.  If you need to walk off lunch, leave the tourists for a walk through the country roads to Pieve di Corsignano, the now almost abandoned 7th century church.  Check out the original baptismal font where both Pope Pius II and his nephew Pope Pius III were baptized but make sure to get the world class gelato from Buon Gusto for the road.

A few kilometers outside Pienza is Podere il Casale.  This is a good spot for an aged pecorino cheese tasting but they also do a truffle hunt, cooking classes, dinner, etc. The Truffle Hunt through the nearby woods is very fun, although a bit pricey and clearly staged by the wily local truffle hunter and his specially trained dog. 

 The highlight is the lunch overlooking the valley where Il Casale chefs cook up your ‘find’ for you and your fellow hunters.  Contact Sandra at info@podereilcasale.it and leave adequate time to get lost the first time. 

Get home early for a nap and rest up for the big dinner later at the Conte Matto.  Managed with warmth and professionalism by Davide Arrigucci, this Michelin Bib Gourmand restaurant is one of the best in all of Tuscany. The elegant menu and sophisticated wine list changes with the seasons, with a few standards like ribolita, the Tuscan vegetable soup, and various seasonal takes on pici pasta. 

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Leave the entire night open for the full Conte Matto experience, including appetizers, a pasta course, secondi, dessert and a traditional digestive, contucci e vin santo.  Reservations recommended for an outside table, or during inclement weather.  

Day 3.  After breakfast, set your GPS to Sinalunga 10 minutes away, a generally nondescript mercantile town with a supermarket, electronics store and other amenities. Find the train station in town, park and walk a block up the hill to Da Forcillo and make a reservation for a late dinner.  Then follow the GPS to the medieval city of Montepulciano, about 25 minutes away. Parking is tricky so go early and grab the first open spot you can wedge into and get ready to walk.  Enjoy the shops and sights of Montepulciano as you do the slow, winding climb up to the top of the hill.  Plan on a late lunch as you wind your way past the many shops, churches and restaurants. You will be surprised to find that even in the most touristy looking place in Italy you can find something on the menu that is memorable.  

On the way up, Osteria del Borgo has great views and good pasta for lunch and wine but save room for that late dinner at Da Forcillo.  As an alternative to lunch, check out Cantina Fattoria della Talosa in the caves/catacombs, Via Talosa 8, near Piazza Grande at the top of the hill.  The cost for the guided tour and tasting is €20 per person and includes a tour of the wine caves and an Etruscan burial site.  The meat and cheese that accompanies the wine tasting is excellent and plentiful but you will leave with room to spare for a big dinner. 

Make sure you check out the incredible glass art store Massimo Cruciani (www.cruciani.com), an artist out of nearby Umbria who does spectacular glass paintings of Tuscany.  Consider dropping a couple of grand for a stained-glass scene of the Tuscan hills, insured and shipped direct to your living room.

Day 4.  This should be your day to seek out the most famous red wine region in Tuscany.  If you guessed Chianti, you would be wrong: Tuscany’s premier wine is Brunello di Montalcino.  For your fellow travelers who aren’t into wine, you can drop them off for cooking lessons at Locanda Demetra, Podere La Buca 221, Via Bellaria, 39-0577-1503199.  Locanda Demetra also does a great farm to table lunch experience if you want to regroup before your afternoon tastings. Reservations can be made on Montalcinocookingschool.com. 

Start your wine tour with a big beautiful Montalcino winery, Banfi.  On the way to Banfi you should do a quick stop at the tranquil 14th century Abbazia Sant’Antimo and check out the old monastery.  For Banfi, email Elisa in advance at hospitality@banfi.it and schedule a hearty lunch pairing.  Don’t miss the Banfi grounds and their glass museum.  If Banfi is too Napa Valley for you, consider the artsy Castello Romitorio in Montalcino or Fattoria dei Barbi, Biondi Santi or one of the quality large Brunello producers on this list for your morning tasting.  http://www.decanter.com/wine/wine-regions/tuscany/best-brunello-producers-know-356813/.  Go big in the morning and small in the afternoon.  

