Sicily May 2026 Tours and Trip packages

Accommodations

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.

Highlights of Sicily - May 2026

4.6

(79 reviews )

No booking fees

Best price guaranteed

This was a fabulous trip, with a well thought-out itinerary enhanced by a wonderful guide, a great group of people, delicious Italian food and beautiful weather.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Catania, Taormina, Sicily, Viagr

Catania, Taormina, Sicily, Viagrande, Noto, Agrigento, Trapani, Palermo

Duration9 days

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Sicily Food & Wine - May 2026

4.7

(40 reviews )

No booking fees

Best price guaranteed

Sicily is a fascinating treasure trove of history and beauty. This trip allows you to experience the Sicilian way of life using food as a lure to explore its villages, towns and landscape as you move from one side of the island to the other.

Food tours

Tour Type

Small Group Tour

Accommodation

Lodge, Villa, Bungalow, Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Palermo, Taormina, Marsala, Agri

Palermo, Taormina, Marsala, Agrigento, Sicily, Syracuse, Catania

Duration8 days

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Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - May 2026

4.8

(102 reviews )

No booking fees

Best price guaranteed

I cant say enough about the actual sites,the tour guide and the driver!!! We were also a very large group and all were so fun and memorable! We always asked about the food and it was not so much part of the memory. The atmosphere of dining in the hotels and food was a 5 at the most. That would be my only disappointment.

City sightseeing

Tour Type

Group Tour

Accommodation

Villa, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Sorrento, Palermo, Sicily

Rome, Sorrento, Palermo, Sicily, Agrigento, Giardini Naxos, Matera

Duration13 days

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Sicily Grand Tour - May 2026

4.5

(13 reviews )

No booking fees

Best price guaranteed

The 15 day tour of Sicily was absolutely fantastic. The best tour guide ever, her name is Milena. A wonderful driver Alessandro. I felt that it was a pretty comprehensive tour of Sicily seeing all the highlights plus more. Fabulous food in restaurants where we ere taken by Milena. Verdict EXCELLENT.

Local culture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Catania, Taormina, Palermo, Cefa

Catania, Taormina, Palermo, Cefalu, Mount Etna, Syracuse, Sicily, Modica, Piazza Armerina, Trapani

Duration15 days

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Sicily - Magna Via Francigena - May 2026

4.6

(14 reviews )

No booking fees

Best price guaranteed

A great way to see Sicily away from the main tourist areas. There was some mud, some territorial dogs to get past and some stiff climbs often at the end of the day to hill towns. But our hosts and other people we met were very welcoming, the food was great and the scenery made the exertion worthwhile. We recommend this walk.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Palermo, Sicily, Corleone, Prizz

Palermo, Sicily, Corleone, Prizzi, Cammarata, Sutera, Racalmuto, Agrigento

Duration8 days

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Best of Sicily (Small Group Tour) - May 2026

(1 review )

Trip customizable

Best price guaranteed

Everything we expected and more. Everything was perfecto.

Food toursCity sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Palermo, Catania, Taormina, Syra

Palermo, Catania, Taormina, Syracuse, Sicily, Mt Etna, Noto, Island Of Ortigia, Agrigento

Duration8 days

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Old World Sicily & Malta - May 2026

4.7

(28 reviews )

No booking fees

Best price guaranteed

I cannot think of one thing the whole trip was fantastic or tour guide Michela , was so fantastic. You truly felt that you were family. She explained everything told us what we expect ahead of time took care of everyone’s needs and still made it so much fun a bunch of us were in our 70s and upper 70s and did not feel that we couldn’t keep up with the tour because it was done so well I think one of the best vacations that we ever took

Walking tours

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Sliema, Taormina, Sicily, Ragusa

Duration12 days

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Best of Italy - May 2026

(1 review )

Trip customizable

Best price guaranteed

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.

Culture shows and excursions

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Palermo

Rome, Florence, Venice, Palermo, Agrigento, Sicily, Taormina, Sorrento

Duration17 days

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Best of Sicily - May 2026

(1 review )

Trip customizable

Best price guaranteed

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

Duration10 days

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Splendours of Sicily - May 2026

Trip customizable

Best price guaranteed

Step into the heart of the Mediterranean with the 'Splendours of Sicily' tour, an 8-day city sightseeing trip beginning and ending in Catania. This thoughtfully guided journey welcomes families, young adults, and seniors alike to experience Sicily's legendary baroque architecture, UNESCO-listed treasures, and captivating local culture. Wander through the storied streets of Catania, marvel at the ancient wonders of Agrigento, and soak in the charm of Campania. With comfortable accommodations, seamless transport, and delicious meals included, travelers of all ages can relax and savor Sicily’s world-renowned cuisine, vibrant traditions, and picturesque landscapes. The unique selling point of this tour is its immersive introduction to Sicily’s layered history and gastronomic delights, all delivered in a leisurely, easy-paced itinerary perfect for families and multi-generational groups. Discover why Sicily is celebrated for its profound beauty, warmth, and cultural richness on this unforgettable tour package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Catania, Campania, Sicily, Agrig

Catania, Campania, Sicily, Agrigento, Palermo

Duration8 days

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Tours and Trip Packages to Sicily in May 2026

Get a customized trip to Sicily in May 2026

18 Trips in Sicily during May 2026 with 278 Reviews

18 Trips in Sicily during May 2026 with 278 Reviews

Highlights of Sicily - May 2026

Sicily Food & Wine - May 2026

Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - May 2026

Sicily Grand Tour - May 2026

Sicily - Magna Via Francigena - May 2026

Best of Sicily (Small Group Tour) - May 2026

Old World Sicily & Malta - May 2026

Best of Italy - May 2026

Best of Sicily - May 2026

Splendours of Sicily - May 2026

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Asia

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Africa

North America

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Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

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

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Tours and Trip Packages to Sicily in May 2026

Get a customized trip to Sicily in May 2026

18 Trips in Sicily during May 2026 with 278 Reviews

18 Trips in Sicily during May 2026 with 278 Reviews