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Top Italy Trips & Tours in May 2025

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Discover Italy in May 2025 on one of these 34 tours hand-selected by the travel experts at Adventure Life. Explore the best of Venice, Valletta, Dubrovnik, Bonifacio, and Taormina during May 2025 as you enjoy village visits, archaeological site visits, wine tasting, cruises, and small ship cruises. 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 34 itineraries in May 2025 and customize it when you contact one of Adventure Life's expert Italy trip planners.
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    • Italy
Discover distinctive Venetian architecture
$6,345
EXPLORE

Classic Italy

Venice to Rome - 10 Day Itinerary
  • Ride the gondola in Venetian canals
  • Discover the Sistine Chapel
  • Explore the Vatican Museums
  • Marvel at the architecture in Siena
  • Savor authentic Tuscan cuisine
  • Enjoy the Tuscan countryside
Starts / Ends:
Venice / Rose Garden Palace
Activities:
Archaeological Site Visits, Cooking Classes, Local Market Visits, Village Visits, Wine Tasting
Activity Level:
Relaxed
Embark on a journey through the timeless beauty of Italy with this 10-day classic tour. Get ready to be awestruck by the splendor of Venice and Florence before heading to the eternal city of Rome. Discover the magic of Venice as you glide through the grand canals on a traditional gondola ride while …
Tour Details
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Manarola, Italian Village in Cinque Terre National Park
$5,703
EXPLORE

Turin, Langhe, and Cinque Terre

Turin to Sestri Levante - 10 Day Itinerary
  • Explore the city of Turin
  • Visit the city's main squares
  • Discover the wine region of Barolo
  • Taste local wine and cheese
  • Experience truffle hunting
  • Walk in Quadrilatero Romano
  • Admire Cinque Terre
  • Swim in the Italian Riviera
  • See the picturesque Santa Margherit
Starts / Ends:
Milan / Milan
Activities:
Hiking, Local Market Visits, Village Visits, Wine Tasting
Activity Level:
Relaxed
Discover the hidden gems of Turin, Langhe's famous wineries, and the picturesque towns of Cinque Terre during this 10-day tour. Begin your journey in the beautiful city of Turin, known as the Paris of Italy. Take a stroll through the historic Quadrilatero Romano, where you'll be transported …
Tour Details
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French Alpine village of Les Contamines-Montjoie
$11,187
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:
Hiking, Village Visits, Wilderness Lodge Exploration
Activity Level:
Challenging
Discover the enchanting surroundings and a breathtaking journey through the French and Italian Alps on this 10-day hiking trip from Geneva to Chamonix Mont Blanc, and admire the highest mountain in Europe and the beautiful landscape of the Alps. Visit the incredible, world-famous mountain resort of …
Tour Details
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Colorful villages line the shores of the Italian riviera
$4,336
EXPLORE

Aeolian Archipelago

Lipari to Salina - 8 Day Itinerary
  • Discover Lipari and Salina
  • Visit a local winery
  • Enjoy a scenic hike in Vulcano
  • Swim in Cala Junco nature reserve
  • Take a walking tour in Stromboli
  • Relax on the beaches of Salina
Starts / Ends:
Milazzo / Milazzo
Activities:
Archaeological Site Visits, Hiking, Village Visits, Wine Tasting
Activity Level:
Relaxed
The Aeolian Islands are a fascinating volcanic archipelago in the Tyrrhenian Sea north of Sicily and are listed on the UNESCO World Heritage Site. On this 8-day tour, explore the beautiful towns of Lipari, Vulcano, Panarea, Stromboli, Filicudi, and Salina. Experience nature and culture, and see the …
Tour Details
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Cortina D Ampezzo, idyllic mountain peaks of Dolomites
$8,318
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, Hiking, Village Visits
Activity Level:
Moderate
Discover the enchanting surroundings of the western alpine region of Italy and hike the Dolomites mountain range on this 10-day guided tour. Take an easy hike to the Tre Cime and visit the Lagazuoi terrace to take incredible photos of the Dolomites. Visit Pesariis, known as the town of the clocks, …
Tour Details
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See the famed Rialto bridge in Venice
$2,496
EXPLORE

Venice Extension

4 Day Itinerary
  • Tour Venice's Grand Canal by boat
  • See monuments and famous churches
  • Visit Mazzorbo's vineyards
  • Create your own carnival mask
  • Explore famous squares and canals
Starts / Ends:
Venice / Splendid Venice - Starhotels Collezione
Activities:
Village Visits, Wine Tasting
Activity Level:
Relaxed
Discover the rich culture of Venice, its history, and UNESCO World Heritage Sites on this 4-day Venetian tour. Enjoy a boat tour on Venice's Grand Canal to explore the city's bustling waterfront and famous historical sites, including St. Mark's Square, Giudecca, San Giorgio Maggiore, …
Tour Details
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Alpe di Siusi
$3,375
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
Activities:
Hiking, Village Visits
Activity Level:
Moderate
Join this 8-day Classic Dolomites Premium Adventure Group Tour in Italy for an exceptional small group tour experience that takes you through the breathtaking landscapes of the Italian Dolomites, a UNESCO World Heritage Site. It's a special blend of adventure, culture, and relaxation, allowing …
Tour Details
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Visit charming Sicily
$2,700
EXPLORE

