TRAVEL INSPIRATION
What to Do in Italy: Essential Experiences, Expert Recommendations, and Hidden Gems
By The Kensington Content Team
Reviewed by Suzanne Palazzolo, Destination Expert
Published March 16, 2026 | Reading Time: 9 mins
TRAVEL INSPIRATION
By The Kensington Content Team
Reviewed by Suzanne Palazzolo, Destination Expert
Published March 16, 2026 | Reading Time: 9 mins
Italy offers an extraordinary blend of art, history, cuisine, and natural beauty, where ancient ruins, Renaissance masterpieces, rolling vineyards, and dramatic coastlines come together in one richly layered journey.
From Rome and Florence to Sicily, Lake Como, and the Amalfi Coast, each region reveals a distinct personality, shaped by local traditions, regional flavors, and centuries of cultural heritage.
With thoughtful timing and expert planning, travelers can go beyond the iconic highlights to enjoy private wine tastings, immersive culinary experiences, and lesser-known towns that showcase Italy at its most authentic.
Italy isn’t just a destination. It’s a feeling. It’s the golden light hitting terracotta rooftops at sunset. The echo of footsteps across ancient stone. The first bite of perfectly charred pizza in Naples. The slow swirl of wine poured by someone whose family has tended those vines for generations.
“Italy captures your heart immediately,” says Kensington Destination Expert Suzanne Palazzolo. “Each region feels completely different, yet everywhere you go, there’s beauty, history, and incredible food waiting for you.”
If you’re wondering what to do in Italy, start here. From Florence and Rome to Sicily and Lake Como, these are the essential experiences, expert recommendations, and hidden gems that bring Italy to life.
Florence is where art, architecture, and appetite come together.
“Watch the sunset from Piazzale Michelangelo,” Suzanne says. “The views are amazing.” As the city glows in soft pink and gold, the Duomo rises above a sea of tiled roofs. It’s the kind of moment that lingers.
In the historic center, marvel at the Cathedral of Santa Maria del Fiore. Climb Giotto’s Bell Tower for sweeping views, then ascend Brunelleschi’s Dome for a perspective that feels both intimate and vast. Explore the Baptistry and its famous bronze doors, often called the “Gates of Paradise.”
And then, of course, there’s Tuscany beyond the city. “Chianti is pure beauty,” Suzanne adds. “Rolling hills and amazing wine.” Private tastings at family-owned estates reveal the stories behind each bottle.
As Emmy-winning storyteller Catie Keogh said after traveling with Kensington last fall, “We met the winemaker whose family has owned this land for generations and were treated to a private tasting.” Moments like these feel personal and rooted in tradition.
For something iconic, rent a Vespa and wind through Tuscany as you feel the breeze in your hair. Catie recalls, “One of the highlights of our trip was the Vespa tour we took through Tuscany with our friends, riding through vineyards and olive groves. It was like something out of a movie.”
And when in Florence, order Bistecca alla Fiorentina. “This is a must,” Suzanne insists. Thick, perfectly grilled, and meant to be shared.
Rome is a city of layers: ancient empire, Renaissance glory, and vibrant modern life coexist in a way that feels effortless.
Start with the Colosseum. “Be sure to see the underground,” Suzanne recommends, as walking beneath the arena floor gives you a visceral sense of the scale and spectacle of ancient Rome. The nearby Forum is also a must-see.
Visit St. Peter’s Basilica for its grandeur and Michelangelo’s dome. Climb to the top for panoramic views over Vatican City and beyond.
For a quieter escape, Suzanne suggests a day trip to Bracciano. “I love this place. It’s beautiful, lakeside, with leisure and a stunning castle.” Overlooking Lake Bracciano, the medieval fortress and relaxed atmosphere feel worlds away from Rome’s bustle.
Naples is raw, vibrant, and unforgettable. Hike to the crater of Mount Vesuvius for stunning views over the Bay of Naples. Then visit Pompeii, a place Suzanne describes as “movingly beautiful, with so much preserved history.” Walking its streets offers a powerful connection to daily life frozen in time.
And the pizza. “Real pizza Napoletana,” Suzanne says with a smile. The soft blistered crust, San Marzano tomatoes, and fresh mozzarella add up to perfection.
