8 Days in Northern Italy: From City Exploration to Countryside Retreat

We landed at Milan-Linate Airport around 10 am and opted for a private transfer to ensure a seamless arrival — something I always prioritize for international trips. Our home base for the night, Speronari Suites, was just two blocks from the Duomo di Milano, making it the perfect spot to rest and recover from jet lag. After checking in, we enjoyed a welcome drink and a €40 dining credit at El Porteño, the hotel's Argentinian steakhouse, followed by a relaxing session in their sauna — much needed after 12+ hours of travel.

For dinner, we dined at Al Cantinone, a cozy spot that feels like an Italian grandmother’s home. Afterward, we took a short stroll to Piazza del Duomo to admire the breathtaking cathedral and enjoy live street music. We ended the night at the Galleria, where we found the famous bull mosaic — legend says spinning on it three times brings good luck!

Today, we explored the breathtaking Duomo di Milano with tickets granting us access to the cathedral, archaeological site and terraces. Climbing the terraces is a must—after ascending 200 steps, we were rewarded with stunning city views and up-close glimpses of the intricate Gothic spires. Since it was Sunday, we also had the unique opportunity to attend part of Sunday Mass, an unforgettable experience regardless of religious background.

For lunch, we headed to Terrazza Aperol, an Instagram-famous rooftop with unbeatable views of the Duomo. Sipping an Aperol Spritz and a Negroni while admiring the cathedral made for a quintessential Milanese moment. The afternoon was spent wandering through Brera, where we discovered charming boutiques, vintage stores (shoutout to ChatGPT!) and stylish finds.

We wrapped up the day with dinner at Obicà Mozzarella Bar, indulging in our first Italian pizza while soaking in one last stunning view of the Duomo.

Next stop: Firenze! We boarded the Frecciarossa in first class, ensuring plenty of legroom and space for our luggage on the quick two-hour journey. Upon arrival, we walked to Hotel Calzaiuoli, a charming four-star stay just steps from the Duomo, Uffizi Gallery and Piazza della Repubblica. A bottle of prosecco and a breathtaking view of the Duomo from our window made for the perfect welcome.

After exploring Piazza della Signoria, we crossed the Arno River and made the climb to Piazzale Michelangelo just in time for sunset. The incline is absolutely worth it — the panoramic view of Florence bathed in golden light was unforgettable. We ended the evening back in the city center with an authentic Tuscan dinner at Osteria dei Leoni.

Florence is packed with sights to explore, so we spent the day wandering, eating and soaking in the city's vibrant energy. We began with a visit to the Cathedral of Santa Maria del Fiore, a UNESCO World Heritage Site, followed by a stop at St. John’s Baptistry. Afterward, we made our way to the San Lorenzo Market and Mercato Centrale, sampling our way through the stalls before venturing outside to browse the leather goods. From there, we crossed the Ponte Vecchio, Europe’s oldest stone bridge, where we enjoyed window shopping for luxury jewelry, watches and other fine items.

A bucket list item for me was to find one of Florence’s famous wine windows. As we explored the Oltrarno District, we were thrilled to locate Babae, one of the most iconic functioning windows. Afterward, we enjoyed a late lunch at Signorvino — while not the most traditional spot, the views of the Arno River and Ponte Vecchio were spectacular. We then headed to Piazza della Repubblica to admire its whimsical carousel before visiting Odeon Cinema, a renovated theater-turned-bookstore that continues to screen classic films.

For our final night in Florence, we kicked off the evening with social hour at Hotel Calzaiuoli, enjoying free drinks before heading to Trattoria ZaZa for dinner. This beloved spot has been a gathering place for both locals and visitors for years, known for serving fresh, high-quality Tuscan dishes. The eclectic decor, mismatched tables, and colorful artwork added to the charm, and the Florentine steak was a true highlight.

We decided to rent a car for the drive into the Tuscan countryside. Though the roads can be a bit challenging, the stunning scenery along the way made it all worthwhile as we headed to Villa Petriolo. This beautifully restored 17th-century villa blends traditional Tuscan architecture with modern comforts, all while embracing sustainability. Everything — from the food and body products to the wine — is either produced on-site or sourced from local farms.

Upon arrival, we spent the day at the Mater Wellness Retreat on the property, indulging in massages and sipping tea while taking in breathtaking views of the surrounding hills. Later, we enjoyed a peaceful afternoon in our private courtyard, sipping the villa’s Aida sparkling wine before heading to Osteria di Golpaja, one of the three on-site restaurants, for an unforgettable dinner.

We started our day with a farm-to-table breakfast before heading back to the Mater Wellness Retreat for a spa day pass. The spa attendant guided us through three pathways: relax, energize or detox. Opting for the relaxation pathway, we immersed ourselves in saunas, steam rooms, cold plunges and serene pools, fully embracing total relaxation. The highlight was unwinding in the hot tub with sweeping views of the Tuscan countryside — an unforgettable experience.

After a delicious lunch, we decided to explore the estate with a farm tour. We strolled through the rolling hills, visiting baby sheep, truffle-hunting dogs, donkeys and pigs. The Villa offers several footpaths, each varying in length and difficulty, allowing us to enjoy the surroundings at our own pace.

On our final day in the Tuscan countryside, we visited the medieval town of San Gimignano. We spent the day exploring its cobbled pedestrian streets, admiring the stunning views and indulging in gelato at Gelato World Cup Champion Gelateria Dondoli — a must for any gelato lover!

In the evening, we dined at PS Ristorante, where we were treated to a six-course tasting menu. This restaurant has earned a green Michelin star for its sustainability efforts, and each course was paired with carefully selected wines. The fun didn’t stop there — during the meal, we played "Blind Man’s Buff." The sommelier picked three wines from different Italian regions, and we had to guess their origins. (Hint: we guessed correctly and won a prize, which came straight from the farm!)

Though we were sad to leave Villa Petriolo, it was time to head back to Milan in preparation for our early morning flight. After returning our rental car in Florence, we boarded a first-class train back to Milan. We checked into the stunning Excelsior Gallia Hotel, where the room entrances resemble bank vaults and the rooms exude modern luxury.

We spent the remainder of the day wandering the city one final time, soaking in Milan’s vibrant atmosphere. For our last evening, we dined at Terrazza Gallia, where we enjoyed expertly crafted cocktails and incredible views of Milano Centrale, making the perfect end to our Italian adventure.