Top Italy Trips & Tours in September 2026

from $13,790

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Hidden Gems of the Croatian Riviera

Dubrovnik - Venice - 8 Day Itinerary aboard Emerald Kaia

• Stroll Piran Venetian architecture
• Admire Opatija coastal views
• Visit Split’s UNESCO-listed palace
• Sail Venice's iconic canals

Starts / Ends

Dubrovnik / Venice

Activity Level

Variable

8-day cruise along the Adriatic aboard Emerald Kaia. Explore the coastlines and islands of Greece, Turkey, Croatia, Italy, France and Spain. Discover rich history, charming streets, and breathtaking landscapes on your unique cruise

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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 $3,150

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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 $2,550

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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 $6,350

NO SS

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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

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 $117,000

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 $1,260

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Rome to Rome

Roundtrip Civitavecchia - 4 Day Itinerary aboard Royal Clipper

• Discover Saint-Florent harbor
• Visit Cap Corse peninsula
• Tour Portoferraio landscapes
• Explore Civitavecchia gateway

Starts / Ends

Civitavecchia / Civitavecchia

Activities

Small Ship Sailing

Activity Level

Variable

Set sail on a 4-day cruise from Civitavecchia aboard the Royal Clipper to explore vibrant Saint-Florent in Corsica and historic Portoferraio in Elba, once home to Napoleon. Enjoy a blend of maritime heritage and cultural landmarks.

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from $15,995

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Italy Cruise: Hidden Treasures from Florence to Venice

Florence -Venice - 12 Day Itinerary aboard Le Dumont-d'Urville

• Discover Renaissance Florence
• Explore ancient Roman ruins
• Savor Corsican old towns
• Taste Sardinian wine culture

Starts / Ends

Florence / Venice

Activity Level

Variable

Uncover hidden Mediterranean treasures on a 12-day luxury cruise aboard Le Dumont d’Urville, visiting Italy, France, and Corsica. Begin in Florence, explore Rome, Sardinia, Sicily, and Bonifacio along the way, and conclude in Venice with exclusive, expert-led experiences throughout.

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from $12,018

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Classic Italy Nature and Wildlife

Tuscan Countryside to Sorrento - 12 Day Itinerary

• Hike trails in Tuscany’s Val d’Elsa
• Enjoy organic wines in Tuscany
• Experience riding horses in Maremma
• Spot dolphins in Pelagos Bay
• Explore Rome’s Appian Way Park
• Cook with lemons in Sorrento Bay

Starts / Ends

Tuscany / Naples

Activity Level

Easy Active

Discover Italy’s wild side on a 12-day Nature and Wildlife Tour through Tuscany, Rome, and Sorrento. Hike the Val d’Elsa, taste wines at sustainable vineyards, ride through Maremma Park, and spot dolphins in the Pelagos Sanctuary. Explore Rome’s Appian Way and end in Sorrento with a lemon cooking class and coastal trek.

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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 $6,293

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Family Friendly Italy

10 Day Itinerary

• Experience Venice as Family in tour
• Explore Florence Art & Culture
• Learn Tuscan Cooking Fun
• Ride Countryside ATV Adventure
• Visit Ferrari Museum Excitement
• Discover Ancient Rome Highlights

Starts / Ends

Venice / Rome

Activities

Wine Tasting, Archaeological Site Visits, Hiking, Cooking Classes, Wildlife Viewing

Activity Level

Easy Active

Discover Italy’s top highlights on a family-friendly adventure through Venice, Florence, Tuscany, and Rome. Enjoy hands-on experiences like mask-making, cooking, and cycling, visit iconic sites such as the Colosseum and Ponte Vecchio, explore the Ferrari Museum, and experience Italy’s rich culture, history, and flavors together.

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from $3,499

10% OFF

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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

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 $6,799

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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

Activities

Urban Exploration, Biking

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 $4,299

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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

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 $3,499

10% OFF

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Sicilian Sunsets & Amalfi Delights

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

• Explore Valletta’s historic port
• Stroll Trapani’s cobbled streets
• Visit medieval Erice
• Indulge in Palermo’s vibrant market

Starts / Ends

Valletta / Naples

Activities

Local Market Visits, Village Visits

Activity Level

Variable

Embark on an 8-day cruise aboard the MY Callisto from Valletta to Sicily and Southern Italy, exploring historic cities and stunning coastlines. Discover Agrigento, Erice, and Pompeii while enjoying exclusive onboard experiences and authentic Sicilian cuisine.

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from $9,460

Save 10%

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Cruising Southern Italy and Sicily – with Smithsonian Journeys

Valletta - Livorno - 9 Day Itinerary aboard Le Dumont-d'Urville

• Explore Valletta's heritage
• Discover Syracuse's history
• Admire Taormina's scenic views
• Experience Naples culture

Starts / Ends

Valletta / Livorno

Activity Level

Variable

Sail on this 9-day Southern Italy and Sicily cruise with Smithsonian Journeys aboard Le Dumont-d'Urville. Start in Valletta, Malta, exploring historic landmarks. Visit Syracuse's Greek and cultural sites and Taormina's scenic views and theater. Explore Reggio di Calabria's coast and museum. Visit Civitavecchia, and conclude in Livorno, Tuscany.

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