From sailing in the bay to an iconic island prison visit – San Francisco makes a perfect city break

“THERE are seven species of shark native to the bay…

Are the exact 10 words I don’t want to hear as I cling on to the edge of USA 76, a retired America’s Cup racing yacht, making its way towards the Golden Gate Bridge from San Francisco’s famous Fisherman’s Wharf.

We’re out of the harbour in no time, as captains Pete and Jon set us to work on the winches.

With a yell of: “Heel!” – a warning for those not on the winches to swap to the boat’s high-side – we turn to the wind and the low side dips toward the water.

This experience is not for the faint-hearted, or the work-shy.

The boat needs 14 crew to operate, and there’s only four professionals onboard, so there’s no option but to get involved. 

I’m handed the wheel as we head past Alcatraz.

“It’s just like driving a car!” says Jon, encouragingly. 

I find no similarities, but the adrenalin rush quickly blows away any hint of jet lag.

The sun is setting as we head under the Golden Gate Bridge, the view straight off a postcard and certainly one you couldn’t get from dry land.

Sailing experiences cost from £87 per person for 21/2 hours (Acsailingsf.com).

Pizza the action

Ready to refuel, we head to Tony’s Pizza Napoletana in Little Italy, a 15-minute walk from the wharf, although we stop at Pier 39 to spy the playful sea lions first.

Founder Tony Gemignani has been crowned World Pizza Champion 13 times, and it’s easy to see why after a slice of the 20in Coal Fired New Yorker, £30 – which is topped with tomato sauce, mozzarella, fennel and calabrese sausage, two types of pepperoni and ricotta, all without a hint of a soggy bottom (Tonyspizzanapoletana.com).

Around the corner is Vesuvio Cafe and, once through the saloon doors, we order the signature Jack Kerouac cocktail, £12, a heady mix of rum, tequila, cranberry and orange juice.

The eclectic bar is famous for its beatnik roots – the walls are lined with artwork and the pours large (Vesuvio.com).

The best views of the city can be found at Dolores Park, so I start the next day with a huge cinnamon-sugar-and-candied-orange-zest-topped morning bun, £4.50, from Tartine Bakery (Tartinebakery.com).

I tuck into it at the top of the park, before grabbing an otherworldly carnitas taco, £3.20, from La Taqueria (Lataqueriasf.com) for a taxi ride to PayPal Park soccer stadium. 

Kicking off

It takes just under an hour – and costs £36 – to reach the home of soccer teams San Jose Earthquakes and newly formed Bay FC, who signed Arsenal Women’s defender Jen Beattie this year.

The atmosphere is festival-like, with a pre-game DJ set, an array of food stalls on the sidelines and a half-time breakdance show.

Even better, tickets start from £11 (Bayfc.com).

The game ends 3-2 to Bay FC so we celebrate back in the city with a creamy gin-based Silver Fizz, £16, at Starlite Lounge, a glitzy rooftop bar with 360-degree views of the twinkling skyline (Beacongrand.com/starlite). 

We’re staying at The Jay, a new hotel in the financial district where rooms are packed with on-trend accents such as crittall-style showers and boucle couches.

Less than five minutes away is the Ferry Building, an indoor market housing artisan bakery ACME Bread Co, where I grab a flaky cinnamon swirl, £3.35, for breakfast, and an elevated cheese sandwich, £7.75, complete with fig jam, rocket leaves and Mt Tam triple cream cheese from the local Cowgirl Creamery, for lunch later (Acmebread.com). 

We could spend hours exploring neighbouring Fog City Flea Trading Post (Shoptradingpost.com) – a treasure trove of indie fashion, home and beauty brands like Bathing Culture, a sustainable local skincare brand (Bathingculture.com) and LA-based Biology Functional Fragrances (Biologyfragrances.com).

But I leave before I convince myself to spend £15 on an adorable avocado toast claw clip.

The JailHouse Rock

Of course, no first time here would be complete without visiting Alcatraz.

The ferry departs from Pier 33, which is a 20-minute walk along the waterfront from the Ferry Building and the self-guided tour of the main cell block is fascinating, although at times unsettling.

Day tours cost £36 per person (Cityexperiences.com).

Back at the pier, the rain sets in so we head to the SF MoMa to get up close to Frida Kahlo’s wedding portrait, Frida and Diego Rivera, and Yayoi Kusama’s Aspiring To Pumpkin’s Love, The Love In My Heart – a huge polka-dot pumpkin sculpture that’s taller than me – as well as works by Matisse, Pollock and Warhol over the seven jam-packed floors. Entry costs £24 per person (Sfmoma.org).

Our last morning inevitably comes too soon.

We order gigantic SMSF Pancakes, £13, with a side of Millionaire’s Candy, £11 – candied bacon that lives up to the hype – at Sweet Maple (Sweetmaplesf.com), and head to Presidio national park, with its many hiking trails (Presidio.gov). 

After a walk along the sands of Crissy Field Beach, we take to the roof of Civil-War-era fortress Fort Point for one final glimpse of the spectacular Golden Gate Bridge and to finish our trip right where it started. 

Photography: Getty Images, Instagram/Tartine Bakery