Lousy brakes and wobbly legs do not fare well in San Francisco. Draped over 43 hills, the city has many dauntingly steep streets.

If you decide to go around on foot – and you should because San Francisco packs a lot in a relatively small area – be ready for plenty of huffing and puffing.

Much of the city’s charm has to do with its topography. On a recent Singapore Airlines media familiarisation trip, there were opportunities, with or without elevation, to take in great scenery – the water surrounding the city; pretty homes hugging the hillsides; the undulating spread of buildings, streets and parks; and the Golden Gate Bridge and the San Francisco–Oakland Bay Bridge elegantly standing guard over the bay.

It helped that during our two days in San Francisco, our small group of Asian journalists stayed at The Ritz-Carlton. Perched on Nob Hill, the hotel is within walking distance of several of the city’s leading attractions and popular neighbourhoods.

These include Chinatown (“the largest Chinatown outside of Asia”); Union Square, where shoppers and their money are soon parted; North Beach, known as San Francisco’s Little Italy; and the bayside Fisherman’s Wharf and the Embarcadero.

Because the city’s cable cars are a National Historic Landmark, riding one of them should be on a first-time visitor’s checklist. But after that, walk whenever you can.

The San Francisco Museum of Modern Art is near the hotel too. Reopened in May 2016 after an expansion project, the museum has the ambition and quality to warrant a visit.

Riding a cable car or a heritage streetcar is a must for a first-time visitor to San Francisco. Better yet, ride it to Fisherman's Wharf. Photos: The Star/Errol Oh

Riding a cable car or a heritage streetcar is a must for a first-time visitor to San Francisco. Better yet, ride it to Fisherman’s Wharf.

Prison break

About 10 minutes from Lombard Street – the “World’s Crookedest Street” – is the waterfront district.

All over the world, people go to places like these for seafood, shopping and to soak up the laidback seaside vibe. But in San Francisco, you can also pretend to be a naturalist studying wild California sea lions hauled out on floats at Pier 39.

The California sea lions at Pier 39 are a unique waterfront attraction in San Fracisco.

The California sea lions at Pier 39 are a unique waterfront attraction in San Fracisco.

From there, it is a short walk to Pier 33 to board a ferry to Alcatraz Island.

The federal prison on the Rock closed more than 50 years ago. Now part of a national park, the island receives about 1.3 million visitors a year.

How things have changed at Alcatraz. It used to house “the country’s most dangerous convicts”, but these days, the only thing visitors should fret about are uneven pavements, cracks and steps.

Alcatraz Island is definitely not for the birds. No visit to San Francisco is complete without a few hours spent at the former federal prison. Photos: Errol Oh

Alcatraz Island is definitely not for the birds. No visit to San Francisco is complete without a few hours spent at the former federal prison.

And when a park ranger urges you to come up with an escape plan, he means you ought to know the ferry departure schedule.

Make sure you allow for the 45-minute audio tour, a rich and smartly written aural re-enactment of life in Alcatraz.

The recording introduces characters such as the prisoner who practised the slide trombone daily despite knowing only three notes, and another who had been taught to crochet by his grandmother and passed on that skill to fellow inmates. After his release, a prisoner who had enjoyed gardening while at Alcatraz, wrote to the warden to request for a rose plant.

These bright moments of humanity are nice touches, but as you walk through the cellhouse, you cannot avoid feeling the suffocation and fear that comes with prisoner status.

The most dangerous room in this building was the dining hall. In the hands of dozens of criminals sitting together, metal knives, forks and spoons could turn into weapons in a flash. And in the kitchen, silhouettes had been painted on the knife rack so that correctional officers could immediately tell if a knife was missing.

The clothing room is one of the first things visitors see when they tour the cellhouse at Alcatraz.

The clothing room is one of the first things visitors see when they tour the cellhouse at Alcatraz.

Genteel living

It is impossible to get enough of San Francisco in merely two days, but we often have to go where our itinerary takes us. If that puts us in the Napa Valley, it is not a bad thing at all.

