Italy Tours in May 2027
Planning for a trip to Italy during May? We offer 240 tour packages to Italy departing in May 2027 that have 6,300 customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Italy on your May holiday.
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Most popular Italy May 2027 Tours
Join one of these handpicked Italy May 2027 tour packages, tailored to the season.
Curated by Alessandra Galassi
Italy travel expert at Bookmundi
Northern Italy’s finest treasures await on the 'Italy’s Treasures: Art, Food & Wine of Italy' trip, a 12-day guided tour from Lake Maggiore to Venice. Experience a harmonious blend of natural beauty, culinary delights, and artistic heritage as you journey through Stresa, Cinque Terre, Tuscany, Florence, and Venice.
Relax by the tranquil Alpine Lakes, explore Cinque Terre’s medieval villages, and ride off-road vehicles through the marble quarries of Carrara. Enjoy a leisurely four-night stay at a Tuscan villa, where you’ll learn the secrets of Tuscan cuisine in a hands-on cooking class. Discover Florence’s Renaissance wonders and the enchanting canals of Venice.
The USP? The immersive culinary and cultural experiences—like cooking in a family-owned villa—set against the backdrop of Italy’s iconic art and landscapes, creating a tour that’s both indulgent and inspiring.
Tour Type
Group Tour
12 days
The Amalfi Coast’s dramatic cliffs and pastel villages are yours to discover on the “Walking the Amalfi Coast” tour, an eight-day trekking adventure starting and ending in Bomerano. Designed for experienced travelers, this moderate-level trip features expertly guided walks through storied towns like Positano, Ravello, and Amalfi itself.
Follow ancient paths across hillsides, explore the haunting remains of Pompeii, and ascend Mount Vesuvius for sweeping views over the Bay of Naples. The highlight is the legendary Path of the Gods, hailed as one of the world’s greatest coastal walks. Enjoy the warm hospitality of a family-run hotel in the quiet village of Bomerano, away from crowded tourist spots.
All accommodations, meals, and transport are included, ensuring a relaxed and immersive experience. The main activity is trekking, supported by decades of local expertise. A special feature of the tour is the combination of iconic walks and authentic Italian hospitality, making it a standout for lovers of both nature and culture.
For a trip that blends Italy’s best scenery, history, and cuisine, this Amalfi Coast adventure is hard to beat.
Tour Type
Group Tour
8 days
Experience the full spectrum of Italian wonders on the 'Wonders of Italy' tour, an 11-day guided city sightseeing adventure starting and ending in Rome. Journey through Lucca, Florence, and Venice, cruise along Cinque Terre’s coastline, and savor a glass of Tuscan Chianti. Perfect for travelers who seek rich experiences at an easy pace, this tour package covers hotels, meals, and all transport. The unique selling point is the hands-on discovery of local crafts, including Venetian glassblowing, which adds depth to the exploration. For anyone longing for an immersive Italian journey, this trip brings the country’s artistry and flavors to life.
Tour Type
Group Tour
11 days
From the sun-drenched hills of Tuscany to the glamour of Capri, 'Italy Bellissimo' is an 11-day city sightseeing tour that captures the spirit of Italy. Starting and ending in Rome, this easy-paced trip takes you through Venice, Montecatini, and more, with highlights including olive oil tasting in an authentic Italian Borgo and evenings spent with new friends. Tailored for those who love culture and conviviality, the tour package covers accommodation, meals, and all transport. Its unique selling point is the seamless blend of classic Italian sights and genuine local experiences, making it an irresistible choice for anyone enchanted by Italy’s charm.
Tour Type
Group Tour
11 days
Embark on a captivating journey that takes you from the piazzas of Rome to the canals of Venice. Discover the rolling hills of the scenic Tuscan and Umbrian countryside. Explore medieval hill towns and visit Assisi, the birthplace of St. Francis. Spend time at a historic winery in the heart of the Chianti region and enjoy a chef-led cooking class with lunch. Discover the masterpieces of the Renaissance in Florence. See glass transformed into exquisite art on Murano Island. Linger in iconic Venice for two nights. Journey to the shores of glamorous Lake Como. Encounter a land rich in history, culture, art, and romance.
Tour Type
Group Tour
10 days
Savor the essence of Italy and Sicily on this 15-day tour package, beginning in Palermo and concluding in Venice. Crafted for seasoned explorers, this itinerary blends effortless sightseeing with immersive cultural experiences. Traverse legendary cities including Agrigento, Pisa, and the romantic canals of Venice. Let your senses come alive as you indulge in fresh Sicilian seafood, wander through Palermo’s lively streets, and stand in awe beneath the Leaning Tower in Pisa’s iconic Square of Miracles. Trace the dramatic silhouette of Mount Etna, soaking in both its natural grandeur and the surrounding local heritage. Each stop offers a tapestry of ancient history and mouthwatering cuisine, promising a journey that’s as colorful as it is comfortable. With accommodation, transport, and meals thoughtfully included, this group tour ensures freedom from everyday worries and more time to relish Italy’s legendary highlights. The unique selling point? An expertly curated blend of historic marvels and authentic regional flavors, making this trip an effortless deep dive into Italy and Sicily’s most celebrated treasures—perfect for those seeking insight and comfort in equal measure.
