Step beyond the standard tourist trail and into the raw, unfiltered history of Van Diemen’s Land. This private experience is curated for those who want a deeper connection to Tasmania’s past. Led by a direct descendant of 17 convict ancestors, you won’t just see the sites—you will hear the personal stories of survival, hardship, and resilience that shaped our island.
Because this is a private tour, we move at your pace, allowing for deeper conversations and access to locations that larger groups often overlook.
Price Includes
What to bring
We’ll start with a scenic coastal drive, taking in jaw-dropping views from Pirates Bay Lookout, then stretch our legs on the otherworldly Tessellated Pavement before exploring the dramatic Devil’s Kitchen, Tasman Arch, and Blowhole—natural wonders carved by time and tide.
At Port Arthur Historic Site, you’ll have time to wander the hauntingly beautiful ruins, learn the stories of those who lived (and died) there, and reflect on Tasmania’s convict legacy. It’s powerful, emotional, and unforgettable.
But the best part? This is a private tour, which means we can mix it up. Fancy sipping a glass of pinot at a local vineyard? Want to swing by Richmond to stroll its charming streets and Australia’s oldest bridge? Craving fresh oysters straight from the source or a warming nip at a Tasman Peninsula distillery? Just say the word—we’ll make it happen.
flexible Pickup Time
10 minutes
Stand above this powerful stretch of ocean. A place many convicts never saw beyond. The cliffs and sea acted like guards, turning nature into punishment.
15 minutes
Explore this remarkable coastal rock formation while discussing how the land itself was part of the isolation system. A punishing terrain out of which escape was nearly impossible.
4 hours
Our longest stop. With entry included, delve past the surface of ruins into the day-to-day experience of convicts. Hear stories shaped by family history and lived hardship. Not just plaques and photo ops
30 minutes
Witness nature’s raw power and learn how rugged coastline features served as psychological and physical boundaries. These dramatic formations help explain why Port Arthur was chosen as a place no one should or could flee from easily..
This is a private tour, which means we can mix it up. Fancy sipping a glass of pinot at a local vineyard? Want to swing by Richmond to stroll its charming streets and Australia’s oldest bridge? Craving fresh oysters straight from the source or a warming nip at a Tasman Peninsula distillery? Just say the word, e’ll make it happen.
Return to the Hobart, we can also drop you off in Hobart CBD if you desired.
iWander Tasmania recommend you have travel insurance that covers cancellation costs.
We have a 24 hour cancellation policy. Cancelling 24 hours prior to a your departure date you will receive a full refund.
Absolutely. One of the biggest benefits of a private tour is that if you find a spot you love, we can stay longer. It’s your day!
Private prices are for individual participant, making it a very cost effective option for larger groups.
A basic level of fitness is all that is needed to enjoy an iWander tour. There isn’t anything demanding but each tour will require some walking, from the bus to the beach, or 30 metres above the trees at the Tahune Airwalk.
Do not hesitate to give us a call. We are an expert team and we are happy to talk to you.