About an hour’s drive north of the city via the Golden Gate Bridge, the Napa Valley is by no means a sprawling wine region. The valley floor is less than 50km long and gets no wider than 8km.

The Napa Valley is picture-postcard wine country that attracts people who enjoy the finer things in life.

The Napa Valley is picture-postcard wine country that attracts people who enjoy the finer things in life.

It makes up for this lack of size with a solid reputation for producing world-beating wines and a capacity to draw people who greatly appreciate (and can afford) the finer things in life. It is hard to go anywhere in this place without encountering something with beauty, taste or craftsmanship, or all three.


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The picture-postcard wine country is promoted not just as a destination for winery visits but also for dining, hospitality, spa treatments and the arts. For example, one of the Napa Valley’s selling points is that it has more Michelin stars per capita than any other wine region in the world. It is telling that an area this small boasts two three-star restaurants and five with one star each.

One of the three-star outlets is in luxury resort Meadowood, where our group stayed for two nights. Charming lodges dot the 100ha private estate and the property is ringed by hiking trails. Close to the centre are two championship croquet lawns, where it is possible to have a couple of hours of genteel fun, wielding mallets and strategy while dressed in the compulsory all-white.

Meadowood guests stay at charming and private lodges like this one. Photo: Errol Oh/The Star

Meadowood guests stay at charming and private lodges like this one.

If Meadowood is beyond your budget and you are OK with missing croquet, search for affordable lodging in the Napa Valley towns of American Canyon, Napa and Calistoga.

Also, if you are there during Cabernet Season, which is from mid-fall to early spring, the weather is cooler and the pace slows down a bit. Hotels and restaurants are then more inclined to offer better rates and packages.

Another reason to time your trip for after the fall harvest, which ends in October, is that you will have higher chances of meeting the winemakers and enjoying the “complete wine-tasting experience” at the wineries. Like the one our group had at Round Pond Estate in Rutherford, an area in the Napa Valley that is said to be particularly good for Cabernets.

But Round Pond is not all about vineyards and vintage. It has organic gardens, olive orchards, an olive mill (one of only two in the county), honeybee hives and a vinegar shed.

The winery can thus provide visitors with a farm-to-table dining experience that features herbs and vegetables from the gardens, and estate products like extra virgin olive oil, red wine vinegar and syrups.

More than just a winery, Round Pond Estate also has organic gardens, olive orchards, an olive mill, honeybee hives and a vinegar shed.

More than just a winery, Round Pond Estate also has organic gardens, olive orchards, an olive mill, honeybee hives and a vinegar shed.

To maintain the Napa Valley as an agricultural preserve, there is a strict definition of a winery, and that precludes most wineries having full-blown restaurants. Instead, they do tastings and wine-food pairings, usually by appointment only.

To add a dash of novelty, Round Pond visitors tour the property in a 1941 red Chevrolet truck. If they stop at the vinegar shed, they will probably take part in a ritual that resembles a gourmet’s version of Holy Communion. They each extend an arm as they file past their host so that he can drip some balsamic vinegar on the back of the hand for tasting (the vinegar, not the hand).

Visitors tour Round Pond Estate in this 1941 red Chevrolet truck. — Photos: Errol Oh/The Star

Visitors tour Round Pond Estate in this 1941 red Chevrolet truck.

To sample red wine vinegar, you use a sugar cube to sop up the vinegar and you then suck on the cube. It is surprisingly quite a treat, and you will find yourself asking for another cube.

There is, however, little pleasure in tasting olive oil if you are a novice. You sip it from a glass and you are instructed to let the oil coat your mouth and slide down your throat. Then comes the burning sensation in the back of the gullet – that peppery assault is apparently a mark of superior stuff – and you cannot help but cough and cough.

It is not an elegant moment, but the rest of the Napa Valley more than compensates for that.


This media trip was sponsored by Singapore Airlines, which flies non-stop from Singapore to San Francisco daily on the A350. For more info, visit singaporeair.com/a350.