It was my 12th trip to Australia when I finally made my way to Tasmania. I had been designing itineraries here for years, sending clients who always came back glowing — and I kept telling myself I’d get there eventually. I had sent so many travelers, and finally it was my turn.
Tasmania is one of those places on the Australian map that is often overlooked, and it should not be. Sitting roughly 150 miles off Australia’s southern coast, it earns your attention from the moment you land: the history of the convicts, the freshest air in the world, amazing scenery, beautiful beaches, unique wildlife, and a food and drink scene that genuinely caught me off guard. They have the freshest produce, amazing seafood, opulent wines, and some of the best craft single malt whiskies that are internationally recognized.
I have been four times now, and all have been between the months of November and April. If you’re already planning an Australia trip — or wondering whether to add a few nights beyond Sydney or Melbourne — Tasmania belongs on your list. Here’s what four nights based in Hobart could look like.
This was a highlight for me as I am a nature lover as well as a food and wine fan. I wanted to see the convict history, I wanted to taste the amazing wines and local specialty foods, I wanted to see the wildlife and waterfalls. Tasmania checked every one of those boxes — and then surprised me with several I hadn’t thought to put on the list.
Hobart is the capital of this small but mighty state and an impressive base to travel from. It’s compact, walkable, and genuinely characterful — and virtually everything I’ve described below is within easy reach.
Day 1: A Private Tour Through Tasmania’s Wine and Whisky Country
Tasmania is recognized around the world for the wines and single malt whisky they produce. The cool climate — a product of those far-southern latitudes — is ideal for cool-climate varietals, and the results are exceptional.
I had a private wine and whisky tasting tour that included two vineyards and ended with a stop at Lark Distillery. It made for one of the most enjoyable days I’ve had in Australia — and that is saying something after more than 20 visits to the country.
We started at Derwent Estate Winery and the Cellar Door Tasting Experience. This historic building dates from 1820 and sits on the Derwent River. Beautiful views combined with beautiful wines made for a perfect start to the day. The winery is built out of straw bales — quite unique for sure!
Then we visited the modern Pressing Matters winery in the Coal Valley. The contrast with Derwent Estate was striking — a completely different variety of tastings that were wonderful, and the staff were so knowledgeable and welcomed us to the estate.
Our last stop was Lark Distillery. The tour through the historic estate, cooperage area, and production areas was very interesting — even for a non-whisky drinker like me. I was told by several people it was fantastic, and I have every reason to believe them.
Insider Tip: Did you know Tasmania is one of the Southern Hemisphere’s most significant hop-growing regions, producing varieties like Galaxy and Vic Secret that have become prized by craft brewers around the world? Hops have been cultivated here since the 1800s, and you’ll see the bines climbing across the Derwent Valley countryside as you drive between tastings. One more thing worth knowing: tour tastings can be customized to your preferred varietal of grape or whisky preference, so don’t hesitate to ask when you book.
Day 2: The Haunting History of Port Arthur and Cascades Female Factory
No visit to Tasmania is complete without confronting its convict past — and the Hobart region offers two of the most powerful ways to do so anywhere in Australia.
Port Arthur
Port Arthur is the best-preserved remnant of a convict colony in Australia — a UNESCO World Heritage Site, and one of the most atmospheric places I’ve ever walked. It is not the only one, but it is certainly the most complete. The remnants of Port Arthur are spooky and truly feel haunted. The scale of what you encounter — the penitentiary, the church ruins, the model prison — gives you a visceral sense of what life here once meant.
Even if your crime was stealing a loaf of bread in England, you could have been sent to Tasmania as a criminal. The stories that the docents share of what the male convicts endured at this location are harrowing — and utterly unforgettable. Plan for at least a half-day; there is far more here than most people expect.
Cascades Female Factory
Back in Hobart, Cascades Female Factory tells the emotional story of convict women and girls — their lives uprooted, the challenges they faced, and the courage they carried as they became part of Australia’s history. Women were transported under the same brutal penal system as the men: convicted of crimes in Britain, shipped across the world, and assigned fates determined by the colony. The well-behaved were sent to work in more comfortable homes; the others endured hard labor for 12 hours a day. To walk through the rooms and cells where they were kept was very eerie as the stories unfolded.
Having a guide at both locations is a must. Truly remarkable experiences.
Day 3: Wildlife at Bonorong and Art at MONA (January 2025)
Bonorong Wildlife Sanctuary
Our morning started with our drive to Bonorong Wildlife Sanctuary. For many of my clients, this becomes the single most memorable stop of their entire Australia trip — and after my own visits, I completely understand why. This was my third visit to the sanctuary, and I find something new each time.
The owner, Greg Irons, is a very passionate advocate for wildlife and his staff. On this visit, he gave us a tour of the wildlife at the sanctuary, the hospital and recovery area, and of course the all-important Tasmanian Devil. They are cute from a distance. The males can reach up to 30 lbs. and the females up to 20 lbs. They are also loud, assertive, and absolutely fascinating to observe up close.
