Grape-land never made our bucket list. We assumed it was hot, humid, dirty, overrun with tourists, smelly, and rife with Gypsies rifling pockets.

All that’s true …

Then a life-long friend retired, snagged a timeshare in Cortona, Tuscany, and invited the old gang over for a June holiday. Within hours of our arrival, the people, history, food, wine, and physical beauty of this travelers’ paradise won us over.

Lana and I arrived in Rome and immediately broke European travel guru Rick Steves‘ taxi rule:  “If you can, get a taxi from an official taxi rank. It lowers the chance that you’ll wind up in unregistered taxis, which are notorious for not playing by the rules.”

After the ten-hour flight and twenty-hour day torched our brains, we stumbled into Roman sunlight, and a portly middle-aged driver — smiling ear-to-ear so happy to see us — uncloaked at the airport curb, tossed our bags into the back of his grimy black unregistered car, drove twenty minutes in circles, then deposited us in front of our hotel for 20 Euros. We wondered why his happiness doubled with a small tip until we caught a taxi ride for the same destination eighteen days later:  10 Euros.

The gregarious hospitality of the happy swindler story was worth the 15 Euros, we figured, and then we got nailed again a few days later in Florence.

Walking down a lightly populated boulevard, we were approached by a well-dressed middle-aged man asking for change. Within two minutes he had his fingers in Lana’s pocketbook playing the I’ll trade-this-two-Euro-piece for two singles … and when we asked him what he needed the change for, he replied:  the telephone.

Although it took reserve to keep my Keen-clad foot out of his Gucci-covered posterior, I laughed at Lana when she said later:  “I’d give him another Euro just to show me how he got his hands in my pocketbook.”

Rome at First Glance

We spent the first day walking around the Trevi Fountain , enjoying the shops and restaurants vibrating with international students, noticing Napoleon’s statue in disrepair and disregard, spying armed guards holding military-grade weapons in front of banks and government buildings, dodging ubiquitous motor-scooters swarming around stoplights — Vespas racing wide open from green to red by suited professionals of both sexes —  watching homeless folk washing feet in public fountains laced with exquisite statues, seeing graffiti sprayed on architecturally perfect limestone buildings throughout the city, ogling grandiose Vatican wealth walled next to Muslim immigrants selling shawls to bare-shouldered-naked-kneed tourists not minding Guru Steve’s advice:

Entry to the Vatican Museums, the Sistine Chapel, St. Peter's Basilica and the Vatican Gardens is permitted only to appropriately dressed visitors. Low cut or sleeveless clothing, shorts, miniskirts and hats are not allowed.

Once lusty shoulder knobs and bony knees are tastefully hidden, one may enter St. Peter’s Basilica and view roughly 50,000 portraits of naked folk. We discovered this at the end our our adventure. The second day we bused to Sorrento via Naples.

Naples

The bus driver stopped and let us stretch our legs at an overlook for ten minutes and then hustled us back inside and barreled through town as though a plague lay in wait.

We didn’t understand his motive as the view out the window was astounding, but days  later when our wine  tour  sommelier told us Naples held the reputation as the drug and crime capital of Europe. Like East St. Louis, West Oakland, and the South Side of Chicago, I reckon Naples contains streets to avoid.

Sorrento

The ocean-hugging romantic getaway across the Bay of Naples was abuzz with tramping tourists, but its lovely weather and cleanliness relative to Rome led to a wonderful stay with unending photographic possibilities, gourmet food, shopping, museums, architecturally unique churches, beautifully maintained walkways, and seaside-views that attract honeymooners from around the globe.

Our friends Mike and Chris — gang of ten members — were in Sorrento with their daughters Bridgette and Cami, so we dined on fresh seafood and pasta and headed back to our respective hotel rooms to gather energy for Capri and Pompeii.

Pompeii

The Pompeii exhibit at the Chicago Field Museum blew my mind back in 2005, but the actual setting places one smack dab in A.D. 79 in one of the prettiest places on earth, and quite modern in its day with running wells, cisterns, toilets, bath houses, shops with “hot plates“, brothels, and a drainage system that cleansed the streets during a rain.

