While Hobart is small and often described as a bit ‘sleepy’, don’t be fooled. Mountainous perimeters, fresh fare from the waterfront, heritage buildings and cobblestoned streets make you feel oddly wistful and at ease, while a handful of trendy eateries will surprise you.There’s also something incredibly restorative about getting off the beaten track for just under a week, to somewhere that is a mere hour flight away. And after spending a sunny summer week admiring the treasures of Tasmania (predominantly on the East Coast), Harrolds can attest to there being plenty to do. You just need to know the right places to go.

That’s exactly why we’re serving you a freshly-trialled, pint-sized travel guide. We’ll cover the crowning jewels, insider tips and essential dressing material for daytime and eveningwear outings in a cool climate. Always remember a chic blazer, a structured tote, some fabulous headwear and something cocooning for when the sun goes down.

Day One: 

Mona takeover.

Mona was the much-anticipated mission on the first day of Harrolds’ Tassie takeover – and for good reason. You’ve likely heard stories of the remote, eclectic and deeply provocative island gallery by the iconoclastic entrepreneur, David Walsh. The utopic (and sometimes dystopic in its art exploration) ‘isle’ of Mona is actually reachable via road or boat on the ‘Mona Roma’ — a series of camo-clad ferries that depart from Hobart frequently each day. We boarded the ‘Posh Pit’ section to recline, quaff champagne and be indulged in small delicacies for the quick, half-hour voyage. Upon arrival, Mona looks like something of a fantasy. As you take in the interactive sculptures, sheer scale and outdoor dining precinct (complete with a live stage and bean bags), it’s clear to see that this is a place of true escapism. We almost immediately forgot that Hobart was just across the way.

To do: 

• Book yourselves in for a wine tasting at Moorilla, Mona’s very own — wait for it — cellar door. Taste unusual and mind-bending wines that challenge what you know about your favourite varietals.

• After some light lubrication, it’s time to bunker down at Faro Bar + Restaurant, Mona’s elusive, exclusive and immersive dining room. We unknowingly entered a live, performative art experience, with numerous musicians playing incredibly quirky masterpieces over lunch. You’ll be bewildered, well-fed, a little bit tipsy and in fits of laughter throughout the feature-length degustation. Expect ‘faux oysters’, ‘edible plastic’, and reimaginations of the Tassie seafood you’ve been long-awaiting in a fine dining context.

• Now, it’s time to experience the gallery itself. Challenging notions of sex and death, Mona’s prestigious curation of maze-like exhibitions will enthrall you in an all-sensory experience like no other. Some dark, perverted and eerie arenas of the gallery walk will leave you feeling beguiled, while others implore you to sit, recline, and study some (very iconic) anatomy. If you know, you know.

• Take yourselves to the Mona gifting boutique and don’t fight your desire to purchase gorgeous coffee table books or elaborately-shaped soaps. Every single touchpoint of the island (from quippy signage to tongue-in-cheek copy at every turn), is thought out with precision. We came away with David Walsh’s biography and a bible on Mona’s inception story. Very eager to voraciously consume these.

• Round out your Mona extravaganza with a drink at golden hour, before your late 6pm ferry departure. We soaked in some afternoon sun and keenly people-watched while sipping on a fine Tassie wine. Bliss.

Day Two: A Journey East.

You may only need a night or two in Hobart, and we decided to bookend our trip with a ‘city night’ at the beginning and a night at the end. This makes it very easy to get back on the plane, and eliminates the need to rush around too much, or do an obscene amount of travel in one day. On our first morning waking up in Tassie, we went for a stroll around Salamanca Square and flitted around some stores, namely the Hobart Book Shop which is a literature enthusiast’s dream. Grab a coffee from Parklane Espresso (a tiny hole in the wall) and grab some Tasmanian talismans. Sadly, we missed the Salamanca Saturday Markets, but they have come highly recommended and we’ll definitely return to witness them one day.

Day two’s mission was to pick up our rental car and zip down the East Coast, to where our Airbnb villa was booked for a two-night stay, with gorgeous pit stops along the way.

To do:

• Before you leave the city, grab brekky at Berta or Jackman & McRoss (for all of the baked goods). Sit alfresco and watch the world go by as you finesse your Instagram uploads from the day prior at Mona.

