I was very excited to learnt his week that b-side, the contemporary arts organisation based on the Isle of Portland in Dorset, is launching a new winter retreat programme combining art, landscape, food and wellbeing. The three-day “bitesized b-side” retreats offer adults a chance to reset creatively, explore the island with local experts, and learn from Dorset artists and makers.
As you can see from the picture, The Island of Portland is quite a small, tied island just 4 miles long and 1.7 miles wide. You've probably heard of the southernmost tip, Portland Bill which lies about 5 miles off the coastal town of Weymouth. The Island is "tied" to the mainland by Chesil Beach.
During January, February and March 2026, b-side will be offering unique weekend stays include coastal walks, illustration and watercolour workshops, yoga, a harbour sauna session, film screenings and communal cooking using local produce - hosted within b-side’s new artist-run B&B on Portland.
Honing in on the demand for creative travel, bitesized b-side is the perfect way to try new things, have the opportunity to be creative whilst on holiday and spend some quality time in a beautiful location. For those looking for something different to a boozy hen do, a spa break or an Airbnb, b-side has the answer.
Workshops are led by respected Dorset practitioners including illustrator Alex Hallett, painter Frances Hatch, and bakery collective Modern Folk. Walks will be guided by Portland historian Andrew Cowling, taking in Fortuneswell, Brandy Row and the harbour front.
What’s Included
- 2 nights’ stay at b-side’s new B&B
- Illustration and watercolour sessions
- Guided coastal and heritage walks
- Yoga and harbour sauna
- Hands-on cooking session with Modern Folk Bakery
- Community lunches, snacks and supper screenings featuring local films
The retreat is priced at £495 per person, with only six places per weekend.
Instead of a generic wellness break, the retreat is designed to connect guests to Portland’s people, history, food and coastline. Bitesized b-side’s co-leads Cat and Poppy describe it as: “A chance to slow down with artists and locals who really know the island. It’s not about ticking off activities - it’s about curiosity, shared tables, salty walks and creativity.”
Rocca Holly-Nambi, director of b-side, said: “We’re seeing a real appetite for retreats that don’t just soothe people, but inspire them. Travellers want to learn something, make something, and connect with the places they visit - not just pass through. These retreats are our response to that shift: slow, local, and led by the artists and makers who live here. Portland is raw and elemental in winter, and creativity thrives in that kind of environment.”
If you live locally, why not check out what's on at b-side all year round or sign up for their newsletter to be kept in the loop.