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Top Italy Trips & Tours in May 2023

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Trevi Fountain in Rome
Sicily
Balate Dorin
Visit charming Sicily
Lipari
Roman Babakin
Hiking on the Amalfi coast overlooking the Tyrrhenian sea
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Discover Italy in May 2023 on one of these 22 tours hand-selected by the travel experts at Adventure Life. Explore the best of Civitavecchia, Portoferraio, Lipari, Syracuse, and Taormina during May 2023 as you enjoy small ship cruises, village visits, small ship sailing, archaeological site visits, and urban exploration. Prices for trips in May 2023 range from $1,250 to $32,680 for a vacation of 5 to 12 days. Choose any of the below 22 amazing itineraries in May 2023 and customize it to make it your own with the help of one of Adventure Life's expert Italy trip planners.
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Scenic view of Dubrovnik
$16,950
EXPLORE

Mediterranean Gems: From Dubrovnik to Naples

Dubrovnik to Naples - 11 Day Itinerary aboard Sea Cloud
  • Explore Gerace
  • Tour the Amalfi Coast
  • Visit Pompeii
  • Explore Dubrovnik
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Relaxed
Marvel at ornate cathedrals and remarkable baroque buildings, explore great sites of antiquity—from renowned Pompeii to the less-visited Greek temples of Paestum—and meander through unspoiled clifftop towns, soaking up breathtaking views. Plus, with a little luck witness the orange glow …
Cruise Details
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Naples at Sunset, Italy
$16,950
EXPLORE

Corsica & Sardinia

12 Day Itinerary aboard Sea Cloud
  • Discover Cagliari
  • Visit Nuraghe Losa
  • Enjoy the medieval city of Alghero
  • Admire Bonifacio's unique views
Starts/ Ends in:
Naples / Naples
Activities:
Small Ship Cruises, Village Visits
Activity Level:
Relaxed
This 11-night voyage is dedicated to the exploration of two fiercely independent islands–Sardinia and Corsica. These islands share many historic elements through millennia of empires and civilizations, but still, maintain their identities and independent attitudes from their governing nations …
Cruise Details
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The city of Bonifacio is built on stunning seaside cliffs along the riviera
$5,755
EXPLORE

Early Summer Mediterranean Style

Civitavecchia to Genoa - 8 Day Itinerary aboard Sea Cloud II
  • Admire Mediterranean beauty
  • Discover elegant Portofino
  • Journey to diverse Elba
Starts/ Ends in:
Civitavecchia / Genoa
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Join the Sea Cloud II on a fantastic cruise along the Italian Riviera. Admire imposing cliffs, white sandy beaches, avenues of cypresses, vineyards and olive groves, traditional villages, and elegant beach resorts which make the place of Napoleon's exile somewhere you would in fact like to be …
Cruise Details
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Colosseum in Rome, Italy
$7,115
EXPLORE

Mediterranean: Civitavecchia to Valletta

9 Day Itinerary aboard Sea Cloud II
  • Admire beautiful Bonifacio
  • Walk around wonderful Naxos
  • Explore the Vatican State
  • Explore Capri and observe its charm
Starts/ Ends in:
Civitavecchia / Valletta
Activities:
Sailing Schooner
Activity Level:
Relaxed
Explore the historical wonders of the Mediterranean on this 8-day small ship cruise sailing from Rome. Enjoy thepicturesque Amalfi Coast with its violet bougainvillea gracing pastel-pink facades, houses perched upon cliffs like swallows’ nests, and perron stairs with views out over the …
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Sicilian landscape in the early evening
$1,890
EXPLORE

Amalfi & Sicily

Civitavecchia Roundtrip - 8 Day Itinerary aboard Star Clipper
  • Gaze upon the Sistine Chapel
  • Snorkel at Palmarola
  • Visit historical Pompeii
  • Wander through the grand Duomo
Starts/ Ends in:
Civitavecchia / Civitavecchia
Activities:
Small Ship Cruises, Small Ship Sailing, Urban Exploration, Village Visits
Activity Level:
Relaxed
Idyllic islands, charming cobbled villages, spectacular scenery, intriguing history... capture the heart of the Mediterranean in a single cruise voyage. Each small harbor is especially suited for small ship exploration. Enjoy the best of the region — from the ancient ruins of Rome and …
Cruise Details
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Woman traveling in Cannes
$2,040
EXPLORE

