Top Italy Trips & Tours in October 2026

from $17,890

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Croatian Coast and the best of the Adriatic

Venice - Dubrovnik - 8 Day Itinerary aboard Emerald Kaia

• Explore Venice's iconic canals
• Sail Adriatic Sea clear waters
• Visit Sibenik historic city
• Explore Korcula medieval town

Starts / Ends

Venice / Dubrovnik

Activity Level

Variable

Embark on an 8-day luxury yacht cruise aboard Emerald Kaia through Croatia, Italy, and Greece. Start in Venice, Italy, and end in Dubrovnik, Croatia. Explore Rovinj, Sibenik, Trogir, Vis, Hvar, and Korcula.

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from $3,420

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Classic Dolomites Premium Adventure

Italy Small Group Tour - 8 Day Itinerary

• Enjoy hiking in the Dolomites
• Hike the spectacular Tre Cime
• See the charming town of Villabassa
• Enjoy the culture of Bolzano
• Visit Monte Piana's open-air museum
• Climb up towards Strudelkopf

Starts / Ends

Villabassa - Niederdorf / Villabassa - Niederdorf

Activity Level

Moderate

Spend your week on an 8-day Classic Dolomites Premium Adventure hiking tour with the help of expert guides from Exodus Travels. Discover some of Italy's most breathtaking scenery while hiking safely and at a pace appropriate for your experience level.

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from $3,075

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Highlights of Sicily

Italy Small Group Tour - 9 Day Itinerary

• Visit the Island of Sicily
• Discover the Valley of the Temples
• Visit Taormina's ancient ruins
• See the Mount Etna in Sicily
• Explore the coastal town of Cefalu
• Visit Syracuse's Archeological Park
• Discover the Zingaro Nature Reserve

Starts / Ends

Viagrande / Taormina

Activity Level

Relaxed

Spend 9 days on this small group journey through the highlights of Sicily to step into a world where ancient ruins stand alongside vibrant cities and picturesque landscapes. Discover ancient ruins, bask in the island's natural beauty, and indulge in Sicily's culinary delights.

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from $2,400

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Highlights of the Amalfi Coast

Italy Small Group Tour - 8 Day Itinerary

• Admire the Amalfi Coastline
• Explore Positano on foot
• Visit Herculaneum and Pompeii
• Ride a boat to the island of Capri
• Walk the Path of the Gods
• Explore the village of Ravello

Starts / Ends

Naples / Naples

Activity Level

Easy Active

Discover one of the most fascinating and romantic destinations in the world, the Amalfi Coast. On this small 8-day group adventure, visit both Herculaneum and Pompeii, see the romantic coastal towns of Amalfi, Positano, and Ravello, and explore the island of Capri on this best-selling tour.

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from $5,690

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Classic Cruise – Italy

Venice - Mantua - 7 Day Itinerary aboard La Bella Vita

• Admire Venice’s grand Basilica
• Explore Doge’s Palace in Venice
• Visit Murano’s glass factory
• Discover Chioggia art-filled church

Starts / Ends

Venice / Mantua

Activity Level

Variable

Experience a 7-day cruise on La Bella Vita, exploring northern Italy from Venice to Mantua, with guided tours of historic sites and art museums. Indulge in local cuisine, wine tastings, and stunning views of the Venetian Lagoon and Po River Valley.

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from $4,200

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Rome, Assisi & Magical Umbria Premium Adventure

Italy Small Group Tour - 8 Day Itinerary

• Visit Roman ruins with a guide
• Visit the Umbrian countryside
• Visit the historic town of Assisi
• Visit local wineries in Montefalco
• Enjoy cooking local Italian dishes.

Starts / Ends

Rome / Rome

Activities

Cooking Classes

Activity Level

Easy Active

Join this 8-day premium group adventure and discover Rome, Assisi, and the magical Umbria Region in Italy with an expert guide. Experience the best of Italy's history, culture, and cuisine in a luxurious and personalized way. Discover the beauty and magic of Italy's cultural and historical treasures on this unforgettable journey.

