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
Cultural tour
7 nights,
hotel-to-hotel
7 meals
included
Headwater
Navigation App
Cultural tour
7 nights,
hotel-to-hotel
8 meals
included
Headwater
Navigation App
Cultural tour
7 nights,
hotel-to-hotel
7 meals
included
Headwater
Navigation App
Overall customer rating, based on 17 reviews
Tap here to filter results
Filter and sort
Holiday type
Cultural tour
Destination
Italy
Departure month
All
Activity level
All
Accommodation type
All
Best for
All
Sorted by
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.
Italy is one hour ahead of the UK all year round, making it a simple destination for short-haul, active getaways without the hassle of jet lag.
Most UK to Italy flights take around 2 to 3 hours-perfect for a relaxed, short-haul active holiday.
Pack comfortable, breathable layers for your cultural tour.
Moisture-wicking clothing, supportive walking shoes, and a lightweight waterproof jacket are musts.
For evenings, casual-smart outfits work well for the local restaurants.
Italy celebrates several national and regional public holidays throughout the year, and while these often bring charming festivals and local colour, they can also affect travel plans-especially in rural or smaller towns.
Key National Holidays in Italy:
• New Year's Day - 1 January
• Epiphany - 6 January
• Easter Sunday & Monday - March/April (varies)
• Liberation Day - 25 April
• Labour Day - 1 May
• Republic Day - 2 June
• Ferragosto (Assumption Day) - 15 August
• All Saints' Day - 1 November
• Immaculate Conception - 8 December
• Christmas Day - 25 December
• Boxing Day (St. Stephen's Day) - 26 December
In addition to clothing mentioned above, it's worth taking:
Walking shoes or trainers
Walking poles (if needed)
Reusable water bottle
Sunglasses and sunscreen
Rucksack for excursions
Hat and sun protection
Travel insurance that covers active activities
Swimwear (for pools or coastlines)
Camera or phone (for taking lots of photos)
Plug adapter (Type C or L)
A good book or journal for downtime
Insect repellent (especially in rural areas)
Sicily, Puglia, Matera, and Tuscany, are ideal-they offer gentle walking or cycling routes paired with excellent food, wine, and historic towns.
May, June, September, and early October are ideal. The weather is warm but manageable-perfect for walking or cycling without the summer crowds or intense heat.
Spring & Autumn: Mild, ideal for activity (15-25°C)
Summer: Hot, especially in the south (25-35°C){NEWFILE}Always check regional forecasts before you travel.
Italy uses the euro (€). Most places accept cards, but carry some cash for small cafes or rural areas
The active travel season generally wraps up by late October, though some areas (like Sicily or Puglia) stay warm into early November.
Sicily, Tuscany, and Puglia are ideal-they offer gentle walking or cycling routes paired with excellent food, wine, and historic towns.
A Headwater active holiday includes self-guided or guided walking and cycling routes through scenic regions, with your luggage transported for you and stays in hand-picked hotels. A cultural tour focuses more on guided sightseeing, local history, and city stays, and more hands-on experiences-with less physical activity. Expect local experiences like traditional bread making on our Journey through Puglia to Matera, or wine tasting on our Sicily's Vino & Volcanoes. Headwater blends both, letting you discover culture at your own pace, often on foot or by bike.
