Unexpected Italy
Street photography of a sweet man watering his plants.
Planning a trip to Italy can be challenging. The expensive add-ons for checked baggage force you to leave your favorite sweatshirt at home, which is just as well since many suitcases wouldn't fit into the trunk of that adorable Italian rental car anyway. And don't get me started on the quaint hotels that don't have an elevator. It isn't until you've carried your burgeoning twenty-four-inch Tumi and your kids' bags up five flights of stairs that you decide it's perfectly acceptable to wear an outfit twice and that you can get by with only three pairs of shoes.
These days, with the assistance of every social media platform and endless travel sites that suggest obvious tourist traps, simply plugging in "10 days in Italy" or "6 days in Spain" into an itinerary creation platform generates a comprehensive travel schedule, including stopovers, hotels, gas stations, and restaurants. That's the safe and preferred way to explore a foreign country, especially if a bonafide travel agency is out of reach.
A clever person once said that life is what happens when you are busy making other plans. If time is abundant while navigating the undulating roads of Tuscany—where the lunch reservation at Giuseppe's is a "soft 1:00 PM"—and you happen upon an impossibly perfect hamlet like Volpaia or Cortona, a towering Medici fortress that envelops a hillside and welcomes visitors to peruse its artisan ceramics and sip on Bianco Vergine Valdichiana, a signature white wine, then veer off your path already.
San Gimignano—difficult to say, but once you have the pronunciation down, you'll want to throw it into conversations and retell the time when you were dared to climb to the top of the tallest tower in flip-flops. The small town is surrounded and fortified by massive medieval walls, protecting the Gothic center and its many tucked-away shops in the backstreets. Whether your destination is Florence or Rome—driving the ancient pilgrim route Via Francigena that passes by "Medieval Manhattan"—missing out on the 800-year-old town with its frescoed churches and traditional Tuscan dishes would surely be one of those regrets to write on the bucket list for future travel.
Tucked away restaurant in Sienna, Italy
Dining within the walls of Tuscan history
Arezzo, Italy
Converted farmhouse is now a boutique 6-room villa on acres of fertile gardens
The city of Arezzo holds timeless, historic monuments that survived the merciless bombings in WWII in Piazza Grande, a square showcasing a miscellany of medieval and Renaissance architecture. To fully appreciate the experience of Arezzo's magic, choose to stay in a farmhouse-converted-hotel or monastery-turned-villa located just outside the 100,000-populated city. These accommodations are as captivating as any lodging in Italy—just ask those who watched Roberto Benigni's classic film, "Life is Beautiful." And equally spectacular in person.
Traveling light in your suitcase and light in your heart will guarantee a memorable experience when deciding to turn left at the fork in the road. "Sinistra! I see a castle in the distance," takes your vacation to another level. Moreover, visiting those quaint Italian villages whose names roll off your tongue as easily as it takes to finish the Nutella-flavored gelato reminds you that although the statue of David is impressive and the Trevi Fountain is iconic, the charming Tuscan villages are there to discover. Wait, we haven't discussed the five towns in Cinque Terre. Sorprendente!
Vernazza, Italy
One of the “Five Lands” in the coastal area within Liguria, the Cinque Terra is comprised of Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore.