10 Best Italy Multiday Tours in May 2027

Combine Italy in May with Nearby Countries for an Unforgettable Trip

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

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Highlights of Italy - May 2027

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How long does it take to fall in love? In a country where history spills from world-class museums and tiny osterias serve up life-changing pasta recipes, eight days might just be enough (but if you have more time, why not extend your adventure?). On this trip, you’ll begin winding your way through the canals of Venice, hiking through the scenic Cinque Terre, soaking up beauty and history of Florence and finishing up in the piazzas of Rome. With plenty of free time for independent exploration and the freedom to discover Italy's history and culture at your own pace, there's no better way to see this popular pocket of Europe.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Hostel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, La Spezia, Florence

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Duration8 days

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Ultimate Italy - May 2027

(9 reviews )

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Our overall experience with GAdventures was outstanding. The CEOs leading the tours were extremely knowledgeable of the cities we visited and always ready to help make the tours exciting and fun. We had at least two days in each of the cites which gave us enough time to explore on our own or with new friends we made along the way. I highly recommend GAdventures and we are already looking for another GAdventure tour next year.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Villa, Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Venice, Lake Como, Montepu

Rome, Venice, Lake Como, Montepulciano, Florence, Cinque Terre

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Duration14 days

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Walking the Amalfi Coast - May 2027

4.7

(427 reviews )

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Basically a perfect week in a beautiful part of the world, good food, great companions, great walks, excellent guide, great weather and fantastic views and experiences...

Trekking and HikingBeach

Tour Type

Small Group Tour

Accommodation

Hotel, Hut, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Bomeran

Amalfi Coast & Campania, Bomerano, Amalfi, Pompeii, Naples

Duration8 days

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Highlights of the Amalfi Coast - May 2027

4.7

(113 reviews )

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An absolutely brilliant trip with a lovely group of people. Wonderful food, scenery and great hotel. Everyday was a completely different experience - a tour with great variety and something for everyone.

Food tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Bomerano, Amalfi, Path Of Gods, Capri, Ravello

Duration8 days

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Jewels of Italy - May 2027

4.3

(52 reviews )

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This trip, while short, provides an in-depth discovery of much of central Italy: Rome and the Colosseum, Florence and the David, Pizza, Verona, and Venice featuring a glass blowing demonstration and optional tour to Burano for a truly unique dinner. The tour also provides an opportunity for time on your own to explore on one’s own pace or visit sites of personal interest. In my case, I could visit Peggy Guggenheim’s museum ( with instructions on how best to get there by our guide) in Venice and have dinner in Rome at a restaurant recommend by an Italian friend.

Adventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence

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Duration7 days

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Discover Puglia: Italy's Ancient Heel - May 2027

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Discover Puglia: Italy's Ancient Heel - May 2027

4.6

(49 reviews )

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An excellent trip. The pace of the trip is perfect. A week flew by and we felt we had been all over the Puglia region. So much to do and see in such a short space of time and yet we managed to relax and get some free time in too. The food was outstanding, the wine was delightful, the people were a pleasure to be around. Every stage of the trip was enjoyable and slightly different.

Food toursLocal culture

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Matera, Lecce, Salento, Alberobe

Matera, Lecce, Salento, Alberobello, Grotte Di Castellana, Ostuni, Otranto

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Duration8 days

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Italy Experience - May 2027

(2 reviews )

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The comfort level trip allows for the traveller to fully experience Italy as a local with their off the beaten track options but with the convenience of travelling comfort, local guidance and added inclusions.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Liguria, Cinque Te

Rome, Venice, Liguria, Cinque Terre and Liguria, Florence, Perugia

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Duration10 days

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Walking in Puglia & Matera - May 2027

4.7

(111 reviews )

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Best price guaranteed

This holiday is a fantastic introduction to the Puglia and Basilicata area of Italy. I enjoyed all of the towns that we visited and would have happily spent more time in Alberobello and Ostuni.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Matera, Puglia, Alberobello, Ostuni

Duration8 days

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Best of Italy - May 2027

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The enduring phrase ‘la dolce vita’ (the good life) truly captures the essence of Italy. On this trip, you’ll spend 14 days discovering the heart of all things Italian on a culturally rich adventure from the piazzas of Rome to the canals of Venice. Discover the Tuscan countryside on a leisurely cycle along Lucca’s Serchio River, peer into Pisa, take to the trails of the Cinque Terre for some stunning coastal views and walk the Portofino Peninsula with its glamourous residents. With time spent wine tasting in rural villages, cruising along Lake Como and relaxing along canals in Venice, you’ll soon understand why Italy remains in the hearts of all who visit.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Cadenabbia, Floren

Rome, Venice, Cadenabbia, Florence, Lucca, Liguria, Asti

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Duration14 days

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Rome to Amalfi - May 2027

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If you want a short trip packed with diversity, this eight-day adventure through southern Italy is perfect for you. Acquaint yourself with Italy's 'Eternal City' (Rome) and get up close and personal with a still active volcano in Naples before witnessing the aftermath of a volcanic eruption in Pompeii. Soak up the sunshine in the coastal town of Sorrento and explore the beautiful Amalfi Coast. This trip promises a blend of history, trekking and culinary delights — a taste of la dolce vita awaits.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Hut

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, P

Rome, Amalfi Coast & Campania, Pompeii, Sorrento, Amalfi

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Duration8 days

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Walking in Tuscany - May 2027

4.9

(226 reviews )

No booking fees

Best price guaranteed

This part of Tuscany was a complete surprise and a total delight. Not only did we have the typical walking through rolling pastureland covered with wildflowers, we also had many walks through shady forests decorated with sun streaming through the new green leaves and over a floor of last years copper leaves before we emerged onto high ridges to enjoy stunning views over still snow clad peaks. A total delight.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Hut, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Tuscany, Pisa, Lucca, Braccicort

Tuscany, Pisa, Lucca, Braccicorti, Corfino, Casone

Duration8 days

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Italian Holiday - May 2027

4.7

(175 reviews )

No booking fees

Best price guaranteed

Very well organized from beginning to end

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, The Vatican, Venice, Veron

Rome, The Vatican, Venice, Verona, Florence

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Duration7 days

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Best of Italy - May 2027

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, Varese

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Duration13 days

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Highlights of Sicily - May 2027

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

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Duration9 days

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All Italy Tours in May 2027

145 Trips in Italy during May 2027 with 5,149 Reviews

Get a customized trip to Italy in May 2027

See Italy tours by duration

Combine Italy in May with Nearby Countries for an Unforgettable Trip

Highlights of Italy - May 2027

Ultimate Italy - May 2027

Walking the Amalfi Coast - May 2027

Highlights of the Amalfi Coast - May 2027

Jewels of Italy - May 2027

Discover Puglia: Italy's Ancient Heel - May 2027

Italy Experience - May 2027

Walking in Puglia & Matera - May 2027

Best of Italy - May 2027

Rome to Amalfi - May 2027

Walking in Tuscany - May 2027

Italian Holiday - May 2027

Best of Italy - May 2027

Highlights of Sicily - May 2027

145 Trips in Italy during May 2027 with 5,149 Reviews

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Food, wine, events and nightlife

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Special interests and hobbies

All Italy Tours in May 2027

145 Trips in Italy during May 2027 with 5,149 Reviews

Get a customized trip to Italy in May 2027

See Italy tours by duration

145 Trips in Italy during May 2027 with 5,149 Reviews