Amsterdam was almost everything you’d want from a city. Then, without meaning to, I stopped going...

Our Return Journeys series explores the joy of a nostalgic trip back to a destination from one’s past – whether a childhood camping holiday or a formative first job abroad.

This week, The Telegraph’s head of fashion Lisa Armstrong returns to Amsterdam. On first trip to the Netherlands, she was barely older than the rowdy Texan high-school students in her care as a tour guide. Returning proved a more refined – but by no means predictable – experience, and a moving one too

I fell in love with Amsterdam when I couldn’t go there. I was 15. Katy, my next sister down at 13, went instead. That’s how it was in the ’70s. Or that’s how it was in our slightly chaotic house. We never went on family holidays. My parents’ business meant summers were their busiest time. Holidays were sourced out to the school and since everyone assumed I’d be hopeless at skiing, the school cruise it was.

Any thoughts of luxury and Jackie O evaporated the nanosecond we embarked. SS Uganda was so basic they probably had to jazz her up when, eight years later, she was pressed into service for the Falklands War. We were packed into huge, below-the-portholes dorms and the seasickness was epic. Batten down, said the teachers. It’s educational.

I looked forward to comparing notes with Katy when she went on the cruise two years later. But somehow the deadline for signing up was missed and in a fit of guilt my mother told Katy to find an alternative educational experience – anything she fancied. She chose Amsterdam. Immediately I was jealous. I knew nothing about the place. But canals – what’s not to like? And Anne Frank.

We weren’t taught about the Second World War or the Holocaust at school. My parents and grandparents never talked about the latter, so I pieced it together from variable sources, including historical romances, Anne, contemporary war footage and later, a trip to Dachau.

Katy’s Amsterdam trip was a whole new level of educational. It was a group trip – accommodation was a barge. Museums, galleries and boring historical tours were extremely optional. The Responsible Adults were barely beyond adolescence themselves, and there seemed to be a lot of something called weed on the menu. No one called social services when Katy got home and recounted her ‘educational’ adventures. My mum probably didn’t know what weed was.

I was 21 before I got to Amsterdam. I’d bagged a job as a tour guide during the university holidays. What a breach of the Trade Descriptions Act (was there one in 1982?). I wasn’t trained (professionally or otherwise), had zero sense of direction, could only notionally read a map and hadn’t been to most of the countries I’d be leading 40 American high-school students across.

But I was taking a degree in French literature and knew how to say, ‘Everywhere I find nothing but base flattery, injustice, self-interest, deceit and roguery,’ in Molière’s native tongue. The tour-guide company, let’s call them Gungho Ltd, agreed I was ideal.

Gungho had oodles of Coles-type notes for guides. So long as you remembered to actually read them you could sound like Alan Whicker meets Mary Beard. ‘When in doubt, smile!’ was my motto. To be fair, it (mostly) worked.

A word about the groups who came on these tours. Some were wild, borderline degenerate. And that was just the teachers, who we were assured would be our moral and authoritative back-ups. ‘Toodle-pip,’ said Gungho at the end of our ‘induction’ day in a dodgy Bayswater hotel. ‘Any problems, our office hours are eight to five.’

Chief ‘back-up’ on my first Amsterdam trip, with 40 friendly but living-it-large Texan students, came in the form of let’s-call-him-Patrick, an anti-establishment charisma machine. We’d barely checked into our third-rate hotel in one of those not-so-picturesque, off-off canal streets, when Patrick took the curriculum for that night into his own hands: late-night opening at the Rijksmuseum or red-light district?

Only one out of the 40 voted for the museum. Let’s-call-him-Alphonse (he really did have a fancy French name despite hailing from Texas) owned the first Fendi wallet I’d ever seen and was the only kid on the tour who, when we reached Venice and were gliding down the shimmeringly beautifully Grand Canal, didn’t ask where McDonald’s was.

It being 1982, there was no way to ask any of the Texas parents for permission. Even if there had been, Patrick didn’t seem the permission type. ‘Don’t worry,’ he told a crestfallen Alphonse and me, ‘it will be educational.’ Where had I heard that before?

I read somewhere recently that the red-light district has been cleaned up and sanitised, and that tourists can be spotted taking a promenade there with their toddlers. That seems more twisted than what Patrick did. I’m not saying it was an elevating experience. It was depressing, exploitative and the live sex-act protagonists were clearly on something that even the 21-year-old me knew wasn’t weed.

I can’t speak for the effect it had on everyone else, but they were all uncharacteristically quiet on the walk home, although dear, studious, on-the-cusp-of-coming-out Alphonse and three others climbed out the window later that night using the hotel’s sheets and were MIA for a few hours. Needless to say, the torn sheets rather than the missing teens tipped the hotel management over the edge from perturbed to downright hostile. Black mark for Gungho Ltd. For years afterward, when I thought of Amsterdam it was through a miasma of sleaze.

Subsequent trips were never so drama-filled but they were more enjoyable. The hotels improved incrementally. I learnt to avoid streets lined with purveyors of plastic tulips and garish pubs. I went once in winter with an Australian who’d moved to the UK because he hated the warm weather in his native land, and the locals were skating on the canals. In summer red and white flowers spilled out of the flower boxes.

