Samuel Shelley
Samuel Shelley
14 Day Trip

Island Indulgence

Two weeks of pure indulgence, Tassie style. Think mountain sunsets, pinot matched with rich dark chocolate, crackling fires and hunting for rare truffles. That’s what we have in store for you.
Day 1

Hobart for two nights

There’s no better way to greet the city than 1,271 metres up, on the peak of kunanyi/Mount Wellington. It’s fresh up here in winter and might even be blanketed in white. All the more reason to give your fave winter jacket some love.

Follow the mountain bends down to Hobart on a bike tour then set sail with Hobart Yachts. There’s everything from tailored lunch cruises to voyages to the secret coves of Bruny Island. Ask the captain about his former pet parrot.

Day 2


Here on a Saturday? Pick up a hand-knitted beanie at Salamanca Market, the country’s largest outdoor market and Tasmania’s most popular attraction.

Don’t miss a ferry trip out to Mona. Opt for the ferry’s Posh Pit, get snug inside and up front with a glass of bubbles. Let David Walsh’s subversive adult Disneyland take you to another world, deep underground where cocktails flow at The Void bar.

Once you’ve emerged from the depths of Mona, have an evening meal at Frank Restaurant not far from where you get off the ferry back at the waterfront’s Brook St Pier. Then it’s a brisk short walk to your two-night stay at MACq01, Australia’s first storytelling hotel. They call it ‘informal luxury.’ It’s bliss.

Couple drinking at The Story Bar, MACq01
Adam Gibson
The Story Bar, MACq01

Day 3

Maria Island

Time to leave Hobart behind and head up the east coast. Cruise to Maria Island from Triabunna with Navigators. There are no cars on the island but plenty of grazing wombats, and they’ll all be wearing their best fur coats. Explore the island on foot or hire a bike once you’re there. You’ll get to Fossil Cliffs or Painted Cliffs much more swiftly and remember, no traffic to worry about. Then again, catch one of the island’s best views at the top of Bishop and Clerk. It’ll take 3-5 hours walking and rocky sections may involve puffing.

Back on ‘mainland Tasmania’ indulge at Spring Bay Seafoods. Spring Bay mussels plucked straight from the nearby pristine waters might be just the thing. This evening, continue on and stay at Freycinet Coastal Pavilions in Coles Bay. Be the first of your friends to stay in a heavenly snug pod this winter.

Day 4

Coles Bay

Set off on a Wineglass Bay Cruise with Duncan. He’s been cruising these waters since starting out as a fishing charter back in 2000. Go up front and ask him where the sea eagle nests are? He’ll point out a nest as big as a queen-size mattress, if the timing is right, or maybe a migrating whale.

Get your legs moving with a walk to Wineglass Bay. Spectacular in summer or in the middle of winter, throw a scarf around your neck and walk to the look out. Those feeling energetic will appreciate the chilled pure sand under bare feet on a wander down to beach level. You might even meet the curious wallaby who likes to go for a beach hop.

afterwards, indulge in fresh Melshell oysters at Dolphin Sands. It’s an oyster shack, it’s a love shack. Crack open a dozen and watch the boys work away out on the farm.

Day 5

Bicheno to St Helens

If you weren’t lucky enough to spot a whale while on Duncan’s boat, spend some time at Whalers Lookout in Bicheno. Surely with a name like that …? At low tide, take a walk out to Diamond Island. There’s also a blowhole that’s well-worth a visit – especially in winter.

For your next mission, we suggest layering up. On the Bay of Fires Eco Tour, the sea breeze can whip. Expect an exhilarating salty taste in your mouth after roaring up and down the coast on a boat built by the skipper.

Let your host and chef at Bay of Fires Bush Retreat cook you a wintery feast over the fire tonight. Then curl up in a warm bell tent and drift away to bush dreamland.

Day 6

St Helens to Launceston for one night

The Pyengana Dairy Company is something else. The cows don’t move particularly fast here. They line up to be milked when they’re ready and then reward themselves with a good back scratch. These happy cows turn out some extremely good milk and cheese. They’ve been making hard cheese here for more than a century. Make sure you take some with you for the road trip.

Next stop, Evandale. Lose hours in the antique stores and galleries here. Be sure to check out the National Trust Store and enjoy some delicate pastries at Ingleside Bakery. Rolling into Launceston, go straight to Waverley Woollen Mills and choose yourself a merino scarf. It’ll come in handy tonight for the Launceston City Ghost Tour. One must be rugged up to hear the chilling tales of the town spirits.

For winter dining, time your trip around the Stillwater Truffle and Pinot Dinner, 28 July. This gala evening is about celebrating Tasmania’s black Perigord truffles and of course pinot. Even more special, 28 July is the night of the blood moon.

Tonight, Hatherley Birrell Collection is home. Look out at a 180-year-old Magnolia and sink deeper into that outdoor volcanic stone bath.

Day 7

Launceston & Tamar Valley

Get your early morning march on today with a walk through Cataract Gorge. It’ll make you feel better when indulging on a full day Tamar Valley wine tour later. Could there be a better combo than pinot and chocolate? Spend the day finding out with cellar doors matching their deep reds to sweet chocolate morsels.

red wine and platter of cheese and fruit at a vineyard
Rob Burnett
Wine and cheese at Josef Chromy cellar door

Stay at Woodbridge Farm, in Relbia. Follow the hawthorn-lined drive up to a heritage-style home built with century-old bricks. Help yourself to the veggie patch and create your own winter feast. The inviting provincial farmhouse table seats up to 10.