Historic Monaco Grand Prix Finals

8 Day Itinerary aboard Royal Clipper
  • Explore Bonifacio
  • Enjoy Portoferraio's vineyards
  • View Monaco's emblematic spots
  • Celebrate Cannes Film Festival
  • Observe prehistoric engraved stones
Starts/ Ends in:
Cannes / Civitavecchia
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
For those who enjoy racing, the world-famous Monaco Grand Prix Finals is a staple stop on this Mediterranean spring sailing cruise. Embark Royal Clipper in Cannes, France, and spend 8 days exploring the Ligurian Sea.Discover Lerici, the largest village on the Gulf of Poets, continue southeast …
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Relax on the Italian coast
$4,490
EXPLORE

Ionian Sea Adventure

8 Day Itinerary aboard Emerald Azzurra
  • Tour Delphi's archaeological site
  • Visit the Aeolian Island of Lipari
  • Explore Cephalonia
  • Cruise the Corinth Canal
Starts/ Ends in:
Piraeus / Civitavecchia
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Join this idyllic 8-day itinerary aboard the Emerald Azzurra sailing the Ionian Sea. Transit the Corinth Canal from Athens, before sailing onwards to the Greek town of Itea for a tour of thearchaeological site of Delphi and the village of Fiskardo in Cephalonia which is considered as the largest of …
Cruise Details
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La Bella Vita
$4,790
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:
Barge Cruising, Biking, Local Market, River Cruise, Village Visit, Wine Tasting
Activity Level:
Relaxed
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
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Relax by the sea near colorful Nice
$3,600
EXPLORE

From the French Riviera to Italian Shores

7 Day Itinerary aboard Le Lyrial
  • Explore colorful Nice, France
  • Wander charming Italian villages
  • See where Napoleon was exiled
  • See historic Civitavecchia
Starts/ Ends in:
Nice / Civitavecchia
Activities:
Archaeological Site Visits, Small Ship Cruises, Village Visits
Activity Level:
Relaxed
Enjoy the Mediterranean's sun-drenched beaches on this 7-day journey from the French Riviera to the Italian Riviera onboard the luxury Le Lyrial. Begin your journey in Nice, a jewel of the French Riviera renowned for its beaches and laid-back atmosphere. Sail to Calvi, Corsica, and explore …
Cruise Details
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Relax on France's colorful coast
$4,530
EXPLORE

Island Hopping in the Mediterranean

Valletta - Nice - 8 Day Itinerary aboard Le Jacques Cartier
  • Explore ancient cities
  • Visit historic cities of Sicily
  • Tour UNESCO-listed Valletta
  • Visit the island of Elba
Starts/ Ends in:
Nice / Valletta
Activities:
Archaeological Site Visits, Small Ship Cruises
Activity Level:
Relaxed
Your voyage begins inNice, the glittering jewel of the French Riviera. Set sail from this sun-soaked port to the island of Elba, where Napoleon spent a period of exile. Sail to Corsica, where the charming Porto Vecchio invites exploration of its historic sites and its surrounding natural beauty. In …
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Stop in beautiful Malta
$4,190
EXPLORE

The Charm of Italian Shores

Civitavecchia - Valletta - 8 Day Itinerary aboard Le Lyrial
  • Cruise the Italian coast
  • Discover Amalfi Coast
  • Visit Sicily
  • Sail by Stromboli volcano
Starts/ Ends in:
Civitavecchia / Valletta
Activities:
Archaeological Site Visits, Small Ship Cruises, Village Visits
Activity Level:
Relaxed
Discover Italy's treasures by taking a cruise along its coast. The first stop on your journey from Civitavecchia is Sorrento. Byron, Tolstoy, Dickens, and Goethe were all enchanted by the town's calm way of life and lovely environment, which clings to the cliffs overlooking the Bay of …
Cruise Details
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Tour the charming city of Valletta, Malta.
$5,860
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 in:
Valletta / Valletta
Activities:
Archaeological Site Visits, Small Ship Cruises
Activity Level:
Relaxed
Cruise around Sicily aboard the new luxury expedition ship Le Bougainville, while exploring mythical places at the crossroads of Eastern and Western civilizations. Discover Sicily's most beautiful historic cities and ancient sites. Valletta, the capital of Malta, will be the departure point. …
Cruise Details
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Explore ruins in Sicily
$7,115
EXPLORE