The sanctuary takes in injured and orphaned creatures of all sizes on the island. If they cannot be rehabilitated, then they become the residents you see on your visit. Every animal here has a story, and the guides share those stories with a level of care and knowledge that makes the visit feel genuinely meaningful — not like a tourist attraction.
After our tour, I went to buy a bottle of water. The line had grown quickly, and all of a sudden Greg was behind the counter helping with orders of food and beverages. That tells you everything about the kind of place Bonorong is — the owner is right there, in the middle of it, every single day.
MONA — The Museum of Old and New Art
On our way back to Hobart, we stopped at MONA (Museum of Old and New Art), often described as the largest privately owned art collection in the world. And since my last visit, it has grown to include the Phrontisterion, which houses David Walsh’s remarkable collection of books, manuscripts, rare volumes, and maps.
To say that David Walsh’s collection is unique and eclectic is an understatement. From antiquities, Christian Orthodox art, and impressionism to modern work and everything in between, there is something for everyone here. Prepare to be provoked. There are several pieces that can start arguments between friends, if you let them.
This needs a full day to visit both the art and the books — which is precisely why they now have a restaurant, brewery, cellar door, and live entertainment on weekends during the summer. It is a world unto itself.
My Top 5 Tips for Planning a Hobart Trip
1. The Best Time to Go
Plan for October through April. Between May and September, the weather gets cold, and some parts of the island receive snow. All four of my visits have fallen within this window — and the temperatures make day-tripping through the countryside far more pleasant.
2. How to Get Around
I always suggest a private guide to get you around. But if you’d like to try self-driving, this is actually a great place to do it. The roads are well-marked, and getting from town to town is quite easy. Just remember: you’ll be on the left.
3. What to Pack
Tasmania is a smart casual destination. Leave the fancy dresses and blazers at home. For virtually any restaurant or experience on this list, nice jeans or chino-style pants will work in any situation. And above all: bring layers! Hobart is on the water and can get chilly in the evening, or if you venture up into the mountains.
4. Don’t Miss the Salamanca Market
Salamanca Market is a must. Block out a full day — Saturday — in Hobart to experience it. This market is full of local artisans and runs from 8:30 a.m. to 3:00 p.m., filling up quickly as the morning goes on. From local jewelers and woodworkers to wool weavers, bakers, and leather workers, there is something for everyone — and the locals come to browse right alongside you, which gives the whole scene an authenticity that tourist markets so often lack. I have brought back local wood products, handmade jewelry, wool items, and local honey — just to name a few.
5. Plan to Stay Longer Than You Think
The one thing I genuinely wish I had known before my first visit is this: Tasmania rewards those who linger. A four-night stay is a wonderful introduction — but it only scratches the surface. If time allows, push further west. The Wild West Coast and Cradle Mountain National Park are landscapes unto themselves, and they deserve more than a day.
Where I Stayed: MACq 01 Hotel, Hobart
This hotel is in a great location along the waterfront, and it is easy to walk to Hobart’s sights from here. It suits families, couples, and singles alike, with very large rooms and a concept that is genuinely unlike anything else I’ve experienced in Australia. There is a theme where all rooms are named after famous — or infamous — people from Tasmania’s history. The fame could be a thief, a prisoner, a hero, a local icon, and much more. Each room has a name and a story behind it.
Don’t miss the storytellers at the hotel — they share the tales of these legends in an evening session that is unlike anything I’ve encountered at any other property. This needs to be pre-booked before your arrival — don’t leave it until you check in. The restaurants on site are very good as well; The Old Wharf is my favorite.
Tasmania Has So Much More — and I’m Already Planning My Return
Tasmania has so much to offer; what I’ve described here is just a taste of the south portion of the island. There are rocky shores and cliffs, impressive swaths of white sand beaches, areas that are home to little blue penguins, the fresh and amazing food, and the friendly people — and so much more to discover across this remarkable island.
And I am far from finished with it. I will go back — to explore the west coast and Cradle Mountain, to do mountain walks, to discover the town of Strahan, to take a boat ride on Lake Gordon, to spend time on Bruny Island, and more. Tasmania is the rare destination that keeps revealing itself — and I suspect it always will.
Over the years, I’ve planned hundreds of trips to Tasmania — everything from multi-day hikes and luxury lodge stays, to visiting an oyster farm for the freshest oysters you’ll ever taste, private wine tastings with a sommelier, tee times on iconic golf courses, and private cruises to Bruny Island for the wildlife. There is no version of Tasmania I haven’t helped someone experience.
If Tasmania has been on your radar — or if this piece just put it there — I’d love to help you plan something extraordinary. Reach out, and let’s start the conversation.
