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Steeped in history and nautical vibes, Simon’s Town offers the best seaside holiday in Cape Town, at a fraction of the cost compared to other areas.

Also read: 11 beautiful beach cottages for a superb summer escape

How it works:
TripAdvisor lists accommodation rated by guests, but as much as we love peer reviews, they don’t offer a comparative voice – so how do we know Number 1 is really the best? Pippa de Bruyn, who has reviewed accommodation for 18 years for the likes of Frommer’s and The Telegraph, scours TripAdvisor and other online sites when researching a destination. For Simon’s Town, she created a longlist of 30 to inspect. The following made the cut.

What we found about accommodation here:
• Like Kalk Bay, Simon’s Town offers the best sea views in Cape Town, with jagged slopes across the bay rising steeply from a glittering ocean in the curved embrace of the Hottentots- Holland Mountains. A view of this is pretty much a prerequisite, and I found plenty of great options.
• I have always coveted the properties that are just a few metres from a beach that is not only washed by translucent waters but home to African penguins. Finding that a few are available to rent was just wonderful. These houses and cottages almost never come on the market; even if they did, I couldn’t afford them.
• Most of the best options are some way from Simon’s Town’s historic high street and charming harbour, so unless you book into the Quayside Hotel you’ll need a car if you’re going to base yourself here.
• You’ll encounter the phrase ‘excellent value’ in a number of reviews – relative to the Atlantic Seaboard, Simon’s Town is a bargain, particularly in winter when the whales come to visit and the Southeaster is hibernating. Rates go up in summer and then shoot up around 15 December to 15 January.
• NOTE: Cape Town is presently on Level 5 water restrictions. Guests may find swimming pools not topped up and gardens not watered. Visitors are asked to take short showers, not baths.


Best-value large house

1. Fisherman’s Cove

TripAdvisor listed but unrated
Wow, what a find! It’s worth raising a toast of thanks to the owner that we can occasionally claim this double-storey Victorian beauty as our very own seaside home. Fisherman’s Cove is beautifully maintained, elegantly furnished and – given its location, just a few metres from Boulders Beach – offers a decadence of space. Up to 13 guests are accommodated in the main house and separate cottage overlooking a garden with plunge pool. The main house is wonderful, with double doors and sash windows filled with blue sea and sky, and a long shaded veranda and balcony with unobstructed views of the penguin colony. The substantial three-roomed cottage, to the side of the main house, is self-sufficient in terms of facilities but is only rented out with the main house. Given the location, views and superior quality, Fisherman’s Cove is extremely good value.
Room tip: The three bedrooms in the main house are the top picks. Note that Eden Cottage is right next door; assuming it’s available, you could extend the gathering for a special occasion.
Cost: From R4500 a night for up to eight people, R250 per person extra. Two-night minimum stay.


Best luxury house

2. Rocamar


Photo supplied.

Somehow, photographs don’t do this house justice. You can see, for instance, that it enjoys a spectacular position: elevated right above Boulders, though the beach is closer than you think – you walk through the garden and onto the boardwalk above it. The views are jaw-dropping. Decor is elegant and classy. With its curved walls and arched windows, tiled floors and shuttered windows overlooking the translucent waters, you could be on the Riviera. (It was built by an Italian family who modelled Rocamar on their holiday house in Saint-Jean-Cap-Ferrat.) But it is the atmosphere that sets it apart, an intangible sense that this home generates serenity and joy in equal measure. It gets pricey during peak season when the rate jumps to R10000 a night, but if budget is not an issue and it’s available, don’t think twice.
Room tip: There are four bedrooms – one has twin beds; the rest are doubles. These share two bathrooms; one is en-suite.
Cost: From R5500 a night (sleeps eight). Minimum two-night stay.


