Italy Tours in May 2026
Planning for a trip to Italy during May? We offer 500 tour packages to Italy departing in May 2026 that have 7,000 customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Italy on your May holiday.
Best Price Guarantee
Best Price Guarantee
We guarantee the best prices on all our tours. If you find a lower price within 24 hours of booking, we'll match it.
Note: Prices may vary based on availability and demand.
Select from 505+ tours
10 Best Italy January Deals
January exclusive deals on Italy May 2026 tours — limited-time massive savings on premium travel packages!
Curated by Alessandra Galassi
Italy travel expert at Bookmundi
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
Southern Italy and Sicily beckon with their distinctive charm and remarkable heritage on the Highlights of Southern Italy & Sicily tour. Beginning and ending in Rome, this 10-day trip is tailored for those who relish cultural exploration and moderate activity. Guided visits reveal the grandeur of ancient Rome and the volcanic wonders of Mount Vesuvius, while free days along the Amalfi Coast and in Taormina and Palermo invite leisurely discovery at your own rhythm. Highlights include the haunting ruins of Pompeii, the storybook trulli of Alberobello, and the ancient cave dwellings in Matera—a true feast for the curious traveler. This tour package brings together a tapestry of UNESCO sites, dazzling coastlines, and local flavors, creating an unparalleled journey through Italy’s southern heartlands. Designed with experienced travelers and seniors in mind, it balances structure and flexibility, allowing you to savor regional cuisine, connect with fellow travelers, and immerse yourself in the rich tapestry of southern Italian traditions. The unique selling point here is the chance to experience both famed destinations and lesser-known gems in one seamless, enriching itinerary.
10 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
Dive headfirst into Europe’s greatest hits with the European Escapade—a 24-day whirlwind tour that starts and ends in London. From Amsterdam’s canals to the romance of Paris, the energy of Berlin, and the sun-soaked streets of Barcelona, this trip packs in legendary cities, Swiss Alps adventures, and exclusive Special Stays at Hopfgarten and Contiki’s Château de Cruix.
Tailored for young adults, this group tour delivers big on iconic sights, lively social scenes, and memorable moments. Upgrade to the ‘Plus’ for twin-share hotel comfort instead of the classic multi-share.
USP: An expertly curated city sightseeing tour package designed for those who want maximum Europe in minimum time—plus the perks of exclusive accommodations and unforgettable group experiences.
24 days
Experience authentic Italian living on the "Local Living Italy—Sorrento" trip, a seven-day trekking and hiking adventure based in the enchanting town of Sorrento. Perfect for travelers who yearn to go beyond surface sightseeing, this guided tour immerses you in the rhythms of daily life along the Amalfi Coast.
Your journey begins and ends in Naples, with highlights including coastal walks, an excursion to the fashionable island of Capri, and a guided visit to the archaeological marvel of Pompeii. The experience is elevated by your stay on an organic lemon farm, where a local family hosts you and introduces you to the secrets of limoncello making and the joys of Italian agriturismo.
With all accommodations, transport, and meals taken care of, you’re free to soak up the region’s stunning landscapes and savor its renowned cuisine. The unique selling point of this tour package lies in its deep cultural immersion—offering you the chance to live, eat, and explore like a true local. If you’re searching for a trip that blends trekking, culinary delights, and authentic hospitality, this Sorrento adventure is the perfect way to live your Italian dream.
7 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
Craving a taste of Italy’s most iconic UNESCO sites in just five days? The "Italy City Break" is your passport to a whirlwind of art, history, and vibrant culture. Starting from Rome, you’ll journey to the medieval town of Assisi—birthplace of St Francis—before heading to Florence, the city where the Renaissance began.
Wander through Florence’s architectural marvels, then continue north to explore the artistic treasures of Bologna, Padua, and the canals of Venice. The adventure doesn’t stop there; Tuscany’s world-renowned vineyards invite you for a final taste of la dolce vita before a return to Rome.
