Italy Itineraries

From the sweeping hills of Tuscany to the winding cobbled streets of Lecce and the fresh alpine air and looming mountains of the Dolomites, Italy is Original Travel's best-selling destination for good reason.

The below itineraries are designed to give you a flavour of the kinds of Italian holidays we can create here at Original Travel, because absolutely every holiday we plan is tailor-made to an individual client's needs, and no two are ever the same.

We believe that life is in the detail, so whether you're in search of the tastiest spaghetti alle vongole Campania, a private tour of the Vatican or the best view point from which to appreciate the beauty of Italy's iconic lakes, speak to our specialists to create your bespoke itinerary.

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Itinerary Ideas

All of the holidays we create are completely tailor-made to you. The sample itineraries below are intended to give you a flavour of what we can do.

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Showing 1 - 12 of 36 itineraries

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: Indicates itineraries that can be done entirely, or partially, by train.

Showing 1 - 12 of 36 itineraries

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Showing 1 - 36 of 36 itineraries

Best for: Couples and Road Trippers
Blissful Beaches and Historic Towns: A Puglia Road Trip
Best for: Couples and Honeymoons
Captivating Culture and Culinary Treats: A Honeymoon in Puglia
Best for: Couples and Honeymoons
Rest and Rejuvenate in Nature: A Four-Day Wellness Holiday in the Dolomites
Best for: Families
Guided Walks & Gondola Tours: A Family Long Weekend in Venice
Best for: Families
Roaming Around Rome: A Four-Day Family Trip
Best for: Couples and Eco Travellers
Romance and Roaming in Italy: London to Lake Como by Train
Best for: Couples
Appreciating Art and Architecture: A City Break in Florence
Best for: Families
Architectural Wonders & Fabulous Food: A Luxury Family Trip to Florence and Tuscany
Best for: Couples and Honeymoons
A Romantic Luxury Getaway to Sicily and Amalfi Coast
Best for: Couples, Honeymoons, Families and Groups
An Italian Mountains & Beach Break: Summer in the Dolomites and Puglia
Best for: Couples, Honeymoons and Eco Travellers
London to Naples, Amalfi Coast and Pompeii by Train
Best for: Families
Pint-Sized Puglia: A Luxurious Family Getaway
Best for: Couples, Solo Travellers and Sabbatical Goers
Art, Architecture & Ancient Cities: A Cultural Sabbatical Through Europe
Best for: Couples and Eco Travellers
Slow Travel Italian Style: London to Puglia by Train
Best for: Families
Hiking, Biking and Mountain Climbing: A Family Trip to The Italian Lakes and Dolomites
Best for: Couples and Honeymoons
Culture and Culinary Treats: A Romantic Trip to Southern Italy
Best for: Couples and Road Trippers
Captivating Culture and Delicious Delicacies: A Road Trip Around Sicily and Malta
Best for: Couples and Solo Travellers
Hilltop Hikes and Wildlife Watching in Italy’s Hinterland
Best for: Couples
Classic Sites and Secret Spots: A Luxury City Break in Venice
Best for: Couples, Solo Travellers and Eco Travellers
Hiking, Biking, Boating & Eating: The Swiss Alps and Italian Lakes by Train
Best for: Couples and Sabbatical Goers
Lovely Lakes, Majestic Mountains and Sparkling Seas: A Luxury Mediterranean Sabbatical
Best for: Couples
Historic Cities, Fabulous Food & Art Tours: Central Italy Train Holiday
Best for: Couples and Eco Travellers
Lakeside Luxury, Cultural Cities and Coastal Charm: An Italian Train Tour
Best for: Couples and Road Trippers
Scenic Walks & Town Tours: A Road Trip Around South East Sicily
Best for: Couples and Road Trippers
A Roman Road Trip: Emilia-Romagna via Via Emilia
Best for: Couples
Ancient Architecture and Cultural Hot Spots: A Luxury City Break to Rome
Best for: Couples, Honeymoons, Families and Road Trippers
Leisurely Lunches & Historic Towns: A Sicilian Road Trip
Best for: Couples and Solo Travellers
Foodie Tours & Cooking Classes: A Gourmet Getaway to Bologna & Emilia-Romagna
Best for: Couples and Solo Travellers
Italian Art and Gorgeous Gardens: An Alternative Florence Getaway
Best for: Couples and Solo Travellers
Sicily's Baroque Beauties: A Tour of Syracuse and Taormina
Best for: Couples and Groups
The Treasures of Tuscany: Exploring Historic Cities & Hilltop Towns
Best for: Couples and Solo Travellers
Pretty Piazzas and Renaissance Art: Luxury Florence and Venice by Train
Best for: Couples, Honeymoons, Families and Groups
Historic Sites and Hilltop Towns: A Luxury Holiday to Rome and Umbria
Best for: Couples, Honeymoons, Families and Groups
Food, Fun & Culture in Italy: A Family Trip to Florence & Umbria
Best for: Couples and Road Trippers
Lakes, Mountains and Cities: Fly Drive Italy
Best for: Couples
Enchanting Islands and Captivating Coastlines: A Getaway to Amalfi Coast, Capri & Rome
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Harriet and Kate L are our 'Italy' experts and as seasoned travellers they have the inside track on the most memorable adventures.

Image of Kate Little
Image of Harriet Harford