Milan blends artistry with sophistication. “The Duomo is a work of art,” Suzanne says. She recommends that you walk its rooftop terraces for intricate spires and city views.
See The Last Supper, Leonardo da Vinci’s masterpiece, in an intimate viewing that rewards advance planning. Then wander the Galleria Vittorio Emanuele II for shopping and ambiance beneath its soaring glass dome.
Bologna invites you to slow down. “Sit in Piazza Maggiore and people-watch with coffee or wine,” Suzanne suggests. Climb Le Due Torri for sweeping views. Visit the University of Bologna, the oldest in the Western world.
This is also the birthplace of tagliatelle al ragù. Remember to order it properly and to never call it spaghetti bolognese.
“Sicily is extraordinary,” Suzanne says. “Trapani is stunning and charming. Off the beaten path.”
Explore the Zingaro Nature Reserve for hidden beaches and coastal walks. Visit Ragusa for its baroque beauty and warm hospitality.
In Modica, taste the island’s famous chocolate. Order brioche con gelato, ice cream tucked inside a fresh bun, a Sicilian must. Discover Taormina for beach and water views. Visit the Valley of the Temples for ancient grandeur. Wander Ortigia Island for atmospheric streets and sea views.
For fewer crowds, head to San Vito Lo Capo, where Caribbean-like beaches stretch along turquoise water.
Lake Como is elegance without effort. Snow-capped mountains rise behind pastel villages. Cypress trees frame grand villas. The rhythm here is slower, more deliberate.
“Arriving in Bellagio by boat is a must,” Suzanne says. Seeing the village from the water reveals its terraced gardens and stone staircases in full cinematic effect.
Explore Varenna, one of the lake’s most charming towns, where narrow lanes lead to waterfront cafés and quiet viewpoints. Visit Villa Carlotta in spring when the botanical gardens burst into color with camellias and azaleas.
For wine lovers, a visit to Ca’ del Bosco in nearby Franciacorta offers a refined tasting of Italy’s answer to Champagne. The combination of lakeside serenity and world-class wine feels indulgent in the best way.
The Amalfi Coast is iconic for a reason. Dramatic cliffs plunge into turquoise water. Villages cling to hillsides in a cascade of pastel color. Every turn in the road reveals another breathtaking view.
In Sorrento, begin in Piazza Tasso, where cafés spill into the square and glasses of limoncello catch the light. Walk through fragrant lemon groves that have shaped the region’s identity for generations.
For sweeping coastal views, hike the Path of the Gods. The trail stretches high above the sea, offering panoramic vistas that feel almost unreal.
From there, explore Capri and the Blue Grotto, where sunlight transforms the cave into an electric shade of blue. Visit Positano for boutique shopping and beachside lunches, or head to Ravello for its gardens and the famed Terrace of Infinity at Villa Cimbrone. With the right timing and guidance, the Amalfi Coast feels less hectic and more intimate, allowing you to appreciate its beauty at your own pace.
Verona is often associated with romance, but there’s far more to discover beyond Juliet’s balcony.
Visit Juliet’s House early to avoid the crowds, then wander toward Piazza delle Erbe, where market stalls and frescoed buildings reflect the city’s layered past. Walk across Ponte Pietra at sunset, when the Adige River glows beneath the arches.
Climb to Castel San Pietro for panoramic views over terracotta rooftops and church spires. It’s one of the most rewarding viewpoints in northern Italy.
Don’t miss the Verona Arena, a remarkably preserved Roman amphitheater that still hosts opera performances in summer. Sitting beneath the open sky as music fills the ancient stone walls is unforgettable.
Whatever your version of Italy looks like, riding a Vespa through Tuscany, sipping wine in a centuries-old cellar, hiking along the Amalfi Coast, or wandering through ancient ruins at sunrise, the right planning makes all the difference.
Your Kensington Destination Expert will tailor your journey around your interests, travel style, and timing, ensuring you experience Italy with depth, access, and ease. From private wine tastings to guided historical tours and lesser-known lakeside towns like Bracciano, every detail is designed around you.
Ready to plan your custom private-guided trip to Italy? Talk to a Kensington Destination Expert today to create a tailored Italy itinerary crafted around your passions and pace.
Experience authentic travel. Request a custom quote today and get one step closer to your personalized trip.
Speak to one of our Destination Experts at 1-888-903-2001