Tailored for young adults and seasoned travelers who appreciate efficient yet immersive sightseeing, this trip ensures you soak up Italy’s best in record time. The guided tour package includes essential highlights, expert insights, and a seamless travel experience.
USP: A curated route through Italy’s cultural heartlands, blending world heritage sites, culinary delights, and breathtaking scenery—making it a perfect short escape for those who want to experience Italy’s essence without compromise.
5 days
See all Italy May 2026 January Deals
Most popular Italy May 2026 Tours
Join one of these handpicked Italy May 2026 tour packages, tailored to the season.
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.
May Departures
2 May, 9 May
Tour Type
Group Tour
8 days
Rome, Venice, and Florence headline the 'Classical Italy' trip—a 5-day sightseeing tour ideally suited for seniors seeking a taste of Italy’s best cities. With all logistics, hotels, and meals included, this group trip allows you to relax and enjoy the highlights stress-free. The real draw is the concise itinerary—offering maximum cultural impact in a short, easy-paced journey designed to delight mature travelers.
May Departures
3 May, 10 May
Tour Type
Group Tour
5 days
Let the Amalfi Coast cast its spell on you during this 8-day food-focused tour, designed especially for seniors seeking both relaxation and cultural immersion. Departing from Naples and ending in Bomerano, this trip weaves through the glamorous island of Capri, the romantic streets of Ravello, and the legendary ruins of Pompeii and Herculaneum.
Based in the peaceful village of Agerola at a family-run hotel, you’ll enjoy a slower pace, savoring fresh Italian cuisine and admiring stunning coastal panoramas from iconic trails like the Path of the Gods. Explore chic Capri by boat, meander through fragrant lemon groves, and delve into the region’s storied past with guided visits to ancient archaeological wonders.
What distinguishes this tour package is its thoughtful blend of culinary delights, scenic walks, and cultural exploration—all tailored to provide comfort and meaningful connection. For those wishing to live la dolce vita while discovering one of Europe’s most dramatic shorelines, the Amalfi Coast awaits.
May Departures
2 May, 9 May
Tour Type
Group Tour
8 days
Few know that northern Tuscany’s Garfagnana is a hidden gem for hikers, boasting dramatic mountain trails and wild national parks. The "Walking in Tuscany" tour invites experienced travelers to discover this lesser-known side of Italy over 8 days of moderate trekking. Set out from Lucca and journey through scenic Braccicorti, Casone, and beyond, returning each night to a welcoming stone farmhouse at the foot of the Apennines. Traditional hospitality and authentic cuisine await after days filled with panoramic hikes. A free day enables exploration of Lucca, Florence, Pisa, or even the Cinque Terre. For those seeking extra challenge, select departures offer tougher treks and a night in a mountain refuge. All accommodations, meals, and transport are included, ensuring a relaxed yet enriching experience. The USP: an intimate trekking escape in Tuscany’s rugged north, where genuine Italian culture and unspoiled nature go hand in hand.
May Departures
2 May, 9 May
Tour Type
Group Tour
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.
May Departures
3 May
Tour Type
Group Tour
10 days
Revel in Italy’s timeless allure on the 'Italian Vistas' trip, a 13-day guided sightseeing adventure that sweeps from Rome to Lake Maggiore. Designed for experienced and senior travelers, this itinerary pairs cultural treasures with the romance of Italy’s most breathtaking landscapes.
Stroll through ancient Pompeii, wander Rome’s Colosseum, cruise to the magical Isle of Capri, and stand in awe before Michelangelo’s David in Florence. Sip Tuscan wines at a local farm, then glide along Venetian canals and meander through Stresa’s scenic streets on Lake Maggiore. Multiple-night stays in key destinations ensure you soak up each locale’s special magic, without ever feeling rushed.
The USP? Extended stays in Italy’s most charming cities and lakeside resorts, allowing for a deeper, more immersive exploration of art, history, and culinary delights—perfect for those who appreciate leisure and luxury in equal measure.
