Places you'll visit








This Italian Odyssey trip invites discerning travelers into a tailor-made, authentic journey through Italy's heart. Experience private tastings, hands-on art encounters, and quiet mornings by shimmering waters as local insiders shape each day to your wishes.
Ready to craft a truly personal adventure? Contact our specialists to design your custom trip to Italy, secure exclusive access, and turn moments into lifelong memories.
| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| Day 1 | Arrival in Venice; private water taxi | Explore Piazza San Marco, Cannaregio, or Lido | Gondola ride or dinner in hidden alleys |
| Day 2 | Private walking tour with St. Mark’s Basilica access | Markets, canal views, and Renaissance gems | Tailor-made restaurant tips from your guide |
| Day 3 | High-speed train to Florence | Visit Duomo, Accademia, and Boboli Gardens | Dinner in lively Sant’Ambrogio |
| Day 4 | Private walking tour of Florence’s historic center | Visit Piazza del Duomo and Ponte Vecchio | Relax with views over the Arno |
| Day 5 | Train to Bologna | Visit museums, gardens, and historic churches | Sunset aperitivo and traditional pasta |
| Day 6 | Drive through Chianti Classico from Florence | Visit wineries, castles, and hilltop villages | Overnight stay with vineyard views |
| Day 7 | Siena private walking tour | Explore churches, artisan shops, and piazzas | Relax in Piazza del Campo |
| Day 8 | Chianti winery and cellar tour | Tasting in architect-designed winery spaces | Enjoy DOCG wine and local pairings |
| Day 9 | Drive to La Spezia, drop off rental car | Private transfer to Cinque Terre | Walk village trails and enjoy fresh seafood |
| Day 10 | Shared sunset boat tour of Cinque Terre | Swim, snorkel, and aperitivo on board | Cruise the coast at golden hour |
| Day 11 | Self-guided day with Trekking or Train Card | Hike trails, explore villages, or relax seaside | Optional dinner in Vernazza or Riomaggiore |
| Day 12 | Breakfast by the water; free time for photos & limoncello | Private transfer to Milan Airport | Depart Italy with unforgettable memories |








Welcome to Venice. After arrival, a private water taxi transfers you from the airport to your accommodation, offering first views of canals and palazzi and a seamless start to your Italy travel.
Wander Piazza San Marco, explore the Cannaregio neighborhood and its local markets, and visit Lido for a coastal taste of Venetian leisure. Enjoy tailor-made suggestions for dining, gondola rides, and hidden alleys that reveal Venice's history and charm.

Discover Venice on a private walking tour with an expert guide, visiting San Giacomo di Rialto, the Rialto Bridge, and St. Mark's Basilica. Explore bustling markets, Renaissance art, and hidden architectural treasures while learning local history and culture.
Skip long lines with basilica access, enjoy stunning canal views, and receive tailored recommendations that shape an authentic Italy trip experience.

Travel from Venice to Florence on a high-speed train, arriving in just over two hours. Spend a free afternoon visiting the Duomo and the Galleria dell'Accademia to see Michelangelo's David, then cross Ponte Vecchio to try fresco painting at Studio Artemisia.
Browse seasonal produce and street food at Mercato Centrale, wander the tranquil Boboli Gardens and Piazza della Signoria, and finish with a tailor-made dinner in lively Sant'Ambrogio.

Enjoy a private Florence walking tour. Cross the medieval Ponte Vecchio for panoramic views of the Arno River and browse centuries-old boutique shops at a relaxed pace with your guide.
Explore Piazza della Repubblica, then continue to Piazza del Duomo to admire Florence Cathedral, Brunelleschi’s iconic dome, the Romanesque Baptistery of Saint John, and Giotto’s Gothic Bell Tower.
Marvel at the Baptistery’s bronze Gates of Paradise as your guide reveals art, secrets, and local stories.

From Florence, take a quick train for a day trip to Bologna. Start at MAMbo for modern art, stroll Giardini Margherita, then explore Museo di Palazzo Poggi and Pinacoteca Nazionale to soak up local masterpieces.
Visit Museo Internazionale della Musica and the Santo Stefano complex, then hike up to the Sanctuary of Madonna di San Luca for hilltop views. Finish in Piazza Santo Stefano with an aperitivo and traditional tortellini or mortadella at a family trattoria.

Pick up a rental car in Florence and drive through the Chianti Classico region between Florence and Siena, winding past rolling hills, vineyards, olive groves, castles, and the hilltop villages of San Donato and Castelnuovo Berardenga.
Visit family-run wineries to tour cellars, taste renowned Chianti wines, and learn traditional winemaking and local history.

Start your Siena private walking tour at the 13th-century Basilica of San Domenico, devoted to St. Catherine. A local guide tailors the route to your interests, revealing hidden chapels, frescoes, and stories that bring medieval Siena to life.
Wander narrow streets lined with historic palaces and artisan shops, then relax at the fan-shaped Piazza del Campo to admire the Palazzo Pubblico.

Discover Chianti Classico in the Chianti area on a shared cellar tour that blends oenology, architecture, and contemporary art. Walk through production areas, barrel cellars, and avant-garde winery spaces crafted for memorable photos and stories.
Savor a curated tasting of Chianti Classico DOCG in striking settings like a suspended tasting room or the intimate Bottaia room.

After dropping your rental car in La Spezia, a private transfer brings you to your base in Cinque Terre. This trip places you in the heart of five fishing hamlets: Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso al Mare.
Explore Parco Nazionale delle Cinque Terre on curated walking routes across terraced vineyards, swim from secluded coves, ride local trains between villages, and taste fresh seafood and pesto with local hosts.

Explore Cinque Terre's rocky coastline on a shared boat tour. Visit hidden beaches, crystal clear coves, and colorful villages while the crew shares local wine and cultural stories, perfect for photos.
Anchor for a swim and snorkeling, enjoy an Italian aperitivo with tapas, then cruise along the Italian Riviera for sweeping panoramas as the sun drops below the horizon, delivering unforgettable sunset memories.

Explore the colorful villages of Cinque Terre at your own pace with a Trekking Card, which includes access to park trails, local bus services, and discounts at museums in La Spezia.
Upgrade to a Train Card for second-class rail travel between Levanto and La Spezia, park entry, Wi-Fi at hotspots, and easy transfers between villages. Expect scenic hikes, coastal views, and smooth logistics, perfect for a memorable day.

Savor your final morning on the shores of Cinque Terre with a waterfront breakfast, a leisurely stroll through pastel villages, time for last photos, and a taste of local limoncello.
At the scheduled time, your private driver will transfer you to the Milan Airport for your departing flight, concluding your Italian Odyssey trip. Arrivederci and safe travels.
