10 Best Italy Multiday Tours in May 2027

Get a customized trip to Italy in May 2027

Plan a multi-country or regional adventure across Italy in May 2027, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy

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Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Combine Italy in May with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

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Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

Matera Sassi European Capital of Culture 2019 - May 2027

Trip customizable

Best price guaranteed

The guided tour make you discover the typical Sassi, a UNESCO World Heritage Site. The itinerary begins in the square Pascoli, with a wonderful view of the Sasso Caveoso and the hill called Murgia. You will pass by the Palazzo Lanfranchi, houses the Museum of Medieval and Modern Art of Basilicata, and the nearby church of the Carmine. The tour continues through the heart of the old buildings to the church of San Pietro Caveoso. Visit to a typical "Casa Grotta (Cave House)" excavated in the rock with furniture of rural culture to the beginning of 1900. You will pass near the cave church of Saint Lucia delle Malve, will visit some of the most important frescoes. The tour continues to the Sasso Barisano following the ancient ravine. Return to the center of town and walk around the baroque area with a visit to the most important churches in this style: St. Clare and St. Francesco di Assisi. End of the tour with the discovery of the Romanesque cathedral.

Walking tours

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, french, german, italian

Destinations

Matera

Duration2 hours

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Discover Castel del Monte (UNESCO) - 2 Hour Guided Tour - May 2027

Trip customizable

Best price guaranteed

In the heart of Puglia is hidden the most important monument of the Middle Ages in Italy, a treasure of beauty and mystery to explore. Castel del Monte was built on top of a hill where you can see a good part of the Puglia Region and the cities of the coast with a beautiful landscape. Castel del Monte is certainly the most important building that has left the Emperor Frederick II Hohenstaufen of Swabia, full of mysteries not fully revealed. At the base of its construction there is always the number 8. After many years of neglect, during which the castle was stripped of furniture and decorations of marble, has become a refuge for shepherds, brigands and political refugees. In 1876 the castle was bought and restored by the Italian state. In 1996 it was declared a UNESCO World Heritage for the perfection of its shape and the harmonious union of cultural elements from northern Europe, the Islamic world and classical antiquity and because it represented the personality of its creator Frederick II Hohenstaufen. The tour you will discover the exteriors and interiors of the 'castle' and describe the secrets of the historical context in which it was built.

Cultural, religious and historic sites

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, german, italian

Destinations

Andria

Duration2 hours

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Private tour of the ruins of herculaneum - May 2027

Trip customizable

Best price guaranteed

See the ruins of Herculaneum, the smaller, but no less impressive, sister of Pompeii, frozen in time by the same devastating volcanic eruption of August 24th 79 AD. Left buried under the rubble of ash until the 1700s, its discovery stunned the world. All of the ancient town lies at the bottom of an archaeological hole, about 75 feet deep. Getting closer, see the area of the marina where 300 human skeletons were found along with a boat (on display at weekends). Discover the garden of the “House of the Albergo”, where quince trees have been replanted following evidence of carbonized roots of the ancient fruit tree. Your next stop is the Council Hall of the Augustali, where beautiful frescoes depict Hercules. Visit the mosaics in the House of Neptune and Amphitrite, and the neighboring store where food and wine containers, carbonised by the volcano, still hang on the walls! Go to the ancient spa, still covered with mosaics from the Roman saunas, gyms, hot rooms, and cold tubs. Finally, see the most spectacular villa of Herculaneum at Villa Dei Cervi, with its luxurious mosaics, frescoes, and statues.

Adventure

Tour Type

Group Tour

Accommodation

Villa

Age Range

5-79 yrs

Operated in

english, italian

Destinations

Amalfi Coast & Campania, Naples

Duration2 hours

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17% OFF TODAY

Great Italian Cities - May 2027

4.8

(201 reviews )

No booking fees

Best price guaranteed

It was a beautiful, historic overview of the heart of Italy. Our guide , was fantastic, caring and knowledgeable.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Munich, Venice, Florence

17% OFF TODAY

Duration10 days

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Gallipoli: guided walking tour in salento - May 2027

Trip customizable

Best price guaranteed

Discover Gallipoli in a walking tour of 2 hours. First stop on the itinerary is the Greek fountain, an example of the Renaissance style inspired by the ancient world (in the past was thought to be of age greek-Roman). Crossing the bridge that connects the old center to the new town, you enter the heart of the city, protected by the big castle. From Antonietta De Pace street walking to the Cathedral, dedicated to St. Agatha, martyred in the city of Catania (Sicily), whose relics arrived in Gallipoli. Then continue to the winding streets of the city, admiring the buildings and the typical houses, and then along the coast with numerous churches of the sixteenth century, including the Church of Purità, St. Francesco of Assisi and the Rosario.