For your afternoon tastings we have two unique and ‘non-guidebook’ suggestions.  Just outside the town of Montalcino is the tiny La Fornace winery.  Email Fabio at info@agricola-lafornace.it for an appointment and make sure it is after the siesta hour.  The tasting experience is in Fabio’s house and is fittingly intimate.  Another wine focused option (versus wine and lunch) is Solaria, right off the main road. To make an appointment call: +39 347 328 4155.   After the tasting, drive up the hill to the town of Montalcino and park by the Fortezza, at the very top.   Lots of wine and wine toys for gifts can be found in Montalcino. For the good food/no views option, try Re Di Macchia if you can get in.  Montalcino has many lovely ‘view’ restaurants, but frankly the food is only average for Tuscany.   Better yet, come home and do a later dinner of a green salad, pizza and gelato with the crowds of locals at Paradiso, the great pizzeria and gelateria on the other side of Trequanda.  The pizza is the show here, but they also have pasta if that’s your preference.  Paradiso is open late, and you can fill up on pizza and dessert and feel virtuous on your walk back to bed.

Day 5.   This is a good hang out and do-nothing day.  Take a long walk through the countryside to the town of Montisi, one of the prettiest of the Cinque Sorelle (5 sister towns) surrounding Trequanda.  

For the less ambitious, pick up some panini at the bakery, get directions and amble down the cemetery road, taking the jungle path to the left.  There is a crumbling old house at the end of the road that makes for a great picnic spot.

As I mentioned, Trequanda has its own winery, Fattoria del Colle.  Take a right turn out of the parking lot, then a left a mile later and you’ll see the sign on the left a few kilometers down the road for the Fattoria del Colle.  Tasting appointments can be made online.  FDC does outstanding local wines and the owner, Donatella Cinelli, has a great Brunello from their Montalcino winery there.  You can walk back from the winery through the vineyards to Trequanda after an early dinner at the Fattoria Del Colle’s panoramic restaurant.  

Or for those in your group who don’t want to hang with the sloths, how about heading into the countryside in search of mineral springs?  Set you GPS to Bagno Vignoni in the cool town on San Quirico.  It’s worth a quick stop before you continue on your way to Bagni San Filippo, the mineral springs stream that all the locals go to.  The stream is free and easy to get to, with several miles of warm mineral baths. The drive there is breathtaking, with classic Tuscan landscapes that will yield the best pictures of your trip. 

 For your lazy day dinner, take an evening drive through the woods to the nearby town of Castelmuzio, where there is a restaurant next to the clock tower in the center of town, Locanda Casal Mustia, that is very good.  The outside tables are the best but they don’t have many and the upstairs seating with its warm service is a fine option if you don’t have reservations.

Day 6.  After a day of relaxation, this might be the day to venture a little further out to Cortona/Prada or Perugia/Assisi.   For shoppers, the Prada Outlet outside Arezzo on the way back from Cortona is a closely guarded secret, with great deals and discounts off last year’s styles.  For Prada, put Via Aretina 403, Montevarchi in your GPS.  The more spiritual should instead do a day trip into Umbria and visit Perugia and Assisi.  Try to find the small pottery town of Deruta (we couldn’t!) and stop there on the way.  Perugia is near Assisi and is not universally loved but I enjoy its size and bustle and the famous Perugia chocolates.  In contrast, Assisi is a place of worship, beloved by followers of the Franciscan order of the Catholic church.  The grand Basilica di San Francesco Assisi at the top of the hill requires that you wade through a sea of tourists and pilgrims. Perugia/Assisi is over an hour each way so for dinner on the way back pick a random restaurant in a roadside town for another memorable meal.

Day 7.  Set your GPS first to the Benedictine abbey at Monte Oliveto Maggiore and enjoy exploring the church and gardens before visiting the ‘tower city’ of San Gimignano.  Don’t miss Monte Oliveto if you love art and history in a uniquely Tuscan setting, with the great 4 walled frescos.  If your timing is good, the chanting Benedictine monks is a special experience.  The gift shop tucked away across from the church has great natural wines, honeys and jams made by the resident monks. Buy enough for gifts and for your own use but remember that like all things fresh and natural from Tuscany, they will not last long in your cupboard.  

