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Tailor-made Italy holidays

Good things happen when we travel

italy lush green landscape next to water

Experience the real Italy on a tailored tour

  • Immersive local experiences

  • Small-scale accommodation

  • 24/7 in-destination support

Soak up the unmistakable charms of Italy, from the vibrancy of its historic cities to the serenity of its rolling countryside, and then there’s the food… One of Europe’s most beautiful and welcoming destinations, our Italy travel specialists are here to share their first-hand knowledge and create a holiday you won’t soon forget.

Special stays including a 15th-century castle and an ancient monk’s residence. Special experiences like Umbrian pasta making and Vespa riding through San Gimignano. Special places such as the Cinque Terre villages and the crystal-clear waters of Cefalu on Sicily. Get ready for a special Italy holiday.

Woman on red vespa countryside behind

Pick your itinerary or build your own

All of our Italy holidays are tailor-made and fully flexible, but to give you some inspiration we’ve created a range of original itineraries, alongside our unique bite-sized trips which allow you to build your own ideal itinerary.

To get started, pick your favourites and send them our way, or simply get in touch for a little expert help.

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A peek at our Italy experiences

Here are a few of our favourite itineraries and bite-sized trips to get things going.

rome vaticano italy at night
Bite-sized trip

Veni, Vidi, Vici!

  • Rome
  • 4 days / 3 nights (flexible)
  • from £ 335.- per person (excluding flights)
View bite-sized trip
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Tuscany & Umbria: La Dolce Vita

  • Pisa - Lucca - Umbria - San Gimigano - Pisa
  • 10 days / 9 nights (flexible)
  • from £ 399.- per person (excluding flights)
View itinerary
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town square barok Ragusa

So Sicily!

  • Catania - Etna - Piazza Amerina - Ragusa - Avola - Catania
  • 12 days / 11 nights (flexible)
  • from £ 899.- per person (excluding flights)
View itinerary
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Trapani salt pans sicily
Bite-sized trip

White Gold!

  • Trapani
  • 3 days / 2 nights (flexible)
  • from £ 170.- per person (excluding flights)
View bite-sized trip
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piazza armeria Sicily city
Bite-sized trip

Sicilian Cuisine in Piazza Armerina

  • Piazza Armerina
  • 3 days / 2 nights (flexible)
  • from £ 105.- per person (excluding flights)
View bite-sized trip
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woman with baby on back

Family fun in Italy

  • Naples - Sorrento - Conversano - Salento - Brindisi
  • 10 days / 9 nights (flexible)
  • from £ 1,379.- per adult (excluding flights)
View itinerary
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Speak to our Italy specialist, David

“Italy is a food fest! I absolutely loved the Italian cuisine before I visited Italy and even more so when I left! Having lived in Rome, I can give you insider tips to make your holiday a truly memorable one.”

Travel Specialist David
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Blue Italian fiat 500

Italy Family Holidays

Looking to plan a family trip to Italy? We can help! Italy is a great destination for children of all ages, and with direct flights from the UK to mulitple airports across Italy, and an extensive transport network, you can travel with ease whilst taking in the sights and sounds of this wonderful country.

Our trips are designed with families in mind, packed with experiences that’ll keep you all entertained. Contact our Travel Specialists about our family-friendly Italy trips and start planning your memorable adventure. 

Why book with Rickshaw Travel

✔ Original holiday experiences

From the mountain villages of the Dolomites to the bustling streets of Naples, our local connections mean that your holiday is anything but ordinary. Small-scale accommodation, unique regional experiences, and the flexibility to tailor-make things just for you.


✔ Expert advice

From your first call to your flight home, your personal travel specialist will be there to share their first-hand experience and ensure you’re fully prepared for your adventure.


✔ Worry-free travel

Seamless transport and logistics, 24/7 local support throughout, full ABTOT financial protection, and sustainability certified by Travelife. Book your holiday with peace of mind.

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Rickshaw brings you closer

We love everything Italy has to offer, from the famous sights of Rome to the glittering water of the Almafi coast, wand everything inbetween. We also love bringing you that bit closer to the real Italy so you can leave having experienced what this passionate country is all about.  

Our travel specialists are passionate about helping you plan a memorable and meaningful trip to Italy. They can share their own experiences and top tips to ensure you have a holiday that is tailored just for you. If you are looking for helpful tips to get started check out our inspiration page.

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Travel with impact

We want to make sure you really get to know the people and the country when you travel to Italy with us. You’ll stay in small-scale hotels and guesthouses so the money you spend directly helps the Italian people thrive. We believe it is essential for us to maintain fair prices so that our guides, hotel owners, and drivers can earn a fair wage. Our goal? That you have an unforgettable holiday to Italy. We ensure that this journey is as sustainable, meaningful, and responsible as possible.

Practical information about Italy

There’s nothing more exciting than booking a holiday to a new destination and looking forward to all the places you are going to visit, but there are also a lot of practical things to consider too. To make it easier for you, we have put together some advice that will help you plan, before and during your trip. Then you can focus on the exciting bit. Get the low down on all you need to know from visas, passport info and money matters to the best time to travel to Italy.

Italian street

Other destinations

Visit other countries in Europe with Rickshaw Travel, we travel to: Greece, Iceland, Lapland and Portugal