I sampled pickled herring breakfasts – my favourite kind – and smoky cannabis cafés (didn’t inhale), wept in the Anne Frank museum, fell in love with van Gogh’s paintings and developed a fascination for Dutch old masters.

Amsterdam was almost everything you could want from a city – grand, cosy, friendly, buzzy, unpredictable and completely walkable. Then, without meaning to, I stopped going. Small children put paid to mini-breaks. Older children meant holidays by the sea… In my mind and my husband’s, it was a place for backpackers (he’d Interrailed there) and carefree 20-somethings.

Then earlier this year, I read Thunderclap by Laura Cumming, an art critic with a passion for 17th-century Dutch art and a talent for making you feel you have to see the paintings she’s writing about in real life. We decided to rail it there – all the way up from Bari in southern Italy, where we’d been holidaying with friends, via Bologna, Zurich and Paris… and yes, the trains still run on time in Switzerland but nowhere else. The food? Never complain about a Great Western Railway sandwich again. On several journeys there was nothing but crisps.

We almost laughed when we finally got to our hotel three hours late – it was so civilised, with round-the-clock delicious tucker. The Pulitzer on Prinsengracht canal was such an upgrade on previous stays, I’d expect someone to bring climb-up sheets and sneak in. I’d heard great things about the comfort, the picturesque location, the inside-outside bars, the Dyson hairdryers, restaurant and new spa – but I wasn’t prepared for the quirk factor.

Carved out of 25 17th- and 18th-century merchant’s houses, every room is different, stuffed with antique and retro finds. We started in The Flower Collector’s Suite, a whimsical two-roomed love letter to the city’s longstanding history of flowers, which only opened this year and reimagines a 19th-century tulip-trader’s home – pink drawing room; dark green, picture-lined bedroom – and because they were so busy, moved on our second night to a smaller one overlooking a large, leafy courtyard.

The prosperous merchants who built these glittering seven-storey edifices, which feel so familiar to anyone who’s walked around Lower Manhattan, would approve of the Pulitzer’s current incarnation, which seems to sum up Amsterdam’s psyche: orderly and conformist on the outside, slightly bonkers inside.

The canals were surprisingly light on tourists. At first glimpse, the endless cobbled streets of red-brick gabled houses look like a model of harmonious urban uniformity. But each one is different, and while most of them have been restored to Architectural Digest degrees of glow-up, with lovely cottage-garden planting in tubs outside, and often in the canals themselves, occasionally you’ll pass one inhabited by squatters and draped in anti-gentrification banners (up the revolution).

Others tilt so precariously, you fear they’re not long for this world. You could fill your days happily criss-crossing the three main canals that form a semicircle around the city’s medieval heart, dipping in and out of cafés (weed-serving or otherwise – there’s palpably less pot aroma in Amsterdam than in London) and browsing the slightly off-kilter homeware and fashion stores.

Amsterdam has its share of chains, but also a local design scene. Róhe, a three-year-old fashion line and Holland’s answer to Toteme, is gaining major cult status, while Ace & Tate eyewear and Wandler bags and shoes have international followings. Make time too for Carmen Amsterdam, a stylish café, guest house and store that prioritises Dutch names. And if after all that you need recharging, there’s the new Beauty House with its bespoke massages and facials just off Prinzengraft, owned by The Putlizer.

You can’t not visit the Rijksmuseum – packed, despite timed entry, and if you want to get within 15 feet of The Night Watch you may have to wait for the crowd to thin – or the Van Gogh Museum. In both we used the audio tours – they’re not bad and ensure you see the highlights.

Better still was the VoiceMap audio walking tour we took around central Amsterdam. We chose one called Power and Politics, which gave us a 90-minute insight into the days when Amsterdam was the centre of the world. If you don’t know VoiceMap, do yourself a favour and download the app. You can choose from 1,300 tours in 68 countries, each priced between £0 and £16 (which you can split if you connect two sets of headphones to one phone), some narrated by local enthusiasts, others by (proper) professional guides, writers and academics.

Power and Politics took us down narrow alleys, past Rembrandt’s magnificent house and the Dutch East India Company HQ (source of so much of Amsterdam’s 17th-century wealth and its lovely-with-a-murky-past architecture), and out into its modern port.

We’d also booked – weeks in advance, as you need to with all Amsterdam’s main attractions – a visit to Anne Frank’s house, now much expanded. They’ve done it sensitively with an excellent audio guide and footage of Miep Gies, one of the people who risked their lives to help the families in hiding, and Otto Frank, Anne’s father who, I realised this time round, died only two years before I first went to Amsterdam.

It may be bigger now, but nestled in the sleek glass extension is the cramped flat where the Frank and van Pels families hid from the Nazis for two years. You enter via a claustrophobic, narrow staircase behind a bookcase. It’s become a popular spot for selfies (weird, inappropriate and officially prohibited, but apparently the only way some can filter an experience). It’s impossible not to be moved by the bravery of those who aided the families, devastated by what they endured, and uplifted by the resilience of the human spirit.

If you see nothing else in Amsterdam, this is the heart of it all; the dark, the light, the good and the ugly.

Rates for a standard room at the Pulitzer start from £412 per night. Rates for the Flower Collector’s Suite, from £850. For more information, visit pulitzeramsterdam.com