Italy is a country that rewards curiosity. Layer upon layer of history, culture, landscape and flavour unfold as you travel - often in ways you don't expect, and always in ways you'll remember.
Our self-guided tours are created to give you Italy at its most authentic and unforgettable. From dramatic coastlines and elegant cities to quiet countryside and volcanic landscapes, these are journeys that go beyond the obvious, combining iconic sights with deeply local experiences. With expert planning, carefully chosen hotels and just the right balance of structure and freedom, you're free to immerse yourself fully in la dolce vita.
Amalfi Coast
The Amalfi Coast is one of Italy's most dramatic landscapes, where colourful villages cling to cliffs above a shimmering Mediterranean. Travel at an unhurried pace through Sorrento, Positano and Amalfi, explore the ruins of Pompeii beneath Mount Vesuvius, and take time to soak up the rhythm of coastal life. With iconic views, ancient history and unforgettable scenery, this is Italy at its most romantic and rewarding.
Venice, Verona & Bologna
From the floating elegance of Venice to the timeless romance of Verona and the rich culinary traditions of Bologna, Northern Italy offers a captivating blend of art, history and everyday Italian life. Travel between cities with ease, explore world-class architecture and galleries, and enjoy moments of quiet discovery alongside famous landmarks. This is a journey through some of Italy's most cultured and characterful cities.
Puglia & Matera
In Italy's deep south, Puglia and Matera reveal a slower, more traditional side of the country. Discover whitewashed hill towns, ancient olive groves and trulli houses, sample local wines and cuisine, and explore Matera's remarkable cave dwellings. Shaped by centuries of history and everyday rituals, this is an immersive journey into Italy's enduring heart and soul.
Sicily
Sicily is bold, beautiful and endlessly fascinating. From baroque cities and lively markets to dramatic coastlines and the shadow of Mount Etna, the island's landscapes and cultures are unlike anywhere else in Italy. Explore ancient ruins, sample distinctive regional flavours, and experience a place shaped by countless civilisations - raw, vibrant and unforgettable.
Explore Renaissance masterpieces, walk ancient streets, taste regional wines or simply watch the world go by from a cafe; our Italian journeys are crafted to feel personal, immersive and genuinely special. These are not rushed itineraries or surface-level sightseeing trip - they are carefully curated experiences designed to connect you to the places, people and stories that define Italy.
Cultural tour
7 nights,
hotel-to-hotel
7 meals
included
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIPCultural tour
7 nights,
hotel-to-hotel
8 meals
included
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIPOverall customer rating, based on 17 reviews
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Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.