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.
DayLocationActivityOvernight
1Venice

• Arrival in Venice and private water taxi

• Explore Piazza San Marco, Cannaregio or Lido

• Gondola ride or dinner in hidden alleys

Venice
2Venice

• Private walking tour with access to St. Mark’s Basilica

• Markets, canal views and Renaissance gems

• Tailor-made restaurant tips from your guide

Venice
3Florence

• High-speed train to Florence

• Visit the Duomo, Accademia and Boboli Gardens

• Dinner in lively Sant’Ambrogio

Florence
4Florence

• Private walking tour of Florence’s historic centre

• Visit Piazza del Duomo and Ponte Vecchio

• Relax with views over the Arno

Florence
5Bologna

• Train to Bologna

• Visit museums, gardens and historic churches

• Sunset aperitivo and traditional pasta

Bologna
6Chianti

• Drive through Chianti Classico from Florence

• Visit wineries, castles and hilltop villages

• Overnight stay with vineyard views

Chianti
7Siena / Chianti

• Private walking tour of Siena

• Explore churches, artisan shops and piazzas

• Relax in Piazza del Campo

Chianti
8Chianti

• Chianti winery and cellar tour

• Tasting in architect-designed winery spaces

• Enjoy DOCG wine and local pairings

Chianti
9Cinque Terre

• Drive to La Spezia and drop off rental car

• Private transfer to Cinque Terre

• Walk village trails and enjoy fresh seafood

Cinque Terre
10Cinque Terre

• Shared sunset boat tour of Cinque Terre

• Swim, snorkel and aperitivo on board

• Cruise the coast at golden hour

Cinque Terre
11Cinque Terre

• Self-guided day with Trekking or Train Card

• Hike trails, explore villages or relax seaside

• Optional dinner in Vernazza or Riomaggiore

Cinque Terre
12Milan → Airport

• Breakfast by the water

• Private transfer to Milan Airport

• Departure from Italy

Places you'll visit

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Day01

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

Venice walking tour with St. Mark's Basilica access

Step into Venice’s winding streets and shimmering canals on a private walking tour with an expert guide. From the lively bustle of San Giacomo di Rialto to the iconic Rialto Bridge and St. Mark's Basilica, each corner reveals layers of history and hidden architectural treasures, a journey that captures the essence of a tour of Venice.

Skip long lines at the basilica, enjoy breathtaking views of the canals, and follow your guide’s insights to uncover the city’s secrets, making this a truly immersive Italian experience.

Saint Mark, Venice
Day03

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

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

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

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

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, a perfect glimpse of what travelers experience on a Tuscany trip.

Wander narrow streets lined with historic palaces and artisan shops, then pause at the fan-shaped Piazza del Campo to admire the Palazzo Pubblico and the rhythm of daily Tuscan life.

Siena
Alessandro

Tips from Alessandro

Italy Travel Expert

quotes

Climb the Facciatone just before sunset. It’s the unfinished façade of Siena’s cathedral extension, and one of the best-kept secrets for a panoramic view without the crowds. The light over the terracotta rooftops is pure magic.

Day08

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

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

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

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

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.

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