Top Italy Trips & Tours in May 2026

from $12,250

$1000 SBC

EXPLORE

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

2for1

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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

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

Air Credit

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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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from $20,290

2for1

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Malta, Sicily & Amalfi Coast

Valletta - Civitavecchia - 10 Day Itinerary aboard Emerald Sakara

• Explore Valletta’s Baroque capital
• Visit Giardini Naxos’ beaches
• Admire Lipari’s scenic cliffs
• Discover Amalfi’s cathedral

Starts / Ends

Valletta / Civitavecchia

Activity Level

Variable

Set sail for a 10-day Mediterranean cruise from Valletta, Malta, to Civitavecchia, Italy, on the Emerald Sakara. Visit Sicilian beaches, Amalfi's historic sites, and enjoy stunning views from Capri and Sorrento, balancing relaxation with exploration.

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from $6,799

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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 $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

Activities

Hiking

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.

Tour Details

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from $4,299

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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 $2,570

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Grand Prix Trials

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Stroll Nice’s Promenade
• Explore Lerici’s coastline
• Visit Portoferraio’s historic sites
• Witness Monaco’s Grand Prix

Starts / Ends

Nice / Nice

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, visiting charming coastal towns like Nice, Lerici, and Portoferraio. Explore stunning beaches and rich history, and witness the Monaco Grand Prix trials before returning to Nice.

Cruise Details

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from $2,570

Air Credit

EXPLORE

Ligurian Sea

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Stroll Nice’s old town
• Discover Lerici’s villages
• Explore Portoferraio’s vineyards
• Relax on Sant’Amanza’s beach

Starts / Ends

Nice / Nice

Activity Level

Variable

Embark on an 8-day cruise aboard the Royal Clipper, sailing from Nice to Monaco while discovering beautiful coastal towns and rich cultural landmarks. Enjoy vibrant local cuisine, stunning beaches, and history in France, Italy, and Monaco.

Cruise Details

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from $2,570

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Ligurian Sea

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Stroll Nice’s old town
• Discover Lerici’s villages
• Explore Portoferraio’s vineyards
• Relax on Sant’Amanza’s beach

Starts / Ends

Nice / Nice

Activity Level

Variable

Embark on an 8-day cruise aboard the Royal Clipper, sailing from Nice to Monaco while discovering beautiful coastal towns and rich cultural landmarks. Enjoy vibrant local cuisine, stunning beaches, and history in France, Italy, and Monaco.

Cruise Details

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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

Wine Tasting, 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.

Cruise Details

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from $15,061

Save 20%

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The Ancient Shores of Sicily and Malta

Roundtrip Malta - 10 Day Itinerary aboard Sea Cloud II

• Explore stunning UNESCO-listed site
• Step into the history of Sicily
• Discover the charm of ancient Erice
• Savor the authentic Sicily flavors
• Explore historic Taormina and Sirac

Starts / Ends

Valletta / Valletta

Activity Level

Variable

Embark on a 10-day Ancient Shores of Sicily and Malta cruise, aboard Sea Cloud II. Explore ancient cities, UNESCO-listed temples, and landscapes shaped by the Romans, Greeks, and Carthaginians. Visit Agrigento’s Valley of the Temples, the Ggantija Temples, and Valletta, stroll medieval Erice, and tour The Godfather’s Castello degli Schiavi.

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from $2,570

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Corsica & French Riviera

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Explore Nice’s old town
• Stroll Portofino’s harbor
• Unwind at Plage Saint Antoine
• Wander Alghero’s medieval streets

Starts / Ends

Nice / Nice

Activity Level

Variable

Set sail for an 8-day cruise on the Royal Clipper, visiting Monaco, Portofino, Corsica, Sardinia, and St. Tropez. Experience stunning landscapes, rich culture, and gourmet dining before returning to Nice with lasting memories.

Cruise Details

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from $2,320

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Amalfi & Sicily

Roundtrip Civitavecchia - 8 Day Itinerary aboard Star Clipper

• Sail across Mediterranean waters
• Visit Lipari for coastal views
• Explore Messina cathedral clock
• See seaside cliffs near Sorrento

Starts / Ends

Civitavecchia / Civitavecchia

Activity Level

Variable

Experience an 8-day Mediterranean sailing adventure from Civitavecchia, exploring Sicily, the Amalfi Coast, and the Aeolian and Pontine Islands aboard Star Clipper. Sail past Stromboli’s active volcano, wander historic Messina, and admire the coastal beauty of Amalfi and Sorrento. Explore Ponza’s unspoiled charm before returning to Rome’s port.

Cruise Details

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from $2,720

Air Credit

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Nice to Rome

Nice - Civitavecchia - 9 Day Itinerary aboard Star Clipper

• Wander Nice’s Promenade des Anglais
• Tour Monaco’s Palais du Prince
• See Portofino’s pastel houses
• Visit Bastia’s Old Town harbor

Starts / Ends

Nice / Civitavecchia

Activities

Small Ship Sailing, Village Visits, Local Market Visits, Archaeological Site Visits

Activity Level

Variable

Set sail on a 9-day Mediterranean cruise from Nice to Civitavecchia aboard the Star Clipper, exploring Monaco, the colorful Portofino, and Corsica’s highlights. Visit Elba to tour Napoleon’s villa and conclude your adventure with access to Rome.

Cruise Details

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from $6,950

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Ancient Shores of the Mediterranean

Malaga to Valletta - 10 Day Itinerary aboard Le Boreal

• Explore Malaga’s coastal old town
• Walk through Algiers’ UNESCO Casbah
• Walk Valletta’s fortified streets
• See Carthage and Byrsa

Starts / Ends

Malaga / Valletta

Activity Level

Variable

Set sail on a 10-day cruise from Malaga to Valletta aboard Le Boreal and explore UNESCO World Heritage Sites, ancient ruins, and vibrant local markets. Discover Roman theaters, Moorish palaces, Arab-Norman cathedrals, and Mediterranean coastlines. Enjoy cultural depth and historic architecture in each port.

Cruise Details

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from $20,130

Save 20%

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Mediterranean Wonders: Sicily, Greece, Sardinia, and Beyond

Spain - Greece - 13 Day Itinerary aboard National Geographic Orion

• Cruise the Mediterranean Sea
• Explore standing stones on Menorca
• Taste Sicilian wine
• Swim at Kefalonia
• Explore Delphi and Corinth Canal

Starts / Ends

Barcelona / Athens

Activities

Kayaking, Stand Up Paddle Boarding

Activity Level

Variable

Embark on a 13-day Mediterranean Wonders Cruise from Spain to Greece aboard National Geographic Orion, explore ancient ruins, medieval towns, and local cuisine. Visit Menorca’s prehistoric stones, Bonifacio’s citadel, Sardinia’s artisan villages, savor Sicilian wine, swim in Kefalonia’s waters, and explore Delphi.

Cruise Details

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from $2,570

Air Credit

EXPLORE

Corsica & French Riviera

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Explore Portofino’s Piazzetta
• Discover Propriano’s lively port
• Wander Alghero’s medieval streets
• Experience Sanary-sur-Mer’s markets

Starts / Ends

Cannes / Cannes

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, visiting beautiful France, Italy, and Corsica coasts. Enjoy vibrant towns, historic sites, fresh seafood, and charming beaches while soaking in the rich culture and stunning landscapes.

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