Italy Uncovered Venice to Rome with Rustic Mountain Towns & Wine Country

Travel Italy’s lesser-known eastern coast, tracing a route from Venetian canals to Rome’s timeless grandeur. Along the way, uncover sparkling mosaics, Renaissance cities, medieval villages, rugged mountains, and wine-producing countryside where heritage, culture, and adventure intertwine.

Welcome to enchanting Venice, with its 117 tiny islands surrounded by a latticework of 150 canals and 400 bridges. As arrival times will vary, today is yours to explore at your own pace. This evening, gather with your fellow travelers for a welcome drink.

This morning, explore the traditional Venetian craftsmanship behind one of the city’s most enduring symbols: the gondola. During an Impact Moment, visit one of Venice’s few remaining traditional boatyards, witnessing the skill and dedication that have kept this time-honored craft alive for centuries. Wrap up the morning at a local café, enjoying a classic Venetian spritz and taking part in the beloved Italian ritual of aperitivo (pre-lunch drink), a pause before lunch at leisure. The afternoon is yours to explore more of the floating city. Perhaps you’ll head out for your own treasure hunt in search of the city’s hidden gems.

Say ciao to Venice as you journey towards the Romagna region, famous for its epicurean lifestyle and its joie de vivre. Your first stop is the charming hilltop village of Dozza, renowned for its vibrant murals, atmospheric lanes, and striking medieval castle. In the afternoon, continue to your hotel, nestled amidst the rolling vineyards of the Romagna countryside, where you’ll settle in for a relaxing 3-night stay. This evening, enjoy an exclusive tour of your resort’s winery, followed by a dinner featuring their own expertly crafted wines.

Grab your passport* and set off for the Republic of San Marino, the fifth-smallest country in the world. Perched atop Mount Titano, this historic gem offers breathtaking views of the Adriatic Riviera and the rolling hills of the Romagna countryside. Spend your free time exploring the Old Town’s fascinating network of fortification towers, walls, gates, and bastions. Later this afternoon, return to your hotel and roll up your sleeves for a hands-on cooking class, where you’ll master the art of crafting pasta staples like handmade tagliatelle. End the day around a convivial table, enjoying the meal you’ve prepared together.

Spend the day uncovering the treasures of Ravenna, a city that rose to prominence during the twilight of the Roman Empire, thanks to its strategic location. As power shifted between the Byzantines and the Goths, Ravenna’s rulers adorned its churches with breathtaking mosaics that still dazzle today. On a guided walking tour, explore the city’s most iconic monuments and marvel at its rich history and artistry. This evening, return to your wine resort and indulge in a wine-paired dinner, savoring the flavors of the region in a truly idyllic setting.

This morning, journey into the Marche region, where rolling hills are lined with olive groves and vineyards. Stop in the hilltop city of Urbino, birthplace of Renaissance painter Raphael, and visit the impressive Ducal Palace — once home to a powerful ruling family and now a showcase of Renaissance art and architecture. Later, continue to the seaside town of Pesaro, where you’ll settle in for a two-night stay.

Today, uncover another side of the Marche — its reputation as a truffle haven, known for both black truffles and the rare white truffle (found only from October to December). Join a truffle hunter and his dogs for a walk through the woods in search of these elusive fungi, followed by an organic, farm-to-table lunch at the family’s farm. The afternoon is free back in Pesaro, birthplace of opera composer Gioachino Rossini, best known for The Barber of Seville and William Tell.

Much of the day is spent traveling by coach as you make your way into the Abruzzo Mountains. Arrive in the medieval village of Santo Stefano di Sessanio, a peaceful, pedestrian-only locale where you’ll walk to your accommodations. Your stay in a unique albergo diffuso serves as an Impact Moment and features rooms set in historic buildings throughout the village, offering a simple, rustic atmosphere.** This evening, connect with local traditions during a hands-on experience making regional cheese and bread, then gather for a dinner featuring what you’ve prepared, embracing the slower pace of mountain life.

Begin your day with a scenic drive across the Campo Imperatore plateau, more than 7,000 feet (2,100 meters) above sea level, with sweeping views of the Gran Sasso peaks, the highest in central Italy. Along the way, stop to enjoy some al fresco arrosticini — grill-it-yourself lamb skewers and a beloved local specialty rooted in Abruzzo’s sheep-herding traditions. Back in Santo Stefano di Sessanio this afternoon, it’s your choice! Join a guided walking tour exploring your village’s fortified layout, stone lanes, and historic buildings -OR- take part in a challenging, guided 4-hour mountain hike to Rocca Calascio, a dramatic stone fortress set high above the surrounding mountains.***

Say goodbye to the quiet lanes of Santo Stefano di Sessanio and journey to the Tirino River, known for its striking blue-green, crystal-clear waters. Set out by canoe and drift along this peaceful waterway, surrounded by gentle currents, reeds, and birdsong in one of Abruzzo’s most serene landscapes. As the saying goes, all roads lead to Rome. After this peaceful encounter with nature, continue your journey to the Italian capital, arriving in the late afternoon for a two-night stay in the Eternal City.

This morning, embark on an extensive walking tour through Rome’s medieval district, a captivating neighborhood that grew atop the ruins of the ancient city. Wander through its narrow cobblestone streets, admire the dark tufa stone buildings, and marvel at the ingenious ways Roman ruins have been repurposed over the centuries. Ascend to the panoramic terrace of the Vittoriano to take in one of Rome’s most breathtaking views. From this vantage point, gaze out over the remnants of the Roman Empire, from the sprawling Forum to the iconic Colosseum. The afternoon is yours to explore the Eternal City at your own pace, soaking in its timeless charm. This evening, come together to celebrate the end of your Italian adventure with a farewell dinner and a toast to the unforgettable journey you’ve shared.

Your tour comes to a close today, leaving you with fond memories of incredible Italy.