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from $105,000

EBD 10%

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Private Charter - Classic Cruise – Italy

Venice - Mantua - 7 Day Itinerary aboard La Bella Vita

• Admire Venice’s grand Basilica
• Visit Adria’s museum
• Tour Ferrara’s castle and cathedral
• Experience Mantua’s Ducal Palace

Starts / Ends

Venice / Mantua

Activity Level

Variable

Experience a 7-day private cruise on La Bella Vita, exploring northern Italy from Venice to Mantua, with guided tours of historic sites and art museums. Indulge in local cuisine, wine tastings, and stunning views of the Venetian Lagoon and Po River Valley.

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from $9,074

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Dolomites Hiking Adventure

10 Day Itinerary

• Visit Pesaris' historic center
• Hike the Mount Coglians
• Visit a local harpsichord maker
• Discover Cortina's mountain scenery
• Hike the spectacular Tre Cime
• Visit a local dairy
• Enjoy the culture of Bolzano
• Tour Venice's Grand Canal by boat

Starts / Ends

Venice / Venice

Activities

Camping

Activity Level

Moderate

On this 10-day tour, hike through the stunning Dolomites mountain range in Italy to see the panoramic vistas, beautiful mountain huts, and serene lakes and pass through enchanting mountain villages.

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from $9,877

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Classic Italy

Venice to Rome - 10 Day Itinerary

• Ride the gondola in Venetian canals
• Discover the Sistine Chapel
• Explore the Vatican Museums
• Marvel at the architecture in Siena
• Savor authentic Tuscan cuisine
• Enjoy the Tuscan countryside

Starts / Ends

Venice / Rose Garden Palace

Activity Level

Easy Active

Explore Italy's rich culture, history, UNESCO World Heritage sites, and gourmet countryside on this 10-day classic Italian vacation. From Venice to Rome, tour the countryside and world-class sites in Florence, Siena, Colle di Val d'Elsa, and Rome.

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from $3,499

Up to 50%

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La Dolce Vita

Naples - Valletta - 8 Day Itinerary aboard M/Y Callisto

• Discover Lipari panoramic viewpoint
• Stroll Taormina’s alleys
• Experience Sicilian wines
• Wander Syracuse’s historic streets

Starts / Ends

Naples / Valletta

Activities

Wine Tasting, Local Market Visits, Archaeological Site Visits, Village Visits

Activity Level

Variable

Set sail on an 8-day cruise aboard the MY Callisto, starting in Naples and exploring the glamorous island of Capri. Discover Sicily's rich history, including Mount Etna and Taormina, before heading to Malta's UNESCO sites, like Valletta and Gozo's ancient temples.

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from $6,299

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Rome, Venice & the Jewels of Veneto

Venice to Rome - 11 Day Itinerary aboard S.S. La Venezia

• Explore Doge’s Palace
• Stroll Burano and Mazzorbo
• Tour Ancient Rome
• Visit St. Mark’s Basilica

Starts / Ends

Venice / Rome

Activity Level

Variable

Sail from Venice to Rome on an 11-day cruise aboard the S.S. La Venezia. Experience early access to St. Mark’s Basilica, Vicenza’s Teatro Olimpico, Murano’s glassblowers, and Rome’s ancient wonders. Explore Chioggia, Burano, and Padua while enjoying unforgettable cultural, historical, and culinary moments.

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from $3,799

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Venice & the Jewels of Veneto

Venice Roundtrip - 8 Day Itinerary aboard S.S. La Venezia

• Experience St. Mark’s Basilica
• Explore Ancient Torcello
• Watch Murano Glassmaking
• Discover Padua’s History

Starts / Ends

Venice / Venice

Activities

Hiking

Activity Level

Variable

Experience an 8-day roundtrip cruise from Venice aboard S.S. La Venezia. Discover the Doge’s Palace, Burano’s colorful houses, Chioggia’s markets, and the Po Delta’s tranquil waterways. Visit castles, art museums, artisan studios, and lively piazzas, while enjoying authentic cuisine and unforgettable views of the Venetian Lagoon.

