Top Italy Trips & Tours in September 2026

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 $7,799

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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 $5,299

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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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Rome to Nice

Civitavecchia - Nice - 8 Day Itinerary aboard Royal Clipper

• Roam Monaco’s opulent streets
• Stroll Alghero’s medieval lanes
• Unwind at Sant’Amanza
• Wander Bastia’s old town

Starts / Ends

Civitavecchia / Nice

Activities

Snorkeling

Activity Level

Variable

Set sail on an 8-day cruise from Civitavecchia to Nice aboard the Royal Clipper, exploring historic sites like Portoferraio and Alghero and stunning beaches in Corsica and the luxurious Monaco. Conclude your journey in Nice, enjoying its vibrant Old Town and the beautiful Promenade des Anglais.

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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 $3,610

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Rome to Athens

Civitavecchia - Piraeus - 12 Day Itinerary aboard Star Clipper

• Explore Ponza’s harbor town
• Discover Sorrento’s ancient cliffs
• View Lipari’s bustling marina
• Wander Syracuse’s baroque piazzas

Starts / Ends

Civitavecchia / Piraeus

Activity Level

Variable

Join a 12-day cruise on the Star Clipper, starting from Civitavecchia and exploring Italy's Pontine Islands, the Aeolian Islands, and Sicily. Discover Greece's historic sites, including Olympia and picturesque Hydra, before concluding in Athens.

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from $2,570

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Corsica & French Riviera

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Discover Portofino’s coastal views
• Wander Propriano’s town center
• Stroll Alghero’s medieval streets
• Visit Ile-Rousse’s coastline

Starts / Ends

Nice / Nice

Activity Level

Variable

Set sail on an 8-day Royal Clipper cruise through the Mediterranean, exploring beautiful coastal towns in France, Italy, and Corsica. Enjoy vibrant markets in Nice, stunning views in Portofino, and relax on St. Tropez’s famed Pampelonne Beach.

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from $2,320

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Amalfi & Sicily

Civitavecchia Roundtrip - 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.

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from $4,499

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Pearls of Italy

Civitavecchia to Dubrovnik - 7 Day Itinerary aboard World Traveller

• Rome historic walking tour
• Hike Monte Rosa trails
• Kotor fortress panoramic views
• Explore old Perithia

Starts / Ends

Civitavecchia / Dubrovnik

Activity Level

Variable

Set sail on a 7-day cruise aboard World Traveller, from Civitavecchia to Dubrovnik, exploring iconic coastal cities and islands. Visit Capri, Lipari, Corfu, and Kotor. Discover ancient ruins, UNESCO sites, and crystal-clear beaches along the way. Enjoy a relaxed day at sea as part of this European itinerary.

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from $6,999

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Greece & Italy Reflections

Venice to Athens - 9 Day Itinerary aboard World Traveller

• Cruise scenic Corinth Canal
• Tour historic Sibenik fortress
• Explore the Delphi ruins
• Discover Parga’s Venetian castle

Starts / Ends

Venice / Piraeus

Activity Level

Variable

Embark on this 9-day cruise aboard the World Traveller from Venice to Athens, exploring the Adriatic and Aegean Seas. Highlights include Venice’s canals, Sibenik’s fortresses, Parga’s vibrant coastal setting, Delphi’s ancient ruins, sailing the Corinth Canal, Nafplion’s Venetian castles, and Athens’ iconic landmarks.

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from $2,570

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Voiles de Saint Tropez

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Explore Nice’s coastal charm
• Discover Lerici’s seaside villages
• Visit Portoferraio’s vineyards
• Swim Sant'Amanza’s crystal waters

Starts / Ends

Nice / Nice

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, exploring the stunning Mediterranean coasts of France, Italy, and Corsica. Journey from Nice to Lerici, Portoferraio, and St. Tropez, enjoying historical sites, breathtaking views, and vibrant local culture.

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from $6,620

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The Best of Croatia

Venice Roundtrip - 8 Day Itinerary aboard Le Boreal

• Stroll Venetian streets in Rovinj
• Explore UNESCO-listed Split center
• Admire Venice’s grand canals
• Visit medieval Korcula island town

Starts / Ends

Venice / Venice

Activity Level

Variable

Cruise through Croatia and Montenegro on an 8-day cruise aboard Le Boreal. Explore Venice, Hvar, Split, Dubrovnik, Korcula, Rovinj, and Kotor with one guided excursion included at each port. Discover coastal towns, ancient landmarks, and scenic bays along the Dalmatian coast. Enjoy unique cultural experiences in every destination.

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from $16,595

EBD

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A Mediterranean Feast

Naples - Lisbon - 17 Day Itinerary aboard Douglas Mawson

• Explore archaeological Pompeii
• Taste Naples' iconic pizza
• Discover the Palace of Caserta
• Visit Monaco's 'The Rock'

Starts / Ends

Naples / Lisbon

Activities

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

Activity Level

Variable

Set sail on a 17-day cruise from Naples to Lisbon aboard the Douglas Mawson, exploring the Mediterranean's rich culinary heritage. Experience local gastronomy and culture while visiting historic sites, traditional villages, and renowned wineries.

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from $12,204

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Mount Blanc Hiking Adventure

10 Day Itinerary

• Enjoy the view of Chamonix
• Hike the Mont Blanc
• Admire the Bioniassay glacier
• Explore Courmayeur Alpine resort
• Hike the old trail valley in Trient

Starts / Ends

Geneva / Geneva

Activities

Wilderness Lodge Exploration

Activity Level

Challenging

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

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from $14,990

OBC

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Spanish Shores & Beyond

Barcelona - Palma de Mallorca - 10 Day Itinerary aboard Emerald Sakara

• Explore Port-Vendres French harbor
• Discover Saint-Tropez Riviera town
• Wander Calvi’s Corsican coast
• Stroll Mahon’s cobbled streets

Starts / Ends

Barcelona / Palma de Mallorca

Activity Level

Variable

Experience a 10-day Mediterranean cruise from Barcelona to Palma de Mallorca on the Emerald Sakara, visiting stunning ports like Monte Carlo and Calvi. Enjoy coastal charm, cultural sites, and luxurious relaxation throughout this captivating journey.

Cruise Details

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from $12,495

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Adriatic Voyage: Croatia, Montenegro and Greece

Split to Athens - 9 Day Itinerary aboard Le Dumont-d'Urville

• Explore ancient Split ruins
• Cruise scenic Kotor Bay
• Visit underground lake Cephalonia
• Transit historic Corinth Canal

Starts / Ends

Venice / Athens

Activities

Kayaking

Activity Level

Variable

Sail from Venice to Athens on a 9-day Adriatic voyage aboard Le Dumont d’Urville. Explore ancient ruins, charming coastal towns, and scenic islands, with plenty of enriching excursions and unforgettable views.

Cruise Details

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from $5,799

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Croatian Dreams

Dubrovnik to Venice - 8 Day Itinerary aboard World Traveller

• Tour Dubrovnik’s UNESCO Old Town
• Discover Split’s Roman ruins
• Tour Opatija’s Lungomare boardwalk
• Tour Piran’s medieval walls

Starts / Ends

Dubrovnik / Venice

Activities

Small Ship Sailing

Activity Level

Variable

Sail on an 8-day cruise from Dubrovnik to Venice aboard the World Traveller. Walk Dubrovnik’s historic Old Town, explore Hvar’s lavender fields and visit Split’s Diocletian’s Palace. Enjoy wine tasting on Vis Island and stroll Opatija’s coastal promenade. Discover Piran’s medieval charm before ending the journey in Venice.

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