Italy Multi-Generation Holidays

We know the destinations we sell incredibly well; our team of consultants have helped our clients travel to 112 countries... so far. Some of our experts have grown up in these destinations, or lived and worked there, but all have travelled extensively within their specialist regions and are perfectly placed to help you plan a holiday full of authentic experiences, from cultural explorations to wildlife wonders and adrenaline-filled adventures.
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Italy multi-generation holiday ideas

A few suggestions to get the holiday planning process started

Our Italy holiday collections

Discover different ways to explore Italy

Couples Holidays

Couples Holidays

Summer Holidays

Summer Holidays

Honeymoons

Honeymoons

Cultural Holidays

Cultural Holidays

Luxury Holidays

Luxury Holidays

Road Trips

Road Trips

Easter Holidays

Easter Holidays

Train Travel

Train Travel

Family Holidays

Family Holidays

City Breaks

City Breaks

Responsible Travel

Responsible Travel

Italy Multi-Generation Holidays Guide

Practical advice and inspiration to help you prepare for your holiday

Practical guide

Best time to visit Italy

Travel Advice & Information

Italy Travel Advice & Information

Blog

What is a Masseria? Explore Italian Luxury

Blog

Italian Lakes Trip Planning: An Expert’s Guide

Blog

Reasons to Visit the Dolomites in Winter

Italy testimonials

30 reviews
4.7 / 5
"Emily really understood what mattered to us and created a trip that felt completely personalised and thoughtfully organised. We had time to relax in Naples after each excursion, our transport provider was friendly and always on time, and it was a pleasure to be looked after by a local, who added an authentic touch to the whole trip. Visiting Herculaneum and Pompeii was a particular highlight - our guide was truly exceptional, making the visits truly memorable with an excellent command of English and an impressive knowledge of world history as well as the sites themselves."
L - UK
Published on 23rd February 2026
"Our Concierge was brilliant and super helpful - we'd recommend travelling with Original Travel based on her help alone! The Concierge was a new thing for us as previous travel companies did not have this feature, and we thought this was invaluable. We particularly enjoyed the food tour in Ragusa, seeing Mount Etna, driving in Ortigia and the sunset in Marsala. It is the first time we have used Original Travel and we were very happy with the service."
M - UK
Published on 29th September 2025
"Emily really listened and understood what I was looking for, and developed a fantastic itinerary based on that. The personalised tour of Siena was a real highlight - I had asked if we could see some James Bond filming locations, and our guide took a lot of time to review the films and take us to the exact streets, balconies, doorways and squares seen in the films. We all loved it, especially our boys, who are James Bond enthusiasts."
G - UK
Published on 29th September 2025
See all Italy reviews

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