Rock formations tumble into the Mediterranean as colorful villas etch themselves into cliffs and sunlight dances through small villages. This is the Amalfi Coast, where nature, history, and culture find a harmony. Touch down in Naples, and it is just a short drive south to your hotel.  Meander through the bewitching coastal landscape to reach a little village perched over the sea, and then take your first early-evening stroll to join the locals who sit on small piazzas as you settle into the Italian experience. Of course, the views are pretty, and the village seems to come from a postcard, but you will soon appreciate that true Italy is far more than what you look at.

Take it easy this morning and follow the aromas of coffee through the narrow lanes as you gaze out over the sea and watch the sub-tropical flora as it surges from surrounding hillsides. Today you will explore the Amalfi Coast beyond your village, beginning with a small-boat Mediterranean cruise. Join the yachts and the catamarans you travel slowly beneath the cliffs, stopping at an island for lunch at a beach restaurant. Exploring Amalfi by land, you can move higher into the cliffs and cross the vine-draped hills to medieval ruins and small Italian cafes. You could get active with some local hikes, but you can also keep it slow, returning to the piazza for a second relaxed evening.

Pompeii was a prosperous city 2,000 years ago, but then Vesuvius erupted and encased the Roman city in ash. Take a walk through the excavated ruins with your guide who will breathe life into Pompeii, narrating tales amid volcano-scorched rock and crumpled temple walls. You will also discover Sorrento, a seaside town of enchanting piazzas, mazy alleys, lush gardens, and dazzling views. In Pompeii, you will need the historical context, whereas in Sorrento, you only need to take a few steps to find the local atmosphere. As in Amalfi, Sorrento has retained its tradition, in spite of its modern popularity. You just need to sidestep the tourist restaurants and stores, and that is easy when you have an excellent local guide.

Montecassino ties the centuries together with a spectacular abbey that gave birth to the Benedictine order, a famous center of medieval art, and then a Nazi World War II stronghold. Although the Abbey has not been rebuilt after intensive bombing, there is still a spirituality that seeps from each wall. Montecassino is an easy stop on the road north to Rome, where a local guide will take you on a neighborhood walk. It will be an introduction to local Rome with the may piazzas, restaurants, traditions, delicacies, and those little things that make any destination so rewarding. You will have three nights in Rome, and your hotel is ideally situated for self-exploration.

The Colosseum will baffle you as it stands so enormous in the heart of Rome. The structure stretches for three tiers, and you will enjoy access to the third, where emperors used to sit and watch the many spectacles. Next door is the Roman Forum, packed full with temple remains and rugged, ruined walkways. Move next to the Pantheon, messages painted on the domed ceiling and more impressions of imperial Rome all around. Your afternoon is left free for your own wandering, or you might want to take it easy, sipping espressos on Piazza Navona and entering one of the churches. You may also want to discover Baroque Rome, the works of Borromini another exquisite city highlight.

Rome is also a wonderful city for watching the world go by, so you can take a chair at an al fresco terrace, order a cappuccino, and surround yourself with everyday beauty. Most of today is left free so that you can continue exploring your version of Rome, whether that is the Empire, the Baroque, or something more contemporary. Later in the day, as tourists leave the Vatican Museums, you will enter for an after-hours tour that showcases the true beauty of what started as a private papal collection.

The Sistine Chapel is also all the more special when nobody else is around as candelabras dazzle without others interrupting your view, and the dozens of galleries and chapels can be appreciated when it is quiet enough to hear your own footsteps. Gaze at Raphael’s masterpieces, take an intimate peek at early Christian sculpture, and get lost in all the artistic detail. The Vatican Museums are, understandably, one of the world’s most popular visitor attractions. By going after hours, you discover what they are truly all about.

Vineyards carpet the landscape as you travel into Umbria, and the Duomo of Orvieto is your compass point with its mosaic-splashed facade visible from afar. You will ascend and then enter through the Cathedral’s vast bronze doors. Inside there are more frescoes, taking you on a journey through Italy’s artistic eras on the walls. Eat lunch at a piazza beneath the Duomo, a traditional trattoria showcasing home-styled Umbrian cooking, and then settle into a small village just outside Perugia, where your hotel still suggests a time of Donini counts. This evening you can dine on a terrace overlooking the vines, inhaling the sultry air of rural Italy. It will be a big contrast to Rome, this being a part of Italy that is strangely overlooked by tourist trails.