Pompeians — enjoying the ultimate in culture and high living at that moment in history, living on a seacoast and hosting trade from the known world while enjoying the amenities of balmy weather and a robust citizenry — had no idea the hammer was coming down.  They didn’t even know that the nearby Vesuvius was volcanic.

On August 23rd A.D. 79 the city celebrated Vulcan, the Roman god of fire.

He rewarded them with a hammer blow the next day,burying the city in six meters of volcanic ash.

The size and scope of the Pompeii site —  plus its history and high culture that catch you unaware — make it a must-see, and British friends tell us that nearby Herculaneum, a UNESCO World Heritage Site lying in the virtual shadow of Vesuvius, is even more impressive.

Capri

It must be duly noted that Lana spent countless hours planning this trip, picking out the best bus tours based on customer ratings and comments on a half-dozen web sites, coordinating hotels, museums, trains, and airline tickets. She read / compared / looked up / analyzed and put together a vacation that unfolded perfectly with few unpleasant surprises, as she has so many times before. All I do is take pictures, write up the story, and admire her ability.

Waking to rainfall, we feared Capri — just a twenty-minutes from Sorrento via the Tyrrhenian Sea– would be a wasted day, but the sun came out on the voyage over, perfect conditions because only 5,000 tourist scampered around the island instead of the usual 10,000 that swarm the island daily.

Sasha, our red-haired tour guide boasting Italian-Russian parentage, met us at the dock and kept us thoroughly amused with historical anecdotes and insights throughout the day, pointing out an Italian Fascist redoubt from the WWII built on a jutting cliff side, and noting that the Greeks believed Capri was the end-of-the-earth. A siren still sits above the rocks luring vessels to her open embrace.

Capri’s known around the world for its blue grotto, a limestone cave that intrepid tourists take turns entering and enjoying the way sunlight reflects off the white stone.

The day –starting with rain and high seas — negated the blue grotto, but our boat driver poked into several other grottoes-not-so-deep-and-famous and gave us the grand tour of the island.

One impressive piece of artwork not far from the docks simply blew me away — Seo Young Deok’s “sculpture” composed of motorcycle chains woven precisely into the shape of a human face — perfect for the scooter-crazy Italians.

Another highlight was the tram ride up to Alta Capri (alta = above) where the views not only took my breath away but jolted me with vertigo, a sign of age perhaps.

The Tyrrhenian Sea continuously cycled through different shades of blue as the sun filtered in and out of the clouds. Few people chose the path below, but folks of all ages rode the tram to the top and rubbernecked a 360 degree view that startles the senses with its beauty via changeable light and islands winking in and out of the horizon.

Orvieto

We took the bullet train to this famous hill-town, but beware boarding trains in Rome.  The schedule displayed for passengers shows trains arriving at certain sidings.  But in reality, high speed trains arrive so quickly they usually beat arrival times, then sit idle on the tracks outside the city while the station assigns them a last-minute arrival siding not listed correctly on the schedule board in Rome.  Which means unaware Americans must run like like O.J.’s leaping luggage to the correct boarding spot at the last second.  Not so much fun for geriatrics with metal knees.

The word Tuscany is derived from the Etruscan culture, which flourished in mid-Italy from 700 BC until Roman assimilation virtually erased it in 400 BC.

During the Middle Ages, [Tuscany] saw many invasions, but in the Renaissance period it helped lead Europe back to civilization. Later, it settled down as a grand duchy. It was conquered by Napoleonic France in the late 18th century and became part of the Italian Republic in the 19th century.  

-- Wikipedia

Orvieto, like Cortona, is a hill town in Tuscany. At first glance, the military advantage of the high ground is obvious, but many of these villages also avoided the swamps covering the low ground, and this is why the region grows such luscious fruit:  the bogs were drained a mere 200 years ago.

The city had a love-hate relationship with the Papacy during the Middle Ages, when it reached a population of 30,000. However, five Popes lived here for a time for “political and strategic purposes.”

In other words, they were run out of Rome and had to wait for the heat to die down before they could re-assume the Vatican.

Major Orvieto attractions include: the Duomo di Orvieto 14th century Roman Catholic cathedral is one of the most spectacular in Italy; the Orvieto Underground leads you through subterranean medieval caves, tunnels and Etruscan wells; the Torre del Moro 13th-Century clock tower chimes on the hour, half and quarter hours; and, Pozzo di San Patrizio (St. Patrick’s Well). Dating to 1537, this well is 62-meters-deep and features two spiral staircases.