After Monte Olivetto, continue to San Gimignano. There are many churches to see, including the Church of Sant’Agostino with its 14^th century frescos.  You can pick up saffron, surprisingly, and for white wine lovers the authentic Vernaccia di San Gimignano, which is delicious cold.  After lunch, head to the walled city of Volterra to see the old Etruscan ruins, the Roman amphitheater and the alabaster arts and crafts that they are famous for.  Set your GPS to take the back roads there and the highway to get home.  Make your last night in Trequanda memorable and try to get to Conte Matto by 9:00 for an arrivederci dinner with Davide.

Cinque Terre– 3 nights

Day 8, 9 and 10.  Say goodbye to Trequanda and head to Cinque Terre and the ‘l’aria fresca’ of the coast.  Leave early as it is a 3.5 plus hour drive from Trequanda to Monterosso al Mare, the first of the five gorgeous villages. Monterosso has a large communal parking lot that you will have to leave your car at throughout your trip.  All five villages are easy to reach via a spectacular hiking trail that snakes along the coast and up and over the hills or via the local train that putters every half hour from town to town.  Keep in mind that lodging is expensive and hard to find even on Airbnb and VRBO during high season unless you book at least 6 months in advance.  Cinque Terre is best discovered on your own–no guidebooks necessary!  You will enjoy hours of debate with your fellow travelers defending Vernazza, Romaggiore, Manarola, Corniglia or even Monterosso as your favorite.

Although Monterosso is the largest (and the least quaint) of the five towns, the lovely Hotel Porto Roca is a great equalizer.  It makes sense to get a standard room (no view) and ditch the room except to sleep and siesta in favor of the gorgeous views throughout the property, the restaurant and the pool. The Cinque Terre trail head comes right to your hotel if you want to hike to the next town, Vernazza.  The route is gorgeous, but you will have to rest along the way with the fresh orange juice guy 84-year-old Angelo Celsi if you are out of shape like I am.  

At least one dinner at L’Ancora della Tortuga in Monterosso (outside table) on a high ridge against the dark blue hues of the Mediterranean cannot be missed.  La Tortuga will be your most enduring memory of Toscana and an evening of dining wonder that will linger with you for years to come. You will need to make reservations weeks in advance for this unsurpassed culinary experience.  You absolutely must insist on an outdoor table when making the reservation and reconfirm the outdoor table (tavola fuori) the day before. 

Siena or Firenze– 2 nights

Day 12 and Day 13.  Siena.  After Cinque Terre, it is time to head back to Roma, via Siena, a 3 hour trip.  No Tuscan holiday is complete, in my eyes, without a full day in Siena, the beating heart of Tuscany and a UNESCO World Heritage Site.  And yes, Siena is crowded so get a room, check in and wait for the crowds to die down in the evening.  Siena is the best shopping you’ll find in Tuscany (not counting Firenze of course), especially ceramics, handicrafts, even shoes and clothes so it makes sense to have that at the end of your trip.

There is a lot to see in Siena but don’t miss the grand Piazza del Campo in the center of town where the Palio bareback horserace is held twice each summer and the magnificent Duomo and Cathedral, second only to the ones in Firenze and Milano.

Alternate Day 12 and 13.  Firenze.   An alternative stopover on the way back from Cinque Terre is Firenze (please don’t call it Florence!).  The drive is a little shorter, at under 2.5 hours, but the crowds are 2 or 3 times as intense as Siena.  For that reason alone, Firenze is listed as an alternative to Siena for the summer after Covid.  There is no city quite as spectacular and also accessible due to its size as Firenze.  Like Siena, you will regret not spending 2 nights here.

The Accademia and Michelangelo’s David is the most famous sculpture in the world but don’t miss the equally powerful Rape of the Sabines in the next room.  

The world’s largest duomo designed by Brunelleschi in the 15^th Century as the Basilica di Santa Maria dei Fiore will be your second favorite screensaver, after one of the Cinque Terre.  The 2 nights will give you a chance to visit the Uffizi Gallery (very crowded) but for the less cultured there is wonderful shopping on Via Calimala (Corneliani-suits), Via Borgo (Angela Caputi-jewelry), Via Dei Pucci (I Fiori dei Tempo-jewelry) and dozens of other tiny side streets.  If you have been looking for that perfect Italian leather jacket, you will be overwhelmed by your choices in Firenze.