Explore the village this morning as there are only a couple of streets, a handful of churches, and some cafes where the locals chatter over coffee and lottery tickets. Age is revered in Italy, especially in rural villages and senior travelers tend to get a very warm welcome in the midst of village life. A visit to Assisi is mixed in with the local encounters today, St Francis’s Basilica a place of faded frescoes and deeply spiritual pilgrims. Like the village, there is a real feeling to Assisi, it being a place that looks good on photos but becomes far more vivid in your memories. A local winemaker stops by your hotel this evening, presenting a vertical tasting through different vintages, the wine complemented by classic Umbrian dining.

Olive groves glisten in the morning light while fig trees line the roadside and vineyards complete the patchwork that makes Tuscany so distinctive. You will enjoy the landscape of nature’s colors, cultivated by humankind over many centuries. Stop at a small vineyard as you travel through the Tuscan countryside with both a tasting and lunch showing a sharp distinction to neighboring Umbria. This afternoon you will be back on the coast, the Tuscan seaside town of Viareggio your base for the next two nights. Unlike nearby Cinque Terre, Viareggio has really retained its Italian feel. There is opera and grandeur, yet also that languorous atmosphere that everyone wants to pick up and take back home with them.

Cinque Terre’s magic was created by its inaccessibility, as for many centuries the fishing villages could only be reached by boat. Today, they are linked by a dramatic coastal road and railway line, and although highly popular with tourists, they are still packed with treasures. Travel next to Vernazza, the bright hues all around as you stroll streets of cobblestone and intrigue. Take the train to the next village and discover its bistros, sampling wine, and olives and citrus and all those dainty treats you do not find outside Italy. It is not far back to Viareggio, and you may be glad to have got away from the crowds, as Italy is more laid-back when you are surrounded by Italians rather than visitors.

Florence will seduce you from your first glance with the golden domes, grand piazzas, and a vernacular that feels aristocratic. The city has a bit of modern bustle as well, not to mention a certain grit and contradiction. Renaissance art and architecture sets the scene, but this is a city with so much more.  Florence is where history is morphing into something new, something just as beautiful yet not what you would expect. It is this Florentine feeling that you can discover today, along with the best of Uffizi, the world’s oldest art gallery. Michelangelo, da Vinci, Raphael, Botticelli are all present, and nowhere has a more revered collection of Italian art, especially not from the Renaissance painters.

There is more art on display that you can imagine, and you will begin with the Galleria dell’Accademia, where Michelangelo’s David is but one of the legends on display. Like yesterday, you will be guided by an art historian and gain insight into del Sarto, Uccello, Ghirlandaio and others that came through this renowned academy. Renaissance Florence can be found by climbing the cathedral dome, but the Renaissance heart also hides down alleys and forgotten streets. These are the focus of your afternoon tour, and places where the vernacular shows glorious attention to artistic detail. There is an experiential Renaissance contrast to enjoy with galleries where masterpieces are given space to shine, and then little old details that are hidden away.

Take the train to Venice, and your hotel is on a canal, accessed by a small boat from the station. This is a city with an uncertain future, and you can feel that as if millennia-old architecture has suddenly taken on an ephemeral characteristic. Today you will explore by water, taking a gondola beneath ancient bridges, cruising alongside palaces and between islands. You can see Venice as the explorers used to first see it, in awe of the inimitability and ingenuity. Disembarking at Piazza San Marco, you can stroll across the square and enter Basilica San Marco after hours. This is the Venetian centerpiece, and it is all the more special when there is nobody else around.

Traveling on a gondola is the quintessential Venetian experience as this is a city of 118 islands, each connected by boats that have hardly changed since the time of Republic. Visit Murano Island to discover ancient glassworks, admire the lavish interiors of Doge’s Palace and find a monastery packed with priceless art and a gallery. Your guide will customize a day to your interests and energy levels, with gondola travel making every moment memorable. By now you will be settled into the Italian rhythm and know a trattoria from a tourist trap, and with your local guide alongside, you can always get an insider’s perspective on where to drink, dine and relax.

Enjoy a relaxed morning in Venice before your short transfer to the airport, a journey mainly by boat. After two weeks in Italy, you will leave with countless photos, but more importantly, a real sense of what Italy is all about.