There’s something so wholesome about winter in the Garden Route – think cool, crisp mornings, golden afternoons and coastlines and nature reserves made for exploring. Whether you’re after laid-back living or something a little more adventurous, there’s plenty to keep you busy in and around Plettenberg Bay. Here are a few of our favourite ways to make the most of the season:


Photos: Gustav Schlechter & Ocean Blue Adventures

1. Whale watching (June–November)

Every winter, the bay comes alive with the ocean’s gentle giants. Southern right whales migrate here from Antarctica to breed, with mothers and calves often spotted just offshore. Book a boat-based experience for an unforgettable look at these ocean visitors.

We recommend: Ocean Blue Adventures – one of Plett’s most trusted and experienced whale watching operators.
Also exciting to note: Recently, Plett had an unexpected visitor – a Pygmy Right Whale! Renowned South African marine mammal scientists are blown away by the rarity of such a sighting in our waters, with only a handful ever having been recorded in Plett.


Photos: Scott Ramsay & The Wanderlust Movement

2. Plett Ocean Festival (4–13 July)

A celebration of all things marine, the Plett Ocean Festival returns this July with an exciting line-up of ocean-focused talks, beach clean-ups, educational activities and more. It’s a fun, family-friendly way to connect with nature and learn about the conservation efforts happening along our shores.

3. Knysna Oyster Festival (4–13 July)

A short drive away, the Knysna Oyster Festival is a must for anyone looking for a fun winter vibe that offers a jam-packed programme of sporting events, live music, and (of course) delicious oysters in every shape and style. It’s one of the region’s most popular winter events, and for good reason.

P.S. if you’re staying at The Old Rectory, speak to our team about booking a shuttle to and from the festival.


Photos: MTO Trails Garden Route

4. The Otter African Trail Run (1–4 October)

This one is for the runners. One of the most challenging and scenic trail races in South Africa, the Otter African Trail Run spans a stretch of coastline that’s as wild as it is beautiful. Whether you’re cheering from the sidelines or taking part yourself, the Otter is a thrilling event to witness – and a great excuse to visit in early spring.

5. Plett ARTS Festival (3–12 October)

From live music to theatre, visual art to pop-up performances, the Plett ARTS Festival transforms the town into a creative playground. With events staged in both traditional and unexpected spaces, it’s a wonderful way to experience the cultural side of Plett. Don’t miss out!

6. Winter Spa Specials at The Old Rectory (until 31 August)

After a day of exploring, there’s nothing better than retreating to the spa at The Old Rectory. This winter, enjoy our limited-time spa specials designed to warm you up and wind you down. Whether it’s a deep tissue massage or a nourishing facial, let our therapists help you reconnect and recharge in our tranquil wellness space. Visit our site to see the main spa menu or check out the Winter Specials now.

7. Explore the Plett Wine Route

Stretching from Harkerville to The Crags, the Plett Wine Route is one of the smallest and most dynamic wine production regions in South Africa. At its heart are a handful of small, privately-owned wine farms (like our sister property, Kay & Monty Vineyards) crafting exceptional still and sparkling wines from the cool-climate varietals that thrive here.

Make a Weekend of It

With our Stay 3, Pay 2 and Luxury for Less offers running until 31 July 2025, there’s no better time to visit. Put on your slippers, settle in by the fire and experience the magic of Plettenberg Bay in winter. Visit our website for more details and to check availability or book online now.