• After driving for a couple of hours straight, you’ll eventually hit some glittering, pure-blue coastline. It will unfold like magic, right before your eyes, and you’ll question how on earth such natural beauty is possible. We made an emergency oyster break at Melshell Oysters, coming hotly-recommended by a good friend (and Tassie expert). This mere, vintage little shack is surrounded by a pavement of empty oyster shells, surrounded by a perimeter of water-view bench seats to sit while you drizzle lemon and indulge. These oysters were some of the largest and freshest of their kind — a must-visit on your East Coast jaunt.

• Milton Wine was our pick for lunch. And when I say lunch, I really mean a silky glass of pinot paired with a triple cream brie and lavosh crackers. This small-scale, picturesque winery overlooks a body of water and boasts daily tastings. If you’re heading towards Bicheno and Bay of Fires, this is a tactical wine break for the drive. We just missed out on a lunch spot at The Waterloo Inn in Swansea, headed up by an ex-Movida chef — one for next time!

• Speaking of Bicheno (touted a “relaxed beachside town” by Discover Tasmania), you’ll want to stock up on a couple of fine Tasmanian wines from The Farm Shed if you’re passing by.  Bicheno is “known for its stellar seafood and proximity to a pair of contrasting national parks”, complete with a bakery, cafés and other spots to refuel. The Farm Shed houses an impeccable, expertly-curated range of Tasmanian-only wines, spirits and brews, designed to showcase the very best that local winemakers on offer.

• After checking in at our secluded, water-surrounded Falmouth villa, we headed to Meresta Eatery in Binalong for dinner. This gave an entirely new meaning to dinner with a view, doused in miraculous evening sunshine, alive with atmospheric energy, and complete with a faultless lookout onto Binalong Beach. We shared a fresh fisherman’s basket and seafood gnocchi over pristine vistas. Go for a walk on the whitest sand before you retreat home to open that bottle of wine you stashed earlier.

Day Three: Shucking and shacking.

A quick trip to our new ‘local’ coffee spot (Swims in Scalamander) was on the cards for our morning routine. This pop-up haven hosts really good lattes and solid, tasty brekky bites like avocado on toast and bacon-and-egg rolls. It’s always pumping, and has people scattered across its sprawling front lawn as they take in — you guessed it — the neverending ocean views.

We were restless with excitement for a midday oyster shucking stint. You can pre-book (in advance is smart) for exquisite oyster tours on the East Coast, to unlock a new party trick and learn about the sheer TLC that goes into growing your favourite champagne accompaniment.

To do:

• We booked in with top-rated and multi-award-winning Oyster Bay Tours, run out of Freycinet Marine Farm. The lovely Declan guided us and other soon-to-be oyster aficionados through a clever and considered experience. We hopped into the shuttle bus and passed a Tasmanian Devil sanctuary on the way to the farm itself, before arriving at the shoreline. They’re not Bottega, but the khaki green ‘waders’ that you’ll step into make for a hilarious, immortalised photo memory of this moment. After wading out into the water and seeing the various life stages of baby and adult oysters, we returned to get to the good part — DIY shucking a dozen of your own oysters, complete with a crisp glass of local riesling and a freshly-made bowl of mussels by Declan. The best mussels you might ever have.

• All of the shucking and upskilling will leave you hungry (again), so a quick visit to Ironhouse Brewery could be on the cards. Share cheese and a Pale Ale on the sweeping balcony, and stare out into the abyss of perfect blue. If you haven’t realised by now, there are no bad views out here.

• Book a late-afternoon tasting at Waubs Harbour Whisky Distillery if you’re into the stronger stuff. But be warned, these potent pours are not for the faint-hearted. This maritime Tasmanian single malt whisky distillery is situated right on the edge of the ocean in Bicheno. If you can muster the strength, the interiors and harbour locus of Waubs make it one of the coolest spots to while an hour away at.

• Dinner should be had next door, at a spot you’ll likely return to the next day. Bicheno’s lauded Lobster Shack came raved about by so many former locals and friends, replete with freshly-farmed, finger-licking, impossibly tasty seafood. You can’t miss out on one of their famed lobster rolls, all juicy, generous and saucy. Pair with calamari and chips, as well as a good rosé. Gaze out at fisherman’s boats, holidayers and locals selling the dream of coastal living down south.

Day Four: The finer things in life.

