All Italy Tours in May 2026

Oct 2025 Nov 2025 Dec 2025 Jan 2026 Feb 2026 Mar 2026 Apr 2026 May 2026 Jun 2026 Jul 2026 Aug 2026

Page 2 of 190 Trips in Italy during May 2026 with 4,793 Reviews

21% OFF TODAY

Super Sales

Best of Italy - May 2026

3.3

(3 reviews )

No booking fees

Best price guaranteed

We highly recommend this Best of Italy tour!!! This tour is a great introduction to Italy and includes the key highlights of this beautiful country. Booking through Bookmundi was easy & the discount appreciated

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Florence, Sorrento, Assisi

Rome, Florence, Sorrento, Assisi, Venice, Lake Maggiore

21% OFF TODAY

Duration13 days

Super Sales

Highlights of Sicily - May 2026

4.6

(78 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

Private Tour of Sicily from Palermo - May 2026

4.8

(4 reviews )

Trip customizable

Best price guaranteed

This is our first private tour and I must say it met all our expectations. Our driver/guide Carlo took very good care of us, told us informative and amusing stories along the way and took us to wonderful restaurants. He made sure all our needs our taken cared of. In Sicily especially I think the private tour is a big advantage as there are many places where only small vehicles can go through. We made the right decision in choosing this tour.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

20-99 yrs

Operated in

english

Destinations

Palermo, Catania, Taormina, Sici

Palermo, Catania, Taormina, Sicily, Agrigento, Marsala, Monreale

Duration8 days

Puglia Coastal Walk - May 2026

4.6

(7 reviews )

No booking fees

Best price guaranteed

Communication when booking and questions afterwards was good. The trip itself was fantastic

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Otranto, Lecce, Salento, Porto B

Otranto, Lecce, Salento, Porto Badisco, Santa Cesarea Terme, Marittima, Marina Serra

Duration8 days

Super Sales

Amalfi Coast Family Adventure - May 2026

4.9

(42 reviews )

No booking fees

Best price guaranteed

If you are thinking about booking this holiday just do it - you won't regret it.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

9-99 yrs

Operated in

english

Destinations

Pompeii, Amalfi Coast & Campania

Pompeii, Amalfi Coast & Campania, Naples, Positano, Vesuvius, Capri

Duration8 days

Via Francigena: Orvieto to Rome - May 2026

4.5

(8 reviews )

No booking fees

Best price guaranteed

A truly memorable holiday which enabled us not only to see parts of the wonderful Lazio countryside that we wouldn’t normally see by car, but also to soak up the atmosphere of the various villages and towns where we stayed.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Orvieto, Bolsena, Montefia

Rome, Orvieto, Bolsena, Montefiascone, Viterbo, Vetralla, Sutri, Campagnano Di Roma, Isola Farnese, Piazza San Pietro

Duration10 days

Super Sales

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

Amalfi Coast Walking - Agriturismo - May 2026

4.8

(91 reviews )

No booking fees

Best price guaranteed

We just returned from our trekking in the Amalfi Coast. It was truly an amazing experience. The Agriturismo was comfortable and relaxing. The family cooked us delicious meals. We met a fantastic group of people. Our guide, Nigel Lewis was knowledgeable, humorous. The experiences offered throughout the week: pasta making, pizza experience and Pompeii/Herculaneum were fun and would encourage everyone to participate in them. The hiking was challenging at times but Nigel helped mitigate this. There were breath taking views!!! Can’t wait to take another trek with Explore!

Walking toursFood tours

Tour Type

Small Group Tour

Accommodation

Resort, Villa, Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Naples, San Lazzaro

Duration8 days

Combine Italy in May with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

View Tours

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

Super Sales

Cycle Cilento & the Amalfi Coast - May 2026

4.7

(99 reviews )

No booking fees

Best price guaranteed

Amalfi coast is one of the most dramatic coastline in the world and this well organised Exodus Trip will guide you on bike along the coastal road all the way to the end (Termini). There are great do-able climbs, long descents, fantastic scenery, great food, great temples and most beautiful gardens - i.e. just about perfect!

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Minori

Amalfi Coast & Campania, Minori, Palinuro, Casalvelino, Paestum

Duration8 days

Tuscany Walking and Wine - May 2026

4.9

(10 reviews )

No booking fees

Best price guaranteed

Want to explore Tuscany without a rushed itinerary? Want a small group? Want to hike to wineries and hill towns? Stay in interesting hotels that are hundreds of years old? A wine and food buff? Then this is for you. I had a great time on this trip. Had a full day in Sienna and a nice orientation tour of Florence (I spent a few extra days) Plus to get to visit lesser known towns that the big companies overlook. My favorite was Pienza. A nice little town that also had my favorite hotel and great places to eat. And yes, we tasted wonderful Italian wines, as well as the best cold cuts and cheeses I’ve ever tasted. And did I also mention hiking to wineries and hill towns? Wonderful sights, with spectacular views. One hike it rained towards the end, but that didn’t dampen our spirits.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Florence, Pisa, San Gimignano, T

Florence, Pisa, San Gimignano, Tuscany, Pienza, Montalcino

Duration8 days

Classic Amalfi Coast - 8 Days - May 2026

4.8

(9 reviews )

No booking fees

Best price guaranteed

It was very well organised. Everything worked smoothly, we had a great holiday.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Positan

Amalfi Coast & Campania, Positano, Amalfi, Maestra Dei Villaggi, Praiano, Naples

Duration8 days

Via Francigena: Best of Tuscany - May 2026

4.6

(28 reviews )

No booking fees

Best price guaranteed

Great trip, all happened as planned.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Buonconvento, San Minia

Tuscany, Buonconvento, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni, Siena, Lucignano D Arbia

Duration9 days

Super Sales

Walk The Prosecco Hills & Hidden Venice - May 2026

4.8

(77 reviews )

No booking fees

Best price guaranteed

Walking on this holiday is varied and well within most people's grasp. Aside from the rolling hills of Prosecco vineyards it includes forest walking and following along side a river. The hotel is most comfortable with large airy bedrooms and updated bathrooms which do not detract from the historic building. It sits within its own grounds including a large swimming pool and a bookable spa. The village of Soligo is small with 3 cafe's and a small shop which stocks a wide range of biscuits, soft drinks and bottled water. There is one sure thing about this holiday and this is you will not go hungry. Lunches are freshly made by the local shop and will keep you going during the walks. The hotel food is second to none and the other resturants we eat at also supplied delicous food. The highlight of this trip is Prosecco in all its forms. I learnt a lot about how the wine was made and how to tell one bottle from another.

Trekking and HikingFood tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Venice, Treviso, Pieve Di Cadore

Venice, Treviso, Pieve Di Cadore, Cison Di Valmarino, Asolo, Conegliano, Pieve Di Soligo