10 Best Italy Multiday Tours in May 2027

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Italian Concerto - May 2027

4.7

(123 reviews )

No booking fees

Best price guaranteed

Great tour at a great price

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Amalfi Coast & Cam

Rome, Venice, Amalfi Coast & Campania, Capri, Florence

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Duration11 days

From

USD 3,925

USD 3,374

Saving

USD 551

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Southern Italy and Sicily - May 2027

4.4

(104 reviews )

No booking fees

Best price guaranteed

All the options were excellent. The local guides walked at a slow pace giving us time to take pictures. Our guide Alfonso and our driver Tito were great. We would take a tour with them anytime

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Pompeii, Rome, Sorrento, Palermo

Pompeii, Rome, Sorrento, Palermo, Capri, Taormina, Agrigento

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Duration10 days

From

USD 3,575

USD 3,051

Saving

USD 524

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Italy Bellissimo - May 2027

4.7

(220 reviews )

No booking fees

Best price guaranteed

Amazing variety of experiences, excellent tour guide and local specialists. I also loved that Trafalgar supports local artists and family run farms. A highlight for me was the Make Travel Matter experience with the weavers.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Capri, Assisi, Venice, Montecatini Terme

Duration11 days

From

USD 3,305

USD 3,206

Saving

USD 99

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Grand Italy & Sicily - May 2027

4.7

(77 reviews )

No booking fees

Best price guaranteed

It covers so many areas in Italy We got exposed to so much history and culture

Wine tasting tours

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Palermo, Sorrento, Capri

Rome, Palermo, Sorrento, Capri, Alberobello, Giardini Naxos, Santa Margherita, Portofino, Lake Maggiore, Venice, Florence

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Duration17 days

From

USD 8,250

USD 6,993

Saving

USD 1,257

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Country Roads Of Northern Italy - May 2027

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Country Roads of Northern Italy - May 2027

4.5

(48 reviews )

No booking fees

Best price guaranteed

Keep the flexibility of the add on activities.

AdventureCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Trento, Lake Maggiore

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Duration10 days

From

USD 4,450

USD 3,841

Saving

USD 609

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Highlights of Matera and Apulia Private Tour - May 2027

(1 review )

Trip customizable

Best price guaranteed

Private Tour around Apulia and Matera beyond our expectations .Very good the Hotel in Matera, Dimora di Metello..but also Tenuta Monacelle near Alberobello. Great local guide and meals. I only think you should had add an extra day in Apulia, 5 days are not enough. Anyway excellent tour and service. Very good value for money

Sightseeing ToursFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

20-99 yrs

Operated in

english

Destinations

Matera, Puglia, Polignano A Mare

Matera, Puglia, Polignano A Mare, Alberobello, Monopoli, Bari

Duration5 days

From

USD 2,310

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Italian Vistas - May 2027

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From the ancient ruins of Pompeii to the chic charm of the Sorrento Coast, embark on a spectacular Italian getaway. Enjoy multiple-night stays in Rome, the charming coastal town of Sorrento, Florence, Venice, and Stresa in the Lake District. Discover the treasures of Classical Rome, including the Colosseum. Walk in the footsteps of the ancient Romans in Pompeii. Take a boat to the enchanting Isle of Capri. See the gems of the Renaissance in Florence, a veritable open-air museum. Marvel at the Leaning Tower of Pisa and stroll the streets of Verona. Stop at a Tuscan winery and farm for a lunch of regional specialties and wines. Tour Venice and walk the Castello district. Cruise to Isola dei Pescatori, one of the scenic Borromean Islands. Delve deeper into its history and culture as you visit some of the world’s most beautiful locales.

Natural landmarks sightseeing

Tour Type

Group Tour

Accommodation

Resort, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Lombardy & the Lakes, Veni

Rome, Lombardy & the Lakes, Venice, Stresa, Sorrento, Florence

Duration13 days

From

USD 4,499

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Italy: Amalfi Coast to Puglia - May 2027

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Stray off the beaten path and explore a new side to the Italy you know and love. Sample wines created from the rich volcanic soil just outside of Pompeii. Soak up the sun with a free afternoon in Positano, home to colorful hillside houses and local posh boutiques. Spend 2 nights in a unique cave dwelling in Matera and your last 2 nights in the Puglia region in a personal converted trullo house. Uncover the Baroque excellence of Lecce, an artisan city of limestone. Make your way through southern Italy and experience the Amalfi Coast and the Puglia region.

