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While the Navy Festival may have had rain on the parade, locals and organisers are hoping for blue Autumn skies as the second edition of the Simon’s Town Festival rolls into the seaside suburb from 15-17 May, with a weekend programme designed to show off the many attractions of this much-loved corner of False Bay. And did you know nearby Boulders Beach was voted one of The World’s 50 Best Beaches this year?
This year’s festival brings together adventure activities, heritage walks, live jazz, open-water swimming, family-friendly events and a few only-in-Simon’s-Town experiences, from a naval-themed treasure hunt to a 1km beer sprint on the town pier!
The festival is produced by Nyati-x and hosted by Bonne Esperance Guest House, with events taking place across town throughout the weekend. The format is deliberately flexible: visitors can book a single activity, build their own programme, or make a full weekend of it.
At the heart of the exploration side of the festival is the Festival Passport, a physical booklet included when you book any activity through the festival website. It can also be bought separately for R50 at the festival information hub at the Willet’s Hotel Courtyard on Saturday (16 May) between 8am and 4pm. It gives access to activities including the High Street Scavenger Hunt and Simon’s Town Skattejag, a self-guided heritage trail through the town. Here’s what else is happening at the Simon’s Town Festival this year:
Friday, 15 May
The weekend gets underway with Vino & Vibes at Bonne Esperance Guest House. The opening reception includes wine, light snacks and a live concert by Proof of Life, running from 6pm to 9pm. Tickets are R300 per person.
Saturday, 16 May
Saturday is the festival’s main Adventure, Culture & Explore Day. Early risers can take to the water with Swim Cape Town for an adventure swim in Simon’s Bay, setting off opposite Bertha’s Restaurant at 8am. There’s also the Klawer Stair Challenge, a self-paced Strava-linked stair climb running from 8.30am to 3pm.
For those more interested in the town’s layered history, two guided heritage walks will run in partnership with CTS Heritage. Nic Wiltshire leads a tour focused on archaeology and Stone Age heritage at 9am, departing from Bonne Esperance, while Jim Hallinan leads an 11am walk exploring the town’s naval, social and architectural development, starting from Willet’s Hotel Courtyard. Both tours cost R150 per person.
Families can head to Simon’s Town School for a Penguin Movie Morning and Awareness session with SANCCOB from 9am to 11am, while the Cape Coastal Rowing Club hosts a rowing regatta from 9.30am. Later in the day, Paddle Experience brings paddle polo to the marina from 2pm.
There are also two self-guided town activities across the day. Simon’s Town Skattejag sends participants along a heritage trail through town, with answers recorded in the Festival Passport. Those racing for the cash prize need to finish at Willet’s Hotel Courtyard to have their time officially recorded. Starts are open from 8.30am to noon, with the route ending by 2pm. Entries start from R300 per person.
The High Street Scavenger Hunt is a slower, curiosity-led route through the town’s main street, with participants encouraged to find answers in any order. Completed entries go into a lucky draw for prizes from local businesses, with the draw taking place before the Beer Sprint.
Music is also a major part of the programme. The Cape Town Jazz Train curates the High Street Sessions on Saturday afternoon and evening, with performances by Ashè Trio at Whyte’s Balcony at 2pm, Hilton Schilder at Natural Yarns Balcony at 4pm, and Reza Khota & Buddy Wells at the Piazza in Willet’s Courtyard at 6pm.
And then there’s Bertha’s Beer Sprint: a 1km race on the Town Pier that involves downing half a pint every 200 metres. It starts at 4.30pm and costs R100 to enter. Probably best not to schedule anything too ambitious afterwards.
Sunday, 17 May
Sunday shifts the focus to Long Beach, where the SprintSplash SwimRun combines open-water swimming and beach running in 1.2km loops. Adult distance options include 2.4km, 4.8km and 7.2km, with entries from R170.
A junior edition for under-12s, covering a 600m route with a parent, starts at 10am and costs R50.
For something gentler, Hot Huts Mobile Sauna and SoundBath will be at Long Beach on both Saturday and Sunday, while the festival closes with Bubbles & Band, a brunch and live jazz concert by the Tete Mbambisa Sextet at Bonne Esperance from 11.30am to 1pm.
What else is there to do?
Beyond the Festival programme, other activities available independently across the weekend include Cape Point e-bike tours, tuk-tuk trips through town, Cape RADD’s Snorkel for Science, shark cage diving, the Simon’s Town Ghost Walk and visits to the town’s naval, submarine, heritage and toy museums.
Simon’s Town Festival: Find out more
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