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Look ahead to your 2024 Holidays with Headwater and join us on a spectacular trip where you can travel from place to place at your own pace in the great outdoors. Our range of self-guided walking and cycling holidays are developed so you can see the best of any location, in the best way possible.

On a Headwater Holiday, you're in control. And our expertly curated itineraries are designed to activate the senses, immersing you deeper into your region's local culture, where you can visit places of historical interest, sample food that epitomizes the local cuisine and enjoy enchanting stays in characterful accommodations. Rest assured, we'll help you find the hidden treasures, the lesser-known path, and the best regional cuisine. You'll soon find there's an incredible world to wander, pedal and absorb in 2024.

Choose your own pace and explore on foot, from rustic country villages to picture-perfect mountain passes.

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Immerse yourself in a region as you take time to uncover historic sites, picturesque villages and sample the local cuisine.

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Soak up the scenery as you explore on two wheels, follow expertly crafted routes whilst we take care of everything else.

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From Michelin Star dining experiences to intimate wine tastings and local cooking classes, you’ll find the best flavours on our gastro-led holidays.

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Our favourite places to stay