A dazzling 23-degree forecast made this a sacred day of winery-going, and spending time in the great outdoors. After another morning coffee and bite at Swims and a quick goodbye to the local sheep, we checked out of our accommodation and dressed up for a visit to the iconic Devil’s Corner Winery.

To do: 

• Originally grabbing our attention on 2022’s season of Masterchef, Devil’s Corner Winery is the pinnacle destination for a full-blown ‘winery day’ in Tasmania. Summoning local produce from Frecyinet Marine Farm  (foreshadowed by our oyster shucking just the day before), and sizzling pizzas courtesy of Tombolo Freycinet, the food is just as good as the vino. That’s saying something. After being poured a stellar lineup of wines at the Cellar Door, we landed on our favourites being the Estate Pinot Noir and the Riesling. They were luxurious.

• Scoop up a complementary picnic rug and park yourself on the Devil’s Corner hill, with your chosen sip. With the right company, you could effortlessly spend hours here, occasionally order a new bottle here and another round of chips there.

• Our accommodation this evening was a one-night-only (not enough) stay at the new Little Beach Co Glamping (LBCG). Laden with sustainable, state-of-the-art infrastructure, gorgeous bathing suites and glamorous bell tents, this is glamping done the Harrolds way. You’ll feel completely immersed in nature, but spoilt by the modern comforts and finishing touches that have been so carefully planned out to execute this unparalleled experience. Explore neighbouring fairy-pools and brave a dip, or sit out on your private deck and take in the sunset with a good book. Anything Deborah Levy is on our proverbial nightstand, and Sunbathing by Isobel Beech is a resounding summertime favourite. There are even private, waterfront villas with canaras and self-contained plunge spas if you’re feeling extra fancy.

• The beauty of LBCG is in its ‘have at home’, locally-sourced dinner offering. With an uncompromising love of local produce, LBC’s founders gather fresh salmon, glorious steaks and plump pumpkins for the crux of your feast. There was also crusty bread, parmesan-tousled salad, dipping olive oil and potato gratin on the menu. After choosing your protein, you’ll be guided to the boujée outdoor cooking stations, where you can prepare your salmon or steak with a glass of wine in hand. Sit down to eat by the firepit or make friends in the dining room with fellow glampers.

Day Five: Nature and Pet Nats.

As they say, all good things must come to an end! It was time to reluctantly leave Little Beach Co and get Hobart-bound for our final evening in the city. We couldn’t depart without factoring in a visit to the veritable star of the East Coast — Frecyinet National Park. And after all of the wining and dining, a hike seemed like a very good idea.

To do:

• It would be silly to go home without visiting Governörs Bicheno, sizing up a gourmet toasted sandwich and an iced latte. Run by some very cool, surfer-looking foodies and boasting the all-white, beachy aesthetic to match, this is the chicest café on the coast. Governörs is also an intimate wine bar on weekend nights during the summer, how fun.

• After a questionably heavy carb-loading, we embarked on our drive to Freycinet National Park, where you simply pay for a parking day pass, slap on some SPF, get into your favourite activewear and plan your bespoke hike. We went for the entry level, hour-and-a-half-ish trek to Wineglass Bay lookout. After what felt like thousands of uphill steps, a beautiful and undisturbed bush gave way to a jaw-dropping, postcard scene.

• If you have time post-hike, visit Frecyinet Lodge for a cocktail at sundown, or check into Saffire for an unbelievably elaborate stay. Anniversaries, special celebrations or midyear ‘just because’ overnighters would be well-spent there.

• After checking into inner-city hotel, The Movenpick, we devised a plan to arrive at Sonny (on a Monday) at 4:30pm to avoid the inevitable waitlines out the front. No bookings here, remember! The intimate, lo-fi wine bar did not disappoint, filling up within a matter of minutes after we got in ‘early’. Prince was playing on vinyl, garlic wafts filled our nostrils and the service was swift. We swished around a few natural wines and relished in the most perfect morsel that is their crab toast with caviar. Savour every bite, or just order several more. Their second venue Ogee has just opened, and rumour has it that the craze will follow.

• Grab a nightcap at The Den (a cosy, chalet-reminiscent bar and eatery), or In The Hanging Garden for a vibier, ‘happening’ spot. We’ve heard The Den is known for their occasional Jazz Nights, and the latter descends into late-night hedonism with DJs and dancing. Pick your night of the week and corresponding dining plans wisely.