Tour Type
Group Tour
15 days
Explore the crossroads of civilizations on "Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast," a 13-day city sightseeing adventure rich in culture and history. Beginning in Palermo and ending in Rome, this moderately active tour immerses you in Sicily’s ancient wonders and southern Italy’s coastal beauty.
Uncover Palermo’s Moorish and Norman heritage, wander through Cefalù’s seaside splendor, and marvel at the Valley of the Temples in Agrigento. In Taormina, visit a local winery for a tasting and agriturismo dinner—an authentic taste of Sicilian life. Journey to the ancient cave dwellings of Matera before exploring Sorrento and Positano, the pearls of the Amalfi Coast. Walk in the footsteps of Romans at Pompeii’s evocative ruins.
With all accommodations, transport, and meals included, this group tour’s unique selling point is its artful blend of ancient monuments, spectacular coastlines, and local culinary experiences—making it the perfect package for those eager to soak up the essence of southern Italy and Sicily.
Tour Type
Group Tour
14 days
Immerse yourself in the timeless allure of Italy with the "Best of Italy" tour, a 13-day journey beginning and ending in Rome. Designed for those eager to experience Italy’s cultural and culinary riches, this group sightseeing trip covers everything from ancient Roman wonders to the Renaissance beauty of Florence. Stroll the historic streets of Assisi, bask in the luxury of Capri’s island life, and enjoy a private guided exploration of Pompeii—a city forever frozen in volcanic time. With accommodation, transport, and meals handled for you, this tour package allows for effortless discovery and indulgence. Its standout feature? Exclusive guided access to world-famous sites and hidden gems, ensuring a truly comprehensive Italian adventure for discerning travelers.
Tour Type
Group Tour
13 days
Northern Italy Including Cinque Terre is a culinary and scenic feast for travelers who appreciate la dolce vita. Over 8 days, begin and end in Milan, journeying through Baveno, Lake Maggiore, and the Italian Riviera. Savor prosciutto and parmigiano in gourmet encounters, and enjoy the high life amid dazzling lake and seaside views. This guided city sightseeing tour includes hotels, transport, meals, and immersive local experiences—perfect for those seeking a blend of relaxation and indulgence. The unique selling point? Its focus on gourmet flavors and breathtaking settings, delivering the essence of Northern Italy in every sense.
Tour Type
Group Tour
8 days
Italy’s timeless beauty unfolds on the "Journeys: Iconic Italy" tour, a sweeping 14-day trip that weaves together the country’s most celebrated cultural, religious, and historic sites. From the canals of Venice to the ancient streets of Rome, you’ll traverse legendary destinations including Florence, Cinque Terre, and the sun-drenched Amalfi Coast.
This small group tour is designed for travelers seeking a deep connection with Italy’s illustrious past and vibrant present. Stand in awe of Renaissance masterpieces in Florence and Venice, explore the haunting ruins of Pompeii side by side with an archaeologist, and pause to enjoy the aromatic lemon groves while winding through coastal villages.
The tour includes comfortable accommodations, seamless transport, and select meals, allowing you to savor every moment without logistical worries. Along the way, discover the art of la dolce vita—from leisurely café breaks to immersive local experiences. The highlight of this package is the unique blend of expert-guided explorations and authentic encounters, ensuring you not only see Italy’s icons but truly experience them. For those dreaming of an Italian journey rich in history, culture, and culinary delights, this tour offers an unforgettable escape through the heart of Italy.
Tour Type
Group Tour
14 days
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Set out on a 22-day grand tour across Europe, discovering the continent’s most celebrated cities and hidden treasures. The Best of Europe tour, beginning and ending in London, is perfectly crafted for experienced travelers and seniors seeking a moderate adventure through Paris, Rome, Amsterdam, Venice, and many more. Explore castles, sip local beers, and take in the beauty of Budapest, Vienna, Prague, and Zagreb on expertly guided excursions. With built-in free days, you’ll have the flexibility to follow your own interests or simply soak up the atmosphere. The standout feature of this tour package is its comprehensive coverage of both Western and Eastern Europe, ensuring an unparalleled variety of landscapes, cultures, and experiences in a single, unforgettable journey.