Most romantic bolthole

3. Eden Cottage

This dinky little corrugated-iron cottage was apparently shipped out from England in kit form and constructed on site in 1899 – since then it has had only three owners. How lucky we are, then, that Basia Swiel, who purchased it 25 years ago, is prepared to share it! Basia, a botanical artist, has decorated the cottage in appropriate style – very low-key and tasteful, sweetly old-fashioned but with furniture and fittings kept in perfect nick. The kitchen-living-dining area is open plan, with doors onto a little veranda-deck with lovely views of the sea – you’re a stone’s throw from Boulders Beach. The house sleeps five in three bedrooms – the two doubles are en-suite; the single room is ideal for a child who will share one of the bathrooms. This is a great choice for a family but equally ideal as a romantic getaway for two. Note that there is street parking only. Pet-friendly on request.
Room tip: If Eden Cottage is unavailable, my next top romantic choice is Cottage A at Bosky Dell, which is a few metres down the road.
Cost: From R1500 a night for four, additional person R200. Minimum two-night stay.


Best hotel

4. Aha Simon’s Town Quayside Hotel

TripAdvisor No. 1 of 1 hotel

Photo supplied.

If you want to be located on Simon’s Town’s pretty high street, strolling distance from a choice of restaurants and bars yet still have great sea views, then this newly revamped hotel is hands-down a winning choice. It has always enjoyed the best location in the village, on Jubilee Square, and a good scale – just two storeys overlooking the working harbour – but now that it’s been completely overhauled (it officially reopened in August), everything is brand new, including the bathrooms, and the decor is in very good taste. It’s a good rate, too – personally, I’d much rather be overlooking this picturesque harbour than the more populous one in the city, and spend the consequent savings at the brilliant wine shop opposite the hotel. The only irritant is that Wi-Fi costs extra – rare these days, and a pity to find such parsimony here.
Room tip: It’s definitely worth the extra R150 for a sea-facing room; the ‘mountain-facing’ rooms actually face the street – though what a pretty street this is!
Cost: Doubles from R920 per person sharing B&B.


Best-value luxury

5. Residence William French

TripAdvisor No. 14 OF 31 B&BS/Inns
William Fabre opened his guest house on the hillside in December 2016; 10 months later he had consistently scored 5 out of 5 on TripAdvisor and 9.9 on I’m pleased to confirm that the raves are much deserved. William spared no expense in fitting and furnishing the rooms, yet he’s kept the rate relatively low – for what you get, this is incredible value. Staying here is not just about getting a luxurious room and access to an infinity pool, but being hosted in a way that really is five-star. It’s William’s home but feels more like a little hotel – there’s always someone on duty (very unusual in a guest house with only five rooms), dinners are a tour de force (served Thursdays to Sundays) and the continental breakfast is the best I’ve had (eggs to order available too, but trust me, you won’t bother). William is the perfect host – laid-back yet attentive, gregarious and charming. As he puts it: ‘Running a guest house is not a job. It’s a vocation, a lifestyle and a philosophy.’ This is a man who walks the talk.
Room tip: I like the new King Room with sundowner perch to enjoy the sea view. The Garden View Queen Room may not have a sea view but it’s gorgeous, has its own courtyard and is the bargain here.
Cost: Doubles from R750 per person sharing B&B.


Best B&B

6. Watercolours House

TripAdvisor No. 6 of 31 B&BS/Inns

Photo supplied.

Splendid views fill each generously proportioned space with light and beauty; waking up in any one of the rooms, you’re tempted to just forego all arrangements for the day. There is a great pool with the same stunning view, and three communal decks shared by just 12 guests (these will not include children as the B&B does not take under-16s). Located in Murdoch Valley, above the road that winds its way to Cape Point, the house has been purpose-built by owners Sharon and Gary Leih to maximise views, space and privacy, and is very tastefully furnished. Sharon is a great hostess, leaving guests to enjoy their peace and privacy but very hands-on should you require advice or bookings. Together with Residence William French, Watercolours sets the bar for five-star hospitality in Simon’s Town.
Room tip: There are only six rooms here; not one dud. If you like the flexibility of self-catering, then book the garden room – it has a kitchenette and dining area, it’s own garden with private seating and sea view, and costs slightly less.
Cost: Doubles from R1000 per person sharing B&B.


