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Top Italy Trips & Tours in May 2025

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Discover Italy in May 2025 on one of these 20 tours hand-selected by the travel experts at Adventure Life. Explore the best of Venice, Valletta, Bonifacio, Dubrovnik, and Taormina during May 2025 as you enjoy cruises, small ship cruises, archaeological site visits, cultural, and wine tasting. Prices for trips in May 2025 range from $1,880 to $112,500 for a vacation of 7 to 16 days. Choose any of the below 20 itineraries in May 2025 and customize it when you contact one of Adventure Life's expert Italy trip planners.
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Explore historic Bonifacio atop the cliffs of Corsica
$7,690
EXPLORE

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:
Archaeological Site Visits, Land & Sea Exploration, Small Ship Cruises, Village Visits
Activity Level:
Variable
Embark on this 8-day Mediterranean Island Voyage with Smithsonian Journeys from Valletta to Nice on Le Bougainville where you can engage in discussions with two Smithsonian Journeys Experts onboard. Explore five Mediterranean islands on one itinerary, starting from Malta and moving on to Sicily, …
Cruise Details
0
Sunset over Palermo
$3,799
EXPLORE

Sicilian Sunsets & Amalfi Delights

Malta - Naples - 8 Day Itinerary aboard Variety Voyager
  • Explore Port Empedocle
  • Discover Trapani
  • Explore Sorrento
  • Explore Palermo
Starts / Ends:
Valletta / Naples
Activities:
Archaeological Site Visits, Small Ship Cruises, Wine Tasting
Activity Level:
Variable
Embark on an 8-day cruise aboard the Variety Voyager from Malta's charming capital, Valletta, through Sicily and Southern Italy. Visit Agrigento's UNESCO-listed Temple Valley, explore the medieval streets of Erice, and delve into Palermo's Mafia history while savoring Sicilian cuisine. …
Cruise Details
0
Explore ruins in Taormina within view of volcanic Mount Etna
$3,699
EXPLORE

La Dolce Vita

Naples - Malta - 8 Day Itinerary aboard Variety Voyager
  • Discover Syracuse
  • Explore Taormina
  • Experience Lipari Island
  • Discover Capri Island
Starts / Ends:
Naples / Valletta
Activities:
Archaeological Site Visits, Small Ship Cruises, Wine Tasting
Activity Level:
Variable
Embark on an 8-day cruise from Naples to Malta aboard the Variety Voyager. Begin your journey in charming Naples, the birthplace of pizza, before heading to the stylish island of Capri, a favorite among celebrities and jet-setters. In Sicily, explore the enchanting town of Taormina, with its narrow …
Cruise Details
0
Blue hour over the city in the shadow of Mount Etna
$3,699
EXPLORE

Mediterranean Serenade

Roundtrip Malta - 8 Day Itinerary aboard Variety Voyager
  • Discover Gozo Island
  • Witness Stromboli
  • Enjoy Catania
  • Explore Valetta
Starts / Ends:
Valletta / Valletta
Activities:
Archaeological Site Visits, Small Ship Cruises, Wine Tasting
Activity Level:
Variable
Embark on an 8-day cruise aboard the Variety Voyager through the enchanting destinations of Valletta, Gozo Island, Syracuse, Lipari, and Catania. Explore the ancient Ggantija temples in Gozo Island, dating back 5500 years. Discover Syracuse's "White City." Sail around the volcanic …
Cruise Details
0
Gondola on Canal Grande at Sunset, Venice
$3,290
Savings
EXPLORE

Venetian Horizons

Venice Roudtrip - 8 Day Itinerary aboard M/Y Callisto
  • Visit Venice's Grand Canal
  • Enjoy fresh seafood delicacies
  • Explore Plitvice Lakes in Croatia
  • Join a truffle hunting experience
Starts / Ends:
Venice / Venice
Activities:
Archaeological Site Visits, Local Market Visits, Small Ship Cruises, Village Visits
Activity Level:
Variable
Set sail on an 8-day Adriatic cruise aboard M/Y Callisto that begins in the city of Venice and winds its way through the coastal towns of Slovenia and Croatia before culminating in the historic city of Ravenna. This eight-day cruise offers a blend of guided tours and free time, allowing you to …
Cruise Details
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The sunny coast of Sardinia
$2,030
EXPLORE

