Long Weekend: Live like royalty at the incredible gothic Pennsylvania Castle on the Isle of Portland

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In Ian McEwan’s novella On Chesil Beach, a young couple honeymooning on the Devon side of the eponymous 18 mile finger of pebbles have such a massive blowout that they never see each other again. If only they’d been staying at the other end of Chesil Beach, on the Isle of Portland, they would probably have had a perfectly lovely time, especially if they’d been staying at Pennsylvania Castle.

The 19th century neo-Gothic building, perched atop a hill overlooking the ocean, has a rich history, having been officially opened in 1800 by Princess Elizabeth, daughter of King George III, and later hosting a meeting between Winston Churchill, General Eisenhower and General de Gaulle as they thrashed out their plans for the D-Day landings (there's a museum about it nearby).

Now you and your mates can sit around the very same table and have equally important discussions because the whole nine-room castle is available to hire (as a single unit only, so no other guests to contend with), making it an incredible destination for a languorous long weekend out of the city.

Getting there

A direct train from Waterloo into Weymouth will take two hours and 40 minutes and it’s a 20 minute taxi ride across the sea to Penn castle (as it’s known to its pals). If you’re intent on taking the old Chelsea Tractor, the drive on a Friday afternoon will take anywhere between three and five hours.

The island

The Isle of Portland (it’s not a peninsula but an island “tied” by Chesil beach, which may or may not be a “tombolo” or a “barrier beach” but is definitely not a causeway) is a rugged old place, hewn from the high quality limestone that takes its name from the island.

If you want to explore, you can hire electric bikes and get a local expert to guide you for an afternoon, taking in the incredible cliffs jutting into the ocean in the direction of Normandy, and visiting not one, nor two, but three imposing Victorian prisons. The more adventurous can don a wetsuit and windsurf or paddleboard down in the harbour.

The castle

You’ll want to spend the majority of your time in and around the castle. It has a big, heated swimming pool, which is excellent for a boozy late-night parties, plastic flute of champagne in hand, stereo cranked up, no neighbours to worry about. There are also manicured gardens overlooking the ocean, and a winding path that leads you directly down to the rocky shoreline.

The en-suite rooms all come with great views, there’s a huge, fully kitted-out kitchen, a conservatory, a study, a library with a grand piano and probably a load of other stuff I didn’t find because the place is so big.

What to eat

The nice people at Penn Castle can organise catering for your stay (the local company they use is great, preparing proper gourmet meals), or you can make the short trip to the island’s main culinary attraction, The Crab House Cafe, a place where the seafood is so fresh it’s still twitching (when I was there the owner was showing off a nice turbot that had just come off the boat) and the oysters are grown round the back. Owner Nigel Bloxham has another, even more casual restaurant a few minute’s drive away called Billy Winter’s, which is great for lunch. You can also arrange a wine-tasting through Penn Castle.

Need to know

To book Penn Castle, go to thepenn.co.uk­, call 01305 820918 or email enquiry @thepenn.co.uk. The minimum stay is two nights and the whole castle can be hired for £5,000 (special packages are available for wedding services and wedding parties); for e-bike hire go to jurassic-electric.co.uk; to book a table at The Crab House Cafe go to crabhousecafe.co.uk or call 01305 788867; for in-castle catering contact rabbitandrose.co.uk