Day 8

Tamar Valley

At Josef Chromy, opt for a Go Behind the Label Tour followed by an decadent, slow lunch. Their award-winning wine is the product of hand-picked fruit, processed within 48 hours of leaving the vine.

If you’ve done your dash with the wine for now, head towards Latrobe and treat yourself to a snowball, a big fluffy mound of marshmallow goodness, at Anvers Chocolates. Continue on to Narawntapu National Park where mighty Forester kangaroos emerge come dusk and long winter beach walks call.

Time your trip around the Devonport Jazz Festival, 28 and 29 July at Ghost Rock Vineyard. They have Sunday music sessions and offer food and wine workshops through Hundred Acre Accommodation, onsite.

a woman and a man standing in restaurant
Harriet Stevens, S. Group
Hundred Acres at Ghost Rock, Alicia Peardon and Justin Arnold

Day 9

Tamar to Cradle for two nights

Dial up the car heat, it’s time for a mountain road trip. Following the Cradle to Coast Tasting Trail, expect to pull over more than once to indulge. At Deloraine Deli staff will gladly pack you a hamper for the road, brimming with the best pickings.

Spend some time at Truffle Tasmania, hunting for truffles with Henry. His face might seem familiar. That’s because he featured on My Kitchen Rules and girls across Australia instantly fell in love with him. Henry is humble and lovely as can be. He’s also very good at finding truffles with his dogs. He’d claim a ‘tummy ache’ in his early days just to get out of school and go truffle hunting.

Get up to Cradle Mountain and begin your winter warming treatment with a whisky or wine by the open fire at Altitude Lounge Bar. Follow up with dinner at Altitude Restaurant. Order your steak seared on a 360°C volcanic stone, sealing in all the natural juices.

Tonight, wrap yourself in the warmth of Cradle Mountain Lodge. Go with the King Billy Suite. You won’t be sorry about that outdoor hot tub or roaring fireplace.

Day 10

Cradle Mountain

Not too long ago the Wilderness Gallery had a makeover. If you’ve been before, come see the new look gallery. Get inspired to get outside (not easy when the heaters are on). Okay, no need to go outside straight away. These two weeks are about indulgence so Waldheim Alpine Spa ticks the boxes with its cosy rugs, fire and steaming spa.

Want to really impress someone? Providing it’s a mild winter day, Cradle Mountain Helicopters offers the chance to take your picnic to a mountain top. That won’t be forgotten in a hurry. Make sure you have that beanie and puffer jacket though!

Tonight, the promise of cheese and wine tasting comes at 4pm. Head back to Cradle Mountain Hotel for a journey through six handcrafted wines, paired with three local cheeses.

Pull up beside a log fire for a hearty dinner. There’ll be no feeding frenzy over your slow-cooked lamb shoulder – it’s all yours. Pick a pinot from the earlier tasting before retreating to your highland cabin.

Day 11

Strahan for two nights

Back on the road and it’s time to head to the west coast. It’s quite a drive to Strahan, but worth every minute. The winter reflections on the Gordon River are amazing. Hop aboard a Gordon River Cruise and yes, it’s never too early for sparkling. Come nightfall, wrap a blanket (provided) around your knees for The Ship That Never Was. For most of the year it’s an open-air performance so don’t refuse said blanket, but from June to August the play takes place at the Risby Cove Theatrette. If you like being called up on stage, hang out in the front row, but they’ll still find you in the back one.

Feast on fresh seafood right down by the water at Risby Cove and then lay your head at Captain’s Rest. The fireplace is a winner and so is the quaint jetty. Edgy and beautifully styled, it’s the place to rest tonight.

Day 12

Strahan day two

Next day, go to the People’s Park for a local meander. Hogarth Falls is one of Tassie’s 60 Great Short Walks and takes you through the sweet-scented forest up to cascading falls. If it has been raining, even better.

Back at the wharf, wander into Wilderness Woodworks and don’t be surprised if you buy what’s being turned by one of the crafty locals. Tonight, watch the sun sink from the hilltop with a glass of pinot while wrapped up in your new favourite Waverley Mills woolly.

Day 13

Strahan to Pumphouse Point

Head to Queenstown and when the whistle blows, hop aboard the West Coast Wilderness Railway. There’s Yulefest in July, adding a festive glow to the carriages.

After travelling under steam, continue on to Pumphouse Point in the Cradle Mountain-Lake St Clair National Park for one or two sleeps. You’ll want to be there for two – sleeping on Australia’s deepest freshwater lake and watching winter mist roll in over the lake is an unforgettable experience. They also have The Retreat, a new high-end offering on the lakeshore for the extra-indulgent minded.

lounge room overlooking lake in the Tasmanian wilderness
Adam Gibson
The Retreat, Pumphouse Point

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Day 14

Head back to Hobart

You won’t want to miss the Wall in the Wilderness on your way home. It’s spectacular. As you wind your way back to Hobart, reflect on the winter break and return home feeling rested and renewed.

Availability of experiences in this itinerary may be subject to opening times, seasonal operation or booking requirements. Please call ahead to plan each day.