Ligurian Sea

8 Day Itinerary aboard Star Flyer
  • Experience a new age of sail
  • Discover Portoferraio's heritage
  • Visit Palombaggia beach
  • Explore medieval Alghero
Starts / Ends:
Cannes / Cannes
Activities:
Biking, Hiking, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Step aboard Star Flyer and discover a new age of sail, where the traditions of the past merge with the amenitiies of the present day. Experience friendly and gracious service and a delightful menu of international foods from the far corners of the earth. Fall asleep to the gentle rhythms of the …
Cruise Details
0
La Bella Vita
$4,950
EXPLORE

Venice and Mantua Cruise

7 Day Itinerary aboard La Bella Vita
  • Tour of historic Venice
  • Cruise on the Canal of the Orphans
  • Tour of Chioggia
  • Enjoy dinner at Villa Ca'Zen
Activities:
Biking, Local Market Visits, River Cruises, Village Visits, Wine Tasting
Activity Level:
Variable
Explore the magical and historical heritage that Italy posses by boarding to La Bella Vita for this 7-day cruise. Travel by Venice's famous monuments and visit the Naval Museum that houses important vessels such as ceremonial barges and warships. Visit Chioggia and enjoy touring the colorful …
Cruise Details
0
Visit charming Sicily
$11,425
EXPLORE

Fiery Sicily and Charming Adriatic Sea

Catania - Dubrovnik - 11 Day Itinerary aboard Sea Cloud II
  • Marvel at volcanic soil in Catania
  • Explore Sicily's poetic masterpiece
  • Learn about Europe's Mount Etna
  • Step into Bari's historic old town
Starts / Ends:
Catania / Dubrovnik
Activities:
Archaeological Site Visits, Small Ship Cruises
Activity Level:
Variable
Embark on an 11-day cruise aboard the Sea Cloud II, exploring Sicily's fiery landscapes and the Adriatic Sea's charming beauty. Begin in Catania, where Goethe found inspiration amidst vibrant orange and lemon trees. Discover Taormina's elegance with a view of Mount Etna. Sailing becomes …
Cruise Details
0
Stop in beautiful Parga
$11,399
EXPLORE

Ionian Interlude

Barcelona - Rome - 16 Day Itinerary aboard World Navigator
  • Explore Venice's canals and cuisine
  • Explore UNESCO-listed sites
  • Relax on Parga's scenic beaches
  • Hike to San Giovanni Fortress
Starts / Ends:
Barcelona / Civitavecchia
Activities:
Archaeological Site Visits, Local Market Visits, Village Visits, Wine Tasting
Activity Level:
Variable
Set sail on an unforgettable 16-day Ionian Interlude cruise aboard World Navigator, exploring the Mediterranean's wonders.. From Barcelona's vibrant streets to Rome's ancient allure, immerse yourself in rich history, culture, and natural beauty. Discover whimsical architecture in …
Cruise Details
0
Piazza Navona, Rome, Italy
$3,030
$100 OBC
EXPLORE

Italy, Montenegro & Croatia

12 Day Itinerary aboard Star Flyer
  • Explore the Sistine Chapel
  • Visit the medieval city of Kotor
  • Cruise through Venice's canals
  • Discover Amalfi's majestic Duomo
Starts / Ends:
Civitavecchia / Venice
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Cruise from Rome to Venice on this 12-day cruise aboard Star Flyer, exploring Italy, Montenegro, and Croatia's historic ports and cultural landmarks. From Civitavecchia's Roman history to Amalfi's medieval charm and Messina's Sicilian delights, enjoy traditional sailing at sea. …
Cruise Details
0
Explore the ancient ruins of Rome
$5,999
EXPLORE

Italy & France Allure

Rome - Barcelona - 8 Day Itinerary aboard World Navigator
  • Visit the Coliseum to catacombs
  • Explore town of San Remo
  • Explore French Riviera in Menton
  • Discover food market in Barcelona
Starts / Ends:
Civitavecchia / Barcelona
Activities:
Archaeological Site Visits, Cooking Classes, Local Market Visits, Village Visits, Wine Tasting
Activity Level:
Variable
Embark on an 8-day Mediterranean voyage aboard World Navigator commencing from Civitavecchia, Italy. Begin by delving into Rome's rich history to picturesque Portofino, Livorno's gateway to Pisa and Florence, and San Remo, famed for its music festival and floral beauty. Explore Menton's …
Cruise Details
0
Explore beautiful Barcelona
$12,799
EXPLORE