On a Course of Longing through Bella Italia

Civitavecchia to Valletta - 9 Day Itinerary aboard Sea Cloud II
  • Explore the Vatican State
  • Admire beautiful Bonifacio
  • Discover Corsica's history
  • Visit the royal Capella Palatina
Starts/ Ends in:
Civitavecchia / Malta
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Explore the historical wonders of the Mediterranean on this 8-day small ship cruise sailing from Rome. Enjoy thepicturesque Corsica Coast with its houses perched upon cliffs like swallows’ nests, and perron stairs with views out over the turquoise sea. Discover Taormina, a stunning town in …
Cruise Details
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Visit the Cathedral of Palmero on your small ship cruise around Sicily
$6,195
EXPLORE

Sicily's Rich Cultural Heritage

Valletta to Syracuse - 9 Day Itinerary aboard Sea Cloud II
  • View the Cappella Palatina
  • Visit Syracuse, a UNESCO site
  • Take a cable car up Mt. Etna
  • Join a cooking class at Lipari
Starts/ Ends in:
Malta / Malta
Activities:
Archaeological Site Visits, Cooking Classes, Small Ship Sailing
Activity Level:
Relaxed
Be a part of this exclusive 9-day cruise and discover the most beautiful sights of Sicily, a magical place full of royal palaces, ancient temples, and heavenly panoramas. Delight yourself with the many facets of the largest Mediterranean island, a fabulously diverse microcosm in its own right with …
Cruise Details
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The clifftop town of Bonifacio, Corsica
$1,890
EXPLORE

Cannes to Rome

8 Day Itinerary aboard Star Clipper
  • Explore Napoleon's birthplace
  • Sail into Bonifacio's harbor
  • Visit Monaco, full of allure
  • Discover Corsica's landscapes
Starts/ Ends in:
Cannes / Civitavecchia
Activities:
Local Market Visits, Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Relaxed
Embark on your 8-day journey from Cannes to Rome. From Cannes, sail to Monaco where you can experience true luxury.Spend time exploring the cliffs ofBonifacio and the beaches in East Corsica. Enjoy the mountainous landscape and tour Napoleon's birthplace of Ajaccio. Set sail for Portoferraio in …
Cruise Details
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A beautiful marina, Cannes at night
$2,040
EXPLORE

Grand Prix Trials

Cannes to Cannes - 8 Day Itinerary aboard Royal Clipper
  • View Monaco's emblematic spots
  • Enjoy Portoferraio's vineyards
  • Explore Europe's top beaches
  • Observe prehistoric engraved stones
Starts/ Ends in:
Cannes / Cannes
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
There is no better way to sail the Mediterranean than onboard a great sailing vessel ship, the Royal Clipper, with tickets to the historicF1Monaco Grand Prixto complete your holiday. Visit Palombaggia, the most famous beach in Corsica. Explore Alguero's bustling historic center, a unique spot …
Cruise Details
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Golden hour in Venice's famed Piazza San Marco
$2,926
EXPLORE

From Renaissance-infused Mantua to the Canals of Venice

7 Day Itinerary aboard MS Michelangelo
  • Discover Emilia-Romagna
  • Enjoy tasting authentic Parmesan
  • Explore the romantic Verona
  • Admire Vicenza's architecture
Starts/ Ends in:
Venice / Venice
Activities:
River Cruises, Village Visits
Activity Level:
Relaxed
From Mantua to Venice, enjoy a unique cruise through the heart of three Italian regions. Your trip starts with the region of Emilia-Romagna and its traditional cuisine: do not miss out on a tour of Parma and Cremona complete with a tasting of authentic cheese and ham! Lombardy welcomes you next …
Cruise Details
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St Tropez, France
$1,890
EXPLORE

Rome to Cannes

8 Day Itinerary aboard Star Clipper
  • Tour a vineyard in Portoferraio
  • Explore Napoleon's birthplace
  • Discover Stintino's beaches
  • Observe the regatta at St. Tropez
Starts/ Ends in:
Civitavecchia / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Relaxed
Join the luxury tall ship Star Clipper on this special cruise which showcases the history, culture, and art of the western Mediterranean. Start in Civitavecchia, the port city of Rome, then sail to Portoferraio. Admire the ancient citadel town of Bonifacio,perched high atop a seemingly impenetrable …
Cruise Details
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