The one holiday to never take when you’re heartbroken

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The desire to flee the familiar when you’re nursing a broken heart is strong, but some destinations can heighten your sense of loss rather than help you forget it.

It’s a rite of passage that few miss. I was 28 years old when I truly felt it for the first time. It was a short relationship that was intensified by timing; he was moving overseas in six months, I was not. It was one of the rare times I threw caution to the wind in hopeful lovesick optimism that somehow it would all work out. Cut to me six months later crying in the bathroom at Sydney International Airport after a gut-wrenching farewell. The next few months were hard. There were reminders of him everywhere. I was desperate for a change of scenery when a Groupon deal too good to miss hit my inbox. This was exactly what I needed. Within two weeks I was boarding a flight with a good friend to Long Island in the Whitsundays.

Woman supping in the Whitsundays
The writer’s trip to the Whitsundays didn’t unfold as planned. (Image: Tourism Australia)

I imagined days spent stand-up paddleboarding, reading by the water and cocktails with my friend would be my ticket to fast-tracking the healing process. I couldn’t have been more wrong. I want to shake my younger self. In what world would a romantic island holiday destination – that literally involves long stretches of time where you do absolutely nothing, are surrounded by couples, and it costs nearly $50 to get a ferry off the island to explore – be a good idea? It seems obvious now. But I feel it is my duty to pass the lesson on. Do not let a cheap, exotic island holiday deal fool you. No matter how broke and desperate you are. You will spend the whole time apologising to your friend for being the world’s worst company.

Woman deep in thought on an island beach
Too much downtime is not the right fit for a post-breakup holiday.(Image: Getty Images / Skynesher)

Other holidays you’ll want to scratch from the list include a tiny home stay – isolation is not your friend, a health retreat sounds like a good idea but no amount of yoga or kale smoothies is going to help, and especially avoid travelling solo during a festive holiday like Christmas – you’ll feel desperately alone; think Cameron Diaz in The Holiday. Sure, she got Jude Law, but there’s a reason the movie ends on New Year’s Eve – that relationship was destined for a fate similar to my own. But where should you go for a post-breakup escape?

According to a recent study by research platform Journo Report, the best place to recover from a broken heart is a city – and there are 10 cities in which you’ll fare better than others. They analysed more than 80 destinations around the world, looking at factors such as the safety index, nightlife, price of hotels and meals for one as well as the number of single-occupancy households to deliver a list of cities that are safe havens for those travelling solo while harbouring heartache.

The street of Hong Kong
Hong Kong is a constant hive of activity. (Image: Getty / Nikada)

Hong Kong, with its culture of dining alone, affordable food and drink, safety and opportunity for connection (30 million international travellers visit annually) came in at number one. Followed closely by London for its vibrant nightlife, slightly cheaper hotels (compared to Hong Kong) and opportunity to meet new people. The city that never sleeps took out third place – unsurprising; who can sleep with a broken heart? But many New Yorkers also live alone, which means the city already caters well to singles. Zurich in Switzerland and Seoul in South Korea came in fourth and fifth respectively.

People on the street in SOHO London
The nightlife in London is a brilliant distraction. (Image: Getty / Marco Piunti)

Need tips, more detail or itinerary ideas tailored to you? Ask AT.

AI Prompt

The best cities to recover from heartbreak at a glance:

  1. Hong Kong
  2. London, United Kingdom
  3. New York, US
  4. Zurich, Switzerland
  5. Seoul, South Korea
  6. Milan, Italy
  7. Geneva, Switzerland
  8. Rome, Itay
  9. Amsterdam, Netherlands
  10. Edinburgh, United Kingdom

But where do you go if you don’t have the funds to splash on an overseas heal-my-heart-holiday? On the surface, a road trip seems like a bad idea, but I think I’ve done my best healing work while driving – blasting a playlist of heartbreak hits, the wind in your hair as you follow the wide-open road makes for some pretty great therapy.

Aerial view of Great Ocean Road
The Great Ocean Road is one perfect coastal towns to visit after the next. (Image: Getty / Alexwise)

The Great Ocean Road consistently tops the list of best road trips in Australia and having made the trip from Melbourne to Warrnambool with a friend I can wholeheartedly vouch for its heart-mending possibilities. I have vivid memories of jaw-dropping sunsets, vibrant restaurants, strawberry picking and long stretches of time laughing and telling stories while driving.