22 days
Italy’s timeless beauty unfolds on the 'Grand Italian Experience'—a 17-day guided city sightseeing adventure starting and ending in Rome. The itinerary travels through Florence, Viareggio, Assisi, and more, offering a rare glimpse of Alberobello’s limestone trulli houses and the romance of Capri. Designed for experienced travelers who savor authentic moments, this tour package includes dinner with locals, explorations of star-crossed Verona, and the tranquil Italian Lake District. With easy pacing, included meals, and comfortable accommodations, the journey’s unique selling point lies in its blend of rare sites and genuine local encounters. If you’ve ever dreamed of living la dolce vita, this trip brings Italy’s magic to life.
17 days
Experience the full spectrum of Italian wonders on the 'Wonders of Italy' tour, an 11-day guided city sightseeing adventure starting and ending in Rome. Journey through Lucca, Florence, and Venice, cruise along Cinque Terre’s coastline, and savor a glass of Tuscan Chianti. Perfect for travelers who seek rich experiences at an easy pace, this tour package covers hotels, meals, and all transport. The unique selling point is the hands-on discovery of local crafts, including Venetian glassblowing, which adds depth to the exploration. For anyone longing for an immersive Italian journey, this trip brings the country’s artistry and flavors to life.
11 days
Craving the flavors and artistry of Italy but short on time? The Taste of Italy tour condenses the country’s finest experiences into an unforgettable 7-day trip. Specially crafted for travelers who appreciate both cultural depth and culinary indulgence, this moderately-paced journey takes you from the ancient streets of Rome to the Renaissance masterpieces of Florence and the romantic allure of Venice. Guided walking tours in Rome and Florence reveal the stories behind iconic landmarks, while a free day in Venice lets you explore at your own pace—perhaps gliding down its legendary canals. The itinerary doesn’t stop there: marvel at the medieval towers of San Gimignano, the rolling vineyards of Siena, and the colorful cliffside villages of Cinque Terre. Savor every moment as you sample top Italian wines and regional specialties, embracing the bella vita lifestyle throughout. Ideal for experienced travelers and seniors seeking a lively yet comfortable adventure, this tour package stands out for its unique combination of sightseeing and gourmet experiences. With thoughtfully selected hotels, convenient transport, and knowledgeable guides, Taste of Italy offers a rich immersion without the rush, ensuring every day brings a new delight for the senses.
7 days
All aboard this exhilarating journey by high-speed train through Italy’s iconic cities of Rome, Florence and Venice. During your 10 days in Italy, conjure up gladiators and chariots in Rome, shop until you drop on Florence’s ancient Ponte Vecchio, strike a pose in Pisa and discover the secrets of Venice on foot like a local.
10 days
Picture yourself wandering through the cobbled streets of Rome, savoring authentic gelato in Florence, and gazing at the sun setting over the Amalfi Coast—this is the essence of the Italy Explorer tour. Spanning 16 days, this comprehensive trip immerses discerning travelers in the heart of Italy’s most iconic destinations. From the ancient ruins of Pompeii to the vibrant canals of Venice, each stop reveals a new facet of Italian culture and history. The itinerary covers must-see highlights such as the Leaning Tower of Pisa, the picturesque villages of Cinque Terre, and the unique trulli houses of Alberobello, culminating with the captivating island of Sicily. Thoughtfully designed for experienced globetrotters and seniors seeking a moderate physical activity level, the tour balances guided city sightseeing with plenty of opportunities to savor world-class cuisine and local wines. Along the way, travelers will enjoy comfortable accommodations, reliable transport, and expert guidance, ensuring a seamless and enriching experience. What sets this tour package apart is its perfect blend of Italy’s timeless art, stunning scenery, and culinary delights, providing a deep dive into both famous sites and charming hidden corners. Whether you’re an art lover, a history enthusiast, or simply passionate about la dolce vita, the Italy Explorer promises a journey filled with unforgettable moments and genuine Italian hospitality.
16 days
The Amalfi Coast’s dramatic cliffs and pastel villages are yours to discover on the “Walking the Amalfi Coast” tour, an eight-day trekking adventure starting and ending in Bomerano. Designed for experienced travelers, this moderate-level trip features expertly guided walks through storied towns like Positano, Ravello, and Amalfi itself.
Follow ancient paths across hillsides, explore the haunting remains of Pompeii, and ascend Mount Vesuvius for sweeping views over the Bay of Naples. The highlight is the legendary Path of the Gods, hailed as one of the world’s greatest coastal walks. Enjoy the warm hospitality of a family-run hotel in the quiet village of Bomerano, away from crowded tourist spots.
All accommodations, meals, and transport are included, ensuring a relaxed and immersive experience. The main activity is trekking, supported by decades of local expertise. A special feature of the tour is the combination of iconic walks and authentic Italian hospitality, making it a standout for lovers of both nature and culture.
