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01. Tell us about your Italy trip

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02. Get proposals from up to 3 experts

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03. Securely book your top choice

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With Insight Guides’ tailor-made Italy trips, the classic sights are only the starting point. Rome, Venice, Florence, and the Amalfi Coast can all be part of your itinerary, along with Cinque Terre hikes, Matera’s cave dwellings, vineyard stays in Tuscany, or time in the Dolomites.

Italy is easy to dream about, but the best trip depends on getting the pace, route, and details right. Our Italy-based local experts help plan your journey around the places, food, culture, and experiences that matter most to you, with the logistics handled before you go.

Browse our Italy trip ideas, then customize your trip with a local expert.

Italy trips by Insight Guides

Crafted with ❤️ by local experts

Cinque Terre National Park UNESCO World Heritage Site, Liguria, Italy
Crafted by Fabio

16 days

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Impressive medieval Assisi town - religious center of Umbria. Italy
Crafted by Fabio

6 days

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Positano
Crafted by Fabio

11 days

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Piedmont in autumn, Italy
Crafted by Fabio

10 days

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Roman ruins in Rome
Crafted by Martina

8 days

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Alberobello
Crafted by Fabio

10 days

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Wooden fishing boats on the old beach of Cefalu, Sicily, Italy.
Crafted by Fabio

11 days

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Colorful fishing boats near the river in Bosa, Sardinia
Crafted by Fabio

12 days

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Riomaggiore is the first city of the Cique Terre sequence of hill cities, Liguria, Italy.
Crafted by Fabio

10 days

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Capri
Crafted by Fabio

10 days

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Tuscany
Crafted by Fabio

6 days

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Meet our Italy travel experts

They will craft your perfect trip

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Fabio
Vetted by Insight Guides
Fabio
Active online: 9h ago
20Years in
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Martina
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Martina
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8Years in
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281Offers
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Marianne
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Marianne
Active online: 17h ago
4Years in
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820Happy
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Valentine
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Valentine
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4Years in
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460Happy
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Anna
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Anna
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4Years in
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240Happy
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Clemens
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Clemens
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12Years in
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940Happy
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Vaseem
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Dimitrios
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Irene
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Irene
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Emilie
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Emilie
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Things to know before your Italy trip

What does a trip to Italy look like?

A typical Italy itinerary might start in Rome, where you can explore the Colosseum, Vatican City, and buzzing trattorias in Trastevere. Then it’s off to Florence for world-class art and Tuscan wine tours, and on to Venice, gliding through its canals by gondola or vaporetto.

But it’s the lesser-known stops that often steal the show: hiking coastal trails in Cinque Terre, marveling at the cave-city of Matera, or skiing and spa-hopping in the Dolomites. Every trip is built around what you want to see, skip, or explore deeper.

Can I customize my Italy trip?+

How far in advance should I start planning?+

Is it more expensive to book Rough Guides tailor-made travel?+

Who are the Italy local experts?+