If you’re craving an Italian escape that’s equal parts elegance, indulgence and old-world charm, let me take you on the exact trip I do when I need an Italian fix. It begins in fashion-forward Milan, winds through vineyard-laced hills and lakeside villages, and ends at a Relais Chateau, family owned Palladian Villa near Venice where the you arrive feeling welcome and leave as family. .
Start in Milan, Italy’s unapologetic capital of style. I checked into Palazzo Parigi, a luxurious Relais & Châteaux property that feels more like a grand private residence than a hotel. High ceilings, velvet drapes, fresh flowers everywhere - it’s Milanese glamour at its best. From here, it’s an easy stroll to the boutiques of Brera, the Duomo, and some of the best people-watching cafés in Europe. Don’t skip aperitivo - it’s a ritual here - and you’ll quickly see why no one’s ever in a rush.
From Milan, rent a car. You could do this itinerary by train, of course—but driving opens up a whole different Italy. The kind with detours to hidden villages, hilltop views, and tiny family-run wineries where tastings are done in someone's living room. The slow roads through Piedmont and Veneto are stunning: lakes that shimmer in the sun, medieval towns perched on cliffs, and the occasional designer outlet that just so happens to have last season’s Italian leather boots at a third of the price.
Just outside Verona, we stayed at Villa Cordevigo, a stunning wine estate and spa hotel housed in a lovingly restored 18th-century Venetian villa. This Relais & Châteaux property is surrounded by olive groves and its own vineyards, offering a tranquil contrast to the buzz of Milan. We borrowed bikes and cycled through the vineyard trails, then stopped for a glass of the estate’s own Bardolino by the pool. The gourmet restaurant, Oseleta, holds a Michelin star, and every bite was as artful as the architecture.
The concierge will set you up with tastings, experiences and even a picnic for your bike tour
Verona itself is romantic and alive with culture. We spent the evening at the Roman Arena under the stars, wrapped in blankets, watching a live performance that felt straight out of a Fellini film. The city is walkable, filled with charm, and worth every step - even if you’re still full from the previous night’s tasting menu.
And then - Mira. You won’t find it on most tourist maps, which is exactly why I love it. About an hour outside Venice, Mira is home to Villa Franceschi, a historic Venetian villa that’s still owned and operated by the Franceschi family. Not in the “we visit occasionally” kind of way - but truly run as a full family affair. The siblings manage the hotel, the parents greet guests and cook in the kitchen, and you can feel the pride in every corner.
Alessandro, who now oversees much of the guest experience, is a walking encyclopedia of local secrets. He personally took us to nearby Italian shoe factories - places that quietly produce high-end footwear for major luxury brands, yet remain almost entirely unknown outside the industry. I came back with shoes I probably shouldn’t have bought, and zero regrets.
We took a day trip into Venice - probably my all time favourite city if you stay off the tourist spots and returned for champagne by the pool. We loved the hands-on cooking class with Alessandro’s father, followed by dinner under the trees at the villa’s beautiful restaurant. Everything we made in the afternoon was transformed into our evening meal. It felt like home - if your home had chandeliers, a private chef, and a very well-stocked wine cellar. My dream would be to get married there one day!
If you’re planning Italy this year, skip the obvious. Land in Milan, take the scenic route through wine country, let Verona and Villa Crespi romance you, and end your journey in Mira—where Italy isn’t just something you see, it’s something you feel.
If you would like me to recreate a private Italy adventure for you please let me know as I would be delighted to.
Want to travel with me? Check out my website here for my upcoming trips including loads of Safaris this year after partnering with an African company.
Fancy an Oceania Cruise at Canadian Dollars at Par… reach out we have that too.
Join us in Tahiti on their newest ship the Vista in March 2026. Info coming soon. Canada at Par pricing too.
Till next week travel pals!
