Traveling to Italy in May 2026? We offer 500+ tours, trips and vacation packages to Italy in May 2026. Our Italy in May 2026 tour packages and trips have 7160+ customer reviews. All the Italy May 2026 tour packages and trips are carried out by hand-picked, qualified local and international Italy tour operators.
Simple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Comfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
Upscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.
Guide Types
Start & End Location
Showing 1 - 10 of 63 results
Price
USD 32USD 12,115
Combine Italy in May with Nearby Countries for an Unforgettable Trip
See tours with itineraries going through multiple countries, including Italy
This tour is the BEST way to see all the infamous spots in Italy, plus local hidden gems, at a reasonable cost and if you are short on time (we had a school break time limitation). It covered everything! We budgeted for the add-ons, especially those with meals, but you could choose to have more free time if you wanted. The food was extraordinary, the bus was roomy and immaculately clean, our driver Antonello was superb, and our Travel Director Anneleis was amazing! She was so talented at integrating the tour highlights, guests, keeping it fun even in the rainy weather, knowledgeable, and able to troubleshoot anything to ensure we had the best experience of a lifetime!! I would love to go back and explore Southern Italy next. The hotels were elegant (only one was just "OK" only because it was in need of some renovations) and the service with our luggage, tipping, etc. was seamless. I highly recommend the Italian Intermezzo tour and Insight Vacations. Favoloso!
Christina organized a fantastic first class itinerary for a 28 day tour of Italy by my wife and me. She was very personable and generous with her time and very knowledgeable of the areas we visited. The trip included incredible private tours with top notch guides and smooth transfers all the way. Any minor glitches were handled promptly and professionally. It was a wonderful experience and we look forward to working with her again in the future.
This tour covered all the best spots in Italy, from Rome to Venice. The guide was super helpful, and everything was well planned. I loved every moment!
We had a wonderful time on this cycling trip in Sardinia!
It was a great route with lots to places to stop along the way. So much good food, and all the accommodation was wonderful. Some of the roads were a bit busy for my liking, not sure if I would be comfortable taking children on those roads but for adults it was fine. A very enjoyable week- a highlight of our month in Italy!
Bicycle tours
Tour Type
Private Tour
Accommodation
Hotel
Age Range
18-99 yrs
Operated in
english
Destinations
Sardinia, Pula, Sant'Antioco, Sa
Sardinia, Pula, Sant'Antioco, Sant Anna Arresi, Chia
Our family of 5 adults recently went to Italy on a 9 day trip to Venice, Rome and Sorrento(Amalfi Coast) with private tours, fast train travel, door to door drivers, and great accommodations; which was all set up by Michael.
Michael was very responsive to my communications, very helpful with trip suggestions to make the trip better, and just overall a great travel planner! I was nervous at first, because I have never completely booked a vacation online without ever meeting the travel planner, but it all worked out great!
We were completely happy with everything about our trip, and will definitely reach out to Michael again when we travel to Italy! There were a couple of small issues that arose over the duration of the trip, but they were handled quickly and without further problem to us. So all was good.
Our private tour guides in Rome, Ornella; and Roberta in Pompeii were incredible. Our Venice tour guide, Cynthia, was awesome too, she did a great job! We did a full day 8 hr tour in Rome of the Colosseum and Vatican, and I would recommend splitting that to two half days if you have the time. It was awesome, but a bit much for one day!! Also, we had a full day Amalfi Coast tour by van, with great driver Antonio, which was supposed to go to Positano, Amalfi, & Ravello, but because the traffic is so bad on the roads, there wasn't time to make it to Ravello. So, I recommend either going by boat, which we hear is faster, or allow more time if you want to see all three villages.
Again, a great trip for the memory books! Thank you MIchael and all of the local operators who worked to make our trip such a success!!
Received excellent service and suggestions for a tour we planned for our son and daughter when they toured the Amalfi Coast in August. Hotels were all in great locations close to the action and all excellent 4 or 5 star. Would definitely use or recommend the tour operator to friends or family.
Countryside and village visits
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
Families keen to explore Tuscan treasures will love the Tuscany Cycle for Families trip, an eight-day self-guided cycling holiday from Pisa to Florence. Designed for all ages, the easy route follows the Arno River past Pisa’s Leaning Tower, Lucca’s Renaissance architecture, Vinci’s birthplace, and Florence’s iconic Duomo. Along the way, enjoy local specialties, visit fascinating museums, and relax in family-run hotels—often with pools and gardens for post-ride relaxation. The standout feature of this tour package is its thoughtfully planned, hill-free itinerary, ensuring everyone can enjoy Tuscany’s beauty and culture at a pace that suits the whole family.
Bicycle tours
Tour Type
Private Tour
Accommodation
Hotel, Villa
Age Range
18-99 yrs
Operated in
english
Destinations
Tuscany, Pisa, Empoli, San Giuli
Tuscany, Pisa, Empoli, San Giuliano Terme, Lucca, Vinci, Florence
Dreaming of the ultimate Italian escape? The 'Best of Sicily' tour is a 10-day guided art and architecture journey that starts in Sicily and ends in picturesque Taormina, weaving through Catania, Lazio, and four other captivating destinations. This easy-paced trip, ideal for families, young adults, and seniors, invites you to savor Sicily's culinary treasures—think artisanal olive oils, local wines, and orchard-fresh fruits—while tracing the footsteps of ancient empires through haunting ruins and timeless hilltop towns. Marvel at the lunar landscapes of Mount Etna and immerse yourself in the region's vibrant culture and natural beauty. With seamless logistics, comfortable group accommodations, and expert guides, the USP of this tour is its deep dive into Sicily’s authentic lifestyle, promising not just a getaway but a trove of cherished memories.
Art and architecture
Tour Type
Group Tour
Accommodation
Hotel, Villa
Age Range
13-99 yrs
Operated in
english
Destinations
Campania, Sicily, Lazio, Catania
Campania, Sicily, Lazio, Catania, Taormina, Agrigento, Palermo
Pressed for time but eager to soak up the Amalfi Coast’s best? The Naples Express & Sorrento - Small-Group Tour is a 4-day sightseeing adventure perfect for families and travelers of all ages. Start in Rome and journey to Naples, where you’ll step back in time at the ruins of Pompeii. Set sail for a day trip to Capri’s idyllic shores, then relax in the charming town of Sorrento, with plenty of free time to explore at your own pace.
The tour includes accommodation, transport, and guided sightseeing, ensuring comfort and ease throughout. The unique selling point? A thoughtfully curated itinerary that captures southern Italy’s must-see highlights in just four days—ideal for travelers who want a rich Italian experience without the rush.
Sightseeing Tours
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
Experience a grand sweep of Italy’s heritage on the 12-day “Irresistible Italy: Rome to Venice” tour, a journey that invites families and travelers of all ages to soak in the country’s timeless allure. Start with private transfers in Rome and delve into the city’s legendary sites, from the Colosseum to the Roman Forum. Sip Chianti in Tuscany, take a coach tour through Florence’s artistic heart, and enjoy the freedom of a 48-hour train card in the picturesque Cinque Terre. Glide along Lake Como’s waters and finish with a gondola ride in Venice, all while traveling effortlessly by high-speed trains. This trip’s unique advantage lies in its blend of guided tours and independent exploration, offering both structure and flexibility for an enriching Italian adventure.
Explorer
Tour Type
Private Tour
Accommodation
Hotel
Age Range
7-99 yrs
Operated in
english
Destinations
Rome, Florence, Venice, Colosseu
Rome, Florence, Venice, Colosseum, La Spezia, Cinque Terre, Milan, Lake Como