Best for nostalgia

7. Dunearn

TripAdvisor listed but unrated
Step into this charming, eclectically furnished, double-storey clapboard house (another I have long coveted) and you’re not sure if it’s 1950 or 1980 – bizarre to find Wi-Fi here! It’s a much-loved rambling family home that has seen very little change in the last 100 years (it was shipped over from Sweden in 1902), so it definitely won’t suit those who prefer modern kitchens and bathrooms. I loved the farmhouse-style kitchen with its walk-in pantry, and the way in which it transports you to another era. The house is very old-fashioned but scrupulously clean. It’s also very secluded – surrounded by a wild garden that is basically an extension of Boulders Beach, with a gate that leads directly onto the boardwalk, and dassies and penguins who treat it as their home. All four bedrooms have the most phenomenal sea and mountain views from their windows.
Room tip: The ‘north’ and ‘south’ bedrooms both have queen beds (and the very best views). Additional pull-out mattresses can be made available for extra children.
Cost: From R2900 a night (sleeps nine, plus two children).


Best-value seafront cottage

8. The Milestone

TripAdvisor listed but unrated
What joy to wake up in this 1920s timber cottage and step onto a lawn that cuffs boulders dropping directly to the ocean, or sit outside and watch the lights flicker on across False Bay. You’re five minutes’ drive from the centre of Simon’s Town but once you’ve stepped through the garden gate, the tranquillity and seclusion is remarkable. It’s close enough to the nature reserve that you’re likely to encounter some kind of wildlife: on terra firma, genets, mongooses or – if you’re very lucky – porcupines and caracal; in the water, otters, penguins, dolphins and seals. The cottage is very cute: simply furnished and well equipped (the kitchen looks brand new), with a wonderful protected braai area and outdoor seating. Named after the stone next to the garage that marked the 25-mile point from Greenmarket Square in central Cape Town, Milestone is also very good value; during peak season, when prices elsewhere leap, Alida Croudace only ups her summer rate by R300 a night. The minimum-stay stipulation could be off-putting if you’re looking for a weekend break, but once you’ve arrived you’ll never want to leave – so just take the extra time off already!
Room tip: There is only one double bed; third bedroom has a bunk bed.
Cost: From R2200 (sleeps six). Minimum four-night stay.


Worth a look

9. Bosky Dell

A ramblin property just above Boulders Beach, its 1850s coach house and stables are converted into five self-catering cottages. Basic but comfy, it’s well-managed and in a good location. Ideal if you’re having a group gathering (there is space for up to 20); if you’re just two or four, I’d opt for A Cottage and The Stables.
Cost: From R450 per person (four to six), R500 per person (two or three), main house from R3000.


10. Whale Song

Very classy beach-chic Salome Gunter interiors; large indigenous garden (with around 30 resident penguins) located 100 metres from Boulders. The house and cottage share wonderful living spaces, a games room and classic veranda.
Cost: From R3000 (sleeps eight).
Contact: 0832798000. Find it on Facebook.


11. A Boat House

Great little B&B. Slightly twee interiors, but who cares when you have the most wonderful views? And it’s walking distance to town (seven minutes). Delivers on service and very good value, with generous extras such as sherry, muffins and fresh milk. If you can, book one of the three upstairs rooms.
Cost: From R700 per person sharing B&B.


12. Blue Waters

Gorgeous interiors and beautiful views, this recently renovated house is located en route to Cape Point. There is a swimming cove, Fisherman’s Beach, three minutes’ walk away. Extremely good value, given the luxury finishes and furniture.
Cost: From R3900 (sleeps six). Minimum two-night stay.


Don’t miss this:

• The penguins, but go early before the tourist hordes arrive (entry to Boulders Beach is R75 adults, R40 kids). Or approach from the sea on a guided kayak trip. 0825018930
• A boat cruise from Town Pier, around the harbour, to Seal Island (to see great whites breaching) or to Cape Point along the cliffs.
• Climbing on board a 1970s submarine, the SAS Assegaai, at the Naval Museum. 0217865243
• The Sweetest Thing patisserie shop (0217864200) and Salty Sea Dog’s fish ’n chips takeaways (0217861918).
• Heading to Red Hill (on the road to Scarborough) for a meal or Saturday afternoon concert at The Cape Farmhouse (0217801246).


This list first appeared in the December 2017 issue of Getaway magazine.

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The December issues features the Tok Tokkie Trail in Namibia (perfect if you dream of sleeping under the stars), 50 things to boost your summer holiday and our ultimate gear guide with the best travel gear, and much more!