Assisi

Is naturally associated with famous homeboy Francis, a.k.a. Francesco Bernardone, who lived here around 1200 AD. This simple friar bridged the gap between Jesus and Martin Luther, calling attention to the materialism of the times and the decadence of the Catholic Church during one of its darker periods.

Today, eight-thousand permanent residents occupy Assisi … while six million tourists stampede through the streets each year. The commercial aspect is a bit daunting, especially when a Saint Francis “statue” springs to life and thanks you for tips.

During his day similar throngs of buyers, sellers, and endless sinners seeking penance crowded the streets and wore out poor Francis. However —  like Jesus rowing to the far side of the Sea of Galilee — Francis would walk forty-two miles through the country to Cortona and relax, meditate, and write at Le Celle (The Cell).

Lana didn’t like Assisi due to its intense commercialism, and heavy crowds. But once she understood it was always this way, and beheld the actual monastery near Cortona where Francis retreated into nature, well.

It all came clear.

Tears flood the eyes and hair stands on the back of your neck when you enter Le Celle.

I’m not a jealous person by nature, but Skip mentioned that he often hikes up to Le Celle to read and contemplate. What a blessing!

Florence

This vibrant city is best viewed in the late fall as June is rife with tourists. At one point a hundred-plus Mexican students paraded by lustily celebrating their soccer victory over Germany, and every restaurant and cafe hummed with activity late into the night.

Jammed with architecture, sculptures, marching bands, entertainers, the best steaks you’ve ever melted in your mouth, and much more, Florence is a must-visit.

Besides the mandatory hackle-raising view of Michelangelo’s David at the Medici family’s Galleria dell’Accademia, check out the Uffizi Gallery (housing Botticelli’s The Birth of Venus, Raphael’s Madonna of the Goldfinch, and Rembrandt’s Self-portrait as a Young Man.

We loved walking the city at night, watching couples enjoying the romantic atmosphere, seeing the architecture in street light, reveling in the gourmet cuisine, and listening to the street musicians earning their keep into the early hours of the morning.

Cortona

This ancient hill-town reaching back to 700 BC Etruscans is a jewel in any visitor’s travelogue-memory.

Fetchingly portrayed in Frances Mayes’ Under the Tuscan Sun, the town’s vibrancy, history, architecture, museums, gourmet restaurants, geography, and kaleidoscopic light combine to hold you spellbound for the entire length of your visit.

Our hosts Skip and Virginia propelled themselves into international-living via elbow grease, perseverance, and brains (is there another legitimate path?) and reside on the northwest side of the city facing sunsets, near the Etruscan wall, on a Roman road overlooking the Cimitero della Misericordia (cemetery). The Roman road leads south to city center, or north through an ancient arch down a quarter-mile stroll to our hotel overlooking the Val di Chiana, or Chiana Valley, where Hannibal destroyed a Roman army in the Battle of Trasimene  in June 217 BC.

Here’s a ten-second video taken at dusk with bats scavenging mosquitoes on the pink horizon, Lake Trasimino shining in the background, and the gang-of-ten enjoying a gourmet meal at Ristorante Tonino, which featured a series of post-dinner solos by inspired opera singers.

Three couples bunked at the timeshare, while Mike, Chris, Lana and I vacationed at the Locanda i Grifi, a sweet hotel just a quarter-mile down the Roman road, an inn we highly recommend due to the nice rooms, great views of the valley, and the hospitality of chef Cristiano, who held a cooking class for us one mid-morning.

Warning: If you really want to enjoy these Tuscan hill-towns, make sure you’re physically up to the challenge of walking up and down 14% grades. Actually, this applies to any kind of foreign travel as the unexpected always occurs, usually involving a physical challenge. Furthermore, driving isn’t feasible in town center due to the inclines, and there’s little room to park. Only the the intrepid locals attempt it.

We enjoyed a leisurely lap around town one sunny morning, passing by Francis Maye’s famous home and the Roman road next to it that’s a shortcut to city-center, all-of-which overlooks the Chiana Valley.

