Travel secrets: where you stay can be a holiday maker or breaker

The key to Airbnb success involves discerning research, beyond price and location. My rule is that user reviews should be unanimous raves.

A shopping tour is part of the Airbnb programme in Tokyo. Tomohiro Ohsumi / Bloomberg

Most people will tell you that where you stay on vacation doesn’t matter, that it’s the city that counts. I’ve unlearned this in my travels, so much so that I’ll pick a city to visit based on the place I can stay. How you experience a city has absolutely everything to do with the place you inhabit, particularly when you travel solo and are left to your own devices. No matter where you venture, the spot you begin and end your day becomes your temporary residence, the framework for the people and places you encounter, the maker or breaker of a holiday.

Great hotel brands understand this, and so they offer a mix of a predictable sameness regardless of where you are with a twist of the local experience. Airbnb is an entirely different equation: absolutely no predictability – you take the chance when you book, based on what’s advertised and users’ reviews, that what you see is what you get – and if you luck out, you get a unique opportunity to live like a local (or, if you so choose, live with a local).

The key to Airbnb success involves discerning research, beyond just price and location. My rule is that the user reviews should be unanimous raves. Keep in mind that hosts are reviewed by guests who are in turn reviewed by their hosts, and so the mutual backscratching is irresistible. I usually amplify a guest’s slightest criticisms, and move on to something else more definitive. I also look for hosts who go out of their way to be distinct, such as providing special amenities or their own local guide to their city, because it’s a sign they view this as a passion project rather than an easy source of rental income. The latter is easy to spot because the reviews mention the host was represented by an agent or the home was lacking in what was promised.

Using this strategy, my Airbnb experiences have been happily more serendipitous than not: in Tuscany, I spent a blissful week with friends in the villa of a figurative painter, whose works, normally on show in London galleries, decorated the walls; and in Sedona, Arizona, my sister and I stayed at a “metaphysical B & B” that offered a sound healing circle with crystal bowls and a horse reiki session that began with a ceremony in a tepee.

But it was my last visit to Tokyo that brought home to me the very best of what’s possible with Airbnb. Initially, I was hesitant to stay in a stranger’s place alone; plus, in Japan, so much gets lost in translation that it helps to have hotel staff for assistance. The price of a week in a Tokyo hotel overrode my resistance. On Airbnb, I found a female “superhost” (Airbnb’s designation for someone with a track record of positive reviews), with a stylishly designed studio in Nihonbashi, whose lovely manner of communicating further dispelled my fears. Nobuko sent me directions in English and Japanese, for the benefit of the taxi driver, and was waiting to greet me. As she toured me around her flat, it was clear my stay would be distinctly Japanese: she gave me two sets of slippers, one for the bathroom and one for the rest of the place, along with Crocs for the balcony, and an amazingly useful portable wireless router to carry for free Wi-Fi everywhere. Her toilet had a small sink on top for washing your hands, which ran the tap water when it flushed, and the separate shower room had a heating fan for drying clothes.

Nobuko left me with maps marking her recommendations on where to eat and shop; some illustrated books on Japan, including the highly amusing Tokyo on Foot: Travels in the City's Most Colorful Neighbourhoods; and, for good measure, origami paper. After my friends arrived to welcome me, she said goodbye, but followed up the next day by WhatsApp saying: "I was happy to have seen you and your friend hug each other with glad voice."

Nobuko's place was so meticulously organised I felt as if I had spent my week inside the tidy mind of Marie Kondo (see The Life-Changing Magic of Tidying Up: The Japanese Art of Decluttering and Organizing). Finding my way through Nihonbashi's pristine alleys, muddling through the grocery store and coming home to my new slipper ritual made me feel as if I had a new life in Japan, a world apart from my previous hotel stay in Tokyo.

However, it was a new Airbnb feature that was the cherry blossom on top of my time there. During the week, I spent three days on a tour during the beta test of its City Guides programme, in which local personalities, vetted by Airbnb, offer themselves up as tour guides, with specialised themes in areas such as fashion, food, fitness and art. (It’s now called Experiences and while at the time it was only for guests with Airbnb bookings, it’s now open to anyone, in select cities, who books through its app.)

In Tokyo, you can spend time in the instruction of sushi chefs and sumo wrestlers, kimono dressers and bonsai masters. I opted for a shopping tour with “pageant producer” Hiroyuki Ishizuka, aka Mr Makeover, who provides style advice in his favourite stores with a dash of Japanese culture as you wander the retail districts. With his photographer friends, Yasuhiro and Mikiko, in tow, we spent our first day browsing the posh shops and architecture of Omotesando, with stops at Comme des Garçons and Issey Miyake, and resting at Wall, a bar with a vertical garden hidden behind an unmarked door of the Costume National Aoyama Complex. The next day, despite a looming tsunami warning, we ventured out in Ginza, getting the VIP treatment at Gucci and Louis Vuitton (where Hiro was once Japan’s top salesperson); leafing through Japanese fabrics at the Mitsukoshi department store, which began selling kimonos in the 17th century; and ending at the 19th-century Kabukiza kabuki theatre. On our last day, we visited Takeshita Street and Laforet mall in Harajuku, the heartland of cosplay and kawaii (cute) culture. “Play is work, work is play, so very happy life,” says Hiro, by way of explanation.

While there was a language barrier, Mikiko was an able translator, and Hiro’s beaming smile of approval, when I tried on an outfit that worked, said it all for me. Each day, I woke up in Nobuko’s tiny, perfect home, excited to meet up with my new Japanese friends, and feeling found in translation.