For myself and my friends’ 50th birthday escape we based ourselves in Cascais, the chic little seaside town just along the coast from Lisbon. We checked in for three nights at Pestana Cidadela Cascais, a stylish hotel set within the walls of a historic fortress overlooking the harbour. It felt special from the moment we arrived: thick stone ramparts outside, contemporary art and a calm, modern design inside.

Our days quickly fell into a wonderfully simple rhythm. Mornings were often spent wandering down to the harbour, watching the boats and soaking up that relaxed, Riviera‑style atmosphere. With everything so walkable, it was easy to dip in and out of the cafés, pop into little boutiques and just enjoy being by the water with friends.

Of course, the beaches were a big part of the trip. Cascais has a string of sandy coves, so we spent our afternoons strolling the promenade, paddling in the Atlantic and finding our favourite spots to sit and chat. Whether we were people‑watching from a beach bar or stretching out on the sand, it was exactly the kind of gentle, sun‑drenched break we had hoped for.

A real highlight was the food. From fresh seafood by the harbour to cosy restaurants tucked into the old streets, every evening became an excuse to linger over local dishes, good wine and even better conversation. Being able to stroll back to the hotel along the cobbles at the end of the night was the perfect way to finish each day.

Cascais turned out to be an ideal choice for a short friends’ getaway: beautiful, easygoing and full of places to eat, wander and unwind together.

If you would love a similar escape with your own group of friends, contact me to start planning a tailor‑made Cascais break crafted just for you