To celebrate our third wedding anniversary — traditionally marked by leather — we couldn’t think of a better destination than Italy, the land of craftsmanship, culture, and cuisine.
Sarah, a seasoned Italy traveller, was eager to return. I, on the other hand, had only experienced Rome from the depths of a hotel basement during a conference. So, with a little persuasion, we planned a road trip to explore some of Italy’s most iconic and romantic destinations: Pisa, Florence, San Gimignano, Lake Garda, and Venice.
Pisa
Our adventure began in Pisa, home of the iconic Leaning Tower. We stayed at the award-winning Palazzo Cini – Luxury Rooms — a beautifully restored 19th-century villa turned boutique B&B. Just minutes from the airport, they arranged a taxi for us, which was both convenient and cost-effective.
Our suite featured a freestanding bath, a separate lounge with a sofa bed, and a private courtyard garden filled with jasmine and orange trees — a serene welcome to Italy.
Pisa is compact and walkable. On our way to the Leaning Tower, we passed through the city’s Botanical Garden, a hidden gem that added a touch of tranquillity to our sightseeing.
San Gimignano
Next, we headed to San Gimignano, a medieval hill town in Tuscany. Famous for its skyline of towers (the Manhattan of the Middle Ages so to speak!) once symbols of family wealth and rivalry — the town is steeped in history. The Duomo di San Gimignano houses frescoes by Ghirlandaio in the Santa Fina Chapel.
We met the charismatic Duccio Nacci, Italy’s first photo gallery owner, whose stunning photography now travels home with us. And of course, we indulged in world-famous gelato at Gelateria Dondoli.
Our stay at Tenuta Guardastelle was unforgettable. This 15th-century farmhouse turned vineyard offers breathtaking views of olive groves and rolling hills. Accommodation is both rooms in the original farmhouse or individual cottages. The wines — especially the Vernaccia di San Gimignano and the rich Irpide Chianti were exceptional. On our anniversary, a Michelin-starred chef prepared a private six-course dinner paired with estate wines, all for just €50 per person.
Florence
Driving through the Tuscan countryside to Florence was a dream. We stayed at Ad Astra Suites, a hidden gem south of the Arno River in a quiet, local neighborhood, but only ten minutes walk to Pritti Palace and 0.6KM from the Ponte Vecchio. The mansion features Europe’s largest privately owned walled garden and as you can see, the view from our room was stunning:
Florence dazzled us with Renaissance masterpieces. We visited the Duomo, Galleria dell’Accademia to see Michelangelo’s David, and the Uffizi Gallery, arguably the finest art museum in the world. The Ponte Vecchio, lined with glittering jewellery shops, was a highlight.
Lake Garda
A four-hour drive brought us to Lake Garda, where we stayed at the elegant Lido Palace in Riva del Garda. This Belle Époque hotel offered every luxury, such as spa, gym, pools, and a fantastic bar — a refreshing contrast to our boutique stays.
Venice
We dropped off our rental car at the airport and took a private water taxi to Hotel Aquarius which is nestled within the Palazzo Pemma-Zambelli. With charming gardens and contemporary rooms embellished with Murano glasswork chandeliers, this boutique hotel felt like a living art gallery, we both thought it was stunning.
The hotel overlooks San Giacomo dell’Orio, a lively square where Venetian dialect still echoes. Two aquariums at the entrance recreate the lagoon’s ecosystem in collaboration with the Natural History Museum of Venice.
We visited Harry’s Bar, St Mark’s Basilica, and shopped for leather anniversary gifts. Using the vaporetto with a day pass was a fun and flexible way to explore the city.
Closing Thoughts
I’m a true convert to Italy. We’re already planning our next adventure, and if anyone needs advice on planning a trip, conference, meeting, or event in Italy, we’d be delighted to help, so why not dispel the winter blues by planning your next trip with us.
Lance