Italian Odyssey trip

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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.

Italian Odyssey trip highlights

  • Venetian canal immersion: Glide past shimmering palaces on a private gondola, meet artisan mask-makers, and discover Venice’s hidden sestieri.
  • Tuscan hilltop and wine: Savor boutique vineyard tastings and a farmer-led cooking class in sunlit hilltowns.
  • Florence artistry and workshops: Explore Renaissance masterpieces with a private guide, then join hands-on ateliers.
  • Amalfi Coast and private boat: Cruise dramatic cliffs and secluded coves on a private boat, stopping at family-run seaside trattorias.
  • Hidden gems and tailor-made discoveries: From ancient ruins to village markets, your bespoke itinerary uncovers off-the-beaten-path Italy moments.
DayMorningAfternoonEvening
Day 1Arrival in Venice; private water taxiExplore Piazza San Marco, Cannaregio, or LidoGondola ride or dinner in hidden alleys
Day 2Private walking tour with St. Mark’s Basilica accessMarkets, canal views, and Renaissance gemsTailor-made restaurant tips from your guide
Day 3High-speed train to FlorenceVisit Duomo, Accademia, and Boboli GardensDinner in lively Sant’Ambrogio
Day 4Private walking tour of Florence’s historic centerVisit Piazza del Duomo and Ponte VecchioRelax with views over the Arno
Day 5Train to BolognaVisit museums, gardens, and historic churchesSunset aperitivo and traditional pasta
Day 6Drive through Chianti Classico from FlorenceVisit wineries, castles, and hilltop villagesOvernight stay with vineyard views
Day 7Siena private walking tourExplore churches, artisan shops, and piazzasRelax in Piazza del Campo
Day 8Chianti winery and cellar tourTasting in architect-designed winery spacesEnjoy DOCG wine and local pairings
Day 9Drive to La Spezia, drop off rental carPrivate transfer to Cinque TerreWalk village trails and enjoy fresh seafood
Day 10Shared sunset boat tour of Cinque TerreSwim, snorkel, and aperitivo on boardCruise the coast at golden hour
Day 11Self-guided day with Trekking or Train CardHike trails, explore villages, or relax seasideOptional dinner in Vernazza or Riomaggiore
Day 12Breakfast by the water; free time for photos & limoncelloPrivate transfer to Milan AirportDepart Italy with unforgettable memories

Places you'll visit

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Venice
Venice
Florence
Florence
Castellina in Chianti
Castellina in ChiantiCastellina in Chianti
Cinque Terre
Cinque TerreCinque Terre
Day01

Day 1: Arrival in Venice

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.

Venice, Italy
Day02

Day 2: Venice walking tour with St. Mark's Basilica access

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.

Saint Mark, Venice
Day03

Day 3: Venice to Florence

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.

florence
Day04

Day 4: Florence historic walking tour

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.

Palazzo Pitti, Florence
Day05

Day 5: Bologna day trip

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.

Bologna
Day06

Day 6: Chianti Classico from Florence

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.

Chianti Region
Day07

Day 7: Siena private walking tour

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.

Siena
Day08

Day 8: Chianti area winery tour

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.

wine windows
Day09

Day 9: Cinque Terre arrival and La Spezia car drop off

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.

Cinque Terre
Day10

Day 10: Cinque Terre sunset boat tour

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.

Cinque Terre
Day11

Day 11: Free day in Cinque Terre

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.

Cinque Terre
Day12

Day 12: Final morning in Cinque Terre

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.

Italian flag