The Good

There’s no better place to begin a sightseeing tour of San Francisco than at Pier 33, from where tour boats set off across the choppy waters to Alcatraz.

Records show that 1,576 prisoners were banished to the maximum security federal penitentiary between 1934 and 1963 and although a number of infamous attempts were made, no successful escapes have ever been confirmed.

Visitors are free to explore much of the island, including the dining hall, exercise yard and what’s left of the warden’s house at their own pace, but almost everyone hurries straight to the cellblock for the award-winning audio tour, jointly narrated by former guards and inmates.

TripAdvisor users ranked Alcatraz the No 1 tourist attraction in the United States for 2018 – no mean feat when you consider the competition.

Passengers fall over themselves to photograph the Golden Gate Bridge during the boat ride, but there are better vantage points. Fort Point is about as close to the much-loved land­mark as it’s possible to get without actually walking or driving across.

For a different perspective, take your pictures of the world’s most famous suspension bridge from Baker Beach, an hour’s walk away along the California Coastal Trail. If you’re lucky, clouds of fog will be rolling in, adding atmosphere to your shots.

On the subject of hazy skies, the north end of the beach was the original site of the Burning Man art festival, from 1986 to 1990, and it’s still a popular spot in which to hang out, drink beer and smoke joints. Afterwards, head to Alamo Square, roll another joint (the recreational use of cannabis became legal in California on January 1, 2018) and ponder how a row of pastel-coloured Victorian houses known as the Painted Ladies have managed to appear in more than 70 films, television shows and advertisements.

For sheer scenery, make your way to Lombard Street, famed for eight impossibly steep hairpin bends festooned with flowers. Then, at the end, where Lombard meets Hyde Street, capture an image of a cable car cresting the hill with Alcatraz shimmering in the distance.

And while we’re checking off iconic locations, hop on a ferry over the bay to Sausalito. The laid-back seaside settlement where artists and day trippers rub shoulders is assured of its place in musical history – in August 1967, singer Otis Redding penned his hit (Sittin’ On) The Dock of the Bay while living on a Sausalito houseboat.

Literature lovers have their own sites of homage. Tours of Steinbeck Country take fans a couple hours south of San Francisco to locales that featured in the novels of the great American writer John Steinbeck.

The agricultural region of Soledad was used as the location for Of Mice and Men, his 1937 classic tale of migrant workers during the Great Depression, and Salinas provided the inspiration for East of Eden (1952). The coastal city of Monterey was the setting for two memorable Steinbeck novels, Cannery Row (1945) and the wine-soaked mis­adventures of Danny and his friends in Tortilla Flat (1935).

Ah yes, wine. California is one of the world’s leading producers and, wouldn’t you know it, Steinbeck Country is just the place to sample a few local varieties. Choose from any (or many) of the more than two dozen vineyards in the Salinas Valley, or try out a tasting room in Carmel-by-the-Sea, 10 minutes from Monterey. You’ll be glad you booked a tour and not a hire car.

The Bad

Visiting the No 1 tourist attraction in the US requires planning. Alcatraz tours often sell out a month in advance and, when booking, be sure to reserve seats on one of the first boats of the morning, as the island jail becomes crowded by 10am. Still, the early start means you can be gazing at the Golden Gate Bridge from Baker Beach by lunch­time.

The panoramic vistas are spectacular, but strong currents make the bay unsafe for swimming and the beach’s reputation as a naturist haven attracting male exhibitionists leaves some visitors less than impressed. As one TripAdvisor reviewer put it: “The good news – great views of the Golden Gate Bridge and excellent weather in October. The bad news – too many nude guys roaming around to take the family.”

Baker Beach might be a former Burning Man hang-out, but stick to beer rather than weed. The same applies for Alamo Square, or any other public place for that matter. Cannabis is legal in California, but only in the privacy of your own home or in a smoking lounge.

Better still, book a wine tour – they’ll be glad for your custom. The industry is feeling the heat after wildfires swept through the state in July. The vine­yards have suffered a double blow, as the resulting slump in visitors has been com­pounded by another round of retaliatory Chinese tariffs on agricultural products, including wine.

Average salaries in San Francisco, the Bay Area and Silicon Valley are among the world’s highest, and property prices are beyond the means of all but the top 20 per cent of earners. At the other end of the scale, homelessness and related social problems are spiralling.

An estimated 7,500 people were recorded as not having permanent accommodation in 2017 and, despite the city allocating US$271 million to address the problem, a shortage of shelter beds has led to an increase in tent camps.

The ad hoc eyesores have spread from parks and underpasses to tourist areas, including Chinatown, which “reeks of urine and faeces from vagrants being allowed to sleep in doorways and streets”, according to one online review.

Things have become so bad that in April, the president of the San Francisco visitors bureau urged city officials to do something about the needle-littered pavements, where intimidating and abusive street sleepers inject drugs in full view of passers-by. Derogatory nicknames like “San Fran Cesspool” and “San Fransicko” are making the rounds on social media, and at least one department store now keeps tents in locked cases to prevent them from being stolen.

The Ugly

The mayor of Osaka, Japan, sister city of San Francisco since 1957, cut ties with its “sibling” this week. The falling-out was over the installation of a controversial statue in St Mary’s Square representing “comfort women” from Korea, China and the Philippines who were forced into sexual slavery by the Japanese army during the second world war.

Getting there

Cathay Pacific, Hong Kong Airlines, Singapore Airlines and United all fly direct from Hong Kong to San Francisco.