Top Italy Trips & Tours in May 2026

from $8,740

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Mediterranean Island Voyage: Sicily, Sardinia, Corsica, and Elba – with Smithsonian Journeys

Valletta - Nice - 8 Day Itinerary aboard Le Bougainville

• Discover Mediterranean islands
• Experience ancient ruins
• Admire Byzantine-Arab mosaics
• Explore medieval towns
• Discover local cuisine

Starts / Ends

Valletta / Nice

Activities

Land & Sea Exploration

Activity Level

Variable

Explore the heart of the Mediterranean on this 8-day Mediterranean Island Cruise with Smithsonian Journeys from Valletta to Nice aboard Le Bougainville. Discover Sicily, Sardinia, Corsica, and Elba's historical civilizations that left mark on these islands' language, cuisine, art, and architecture.

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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

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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 $2,475

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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

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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 $2,080

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Amalfi & Sicily

Civitavecchia Roundtrip - 7 Day Itinerary aboard Star Clipper

• Explore Civitavecchia wonders
• Discover Lipari lively streets
• Witness Stromboli’s volcano
• Experience Amalfi seaside views

Starts / Ends

Civitavecchia / Civitavecchia

Activities

Small Ship Sailing

Activity Level

Variable

Embark on a 7-day cruise aboard the Star Clipper, starting from Civitavecchia and visiting Italy's beautiful coastal spots like the Aeolian Islands and Amalfi. Conclude your journey with easy access to explore Rome.

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from $117,000

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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 $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 $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

Local Market Visits, 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 $12,250

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A Circumnavigation of Sicily with Smithsonian Journeys

Valletta - Valletta - 9 Day Itinerary aboard Le Bougainville

• Take a loop around Sicily
• Discover Sicily's beautiful cities
• Visit Syracuse
• Explore Palermo

Starts / Ends

Valletta / Valletta

Activity Level

Variable

During this 9-day cruise around Sicily aboard the new luxury expedition ship Le Bougainville, you'll be able to explore mythical places at the crossroads of Eastern and Western civilizations. Discover Sicily's most beautiful historic cities and ancient sites.

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from $17,490

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French & Italian Rivieras with Corsica

Civitavecchia (Rome) - Nice - 8 Day Itinerary aboard Emerald Sakara

• Explore Corsica’s Calvi
• Taste Livorno’s seafood
• Walk historic Porto Venere
• Experience Monte Carlo culture

Starts / Ends

Civitavecchia / Nice

Activities

Village Visits

Activity Level

Variable

Sail on this 8-day Western Mediterranean cruise from Civitavecchia to Nice aboard Emerald Sakara. Explore Corsica’s Calvi, Tuscany’s Livorno and Marina di Carrara, the UNESCO-listed town of Porto Venere, the coastal gems of Santa Margherita Ligure and Portofino, and the glamorous cities of Monte Carlo and Nice.

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from $3,610

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Italy and Croatia

Civitavecchia - Venice - 12 Day Itinerary aboard Star Clipper

• Explore Ponza’s colorful harbor
• Discover Amalfi’s grand Duomo
• Admire Lipari’s volcanic beauty
• Wander Taormina’s ancient lanes

Starts / Ends

Civitavecchia / Venice

Activity Level

Variable

Set sail on a 12-day cruise from Civitavecchia to Venice on the Star Clipper, exploring Italy and Croatia's hidden gems like Ponza and Otranto. Experience historic towns and local cuisine, and enjoy onboard relaxation and adventure across beautiful coastal seas.

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