Planning an Unforgettable Multi-Family Winter Trip to Caernarfon in North Wales

When we visited Caernarfon last June, it was, in true British fashion, grey, damp, and persistently gloomy. I was annoyed at the time because I generally rely on the sun to act as my Automatic Photographic Enhancer™, but looking back at the photos a year later, I’ve realised that the clouds actually suit the place. If you’re currently the designated Adult in Charge of organising a trip for 50+ people, you’ll find that Caernarfon’s slightly moody atmosphere is actually quite forgiving.

The Castle: A Strategic Hiding Place

The centre of everything is the Castle. Edward I started building it in 1283 as a way to loom over the Welsh, and 700 years later, it’s still very good at looming. It cost about £12,000 back then (roughly £5 million today) which is a lot of money for something they never actually bothered to finish.

For a group of fifty, the castle is a godsend. It’s essentially a giant stone labyrinth where you can "lose" the more energetic members of your party for a few hours. I personally spent a significant amount of time climbing the steep, dark stairs of the Chamberlain Tower. There is something grounding about laying your hands on cold stone that has seen seven centuries of rain. It puts your own logistical problems back into proportion.

The Black Boy Inn

Eventually, the wind will win, and you’ll need to retreat. My dad and I have headed to the Black Boy Inn for food before, and it is exactly the kind of place you want to find when your extremities are starting to go numb. It dates back to the 16th century, so the ceilings are low, the fires are real, and the atmosphere is thick enough to lean against.

If you’re trying to feed fifty people, my advice is to abandon any hope of a synchronised seating plan. It’s much better to let people drift in and out in small, manageable clusters. Or, if the weather is particularly "atmospheric," just buy a mountain of fish and chips from the harbour and eat them back at the accommodation. It’s less formal, and nobody has to worry about which fork to use.

Winter Walks and Colourful Houses

The walk along the Menai Strait is a reliable way to reset the group’s collective mood. In the winter, the air smells like salt and distant woodsmoke. It’s the kind of walk that clears your head and ensures everyone is tired enough to stop arguing by 8:00 PM.

One thing I didn't expect to love was the town itself. Just outside the medieval walls, there are rows of houses with these incredibly bright facades that refuse to match the weather. Even on a day that looks like a grayscale filter, they provide a much-needed hit of colour.

Practical Notes for the Organiser:

• The Museum: There’s a Royal Welch Fusiliers Museum inside the castle. It’s warm, it’s dry, and it’s a perfect place to wait out a heavy downpour.

  
  

• The Stairs: The spiral staircases in the towers are beautiful but also quite smooth. In the damp, they become a high-stakes game of balance. Wear shoes with actual grip.

  
  

• Parking: Don't attempt to park 15 cars on a medieval side street. Use the harbour multi-storey. Your blood pressure will thank you.

  
  

Ultimately, Caernarfon is a town built to survive the elements and the centuries. It can certainly survive your extended family. Bring a waterproof jacket. Don’t wait for the sun.