Italy's Great Cities

Day 1

Welcome to beautiful Bellagio

Grand Italy begins beside one of the world’s most beautiful lakes. Arrive in Bellagio, the enchanting village situated where Lake Como’s waters meet, surrounded by magnificent villas, mountain scenery and the timeless elegance of Northern Italy.

After settling into our Bellagio hotel, meet your Now Journey Tour Captain and fellow travelers for a gentle Discovery Walk through the village’s picturesque lanes, charming waterfront and inviting piazzas.

Tonight, gather for our included Welcome to Lake Como Dinner—a beautiful beginning to the Journey ahead.

Day 2

Bellagio and the beauty of the lake

After breakfast, explore Bellagio with your Tour Captain before taking to the water for an included private lake experience. Magnificent villas, picturesque villages and dramatic mountains create one of Italy’s most breathtaking landscapes.

The afternoon is open to linger in town, relax at the hotel or follow your Tour Captain’s recommendations.

Day 3

Onward to beautiful Venice

After breakfast, leave Lake Como for Milan and continue by high-speed train to Venice. On arrival, a private water taxi carries you from the Venice railway station through the canals to your hotel in the heart of San Marco.

Later today, meet your Tour Captain and begin our Discovery Walk — a signature Now Journey touch: a short orientation through Venice’s highlights, including Piazza San Marco, the Campanile, the Grand Canal, and more. It’s the perfect warm-up before tomorrow’s immersive guided tour.

Day 4

Venice: the Story begins

Discover Venice’s hidden corners and layered history with our incredible local guide as you explore St. Mark’s Basilica, the Doge’s Palace, the historic prisons and the Bridge of Sighs—along with the story of Casanova. Venice emerges not as a postcard, but as a republic shaped by power, intrigue, faith and extraordinary beauty.

Included Admissions and Expert Guiding: Explore St. Mark’s Basilica and the Doge’s Palace with the admission arrangements published for this Journey. Standard security procedures and attraction access requirements still apply.

Day 7

Tuscany: a day of flavor and tradition

The landscape shifts as rolling hills and cypress trees guide you into the Tuscan countryside. Begin in San Gimignano, famed for its medieval skyline and artisan streets, with a toast of Vernaccia, the town’s signature white wine.

Settle into a family-run Tuscan estate for a guided cellar visit, curated tasting and leisurely farm-to-table lunch. Later, a scenic journey carries us to Cortona, where your Tour Captain handles check-in at our charming Cortona hotel before leading a gentle Discovery Walk into the historic center.

Day 8

Cortona: slow moments and simple pleasures

Enjoy a full day at leisure in Cortona. The day can be as quiet or active as you wish: a long piazza morning, a countryside walk or time exploring Cortona’s upper streets and Etruscan layers.

Your Tour Captain can help shape the day around your style, and the evening remains open for a relaxed night in one of Tuscany’s loveliest hill towns.

This evening, your Tour Captain will invite you to join the group for an optional dinner, or the evening is entirely yours.

Day 12

Pompeii, Sorrento and the coast

Leave Rome as the Journey turns south toward Pompeii, the remarkable Roman city preserved beneath volcanic ash for nearly 1,700 years. On our included expert-guided archaeological visit, walk its ancient streets and enter the human story revealed through homes, shops, public spaces and the everyday details of a city interrupted in time.

After Pompeii, continue to Sorrento on the beautiful Sorrento Peninsula. Following hotel check-in and time to refresh, your Tour Captain leads a Discovery Walk through the heart of town as our final coastal chapter begins beside the Bay of Naples.

Day 13

The coast at your own pace

Today is intentionally open for the coast. Follow your Tour Captain’s recommendations through Sorrento’s historic streets, settle into a seaside café, browse local shops, linger over a long lunch or simply relax at the hotel and let the Bay of Naples set the pace.

Guests who want a fuller day may choose the optional private boating experience to Capri and Anacapri. Depending on the confirmed excursion design, weather, sea conditions and local access, the day may include open-air island transportation, an opportunity for the Monte Solaro chairlift, selected grottoes and optional swimming. This optional experience is not included in the Journey price.

Day 14

Arrivederci, Italy

As the Journey closes, your Tour Captain or the Now Journey team can assist with practical departure guidance.

An optional transfer to Naples Airport may be requested separately and is not included in the base Journey. The transfer is $125 per person with a minimum of two travelers, or $250 for one traveler. If you would like more time in Southern Italy, ask about extending your stay when appropriate and subject to availability.

From the mountain-framed waters of Lake Como and the enchanting lanes of Bellagio to Venice’s canals, Florence’s masterpieces, Tuscany’s vineyards and Rome’s ancient treasures, Grand Italy has taken us through some of Italy’s most remarkable places.

Now, beside the beautiful Bay of Naples, our Journey comes to a close—with new friendships, wonderful memories and stories we’ll be sharing for years to come.