WINTER ITINERARY

Winter in Plettenberg Bay: A Cosy Coastal Itinerary from Stanley Island

There’s something undeniably magical about winter on the Garden Route. While the crowds thin out and the air turns crisp, Plettenberg Bay comes alive in its own quiet, golden way — offering cozy adventures, misty mornings, and fireside evenings. Here’s how we love spending winter days from the comfort of Stanley Island.

MORNING WALKS ON KEURBOOMS BEACH

Start your day with a fresh coastal breeze and a walk along Keurbooms Beach, just a short boat ride from the island. In winter, the beach is beautifully empty, the waves bold and blue, and the air just chilly enough to make a hot coffee afterward feel well-earned.

WINE FIRESIDE TASTINGS AT LOCAL ESTATES

Plettenberg Bay is home to some of South Africa’s most exciting boutique wine farms. Spend a slow afternoon wine tasting at spots like Kay and Monty, Newstead, or Lodestone — where crackling fireplaces, gourmet platters, and award-winning bubbles make the perfect winter pairing.

EXPLORE TSITSIKAMMA NATURE RESERVE

A short scenic drive brings you to Tsitsikamma National Park, where forest trails, river crossings, and dramatic coastal views await. Whether you're up for a relaxed walk along the boardwalk or a heartier hike deeper into the reserve, this is where nature truly shows off — even in the cooler months.

SUNDOWNERS AT ROBBERG NATURE RESERVE

Pack a blanket and a flask of something warm and head up to Robberg for sunset. With panoramic views of the bay and the crashing waves below, it’s one of the best spots to watch the winter sky shift from gold to pink to deep blue.

KEURBOOMS RIVER BOAT CRUISE

For something a little more laid-back, enjoy a tranquil boat cruise up the Keurbooms River, where the still water mirrors the forest canopy and time slows down. Bring a picnic, bring a blanket — and just float.

BACK ON STANLEY ISLAND....

Round off the day with sundowners at Stowaway, where our 2-for-1 Sunset Specials warm things up every Monday, Wednesday, and Friday. Thursdays are for Date Night: a cozy dinner for two featuring seasonal dishes and a bottle of wine. And if you're lucky, you might spot zebras wandering past on your walk home.

EXPLORE THE LOCAL ART + CRAFT SCENE

Winter is a wonderful time to slow down and enjoy the local creativity Plett has to offer. Visit Old Nick Village, where artisans showcase handmade ceramics, textiles, and art. Grab a coffee, browse the studios, or shop for something unique to take home. Or check out some of the local shops in town such as Salt and Little Victory Clothing.

SPA DAYS + SELF-CARE

What’s winter without a little indulgence? Treat yourself to a spa day at nearby wellness spots like Forest Nature Spa or Zinzi Spa. After a day of exploring, a warm stone massage or a deep soak is the perfect reset.

WHALE WATCHING

Winter marks the beginning of the whale migration season along the Garden Route. From as early as June, you might spot Southern Right or Humpback whales breaching just off the coast — especially from Robberg, Lookout Beach, or even during a river cruise.

BREAKFAST WITH A VIEW

If you’re headed into town, stop for breakfast at local favourites like Le Fournil de Plett, Down to Earth or The Palms. Warm croissants, river or mountain views, and a quiet winter morning? Yes please.

STORM WATCHING (IF YOU ARE LUCKY)

There's something strangely romantic about watching a winter storm roll in from the comfort of a cozy room. Stanley Island offers the perfect vantage point to wrap up, light a fire, and sip on something strong while nature puts on a show.

BONUS: CURL UP + STAY A WHILE

With winter accommodation specials, Stanley Island is the perfect base to explore it all. Think soft blankets, peaceful mornings, and a new coffee shop on its way to fuel your mornings.