Pestana Churchill Bay

The Pestana Churchill Bay overlooks the horseshoe bay of Câmara de Lobos — the fishing harbour Winston Churchill came to paint in 1950 — occupying the town's former Council Chamber and fish market, the first hotel ever opened in its historic centre.

The 57 rooms are styled after Churchill's Madeira canvases, with the harbour, boats and banana-coloured houses framed in the windows. Below, the promenade's poncha bars and espetada restaurants start at the door.

A restaurant of regional flavours, a waterfront bar and terrace, a sauna and the panoramic rooftop pool above the masts complete the stay. It is the most picturesque working harbour on the island — and this is the only bed directly on it.