For dinner there are many choices, but I always enjoy Il Parione and its intimate but casual cellar dining room.  Ristorante Sabatini and Ristorante Fellini (for seafood emphasis) are both excellent but more formal. The restaurants are awesome in Firenze but look good it you going out in this stylish city.

A good hotel choice is the Davanzati, a 5 minute walk from the romantic Ponte Vecchio. If you would rather spend your money on food and shopping, the well located but otherwise mediocre hotel Due Fontane isn’t bad since you won’t be spending much time in your room. 

Fiumicino/Rome Airport– 1 night

Day 14. Fiumicino Airport Hilton.  Drive back to Fiumicino Airport and turn in your car.  You can stay the night at the Airport Hilton (not to be confused with the cheaper Garden Hilton near the airport) and walk directly from the hotel to your terminal for that early morning flight.  The Airport Hilton is, well, the Airport Hilton, strangely comforting in its predictability.

To round it off, here are my Top 10 Tips for your Tuscan holiday:  

• Rent your car at the airport in Rome, which is in the airport parking garage, a short walk from the second-floor terminal lobby.  Renting a car is relatively cheap and you absolutely need a car to explore Tuscany.  The roads are great and the driving easy, at least until you get into a town. Try not to drive in the chaotic big cities or venture down the tiny streets in the old Tuscan villages.  Park and walk!  
• Remember that in Tuscany most restaurants close by 1:30 so pull off the road at the Autogrill (surprisingly good) if you are hungry. Contrary to myth, although dinners start late, around 8:00, it is hard to get seated after 9:30.
• Buy a good GPS with current Italy maps loaded on because you don’t want to rely solely on Waze or Google Maps.  Cell coverage is getting better all the time but when you hit a dead spot you will wish your car had the satellite signal.  
• Foodies will be surprised to discover that there is rarely much difference on pricing between ‘fancy’ and ‘family’ restaurants.  The spread is usually around €3 for pasta dishes and rarely more than €5 for secondi. The nicer restaurants will expect you to buy all 4 courses, which is the big cost difference.
• Don’t let the slow, sometime poor service ruin your meal.  Be patient, drink a lot, don’t take it personally.  If you are polite and persistent you will get a smile.
• There are no bad restaurants in Tuscany, and this is a great excuse to free yourself from the guidebooks and websites and explore for yourself.  At dinner, remember to order the entrees and not just the primi (pasta) courses if you can afford it, even if you aren’t super hungry.  In Tuscany, the restaurant holds the table for you all night.
• Always go with the house wine in Tuscany, il vino di casa.
• Leave a small tip (10%) at dinner as a nod to being an appreciative guest in their country.  A euro per head at breakfast and lunch will earn you a big ‘grazie mille’ and VIP service the next time.
• Men, please dress nicely for dinner: the locals always do!  A clean dress shirt (no T-shirts), belt and black pants (no blue jeans or khakis) are good rules, with a jacket added for a nicer restaurant.  Never ever go to dinner in shorts unless you want the chef to spit something green and vile into your spaghetti. 
• There will be deals this year on flights and rooms but be prepared for a rush for August and September reservations. Please book your rooms directly through their website (rather than Booking.com or Orbitz) and pay a deposit now to help with the cash flow crisis.  It will also guaranty a nicer room and a warm reception when you check in. 

Finally, this is an itinerary for a middle of the road traveler.  It is neither a budget nor a luxe experience, just a great experience.  You will notice my bias against Airbnb but there are nice places on there as well if you don’t need the amenities of a hotel and don’t mind navigating around the language barrier.  The hotels in Cinque Terre and Firenze will be in the €350-€450 a night range so I have balanced the costs out with your stay in Trequanda. The travel experience should never be just a parade of fancy hotels and elegant restaurants picked out for you by TripAdvisor, even if you can afford to do that.  Tuscany is a blend of the simple and the sophisticated, accessible to the wildly spontaneous and the detailed planners.  For me, it is the elixir that will make me feel younger as I know I grow older.  For your hosts, your willingness to travel beyond your comfort zone in the year of Covid-19 will be life changing.  

Indrajit Obeysekere