For a trip that blends Italy’s best scenery, history, and cuisine, this Amalfi Coast adventure is hard to beat.
8 days
From the sun-drenched hills of Tuscany to the glamour of Capri, 'Italy Bellissimo' is an 11-day city sightseeing tour that captures the spirit of Italy. Starting and ending in Rome, this easy-paced trip takes you through Venice, Montecatini, and more, with highlights including olive oil tasting in an authentic Italian Borgo and evenings spent with new friends. Tailored for those who love culture and conviviality, the tour package covers accommodation, meals, and all transport. Its unique selling point is the seamless blend of classic Italian sights and genuine local experiences, making it an irresistible choice for anyone enchanted by Italy’s charm.
11 days
Rome, Florence, Venice—names that conjure centuries of art, culture, and history. The Jewels of Italy tour is a 7-day guided adventure that encapsulates the essence of Italy’s most enchanting cities, designed with both seniors and experienced travelers in mind. Explore the Leaning Tower of Pisa, marvel at Florence’s Duomo, and glide through Venice’s Grand Canal. With comfortable accommodation, included meals, and expert guides, this easy-paced trip ensures you enjoy every landmark without the rush. The USP: a thoughtfully curated tour package that delivers Italy’s timeless magic in just one unforgettable week, perfect for families and culture lovers alike.
7 days
Discover Sicily, the scenic Italian island forged over centuries by Phoenician, Greek, Roman, Arab, Norman and Spanish rulers. On this comprehensive adventure, we explore the very best bits, starting on the volcanic slopes of Mount Etna, before continuing to the towns of Syracuse, Agrigento, and Selinunte – all World Heritage sites. A hike in Zingaro National Reserve offers magnificent views over the coast, while there’s also plenty of opportunities to discover the history and heritage of the biggest island in the Mediterranean.
9 days
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Top Italy Tour Activities for May 2027
From cultural, religious historic sites tours to city sightseeing and others, here are some popular tour activities in Italy with departures in May 2027.
Italy May 2027 Tours for all Age Groups
Italy tours in May 2027 designed for all ages—families, young adventurers, seniors, and everyone in between.
Reviews of our Italy Tours for May
Feedback from guests who toured Italy during May.
Deborah T. | Traveled in May
You get an excellent overview of all the varied regions, history and culinary traditions of the people of Italy. The scenery is outstanding and my dream of seeing Pompeii was the capstone. I majored in archaeology in college so seeing all of the sites we studied was a wish come true. And visiting the Vatican museums, upon coming out int St Peter’s Square, we happened upon the weekly Papal Audience which was a fun bonus as Pope Leo is from just down the road from my home!
Amy L. | Traveled in May
It was a fabulous tour and I had such a wonderful time, I loved the format of staying in one town (Montecatini-Terme was so perfect), unpacking once and exploring each day. San Gimignano and Lucca were both amazing and I love the wine tasting, cheese farm and cooking class/dinner. It really was all just amazing and Savio was an absolute GEM!
Anonymous | Traveled in May
Awesome scenery, a very responsible driver who followed Insights driving policies and procedures, the guide went above and beyond if there was an issue which showed how awesome insight are.
Anonymous | Traveled in May
It was a whirlwind itinerary but it provided all the highlights I wanted to see in each country. I checked other travel companies but they did not have all the spots I wanted to see
Ruth Cr | Traveled in May
The tour was well organized and the leader very helpful and knowledgeable.The bus driver was excellent and we felt safe and cared for.The places visited were of interest and the hotels comfortable and clean.
Carolyn | Traveled in May
This was an amazing trip! From meeting the group at the airport to the drop off a week later everything went really smoothly. Gennaro was our guide for the week. He was fantastic! His love for the Amalfi coast was evident everyday. He did a fabulous job of giving us a sense of what life is really like there. He was so eager to share all of his knowledge. It made the trip even better. He was patient and kind and kept us moving and on time with any bus or ferry trips we had each day. It felt like he knew all of us right away. We had a very cohesive group. I feel like I made friends for a lifetime. Staying at the farm in San Lazarro was even better than I expected. The family were such gracious hosts. The food was fabulous. Pasta and cheese making was so much fun. The accommodations were spotless. The hiking was definitely rigorous but we kept each other going. Gennaro was a great motivator and very encouraging to everyone. The views were well worth the hikes! I loved that we had time to swim a few times if we chose. The Mediterranean was gorgeous. I would highly recommend this trip and especially Gennaro!
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Plan a multi-country or regional adventure across Italy in May 2027, with help from a local expert.
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Popular May 2027 Destinations in Italy
- Rome May 2027 Tours
- Venice May 2027 Tours
- Florence May 2027 Tours
- Milan May 2027 Tours
- Naples May 2027 Tours
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