Driving off road in Tasmania
A Tassie road trip offers up just the right balance of adventure and city highlights. (Image: Tourism Australia)

I’d also recommend a road trip around Tasmania. I spent seven days with a friend driving the winding roads of the island state from Launceston and back via Cradle Mountain, Hobart and Coles Bay after another breakup. I poured my energy into planning each day – there was no way I was leaving this trip to chance. My friend, just as enthusiastic for me to be over my most recent heartbreak as me, infused the trip with as much fun and energy as she could muster.

Woman swimming at Wellington Park in Southern Tasmania
Making new memories with friends is the best remedy. (Image: Tourism Australia)

But as I write this a decade later, recalling all the trips I made while nursing a broken heart, perhaps the real medicine wasn’t the destination at all but the people I got to share it with. There are few heartbreaks in life that a good friend, a well-planned trip and time can’t heal. Hang in there (and never book an island holiday).

Where have you travelled to recover from a broken heart? Share in the comments below.

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Katie Carlin
Katie Carlin is Australian Traveller's Head of Content and when she’s not travelling or behind her computer, she’s hosting a dinner party (likely cooking an Alison Roman recipe), at brunch, working on extending her running k’s, or has her nose buried in a book. She joined Australian Traveller in 2018 and is responsible for leading the editorial team across print, digital, social, email and native content. Her job is to make sure we create content that connects readers to incredible experiences in Australia and beyond. In addition to sharing her expertise on travel through industry speaking engagements, Katie appears onToday, A Current Affair and various radio segments. With a BA in Communications majoring in Journalism and a career that has spanned roles at Fairfax Media and Are Media writing for titles such as The Sydney Morning Herald, The Age, and various lifestyle brands, she brings a wealth of experience to her role. Her most impactful trip to date has been swimming with whale sharks on Ningaloo Reef. For her next trip she is longing to experience the romance of train travel – hopefully on The Ghan or Indian Pacific.
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Art, wine & fireplaces: 8 reasons Bowral is the ultimate winter getaway

(Credit: Destination NSW)

    Carla Grossetti Carla Grossetti
    The Southern Highlands earns its title as Australia’s top country town in the cooler months, and it’s worth every minute of the 90-minute drive from Sydney.

    Many Sydneysiders head to the Southern Highlands in spring for the tulips. It’s one of the most stunning spring carnivals in Australia. But the ones in the know come to Bowral in winter.

    The first thing you notice at this time of year is the quality of the light. It catches the tangled limbs of the gums and tints the fields, farms and forests a pretty shade of Granny Smith green. And then, a world-class art museum, an impressive network of walking trails, great shops, cosy restaurants and bars and luxury accommodation take centre stage, making Bowral a place you want to linger as the mercury drops.

    Just 90 minutes south of Sydney, a Bowral winter getaway is the coolcation city folk desperately need. Here are eight reasons to pack a good coat and head for the Southern Highlands.

    1. Check in

    aerial of Ardour Milton Park Bowral in winter
    Check in to the gorgeous Ardour Milton Park Bowral. (Credit: Destination NSW)

    Ardour Milton Park Bowral rises like a hologram in the hazy green light as you turn onto Horderns Road. A $10 million refurbishment of the grand 1910 estate was completed in early 2026, and the beautifully restored hotel now includes 44 guest rooms washed in sage green, cobalt blue and dusty blush. The dining room at Horderns Restaurant continues with a botanical theme – earthy banquettes, floral touches throughout – and a menu that moves with the seasons.

    After enjoying slow-braised Cowra lamb and a second glass of red, move to the Polo Bar, which has a fireplace and views across the estate gardens. Build a grazing board from the dedicated Charcuterie Room and take it outside while the light lasts. If the sky clouds over, use this as your cue to enjoy a next-level spa experience at Èliva.

    2. Hunt for treasure

    couple exploring Dirty Janes bowral
    Find vintage treasures in Dirty Janes. (Credit: Destination NSW)

    Winter is the perfect season to lose an afternoon inside Dirty Janes Bowral. Over 1600 square metres of covered space houses 90 individual sellers of everything from mid-century furniture to industrial lighting, antique silverware, vintage clothing and objects whose previous lives you can only imagine. Enjoy a bit of off-the-cuff banter with your fellow fossickers in between searching for that must-have military jacket or vintage silk scarf.