Walking tours

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, french, german, italian, spanish

Destinations

Gallipoli, Salento

Duration2 hours

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13% OFF TODAY

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Hiking in the Dolomites - May 2027

No booking fees

Best price guaranteed

Discover the Dolomites on a small group hiking adventure. With easy to moderate walks, conveniently located accommodation and a knowledgeable local leader to keep everything running smoothly, this trip offers an active yet leisurely way to explore one of Italy’s most iconic mountain ranges. Base yourself in the alpine town of Dobbiaco – surrounded by pointy peaks and lush meadows – and spend eight days hiking through UNESCO World Heritage-listed landscapes, kicking back in village inns and refuelling with hearty mountain food – apple strudel, anyone?

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Guest House, Hotel, Hut, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Venice, Dobbiaco, Lake Braies, B

Venice, Dobbiaco, Lake Braies, Brunico, Cortina D’Ampezzo, Bolzano, Tre Cime Di Lavaredo

13% OFF TODAY

Duration8 days

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Wine tasting in a typical “masseria” - May 2027

Trip customizable

Best price guaranteed

Visit to a typical winery in the Apulia region (Southern Italy), a few steps from the Cathedral of Trani and the sea, surrounded by countryside. The winery is located in a beautiful old stone farmhouse "Masseria" in the countryside. You will visit the magnificent vineyards and through a pleasant walk, explore the cellars with wooden barrels where they are stored different types of wine. Some wines take their name from the important medieval castle in this area, Castel del Monte. At the end of the tour there will be a wonderful wine tasting or the characteristic "Moscato di Trani", a sweet dessert wine.

Wine tasting tours

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, german, italian

Destinations

Trani

Duration2 hours

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18% OFF TODAY

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Italy: Highlights of Sicily - May 2027

No booking fees

Best price guaranteed

Calling all sun-seeking adventurers! Take an eight-day trip to Sicily and explore dramatic cliffside villages, soak in the Sicilian sunshine and take in the scenic views of clear waters (did we mention the deliciously fresh seafood?). From the volcanic valleys of Mt Etna to the timeworn streets of Syracuse and the Baroque wonders Ragusa, get ready to discover the varied sides of Sicily. Take a step back in time as you explore the ruins of the Valley of the Temples and learn of the rich anti-Mafia history in Palermo. Eat good food, drink local wines and learn about the region with a handy local by your side – there's a reason everybody loves Italy!

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Catania, Syracuse, Agri

Palermo, Catania, Syracuse, Agrigento, Marsala

18% OFF TODAY

Duration8 days

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18% OFF TODAY

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Premium Sicily - May 2027

No booking fees

Best price guaranteed

Explore Sicily and see how much this island in the heart of the Mediterranean has to offer. Join an expert local leader on a fully immersive 10-day Premium journey – with a sprinkling of Arab, Norman, Greek and Roman influence, this region is a hive of history and culture. See intricate mosaics, towering palaces, crumbling ruins and marble-lined laneways. Head out of the main hubs to discover Mount Etna – Europe’s largest active volcano. Taste Genovesi, arancini, local dishes like caponata and cannoli, and take a traditional cooking class to get the most out of Sicily’s celebrated cuisine. With Exclusive Experiences and a gorgeous Feature Stay in the countryside, what are you waiting for?

City sightseeingAdventure

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Catania, Marsala, Agrig

Palermo, Catania, Marsala, Agrigento, Siracusa

18% OFF TODAY

Duration10 days

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Bari historic walking tour shore excursion - May 2027

Trip customizable

Best price guaranteed

Explore the city of Bari, famous around the world to preserve the relics of St. Nicholas of Myra, venerated as a saint by the Catholic and Orthodox Churches. Discover its history and heritage in this 3-hour shore excursion. St. Nicholas he became famous even outside the Christian world because his figure has given rise to the myth of Santa Claus (or Klaus), symbol of the Coca Cola Company. Discover the Basilica of St. Nicholas, built in the twelfth century to preserve the relics of St. Nicholas of Myra, is considered one of the most beautiful examples of Romanesque architecture. The walk will continue to the Cathedral of St. Sabino of the eleventh century until the Norman-Swabian Castle Fortress built in the twelfth century by Roger the Norman, and after the destruction by William I of Sicily, was rebuilt by Frederick II Hohenstaufen. The tour will end with the visit of Mercantile square and the Column of Justice Free time to buy typical local products