May Departures
16 May, 8 Jun
Tour Type
Group Tour
13 days
The rolling hills and timeless charm of Tuscany await on the "Spotlight on Tuscany" tour, a 9-day art and architecture adventure through Italy’s most cherished region. Starting and ending in Montecatini Terme, this moderate-activity trip is crafted for those who revel in culture, history, and authentic flavors.
Enjoy a 7-night stay in the renowned spa town of Montecatini Terme, your base for exploring Pisa, Florence, San Gimignano, and Lucca—Italy’s best-kept secret. Learn the region’s history at WWII’s Gothic Line and the Museum of Liberation. Delight in hands-on experiences, from a Tuscan cooking class to cheese tastings at a local farm. Savor world-class wines and the region’s celebrated cuisine, and enjoy free time to wander Florence’s artistic treasures.
With accommodations, transport, and meals included, the unique selling point is the blend of immersive culinary and cultural activities, ensuring each traveler connects deeply with the heart of Tuscany in a single, thoughtfully curated tour package.
May Departures
6 May, 13 May
Tour Type
Group Tour
9 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.
May Departures
7 May
Tour Type
Group Tour
17 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.
May Departures
15 May, 4 Jun
Tour Type
Group Tour
13 days
Let the Prosecco Hills of Italy surprise you with their tranquility and beauty, all while you enjoy a curated trekking tour that places you at the heart of this world-renowned wine region. The "Walk The Prosecco Hills & Hidden Venice" trip, crafted for experienced travelers seeking both culture and adventure, offers eight days of guided hiking through vineyard-clad slopes sheltered by the Dolomites. Despite the fame of Prosecco, these hills remain uncrowded and authentic, making each day’s walk a discovery of hidden gems. Stay at a luxurious four-star hotel along the historic Prosecco Road—the oldest wine route in Italy—and savor tastings of regional cuisine paired with the area’s celebrated sparkling wine.
As you traverse the landscapes from Pieve Di Cadore to Treviso, Pieve Di Soligo, and beyond, each step immerses you deeper into the Italian countryside’s rhythms. The journey’s highlight is an alternative day trip to Venice, where you’ll explore less-visited neighborhoods and step inside a master artisan’s workshop, gaining rare insight into traditional Venetian life. Throughout, the emphasis on local interaction and cultural immersion sets this tour apart, allowing you to experience Italy beyond the usual tourist routes.
With accommodation, transport, and meals seamlessly arranged, this trekking tour balances moderate physical activity with plenty of indulgence and relaxation. The unique selling point lies in its blend of off-the-beaten-path hiking and exclusive cultural experiences, including a Venice visit far from the crowds. If you value authentic discovery and fine wine, this tour package is your gateway to some of Italy’s best-kept secrets.
May Departures
16 May, 13 Jun
Tour Type
Group Tour
8 days
See all Italy May 2026 Tours
Top Italy Tour Activities for May 2026
From art architecture tours to cultural, religious historic sites and others, here are some popular tour activities in Italy with departures in May 2026.
Italy May 2026 Tours for all Age Groups
Italy tours in May 2026 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.
James M. | Traveled in May
Packs a lot into the 10 days. A wonderful introduction to Italy for anyone (such as myself) who had not previously visited. The local guides were all very engaging and knowledgeable, and a big plus. As others have noted, "Easy Pace" is perhaps a slight misnomer -- there was quite a bit of walking! But nothing that we couldn't handle and we very much appreciated all the opportunities to experience Italy "on the ground." We hope to travel with Insights again!
Anonymous | Traveled in May
Most was excellent except for the second accommodation hotel Poiano it was too far from the lake Garda and there was sewerage smell within the room,it was quite clean but it was not really a hotel it was like a holiday camp. Our director was great and very informative with a sense of humour, our last supper was very special I say this as I went and did another trip in Paris with Trafalgar and it was not, so have something to compare it to but all in all I enjoyed it another thing is it was not overcrowded on the bus whereas in Paris there were too many people in the group.Allin all I enjoyed it. Regards Jill Pastine
Anonymous | Traveled in May
Absolutely wonderful tour and great itinerary! Highly recommend for a tour of Northern Italy. Travel time was planned smartly and efficiently to ensure the time was spent well. It's easy to add another extension before or after the group tour as well with Milan as a central location.
