Explore Portland

With its rich history and amazing landscape, the Isle of Portland is the perfect setting, whatever your occasion

Connected to the mainland by the breathtaking sweep of Chesil Beach, the Isle of Portland offers a magnificent blend of beauty and excitement. As a major feature of the Jurassic Coast – a UNESCO World Heritage site – Portland is well known for its fascinating landforms and breathtaking sea views. With two castles, three lighthouses and a charming array of hidden gems, there’s certainly plenty to see and do, whether you’re here with family, friends or colleagues.

  • Leisure

    Dorset’s extensive coastline offers all sorts of water sports, from diving to windsailing and sea angling to kite surfing. But if you don’t fancy getting wet, the unique local landscape offers superb walks and bike rides, historic sites and plenty of shopping opportunities. Please see Activities@ThePenn for a full list of available options. Photo © Ed Peers



    If a swim in our pool or a sit by the fire isn’t enough, spa treatments can be arranged in the comfort of the Castle.


    Chartered boats can be arranged for you to go out on the Olympic sailing waters, with power boats and yachts available from Portland Harbour.

    Pubs and restaurants

    If you’re looking for a night out on the island, The Crab House Café, Quiddles and The Cove House Inn all offer exceptional food at reasonable prices. If you venture in Weymouth Al Molo is always worth a visit.
  • Rufus Castle

    Also known as Bow and Arrow Castle, Rufus Castle is a ruined 12th century, Grade I listed castle that is clearly visible from The Penn. The ruins you will see today are the remains of the late 15th century castle built over the earlier castle.

    Portland Castle & Castletown D-Day Museum

    Situated on the north of the island, Portland Castle was built in the 1540s to protect against French and Spanish invasion – one of Henry VIII’s finest coastal forts. At Portland Castle, you can tour the Tudor kitchen, step inside the Great Hall, enjoy the stunning views out to sea from the gun platforms and explore the glorious heritage garden.   Also in Castletown you will find the D-Day centre, a family attraction offering an immersive experience of a wartime dockyard on the Isle of Portland.

    Portland Bill

    Standing proudly at the southern tip of Portland and keeping watch over the seas, Portland Bill’s three lighthouses and dramatic coastline give it an edge-of-the-earth feel. The current lighthouse is over 100 years old and the area lies on a major bird migration route, making it very popular with bird watchers and nature lovers the world over.

    Chesil Beach

    Stretching over 18 miles from Portland to West Bay lies the spectacular Chesil Beach. The Beach and The Fleet behind it form part of a UNESCO World Heritage site, and it is also the location for Ian McEwan’s acclaimed novella ‘On Chesil Beach’.

    Church Ope Cove

    Lying just below Pennsylvania Castle, on the eastern side of Portland, is the sheltered Church Ope Cove, a tranquil pebbly beach that’s perfect for fishing and swimming. It’s a great spot for diving too, with several shipwrecks just off the coast. Photo © Peppermint Love Photography