    Around the corner, find the Instagram-famous front door of FoundAntiques, though the real finds are deeper inside. Bring cash, wear comfortable shoes and leave some room in the boot.

    kids posing with donald bradman statue in bowral's The Bradman Museum
    Learn about an Aussie legend at The Bradman Museum. (Credit: Destination NSW)

    Ngununggula – meaning ’belonging’ in the language of the Gundungurra First Nations people – is the region’s first dedicated regional gallery, housed inside the sustainably transformed old dairy building at historic Retford Park. The onsite White Cottage Gallery and restored grounds of the former Fairfax estate reward a slow wander. Find a spot to sit in the courtyard filled with rivulets of winter light and enjoy the plaintive call of a currawong carrying across the heritage-listed grounds. It’s one of the best things to do in Bowral.

    Add Bowral Honey Farm for a hands-on harvest experience, then continue into town to the Milk Factory Gallery to admire eclectic works by local artists in a converted industrial space. The Bradman Museum also knocks it out of the park. Australia’s largest dedicated cricket museum sits beside the heritage-listed Bradman Oval, where a young Sir Donald Bradman first picked up a bat.

    4. A taste of France

    table spread at Lucette bowral
    Enjoy a taste of France at Lucette.

    For a taste of France without the airfare, husband-and-wife team Julien and Romy Besnard – of long-loved Franquette Crêperie – have opened Lucette, a French cafe-bistro with Paris-born chef Guillaume Dubois at the helm. Dubois brings serious pedigree from Michelin-starred kitchens in France and Sydney’s former two-hatted Monopole, and it shows. Start your day with pastries for breakfast and bookend it with boeuf bourguignon for dinner. The chocolate mousse, freckled with Guerande Salt, is the kind of dish that will make you feel smug about the decision to drive south. Join the Sydneysiders dressed in charcoal coats, boots and black tights who’ve already worked this out; the whole scene is worthy of splicing it into an Instagram reel.

    Francophiles should also be across Julien’s Bowral Brasserie – led by Frenchman Julien Viel, who also found his way to the Southern Highlands and stayed.

    5. Indulge in a tipple

    Centennial Vineyards bowral in winter
    Spend time amongst the local vines. (Credit: Destination NSW)

    The drive to Centennial Vineyards passes through a beautiful woodland idyll, the countryside a fuzz of green all around. Inside the Barrel Room, a tasting flight of cool-climate pinot noir, chardonnay and reserve shiraz viognier flaunts how well the Southern Highlands does winter.

    This is a region that takes its cool-climate wines seriously, and the pinot noir is one of the stars – a gentle, easy-drinking style with red cherry aromas. Follow your tutored cellar door tasting with another glass of wine in the Terrace Bar, which overlooks the vineyard and manicured grounds.

    6. Blend your own gin

    Millsheds Distillery & Bar
    Pop into Millsheds Distillery & Bar. (Credit: Mattia Panunzio)

    Millsheds Distillery & Bar is somewhat of a local secret. The award-winning small-batch operation produces gin, vodka and liqueurs using Australian botanicals and has picked up silver medals at both the London Spirits Competition and International Wine & Spirit Competition. Beyond the tasting paddle, the hands-on blending masterclass – where you design and leave with two bottles of your own custom gin – is the experience to book, while the terrace bar that wraps around the courtyard is a fine place to settle in afterwards.

    7. Go for a walk at dawn

    Switch your phone off sleep mode and set your alarm to early. Mt Gibraltar rises to 864 metres just east of Bowral’s main street and offers the best views in town. You will pass a raggle-taggle bunch of hikers on the way up to the summit, all making the same quiet pilgrimage into the crisp high-altitude air. On a clear morning, the bony ridges of the ranges come into sharp relief against the light. The return loop takes roughly 90 minutes. A flat white in Bowral tastes considerably better after completing one of the scenic walking trails.

    8. Cosy up by the fireplace

    Aspinalls Whisky Bar & Lounge at the Berida Hotel
    Get cosy in the Berida Hotel’s whiskey bar.

    A cosy bar is the perfect complement to winter in Bowral, and there are a few worth committing to. Aspinalls Whisky Bar & Lounge at the Berida Hotel is built for long, languorous evenings. Take a seat beside the fireplace laden with gnarled logs and work your way through a few whiskies and bar bites like Rangers Valley beef tartare, or salt cod and potato croquettes.

    At Hickory’s within Peppers Craigieburn, well-dressed waiters in denim and leather move quietly between tables, and the cosy fireplace in the adjoining guest lounge attracts an Escape to the Country crowd.

    Start planning your Bowral escape at visitsouthernhighlands.com.au.