Winter is an ideal time to visit Tasmania’s historic sites, where the stories might just be as chilling as the night air. As you explore, it’s hard not to speculate about what life may have been like for the brave souls from days past, who faced the cold without heaters or puffer jackets. It’s a memorable way for young minds, and their grownups, to connect with the past while making the most of the Off Season magic.

Between 1804 and 1853, over 70,000 convicts were transported to Tasmania, helping build the roads, bridges, and buildings that still shape the island today. The most iconic of these is the Port Arthur Historic Site (portarthur.org. au), Australia’s best-preserved convict settlement. Spread across 100 acres, it’s home to more than 30 fascinating historic buildings and ruins, just waiting to be explored. With space to roam, hands-on activities, and kid-friendly tales woven into the experience, it’s a day out the whole family can enjoy.

If you’d prefer to leave the planning to someone else, take a day tour with Experience Tasmania Tours and Charters (experiencetas.com.au). The tour combines convict tales with scenic views of the rugged Tasman Peninsula. During the Off Season, kids travel free with a paying adult. The itinerary includes a visit to historic Richmond Bridge, entry to Port Arthur, and a stop at the Chocolate Foundry. Tours depart from Hobart at 8:45am, returning by 5:30pm, with entertaining and informative commentary from your driver.

For those who want to experience a more mysterious side of history, consider joining Port Arthur Ghost Tours (portarthur.org.au) after night falls. Rug up and be guided through the ruins on a lantern-lit 90-minute ghost tour.

The cool air and an eerie atmosphere make it a spine-chilling experience as you hear about the spirits said to linger in this historic site.

But Port Arthur wasn’t the only gaol in Tasmania. Richmond Gaol (richmondgaol.com.au), Australia’s oldest intact gaol, was built five years before Port Arthur. A visit here offers a fascinating window into Tasmania’s convict era, where you can peek inside tiny solitary cells and hear stories of infamous inmates like Ikey Solomon, said to have inspired Charles Dickens’ Fagin in Oliver Twist. It’s an eye-opening experience that brings history to life, perfect for a rainy-day excursion.

Before being sent to these infamous sites, many convicts were processed at the Hobart Penitentiary. Established in 1821, it was originally known as the Hobart Prison Barracks. The surviving Penitentiary Chapel was completed in 1834 and is now open to visitors. Explore the site and learn about the harsh realities of convict life, including the gallows where many met their end. Unshackled Hobart Penitentiary (nationaltrust.org.au/places/penitentiary) offers tours where you can honour convict ancestors at the Convict Memorial by writing their names on a Forget-Me-Not and placing them on the Memorial Wall, ensuring their legacies live on.

Long before the convicts, the Palawa (Tasmanian Aboriginal) people lived on this land for tens of thousands of years. You can learn more about their deep and enduring connection to Country on a guided tour with tunapri (tunaprisciencenatureculture.rezdy.com) in Burnie. “tunapri” means “to understand” in palawa kani, the language of the Palawa people. On one of their family-friendly tours, you’ll walk in the footsteps of the Palawa and gain a meaningful insight into their culture.

During the Off Season, their tunapri Patuyala tour is a 90-minute walk that explores the natural and cultural wonders of the north west, and includes a hands-on cultural craft activity the whole family can enjoy.

If you’re curious about Tasmania’s military history, the Anglesea Barracks in Hobart is the place to go this Off Season, Australia’s oldest military establishment still in use. During the winter school holidays, Tasmania’s Most Haunted (tasmaniasmosthaunted.com.au) invites kids to become paranormal investigators. Armed with real ghost-hunting tools, kids can search for clues left by “Old Jack,” a mischievous ghostly warden, as they explore the supposedly haunted hallways of this military gaol.

For a peek into 19th-century entertainment, visit Hobart’s Theatre Royal (theatreroyal.com.au), Australia’s oldest working theatre, opened in 1837. Take a behind-the-scenes tour and learn about its colourful past, the performers who graced its stage, and the rich history of one of Tasmania’s cultural treasures.

Tasmania also has a rich mining history, and a visit to the Beaconsfield Mine and Heritage Centre (beaconsfieldheritage.com.au) provides insight into the gold mining history of the West Tamar. The site is famous for the dramatic 2006 mine rescue. Visit after dark for a 90-minute evening tour that’s both gripping and family-friendly, exploring interactive exhibits and local tales.

After all that exploration, why not cap it off with a family portrait, old-school style? At Olde Time Portraits (oldetimeportraits.com.au) in Blackman’s Bay, you can dress up in Victorian or gangster-themed costumes for a unique family photo. Complete with authentic props and clothing, these portraits make for a special keepsake to remember your time exploring the island’s history in the Off Season.