Travel / 48 hours in
48 Hours in Portland and Weymouth
What to do in Portland
Portland Castle’s squat rounded seaward form was designed to deflect an incoming cannon shot – photo: Martin Booth
My ten-year-old daughter Lois was desperate to go for a swim as soon as we arrived on the Isle of Portland, connected to Weymouth by the shingle spit of Chesil Beach. The sea was much too rough on our first two days but fortunately, on the morning of our departure we walked the short distance from our B&B to Castletown where there is a delightful secluded beach next to Portland Castle, one of Henry VIII’s coastal artillery forts. (If you fancy something warmer than seawater, try the nearby Island Sauna.) Just off the coast of Castletown are two Mulberry harbours used in the invasion of Normandy in June 1944 and back on dry land is the fascinating Castletown D-Day Centre.
The Sherman was the most widely used battle tank used by the Allies during the Second World War – photo: Martin Booth
Portland’s name is world renowned thanks to Portland stone which has been quarried on the island since Roman times and used in public buildings such as St Paul’s Cathedral in London and the United Nations Headquarters in New York. Wander around the former Tout quarry which is now a sculpture park and nature reserve. Look out near here for memorials to the crew of the submarine HMS Sidon and the warship HMS Foylebank, as well as the Olympic rings also overlooking Portland Harbour, once the largest man-made harbour in the world, where the sailing events in 2012 took place.
The Olympic rings overlook Portland Harbour where the sailing events took place in 2012 – photo: Martin Booth
What to do in Weymouth
I took part in Weymouth parkrun on Saturday morning in Lodmoor Country Park, which also has the Sea Life Centre with the UK’s largest collection of marine creatures; SandWorld, featuring incredible work by some of the world’s leading sand sculptors; a model railway; and a nine-hole pitch and putt course. Back in the town centre, keep a look out for a replica of the bathing machine used by King George III who was a frequent visitor to Weymouth. His first visit in June 1789 was to convalesce from his first bout of mental illness, at a time when many doctors recommended sea bathing as a cure for many ailments.
is needed now More than ever
A statue of King George III overlooks a bathing machine which used to transport the monarch into the sea – photo: Martin Booth
On the sandy beach where the king’s bathing machine was pushed on the way out into the sea are numerous beach volleyball courts, with Weymouth the first place in the UK where the sport was played and every July hosting the country’s most prestigious tournament. Throughout 2025, We Are Weymouth is showcasing the town’s rich history through stories, images and exhibitions “celebrating the memories made and the lives lived here” as part of their #WeyBackWhen campaign.
St Alban Street is Weymouth’s most picturesque thoroughfares – photo: Martin Booth
Where to eat in Portland and Weymouth
As the hatches were battened down on our first evening, every man, woman and their dog seemed to have the same idea of eating at the Cove House Inn, an 18th-century pub overlooking Chesil Beach. So make sure you book your table here if you can. Instead, we opted for excellent takeaway pizzas from the Portland Pizza Company, whose wood-fired oven is within a converted horsebox further down the beach. Overlooking the far end of Chesil Beach and also in Chiswell is Quiddles, where we enjoyed the view as much as the toasties and paninis.
Quiddles is at the far end of Chesil Beach in Portland – photo: Martin Booth
In Weymouth, you can find some of the best fish and chips on the Jurassic coast at Bennett’s on Trinity Road overlooking the harbour. My mackerel fillets were delicious – line-caught and lightly fried in Bennett’s “famous” batter – while my wife and two daughters all had the seafood basket with salt and pepper squid, butterfly king prawns, cod bites, calamari rings, a sweet chilli sauce and fish presented within a miniature fryer.
Bennett’s seafood basket costs £13.95 – photo: Martin Booth
Where to drink in Portland and Weymouth
For a small island, Portland is not short of places to drink, especially in Fortuneswell. The George Inn was King George’s watering hole of choice when he was on the island but I found myself on Friday evening at the Britannia Inn, whose landlord Tim had kindly agreed to put on Bristol versus Bath in the Premiership semi-final when I popped in earlier in the day to ask if he was showing the game. As Bath dominated the second half, I drowned my sorrows with pints of Westwood Ales’ Mad Hatter and 360° Brewing Co’s Tacoma while Tim and another punter played darts. I would have had a more enjoyable evening in the same pub if I had chosen to read a novel from the book exchange in one corner. The oldest pub in Weymouth is reputed to be the Black Dog on St Mary Street, dating back to the 1500s. For the best coffee in town, head to Finca on St Thomas Street, whose coffee is roasted at their own roastery in Dorchester. There are pastries galore and antique maps of the town on the walls.
Old maps of Weymouth line the walls of Finca – photo: Martin Booth
Where to stay in Portland
We stayed at bnb-side in Fortuneswell on Portland, a perfect spot from where to explore the island fuelled by a buffet and a full English breakfast each morning. Up some steep stairs, there are six en-suite bedrooms here. Off the breakfast room there is a spacious balcony with a view of the rooftops of Fortuneswell and Chiswell, and beyond to West Bay. Even better, guests staying at bnb-side help support b-side, a Portland-based not-for-profit community-driven arts organisation.
bnb-side’s spacious balcony offers a panoramic view of Portland – photo: Martin Booth
Main photo: Martin Booth
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