Walking tours

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, french, german, italian

Destinations

Bari, Puglia

Duration2 hours

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Private walking tour of pompeii - May 2027

Trip customizable

Best price guaranteed

Enjoy a 2-hour walking tour of Pompeii and experience life in an everyday Roman town, with your own personal guide. Tours can be tailored to your own interests and physical abilities, but aim to take in at least one site from each type of building. Start at Porta Marina, one of the best preserved city gates. Walk along the original basalt road of volcanic rocks, looking down at hundreds of little white travertine spots used to reflect torch light. See big blocks of basalt emerging from the road, used by pedestrians to avoid getting wet when it rained. Explore the buildings of the Forum, such as the Temple of Apollo, Temple of the Emperor, and Macellum market. You will also see a display of human casts of the Pompeii residents caught by the volcano in the exact pose that they died. Discover the Roman equivalent of today’s fast-food restaurants, and see the bakeries of Pompeii, where carbonized loaves of bread where found during the excavations. Continue to the former Red Light District to see Roman frescoes of erotic images. And visit one of the city’s 3 theaters, either at the outdoor arena for public performances, the indoor theater for mime and poetry, and the outdoor theater for tragedies and comedies.

Adventure

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, italian

Destinations

Pompeii, Amalfi Coast & Campania

Pompeii, Amalfi Coast & Campania, Naples

Duration2 hours

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Ancient Rome Segway Tour - May 2027

(2 reviews )

No booking fees

Best price guaranteed

Writing reviews is just not for me, but I'm glad to be writing my first review about this amazing experience. It was such a pleasant, fun, and thrilling tour. My husband and I have a lot of appreciation for historical architecture and our guide Eugene did a fantastic job with showing us some of thee best spots to take in the beauty of Rome. He was very informative and has a great amount of interesting knowledge about the history. Very friendly and professional and overall a delightful tour guide. I was skeptical about riding a Segway, but it was actually an enjoyable way to get around for siteseeing. Eugene was patient and helped alot with being able to maneuver around the city safely.

Segway tours

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, french, german, dutch, italian, spanish

Destinations

Rome

Duration3 hours

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18% OFF TODAY

Super Sales

Premium Puglia - May 2027

No booking fees

Best price guaranteed

Dreamy beaches, inspiring architecture and ancient wonders come together on an eight-day Premium adventure through Italy’s Puglia region. Understated and unbelievably beautiful, this lesser-visited corner of Italy delivers in historical, cultural and natural sights. Begin in the coastal town of Bari, admire unusual trulli buildings in Alberobello, stay in a former palace in Nardo, explore ancient sassi homes in Matera and discover the well-preserved ruins of Pompeii. With a local leader by your side and expert guides joining you along the way, you’ll really get a kick out of this adventure.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Bari, Naples, Polignano A Mare

Bari, Naples, Polignano A Mare, Nardò, Matera

18% OFF TODAY

Duration8 days

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Rome by electric bicycle private tour - May 2027

(1 review )

No booking fees

Best price guaranteed

We had a E bike tour with Jiulio in Rome yesterday, it was fun, interesting, Julio had a lot of knowledge , patience, we enjoyed every second of the tour!

Scooter and electric bike tours

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, german, dutch, italian, spanish

Destinations

Rome

Duration3 hours

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All Italy Tours in May 2027

Page 7 of 115 Trips in Italy during May 2027 with 3,853 Reviews

See Italy tours by duration

Get a customized trip to Italy in May 2027

Combine Italy in May with Nearby Countries for an Unforgettable Trip

Matera Sassi European Capital of Culture 2019 - May 2027

Discover Castel del Monte (UNESCO) - 2 Hour Guided Tour - May 2027

Private tour of the ruins of herculaneum - May 2027

Great Italian Cities - May 2027

Gallipoli: guided walking tour in salento - May 2027

Hiking in the Dolomites - May 2027

Wine tasting in a typical “masseria” - May 2027

Italy: Highlights of Sicily - May 2027

Premium Sicily - May 2027

Bari historic walking tour shore excursion - May 2027

Private walking tour of pompeii - May 2027

Ancient Rome Segway Tour - May 2027

Premium Puglia - May 2027

Rome by electric bicycle private tour - May 2027

Page 7 of 115 Trips in Italy during May 2027 with 3,853 Reviews

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All Italy Tours in May 2027

Page 7 of 115 Trips in Italy during May 2027 with 3,853 Reviews

See Italy tours by duration

Get a customized trip to Italy in May 2027

Page 7 of 115 Trips in Italy during May 2027 with 3,853 Reviews