Italian Confidential

Over the past few years, I have had the pleasure of visiting Southern Italy for two key moments in my life: the first being my honeymoon, where my Italian-Canadian husband introduced me to the Italy he knows, and the second being his sister’s Sicilian wedding, where my entire extended family introduced me to the Italy they know. My in-laws have deep roots in the south, and now, so do I. So instead of putting together the traditional Sip, Stay, Shop travel diary, I’ve chosen four places in the most intense Italian sud—an area still largely undiscovered by tourists— that I simply have to see again. —Kelsey Klassen

MASSERIA SUSAFA: Pulling up to the villa in the hills of central Sicily where my sister-in-law was hosting her wedding literally took my breath away. After a white-knuckle drive along a charmingly winding and washed-out dirt road, the unexpected appeared: a meticulously landscaped pine drive, leading to a steel and stone masseria, or country estate, rosemary hedgerows, and then golden wheat fields as far as the eye could see. Primarily a boutique wedding and agritourism destination for in-the-know Europeans, anyone can, and should, brave the drive to bask in the sights, smells and tastes of this 300-year-old working Italian farm. Masseriasusafa.com

OTRANTO: A whitewashed slice of Greece near the tip of Italy’s stiletto, Otranto is a paradise waiting to be discovered. The coastal drive to get there—dotted with hidden swimming grottos and seafood to nourish the soul—makes the day of travel from Naples worth it alone. An ambling walk from our hotel, the Relais Valle Dell’Idro, gently guided us towards the seaside resort’s impossibly romantic central promenade, filled with Italian day-trippers and sun-kissed families sharing plates of frittura mista. Flanked by a soaring medieval fortress at one end and a quintessentially Italian beach at another, time ceases to tick by in the distance between the two. Otrantohotel.com

AMALFI COAST: The Amalfi Coast is hardly a secret; however, the travellers who venture beyond Rome and Naples to this dizzyingly improbable UNESCO World Heritage Site rarely go past the renowned towns of Sorrento and Positano. This is for two good reasons: 1) They are beautiful. And 2) Tourists are warned explicitly to not drive the hazardous Amalfi Coast road. Before she immigrated to Canada, though, my mother-in-law used to summer on the Amalfi Coast as a teen, so my husband and I have made a point of seeing it all. Listen to church bells peal out over the Piazza del Duomo in Amalfi, relax in sundrenched Praiano, buy lemons from a roadside stall in family-friendly Maiori, catch a boat to a hidden cove from the beach in wee Erchie (where we base our stays, at the Limoneto di Ercole apartments), and eat the freshest catch of the day in authentic Cetara. Then leave it all in the glowing rearview and go see the ruins of Pompeii. Limonetodiercole.com 

TAORMINA: Long a playground for the rich, and richer, Taormina is a spectacularly situated resort destination on the east coast of Sicily. In addition to boasting world-class luxury shopping and azure-blue beaches, Taormina is also just a helicopter ride away from the volcanic spectacle of the Aeolian Islands. I suggest booking a vacation rental through VRBO.com. Keep peak season in mind–Taormina is Sicily’s most popular summer getaway—and if you get the chance, try to catch a touring pop star performing in the city’s ancient Teatro Greco. Teatrogrecotaormina.com

Image credits: iStockphoto.com