Beach

Tour Type

Group Tour

Accommodation

Resort, Villa, Hotel, Hut

Age Range

1-99 yrs

Operated in

english

Destinations

Bari, Naples, Alberobello, Monop

Bari, Naples, Alberobello, Monopoli, Lecce, Minori, Matera

Duration14 days

From

USD 4,699

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Rome and Tuscan Highlights - May 2027

4.8

(48 reviews )

No booking fees

Best price guaranteed

I chose this trip because of the 6 nights in Tuscany - Montecatini Terme. Cinque Terre, Lucca, Siena and San Gimignano were highlights of this tour. The food for the special dinners was amazing. Rosella and Massimo kept things on track. Organizing and coordinating tickets, transportation (2 ferries, train and bus) and firsthand knowledge of the areas visited was well exhibited by Rosella. The specialty tour guides were knowledgeable and added extra flair to the excursions. Enjoyed the trip immensely.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Montecatini, Florence, Vin

Rome, Montecatini, Florence, Vinci, San Gimignano

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Duration9 days

From

USD 2,750

USD 2,357

Saving

USD 393

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Italy Coast to Coast by E-bike: Puglia to Amalfi Coast - May 2027

(4 reviews )

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This was the first time that this trip had been run using E-bikes, so everyone was keen to see how the trip would unfold. We were introduced to our bikes on the first evening, and because of a change of hotel we had the opportunity to cycle into Monopoli, and return in the dark after an amazing first meal. When I checked the itinerary I could see that the first two rides were going to be the most challenging in terms of ascent and distance, but I quickly realised that E-bikes are a great leveller. There are four levels of assistance, with turbo being the most powerful. The motor rewards effort, the faster you peddle, the more assistance it gives you, up to its maximum speed - these bikes are not chipped like the delivery cycles that whizz around around our streets bringing takeaways to the masses. Each person in the group decided how much effort to put in, getting up the many hills, but hats off to the one person in the group who rode the whole way on an ordinary bike . . . . and he was not at the back. Respect!! With uphills come downhills, and there were plenty of those. Long sweeping downhills that went on and on. Great fun. We were well fed and watered on this trip, both at lunchtime and in the evenings, and for the most part the weather behaved itself.

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Hut, Resort, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Sorrento, Monopoli, Matera, Cast

Sorrento, Monopoli, Matera, Castelmezzano, Monte Sant'Angelo, Paestum, Salerno

Duration8 days

From

USD 5,850

USD 5,675

Saving

USD 176

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Northern Italy Including Cinque Terre - May 2027

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Northern Italy Including Cinque Terre - May 2027

4.5

(98 reviews )

No booking fees

Best price guaranteed

Very enjoyable, with a variety of interesting locations.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Baveno, Italian Riviera

Milan, Baveno, Italian Riviera, Cinque Terre, Lake Maggiore

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Duration8 days

From

USD 2,395

USD 2,021

Saving

USD 374

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Rome & the Amalfi Coast - May 2027

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From Rome to the rocky cliffs of the Amalfi Coast, take in the best of southern Italy. Uncover classic Rome’s myriad treasures and discover Pompeii’s ruins. Explore the breathtaking scenery of Italy’s coastline, from the dramatic beauty of the Amalfi Coast to the charms of seaside Sorrento. Stop at a winery for a taste of Lacryma Christi, learn how homemade cheese is made, and sip homemade limoncello. Featuring stays in two of Italy’s most beloved locales, experience the country’s renowned food, culture, history, and landscapes.

BeachChill out

Tour Type

Group Tour

Accommodation

Resort, Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, Amalfi Coast

Duration10 days

From

USD 4,399

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Best of Italy and Sicily - May 2027

4.7

(55 reviews )

No booking fees

Best price guaranteed

The Hotel were ok but did not cater to the tourist. The rooms did not have the use of the fans and found the air stagnant. A little air moving would helped. The Hotel in Sicily in Jiardini Naxos, Caeser palace, found the hotel desk determinitly unhelpful.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Palermo, Assisi, L

Rome, Venice, Palermo, Assisi, La Spezia, Florence, Monreale, Agrigento, Taormina, Sorrento, Capri, Vatican City

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Duration15 days

From

USD 5,225

USD 4,422

Saving

USD 803

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Country Roads Of Tuscany & Central Italy - May 2027

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Country Roads of Tuscany & Central Italy - May 2027

4.9

(24 reviews )

No booking fees

Best price guaranteed

Great way to see the true Italy

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice

6% OFF TODAY

Duration9 days

From

USD 4,025

USD 3,768

Saving

USD 257

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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.

All Italy Tours in May 2027

Page 3 of 64 Trips in Italy during May 2027 with 3,105 Reviews

See Italy tours by duration

Italian Concerto - May 2027

Southern Italy and Sicily - May 2027

Italy Bellissimo - May 2027

Grand Italy & Sicily - May 2027

Country Roads of Northern Italy - May 2027

Highlights of Matera and Apulia Private Tour - May 2027

Italian Vistas - May 2027

Italy: Amalfi Coast to Puglia - May 2027

Rome and Tuscan Highlights - May 2027

Italy Coast to Coast by E-bike: Puglia to Amalfi Coast - May 2027

Northern Italy Including Cinque Terre - May 2027

Rome & the Amalfi Coast - May 2027

Best of Italy and Sicily - May 2027

Country Roads of Tuscany & Central Italy - May 2027

Page 3 of 64 Trips in Italy during May 2027 with 3,105 Reviews

Combine Italy in May with Nearby Countries for an Unforgettable Trip

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Food, wine, events and nightlife

Adventure and sport

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Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Italy Tours in May 2027

Page 3 of 64 Trips in Italy during May 2027 with 3,105 Reviews

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Page 3 of 64 Trips in Italy during May 2027 with 3,105 Reviews