Timeless Tastes & Treasure

Barcelona - Venice - 15 Day Itinerary aboard World Navigator
  • Visit Barrakka Panoramic Lifts
  • Explore French Riviera and Old Nice
  • Visit the town of Côte d'Azur
  • Do truffle-hunting in Tuscany
Starts / Ends:
Barcelona / Venice
Activities:
Archaeological Site Visits, Local Market Visits, Urban Exploration, Wine Tasting
Activity Level:
Variable
Embark on a 15-day Timeless Tastes & Treasure Cruise from Barcelona to Venice aboard World Navigator. Along Valletta's Grand Harbor, start with the Barrakka Panoramic Lifts, for a sunset with an extended evening in port. Enjoy a late night in Monte Carlo, to explore the scenery of the …
Cruise Details
0
Bonifacio, Corsica, France
$1,880
EXPLORE

Corsica & French Riviera

7 Day Itinerary aboard Royal Clipper
  • Discover Portofino
  • Explore Bastia
  • Discover Sant' Amanza
  • Experience East Corsica
Starts / Ends:
Cannes / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on a 7-day cruise aboard the Royal Clipper in Cannes, France. This glamorous city is known for its luxurious lifestyle and the famous Cannes Film Festival. Next, visit the picturesque fishing village of Portofino, Italy, with its colorful houses and stunning views. Explore the beautiful …
Cruise Details
0
View of Hvar harbor
$12,390
EXPLORE

Croatian Coast and the Best of Adriatic

Venice - Dubrovnik - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Rovinj
  • Experience the attractions of Zadar
  • Discover Sibenik
  • Marvel at Hvar Town
Starts / Ends:
Venice / Dubrovnik
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Begin your 8-day cruise of discovery in Venice, the gateway to Croatia. Cruise aboard the Emerald Azzurra and explore some of the Adriatic's most iconic destinations, including Rovinj, Zadar, Sibenik, Hvar, Split, Korcula, and Dubrovnik. Take a tour of Rovinj and visit the hilltop church of St. …
Cruise Details
0
City of Dubrovnik
$3,890
EXPLORE

Adriatic Jewels

Venice - Dubrovnik - 8 Day Itinerary aboard M/Y Callisto
  • Visit a UNESCO World Heritage site
  • Discover Rovinj in Croatia
  • Visit St. James Cathedral
  • Try a truffle hunting & wine tour
Starts / Ends:
Venice / Dubrovnik
Activities:
Archaeological Site Visits, Small Ship Cruises
Activity Level:
Variable
Embark on an 8-day Adriatic cruise, starting in Venice and concluding in Dubrovnik, aboard M/Y Callisto. From the moment of embarkation in Venice, you'll be treated to exceptional service and unique experiences. Explore Rovinj’s charming old town, join a truffle hunt in Istria, and …
Cruise Details
0
A beautiful marina, Cannes at night
$2,030
EXPLORE

Corsica & French Riviera

8 Day Itinerary aboard Star Flyer
  • Experience Cannes
  • Discover Ile Rousse
  • Explore Calvi
  • Enjoy St. Tropez
Starts / Ends:
Cannes / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on an 8-day cruise to and from Cannes aboard the Star Flyer. Discover the Mediterranean's charm with visits to glamorous Cannes, scenic Portofino, the quaint towns of Ile Rousse and Calvi in Corsica, the serene beauty of Plage Saint Antoine and Saint-Raphaël, and the vibrant …
Cruise Details
0
Part of the beautiful French Riviera, Monaco sits high on a cliff.
$2,030
EXPLORE

Grand Prix Finals

Cannes - Civitavecchia - 8 Day Itinerary aboard Star Flyer
  • Explore Cannes
  • Sail through St. Florent
  • Discover Ajaccio's stylish allure
Starts / Ends:
Cannes / Civitavecchia
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Set sail on an incredible 8-day cruise aboard Star Flyer for the ultimate Grand Prix Finals. From the glitzy shores of Cannes to Monaco's legendary domain. Discover vibrant harbors and ancient citadels in St. Florent and Bonifacio, and dive into Ajaccio's stylish vibe, the birthplace of …
Cruise Details
0
Ruins Athina Pronaia temple in Ancient Delphi
$15,696
Savings
EXPLORE

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:
Small Ship Cruises
Activity Level:
Variable
On this 13-day Mediterranean Wonders: Sicily, Greece, Sardinia, and Beyond Cruise from Spain to Greece aboard National Geographic Orion, traverse the Mediterranean Sea to explore ancient ruins, medieval towns, and culinary delights from Spain and Sardinia to Corsica and Greece. Walk among …
Cruise Details
0
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