A Taste of Italy: Discovering Florence and Venice in the Shoulder Season

This spring, I had the opportunity to visit two of Italy’s most iconic cities—Florence and Venice—on a recent familiarity trip designed to deepen my firsthand knowledge of luxury travel experiences in the region. Visiting during the shoulder season, just before peak summer crowds descend, allowed for a more relaxed pace, better access to popular sites, and a chance to connect more authentically with each destination.

Florence: Renaissance Reverence, Shopping, and Culinary Excellence

Florence is a city that wears its history with quiet confidence. Every street corner offers a visual reminder of its Renaissance legacy—from the intricate façades of 15th-century chapels to open-air sculptures in lively piazzas. Walking through the historic center, a UNESCO World Heritage site, it’s easy to feel immersed in centuries of art, thought, and political influence.

The Duomo, with its red-tiled dome engineered by Filippo Brunelleschi, dominates the skyline and rewards those who climb its narrow stairs with sweeping views over the city and the Tuscan countryside beyond. Just steps away, the Baptistery’s bronze doors—known as the "Gates of Paradise"—are as dazzling as their nickname suggests.

Florence’s museums offer a concentrated dose of world-class art. If you have visited before, you know all about the Uffizi Gallery.  What you may not know is that they have recently opened the walkway that connects the Uffizi with the Boboli Gardens.  About 750 meters long, it was built by architect Giorgio Vasari in 1565: the Medici family used it to reach Palazzo Vecchio from Pitti Palace undisturbed and without running risks to their safety. Closed in 2016 to allow it to be brought up to safety standards, it has been fully restored.  It is now available to visit – but book the private tour, otherwise it’s just a long walk with no context.

One of the most meaningful moments of the trip was our private tour of the Basilica di Santa Croce, a stunning example of Florentine Gothic architecture and the final resting place of many of Italy’s most celebrated figures. With an expert guide, we explored the church’s ornate chapels and vast frescoes by Giotto, gaining a deeper appreciation for its artistry and spiritual significance.  We stood before the tombs of Michelangelo, Galileo, and Machiavelli in near silence—a rare and unforgettable opportunity to connect with the giants of Italian history.

One of the most enjoyable parts of this visit was staying in a restored palazzo-turned-luxury-hotel, where historic charm is balanced with modern comforts. Waking up to the sound of church bells and enjoying breakfast in a quiet courtyard felt like an invitation to slow down and soak in the rhythm of Florentine life.

The city is also a shopper’s paradise. Florence is the birthplace of several iconic Italian fashion houses—Gucci, founded here in 1921, now operates an immersive boutique and museum known as Gucci Garden. Housed in a former palace in Piazza della Signoria, the space combines fashion, art, and curated gastronomy. Nearby, the Ferragamo flagship store and its adjacent museum trace the evolution of Italian style from custom-made shoes to high fashion.  I was in heaven!

For clients who value craftsmanship and exclusivity, Florence’s leather workshops are a true draw. Many of these family-run ateliers have been handcrafting gloves, belts, and handbags for generations. A guided shopping tour can include private appointments where clients can see artisans at work and even order custom pieces.  We can even book a chance for you to create your own leather masterpiece!

Venice: Quiet Canals, Timeless Craftsmanship, and a Grand Arrival

After Florence, we took the train to Venice, ever romantic and mysterious. It felt especially serene during the shoulder season. The absence of large crowds meant that even the most visited areas—like Piazza San Marco and the Rialto Bridge—were approachable and enjoyable.  But don’t be surprised to discover that Venice is bustling, even in March. 

Upon arrival, we were greeted by an unforgettable sight: the Amerigo Vespucci, the majestic tall ship of the Italian Navy, docked in the Venetian harbor almost directly in front of our hotel. With its black and white hull, gleaming brass fixtures, and towering sails, the ship was preparing for its annual training voyage for naval cadets. Often referred to as the most beautiful ship in the world, the Amerigo Vespucci is not only a feat of engineering but also a floating symbol of Italian pride and tradition. Watching it at rest in the lagoon, framed by the domes and bell towers of Venice, felt like a moment suspended in time.

Accommodations in Venice range from grand canal-side palazzi to quiet boutique hotels tucked into residential neighborhoods. I stayed at a luxury property in the Castello district, which offered both proximity to major landmarks and the calm charm of a less touristed area. It’s a former convent with a stunning interior and some of the best service I have ever experienced.

Another standout experience was a leisurely afternoon on Burano, the colorful island known for its lace-making tradition and vibrant fishermen’s homes. After a short boat ride from Venice, we wandered through quiet canals and narrow lanes, enjoying the calm pace and postcard-perfect scenery. The island's cheerful façades are more than just pretty—they represent a long tradition of fishermen painting their homes in bright colors to spot them easily from the sea. We enjoyed a wine tasting at a family-owned enoteca, where we sampled crisp white wines from the Veneto region and learned about small producers not often found abroad. Ask me about their wine – which is sold in a Murano glass bottle.  Yep.  I was sold!  This was followed by a seafood-focused lunch in a restaurant famous for it’s fresh seafood and incredible risotto! Burano, with its mix of color, tradition, and culinary charm, was a refreshing contrast to the grandeur of Venice proper.

Back in Venice, we were treated to a private tour of the hidden rooms of the Doge’s Palace.  What a treat! Taking the time to see the treasure and the Doge’s private rooms was incredible – and something we could book for you too.Dining was a pleasure in itself. From cicchetti bars serving small bites with a glass of local wine to elegant dinners with views of the Grand Canal, the city offers a wide range of gastronomic experiences. A standout meal included risotto al nero di seppia (squid ink risotto), a Venetian classic prepared with care and paired with a delicate white from Friuli.

Why Travel in the Shoulder Season?

Traveling in the shoulder season—typically March to mid-April or late October to November—offers a number of advantages that elevate the overall travel experience. The weather is milder and more pleasant for walking tours, boat rides, and alfresco dining. Accommodations often have better availability and more flexibility for upgrades or special requests. And, perhaps most importantly, there is room to breathe—whether you're admiring Renaissance frescoes, strolling along quiet canals, or simply enjoying a cappuccino in a sun-drenched piazza.

These months also offer a chance to experience local life more fully. With fewer visitors, cities like Florence and Venice return to their natural rhythms. You’re more likely to strike up a conversation with a local, discover a neighborhood trattoria that isn't listed in guidebooks, or stumble upon a seasonal market selling fresh truffles or handmade linens.

Most memorably, the quieter season opens doors to exclusive opportunities that are harder to access during peak months—like our private tour of Santa Croce. Standing in the cool stillness of the basilica, with Giotto’s frescoes towering above and the tombs of Italy’s greatest minds at our feet, we felt the full weight and wonder of Florence’s cultural legacy. It’s experiences like these—quiet, personal, and steeped in meaning—that truly define luxury travel.