The Piazza della Repubblica is the heart of town, where we lunched and people-watched while discussing the length of the trip between gnawing on our mother’s ankles under the kitchen table in the late 1950’s … to this spot where Saint Francis hung out for recreation and Hannibal slaughtered the Romans.

Other highlights included The Museum of the Etruscan Academy, a tour of the famous cemetery below the time share, and a tour of the Stations-of-the-Cross that ended above our hotel at the Basilica di Santa Margherita, where its namesake lies in state like a slab of dark jerky, drawing gawkers inevitably spilling donations into a handy cup. The interior architecture is a wonder to behold.

Cortona is so packed with delights that it would take a decade of living there to search them all out. We jammed in as much as possible, however, and never lost the idea that we were on parade as well.

Living in a small Italian hill-town, and having lived in a small town in south Georgia, I understand that you can recognize a family gene pool by the lift of an eyebrow, or the length of a neck, or a way of walking.

-- Francis Mayes

The Villa S. Anna

We visited several Tuscan wineries and all were unique, but Villa S. Anna Winery — owned for nearly two hundred years by Simona Ruggeri Fabroni’s family near Montepulciano — tops the list due to Simona’s wonderful personality, storytelling ability, and deep knowledge of the business from five decades of managing all aspects of the enterprise.

After serving a wonderful lunch, Simona lead us through the grounds and cellars, sharing insights other wineries lacked — e.g., instead of removing cellar wall mold, it’s maintained at a certain humidity so the wine ages at a steadier rate. Newer wineries avoid this hassle, but the results are less predictable.

Sometimes the Scottish blood is an inconvenience.  For example, sane people toss out most of their wine while sip-sip sipping throughout a day-long wine tour.

But if pinching pennies and looking for dimes on city streets is a natural inclination, then drinking all the wine poured out at wine-tastings is elemental.

But don’t do it.

Here’s the result if you think you’re going to win that particular battle, so hold your cell phone sideways.

The Vatican

Our dream days in Cortona ended with a wonderful lasagna dinner at Skip and Virginia’s followed by several hours of joyful banter, video-making, and wine-tasting.  Then it was time to plan for the next gang-of-ten rendezvous, followed by hugs and farewells.  The blessing we have in each other is lost on none of us, and a week together in Cortona deepened the bonds even further.

We returned to Rome for the last two days, viewing the Vatican, walking as much as possible for photos, and loving the seaport at Fiumicino,  next to the airport.

The Vatican is so vast and full of unending surprises that no blog of this size could explain it. The picture above captures the average reaction upon entering The Papal Basilica of St. Peter, the main hall reaching a height of 448 feet.

Our university-art-school-trained guide lead us through a maze of huge rooms and hallways filled with artwork, spilling thousands of interesting tidbits that my mind couldn’t fully process, but I do remember that during Michelangelo’s work on the Sistine Chapel,  Pope Julius II was plagued by some minor official’s poor behavior, so when Michelangelo asked Julius who needed to fill the hell space in the bottom right corner, the Pope suggested the same minor official — and then added that this guy needed a viper attached to his scrotum for all eternity. The sort of thing males remember from art museums.

Fiumicino

We spent the last two days strolling arm-in-arm through the streets of Rome and across the beaches of Fiumicino, watching women jostle over sale items, enjoying one last gang-of-eight meal, and watching the fishing boats arrive and unload the day’s catch.

Don’t underestimate this sleepy little city next to the airport as it jumps alive to the sound of fishing boats returning — reminding me of the Hannibal, Missouri of Mark Twain’s youth — and there are dozens of excellent street-side cafés, restaurants, and bars to explore while public beaches allow blue-collar travelers a gander at the blue-collar locals.

The Takeaway?

Don’t let preconceived notions keep you from enjoying Italy as its pleasures far outweigh the hassles for 52.4 million visitors per year, but go physically prepared for international travel.

Italy provides more to do than several lifetimes of exploration could cover, and the mix of ancient history and current vibrancy intoxicates the senses beyond the legendary food and drink. Enjoy it with old buds if possible, then savor those times together whenever you reunite.

An old friend never can be found, and nature has provided that he cannot easily be lost.

Samuel Johnson