Treasures of Sicily

Italy Small Group Tour - 9 Day Itinerary
  • Visit the Island of Sicily
  • Discover the Valley of the Temples
  • Visit Taormina's ancient ruins
  • See the Mount Etna in Sicily
  • Explore the coastal town of Cefalu
  • Visit Syracuse's Archeological Park
  • Discover the Zingaro Nature Reserve
Starts / Ends:
Viagrande / Taormina
Activities:
Archaeological Site Visits, Hiking, Village Visits, Wine Tasting
Activity Level:
Relaxed
Explore the Treasures of Sicily on this 9-day small group tour from Viagrande to Taormina, a collection of extraordinary wonders found on the beautiful Italian island of Sicily. Sicily is home to well-preserved Greek temples showcasing the island's ancient past. The Valley of the Temples in …
Tour Details
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Explore Italy's colorful Amalfi coast
$2,248
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
Activities:
Archaeological Site Visits, Hiking, Village Visits, Wine Tasting
Activity Level:
Easy Active
On this 8-day small group tour, explore the breathtakingly beautiful region of Italy, the Amalfi Coast, located along the southern coast of the Sorrentine Peninsula. See the dramatic cliffs, picturesque villages, and crystal-clear waters. Visit the charming town of Positano, known for its colorful …
Tour Details
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Panoramic view of the historic town of Assisi
$4,500
EXPLORE

Rome, Assisi & Magical Umbria Premium Adventure

Italy Small Group Tour - 8 Day Itinerary
  • Visit Roman ruins with a guide
  • Visit the Umbrian countryside
  • Visit the historic town of Assisi
  • Visit local wineries in Montefalco
  • Enjoy cooking local Italian dishes.
Starts / Ends:
Rome / Rome
Activities:
Archaeological Site Visits, Cooking Classes, Hiking, Village Visits, Wine Tasting
Activity Level:
Easy Active
Embark on this premium small-group adventure through the heart of Italy and explore the timeless beauty of Rome, Assisi, and Umbria. This 8-day tour will take you through some of Italy's most beautiful and historic regions, where you'll experience unforgettable moments and create lasting …
Tour Details
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Cortina D Ampezzo, idyllic mountain peaks of Dolomites
$6,916
EXPLORE

Dolomites Explorer

Bolzano to Venice - 8 Day Itinerary
  • Enjoy the culture of Bolzano
  • Visit Bozen's main local attraction
  • Hike the Parco del Respiro
  • Visit the Abbey of Novacella
  • Cable car ride to Castelrotto
  • Visit a local dairy
  • Discover Cortina's mountain scenery
  • Hike the spectacular Tre Cime
  • Tour Venice's Grand Canal by boat
Starts / Ends:
Venice / Venice
Activities:
Hiking, Local Market Visits, Village Visits, Wine Tasting
Activity Level:
Moderate
Explore the western alpine region of Italy and see the Dolomites mountain range on this 8-day journey. Drive through stunning mountain scenery from Bolzano to Cortina d’Ampezzo, and experience true masterpieces of nature in the alpine region, award-winning views, serene lakes, and an …
Tour Details
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View of Varenna town at Lake Como, Italy
$6,121
EXPLORE

Lake Como, Milan, and Amalfi

10 Day Itinerary
  • Ride a boat on Lake Como
  • Explore the village of Varenna
  • Visit Piona Abbey in Colico
  • See the Gothic Art in Milan
  • Visit the Duomo di Milano
  • Stroll around in Galleria Vittorio
  • See archaeological sites in Pompeii
  • Admire the coastline of Amalfi
  • Enjoy scenic drives in Italy
Starts / Ends:
Milan / Naples
Activities:
Archaeological Site Visits, Small Ship Cruises, Village Visits, Wine Tasting
Activity Level:
Relaxed
Join this 10-day tour to explore Lake Como, Milan, and the famous and dramatic Amalfi Coast. Explore the treasures of Lake Como on a private Venetian-style boat for a picturesque ride across Lake Como. Visit the Cistercian Santa Maria di Piona Abbey, a masterpiece of Lombard architecture. After the …
Tour Details
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Explore ruins in Taormina within view of volcanic Mount Etna
$3,699
EBD
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
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
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Sunset over Palermo
$3,799
EBD
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
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Blue hour over the city in the shadow of Mount Etna
$3,699
EBD
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
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Walking the Tuscan countryside at sunset
$2,770
EXPLORE

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, Village Visits, Wine Tasting
Activity Level:
Easy Active
Experience Tuscany's best on this 8-day tour. Begin at the family-run Hotel Le Renaie, then explore the Via Francigena from Gambassi Terme to San Gimignano, followed by a sensory wine tasting at a Certaldo estate. Discover the Chianti region's vineyards with a scenic walk and optional …
Tour Details
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Colosseum in Rome, Italy
$1,918
EXPLORE

Rome Extension

4 Day Itinerary
  • Admire Michelangelo's masterpiece
  • Explore the Vatican Museums
  • Visit Roman ruins and monuments
  • See the Colosseum Belvedere
Starts / Ends:
47 Boutique Hotel - Rome / 47 Boutique Hotel - Rome
Activities:
Archaeological Site Visits, Urban Exploration
Activity Level:
Relaxed
Discover the heart of Italy and immerse yourself in the enchanting city of Rome during this 4-day tour. Experience the city's most iconic landmarks and UNESCO World Heritage sites. Witness the grandeur of ancient Rome and explore famous ruins like the Colosseum, Roman Forum, Foro di Cesare, and …
Tour Details
0
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