Italy's Great Cities

Begin in signature Now Journey style with a warm arrival welcome and included private water taxi transfer from Venice Marco Polo Airport to the hotel in the heart of San Marco. Check in, refresh, and let Venice begin gently.

Later, meet your Tour Captain for a Discovery Walk through Piazza San Marco, the Campanile, the Grand Canal and the practical rhythms of the Journey. That evening, gather for a Venetian opening dinner with regional Italian cooking, wine and premium beverages included.

With our expert local guide, explore Venice's hidden corners and layered history as you visit St. Mark's Basilica, the Doge's Palace, the historic prisons, and the Bridge of Sighs. The day reveals Venice not as a postcard, but as a republic shaped by power, intrigue, faith and extraordinary beauty.

Later, enjoy an included gondola experience through the city's quiet canals, accompanied by live musicians. Your Tour Captain can point you toward a favorite local restaurant for an optional dinner afterward.

After breakfast, Venice gently fades behind you. A private boat transfer brings you to Venezia Santa Lucia, where you board a comfortable high-speed train bound for Florence—a seamless transition from lagoon light to Renaissance stone.

On arrival, your Tour Captain leads a Florence Discovery Walk through the heart of the city, including Giotto's Campanile, the Baptistery, the Duomo and Ponte Vecchio. That evening, gather for a hosted Tuscan dinner with regional specialties, local wines and premium beverages.

Florence comes alive through art, architecture and story. Enjoy skip-the-line entry to the Accademia to see Michelangelo's David, then continue through the historic center with your guide: Santa Maria del Fiore, Giotto's Bell Tower, the Baptistery, the Gates of Paradise, Piazza della Signoria and Piazza della Repubblica.

The afternoon is intentionally open. Wander, shop, linger over lunch, visit Santa Croce, climb the Duomo, explore the Uffizi or choose a privately arranged museum experience.

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.

Then settle into a family-run Tuscan estate for a guided cellar visit, curated tasting and leisurely farm-to-table lunch. Continue to Cortona, where your Tour Captain handles check-in before leading a gentle Discovery Walk into the historic center.

Enjoy a full day at leisure in Cortona. Make it as quiet or active as you wish: a long piazza morning, a walk through vineyards, a cooking class, horseback riding, a Siena day trip, a monastery visit or time exploring Cortona's upper streets and Etruscan layers.

Your Tour Captain will help shape the day around your style. The evening remains open for a final Cortona dinner or an unhurried night in one of Tuscany's loveliest hill towns.

Continue south toward the Eternal City. After arrival and check-in near the Pantheon, your Tour Captain leads a Discovery Walk through the heart of Old Rome.

Begin with the Pantheon, then continue through Piazza Navona, Campo de' Fiori and Largo di Torre Argentina. That evening, gather for a hosted welcome dinner featuring the flavors of Lazio.

With privileged entry, explore the Vatican Museums, stand beneath Michelangelo's Sistine Chapel, and continue into St. Peter's Basilica and Square. Your guide brings context to the art, ritual, architecture and living pageantry of Vatican City.

The afternoon and evening are open. Explore Trastevere, Campo de' Fiori, a hidden wine bar or a quieter Roman corner with suggestions from your Tour Captain.

Set out through Rome's ancient heart, where ruins and modern life share the same streets. Visit the Colosseum and Roman Forum with admission and guiding included, then trace the shape of empire through Palatine Hill, Capitoline Hill, triumphal arches and views toward Trajan's Market.

Tonight, join your Tour Captain for a special Farewell to Rome dinner—a final hosted evening to reflect on the canals, masterpieces, hill towns and ancient stones gathered along the way.

Breakfast is included this morning if your departure timing allows. Guests ending in Rome may request departure guidance for Rome Fiumicino or Ciampino Airport, and extra nights can often be arranged when available.

For many travelers, Rome becomes the perfect finale: a final espresso near the Pantheon, one more walk through ancient streets, and the feeling that the essential Italian story has come full circle.