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Top Italy Trips & Tours in May 2026

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Discover Italy in May 2026 on one of these 19 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2026 as you enjoy Archaeological Site Visits, Village Visits, Local Market Visits, Hiking, and Small Ship Sailing. Prices for trips in May 2026 range from $2,080 to $33,800 for a vacation of 7 to 13 days. Choose any of the below 19 itineraries in May 2026 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
from $7,790
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
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.
Cruise Details
0
Sicilian landscape in the early evening
from $2,080
EXPLORE

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
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.
Cruise Details
0
Alpe di Siusi
from $3,225
EXPLORE

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
Starts / Ends
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.
Tour Details
0
Explore Italy's colorful Amalfi coast
from $2,475
EXPLORE

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.
Tour Details
0
Cortina D Ampezzo, idyllic mountain peaks of Dolomites
from $9,074
EXPLORE

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, Cooking Classes
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.
Tour Details
0
Tour the charming city of Valletta, Malta.
from $9,450
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.
Cruise Details
0
Civitavecchia, the historic port city that opens the gateway to Rome.
from $3,610
EXPLORE

Italy, Montenegro 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
Activities
Small Ship Sailing
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.
Cruise Details
0
Part of the beautiful French Riviera, Monaco sits high on a cliff.
from $2,570
EXPLORE

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
0
Sant'Amanza beach, Corsica, France
from $2,570
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
0
Gondola on Canal Grande at Sunset, Venice
from $4,090
EXPLORE

Venetian Horizons

Venice Roudtrip - 8 Day Itinerary aboard M/Y Callisto
  • Visit Venice's Grand Canal
  • Enjoy fresh seafood in Piran
  • Explore Plitvice Lakes in Croatia
  • Experience truffle hunting in Koper
Starts / Ends
Venice / Venice
Activity Level
Variable
Embark on an 8-day Adriatic cruise aboard M/Y Callisto, starting in Venice and visiting coastal towns in Slovenia and Croatia before ending in Ravenna. Enjoy guided tours and free time to explore iconic sites, beautiful landscapes, and rich cultural heritage.
Cruise Details
0
The sunny coast of Sardinia
from $2,570
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
Activities
Village Visits
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
0
Ancient theater of Taormina Sicily Italy with Etna erupting volcano at sunset
from $14,357
EXPLORE

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
Activities
Wine Tasting
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.
Cruise Details
0
Beautiful Amalfi Coast
from $2,320
EXPLORE

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.
Cruise Details
0
Part of the beautiful French Riviera, Monaco sits high on a cliff.
from $2,570
EXPLORE

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
0
Sunset over Palermo
from $6,950
EXPLORE

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
Activities
Local Market Visits, Archaeological Site Visits, Urban Exploration
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
0
French Alpine village of Les Contamines-Montjoie
from $12,204
EXPLORE

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.
Tour Details
0
Wander the cobbled streets of Rovinj
from $3,990
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
Activity Level
Variable
Set sail on an 8-day Adriatic cruise aboard M/Y Callisto, sailing from Venice to Dubrovnik. Explore historic towns like Rovinj, Senj, and Kotor, and marvel at natural wonders such as the Plitvice and Krka Waterfalls. This adventure combines cultural heritage, natural beauty, and culinary delights, making it a truly unforgettable experience.
Cruise Details
0
Ruins Athina Pronaia temple in Ancient Delphi
from $16,172
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
Hiking, Land & Sea Exploration, Kayaking, Stand Up Paddle Boarding
Activity Level
Variable
On this 13-day Mediterranean Wonders Cruise from Spain to Greece aboard National Geographic Orion, explore ancient ruins, medieval towns, and culinary delights. Visit Menorca's prehistoric stones, savor Sicilian wine, swim in Kefalonia's waters, and explore Delphi.
Cruise Details
0
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