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from $7,340

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Authentic Mediterranean Shores

Valletta Roundtrip - 10 Day Itinerary aboard Le Boreal

• Walk Valletta’s historic streets
• Visit Palermo’s Palatine Chapel
• Discover Lipari’s volcanic cliffs
• Explore Trapani’s cultural sites

Starts / Ends

Valletta / Valletta

Activity Level

Variable

Embark in Valletta for a 10-day Mediterranean cruise to Sicily and southern Italy aboard Le Boreal. Explore Syracuse, Palermo, Lipari, Taormina, and Pompeii. Visit temples, amphitheaters, cathedrals, and volcanic sites. Enjoy views of Stromboli and Etna, then return to Malta aboard a luxury ship with cultural programming and refined comfort.

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from $3,000

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Tuscany Walks & Chianti Wines

Italy Small Group Tour - 8 Day Itinerary

• Taste wines at Certaldo
• Explore Radda in Chianti
• Visit Siena’s stunning duomo
• Discover Florence’s Renaissance art
• Learn about Tuscan wines

Starts / Ends

Certaldo / Florence

Activity Level

Easy Active

Discover Tuscany on this 8-day tour. Explore the Via Francigena, savor wine tastings, visit Siena and Florence, and enjoy scenic walks through Chianti vineyards and San Gimignano.

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from $7,299

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Grand Highlights of Italy & Slovenia

Ljubljana to Rome - 14 Day Itinerary aboard S.S. La Venezia

• Explore Lake Bled from Ljubljana
• Visit Doge’s Palace
• Tour the Vatican City
• Taste Chioggia Wines

Starts / Ends

Ljubljana / Rome

Activity Level

Variable

Discover Slovenia and Italy on a 14-day cruise from Ljubljana to Rome aboard S.S. La Venezia. Visit Lake Bled, Venice’s Doge’s Palace, Chioggia’s markets, and the ancient wonders of Rome. Savor regional wines, explore medieval towns, and enjoy private after-hours access to St. Mark’s Basilica.

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from $4,799

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Slovenia, Venice & the Jewels of Veneto

Ljubljana to Venice - 11 Day Itinerary aboard S.S. La Venezia

• Visit Doge’s Palace early
• Walk Ljubljana's historic center
• Discover scenic Lake Bled
• Watch Murano glassblowing live

Starts / Ends

Ljubljana / Venice

Activities

Biking

Activity Level

Variable

Sail from Ljubljana to Venice on an 11-day Slovenia, Venice & the Jewels of Veneto river cruise aboard S.S. La Venezia. Visit Lake Bled, explore Postojna Caves and enjoy early access to St. Mark’s Basilica. Cruise through the Venetian Lagoon and discover vibrant Burano, Torcello, Chioggia, and Murano, plus historic cities like Padua and Vicenza.

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from $3,918

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La Dolce Vita along the Italian coastline

Roundtrip Nice - 8 Day Itinerary aboard MV La Belle des Océans

• Tour Lucca or Florence from Livorno
• Visit Napoleon’s home on Elba
• Cruise past Maddalena Islands
• Walk Alghero’s old walled town
• See beaches at Porto Cervo
• Explore Cinque Terre or Portofino

Starts / Ends

Nice / Nice

Activities

Urban Exploration

Activity Level

Variable

Cruise the Italian coast on this 8-day trip from Nice. Stop in Livorno, Elba, Alghero, Porto Cervo, Porto Santo Stefano, and La Spezia. Explore old towns, enjoy wine tasting in Tuscany, visit Napoleon’s home, relax on quiet beaches, and tour the Cinque Terre or Portofino. Return to Nice with lasting views, local flavors, and rich coastal charm.

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from $6,210

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Cruising the Mediterranean: Sicily, Sardinia, and Mallorca – with Smithsonian Journeys

Valletta - Barcelona - 8 Day Itinerary aboard Le Boreal

• Visit UNESCO sites in Valletta
• Indulge in Sicilian seafood
• Stroll Mahon's colorful streets
• Transit the Corinth Canal passage

Starts / Ends

Valletta / Tarragona

Activity Level

Variable

Embark on an 8-day Le Boreal cruise from Valletta to Barcelona. Visit Sicily’s historic cities, Sardinia’s archaeological treasures, and the Balearic Islands’ stunning landscapes. Shore excursions, transfers, and expert-led discussions with Smithsonian Journeys.

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