Ian Ei | Traveled in May
the itinerary was wonderful and saw all the major sites as well as many unexpected and equally interesting places. in a large part the success of the tour was the great leadership from Danielle Lampoon and our driver.
Onnalee O. | Traveled in May
The trip was amazing- relaxing while still seeing plenty! It was a good balance of culture/cute towns & wine tasting. Also, don't skip out on the leather belt making in Florence, Ihad a blast doing that! Our trip manager was absolutely amazing & we also had the best dressed coach driver in all of Italy . It was also nice to stay in one hotel for the majority of the trip. It made it so that we could really 'unpack' & really soak in the Tuscan lifestyle.
Theo Lucas | Traveled in May
Sicily is one of these hidden gems from Europe that you don’t hear much about… so it’s great that this tour allows people to explore it!! I heard about Sicily a while back and have wanted to visit it ever since, and I’m glad I went with Charlie’s company to do so. The itinerary was super fun and varied, the guides were great, the accommodations were lovely. Charlie really knows what he does. I recommend this tour to anyone who wants to explore cute European towns.
Traveler Photos For Trips in Italy
Get a customized trip to Italy in May 2026
Plan a multi-country or regional adventure across Italy in May 2026, with help from a local expert.
Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy
Recommended by
Keep Exploring Italy
Tour Types
- Italy Tours
- Italy Eco Tours
- Italy Travel Deals
- Italy Group Tours
- Italy Guided and Escorted Tours
- Italy Tours for Senior Citizens
- Italy Solo Trips
- Italy Experienced Travelers Trips
- Italy Budget Tours
- Italy Tailor-made Vacation Packages
- Italy Customized Tours and Trips
- Italy Small Group Tours
- Italy Private Tours
- Italy Self Guided Tours
- Italy Tours for Young Adults
- Italy Family Tour Packages
- Italy Tour Operators
Popular Destinations
Popular Activities
- Cultural, religious and historic sites Tours
- Art and architecture Tours
- City sightseeing Tours
- Explorer Tours
- Walking Tours
- Trekking and Hiking Tours
- Sightseeing Tours
- Food Tours
- Natural landmarks sightseeing Tours
- Museum and gallery visits Tours
- Bicycle Tours
- Countryside and village visits Tours
- Wine tasting Tours
- Local culture Tours
- Cruise Tours
- Adventure Tours
Upcoming Departures
Trips per Durations
Trending Travel Guides
- Hiking in Italy: The 7 Best Trails
- 7 Best Wineries in Tuscany
- Rome in Winter: An Essential Guide
- Italy in Winter: Top 8 Destinations
- A Complete Guide to Colosseum: A Must Visit
- Top 3 Amalfi Coast Itineraries: Plan a Perfect Trip
- Top Italian Lakes To Visit In Italy: A guide to Italian lakes
- Things to Do in Italy
- Hiking in the Dolomites: Everything You Need to Know
- 10 Best Places to Visit in Italy
- Planning a Trip to Italy: Travel Tips and Advice
- Great Italy Itineraries: How Many Days to Spend?
- Italy in One Week: 4 Recommended 7-day Itineraries to Italy
- Off the Beaten Path in Italy: Top 10 Hidden Gems in Italy
- Italy in 10 Days: 4 Recommended 10-day Itineraries to Italy
- Italy in 2 Weeks: 3 Recommended 14-day Itineraries to Italy
- Italy in October: Weather, Festivals and More!
- Italy in September: Weather, Wine Expos and More!
- Italy in July: Weather, Beaches and More!
- Summer in Italy: Weather, Top Destinations and More!
- Venice to Murano: How to Travel
- Milan to Lake Como: How to Travel
- Rome to Naples: How to Travel
- Venice to Naples: How to Travel