The Ultimate Winter Road Trip

The Ultimate Winter Road Trip for Big Experiences

When the temperature drops, it’s time to turn up the adventure. Winter along the Grand Pacific Drive isn’t just about scenic pit stops and coastal views – it’s about chasing those once-in-a-lifetime moments. 

Picture this: skydiving over a sun-kissed coastline, spotting humpbacks breach just offshore, wandering through world-class art museums, or stargazing under a velvet sky on a white-sand beach.

From the wild to the whimsical, the South Coast and Southern Highlands are packed with experiences that make you feel alive, even when your breath fogs up the air. 

Ready to chase some grand winter magic? Let’s hit the road.

Wollongong: Thrills, Tranquillity & Wildlife Encounters

Wollongong knows how to do grand – and winter is one of the best-kept secrets for making the most of it. First up: skydiving. Yes, skydiving in winter. With clearer skies and calmer winds, cold-season jumps with Skydive Sydney–Wollongong offers unbeatable views of the coast, the mountains, and your courage levels skyrocketing. You’ll free-fall over one of Australia’s most iconic beaches, and the bragging rights are as epic as the experience.

Balance the adrenaline rush with a soul-soothing visit to Nan Tien Temple, the largest Buddhist temple in the Southern Hemisphere. Wander through peaceful gardens, admire the intricate architecture, or even join a mindfulness session – it’s the perfect way to reset and recharge on your journey.

And for something wildly heartwarming? Head just north to Symbio Wildlife Park, where you can hand-feed kangaroos, snap a selfie with a koala, or meet exotic animals from around the globe. It’s family-friendly, feel-good, and pure winter magic.

Shellharbour: Whale Tails, Jet Thrills & Mini Golf Madness

Shellharbour may be small in size, but it delivers big on adventure – especially in winter. For starters, this is prime time for whale watching with Shellharbour Wild. Set sail on a coastal cruise and watch as majestic humpbacks breach, slap their tails, and glide gracefully along their migration path. It’s the kind of experience that makes you gasp out loud – and maybe shed a little awe-inspired tear.

If you prefer your thrills in the sky rather than at sea, buckle into the cockpit with Jetflight Shellharbour. This is no ordinary scenic flight – you’ll soar above the South Coast in a real ex-military jet before diving into an adrenaline-fuelled aerobatic routine of loops, rolls, and wingovers. It’s wild, unforgettable, and definitely one for the bucket list. While you are at Shellharbour Airport, make sure you visit the HARS Aviation Museum, here you can climb into the cockpit of an F-111 jet fighter while it’s still on the ground and take a walk on the wing of the record-breaking jumbo jet – Qantas Boeing 747.   

Then, bring it back to ground level with a dose of competitive family fun at Mini Golf at The Links Shell Cove. This isn’t your average mini golf – it’s a big on fun scaled-down replica of a real golf course, complete with bunkers, greens, and a challenge level to suit everyone from pint-sized beginners to expert golfers. It’s the perfect way to wind down after a big day – or to fire up a little friendly competition before your next adventure!

Kiama: Tree-Top Views, Coastal Cruising & Creative Moments

Kiama is the kind of place that invites you to slow down, look up, and lean into the joy of discovery – whether you’re gliding through a rainforest canopy, pedalling beside ocean views, or getting inspired by local makers.

Start your day above it all at Illawarra Fly Treetop Adventures, where panoramic rainforest views stretch all the way to the coast. Wander the elevated steel walkway that winds through the canopy or climb the spiral stairs of Knights Tower for a breathtaking lookout. Feeling brave? Clip in for the Zipline Tour – Australia’s highest – and soar between tree platforms with nothing but the wind (and a lot of laughter) in your ears. It’s a forest experience like no other, and it’s even better in the cool, clear winter air.

Next, swap the treetops for the coastline with a spin on two wheels from Kiama Cycles and Sports. With gentle power-assisted rides, you’ll cruise along seaside paths and winding country roads, taking in all the charm of the region without breaking a sweat. Whether you’re a weekend wanderer or a cycling pro, there’s a route to match your pace – and the views are worth every turn of the pedals.

Round out your visit with a dose of handmade magic at Soul Clay Studios in Gerringong. This welcoming creative hub is home to a community of ceramic artists crafting beautiful, functional pieces in the heart of town. Watch the artists in action, browse the shelves for a one-of-a-kind souvenir, or take a behind-the-scenes peek into the studio where each piece is thoughtfully made. Or why not enjoy a one-off air dry or wheel throwing class? It’s art you can touch – and take home.

Shoalhaven: Whales, Stars & Deep Connection to Country

Down in the Shoalhaven, we invite you to slow down, look closer, and feel something deeper – whether it’s the stillness of the bush, the vastness of the night sky, or the heartbeat of ancient culture.

Begin your journey at Woebegone Freedive, where adventure and nature collide in an unforgettable way. Dive into the crystal-clear waters of Jervis Bay, where you’ll explore the stunning seal colonies, migrating humpback whales, hidden sea caves, and pristine white sandy beaches. Whether you’re embarking on a beach or boat snorkelling expedition or seeking to refine your skills with a Freedive training course, Woebegone Freedive offers the ultimate underwater experiences. Don’t miss their biggest winter treat – the Swim with Whales Expedition, running from June to October. This extraordinary opportunity lets you swim alongside the majestic humpback whales in their natural habitat, a truly once-in-a-lifetime adventure.

As night falls, swap gallery lights for starlight with Jervis Bay Stargazing. Led by a passionate astrophysicist, this unforgettable beachside experience lets you explore the cosmos far from city glare. With the waves as your soundtrack, you’ll learn how to read the sky, track satellites, and even spot shooting stars – all while being wrapped in the wonder of where the sea meets the stars.

For a truly grounding and powerful experience, join Gadhungal Marring’s Raymond Timbery in Huskisson for a cultural immersion that will stay with you long after your trip. From smoking ceremonies and dance to bush food knowledge, mangrove walks, and yarns around the fire, these on-country teachings are a profound way to engage with the living culture of the First Nations people – and see this land through a different lens.

Southern Highlands: Scenic Drives, Cosy Fires & Wine for Days

Winter in the Southern Highlands is crisp, calm, and quietly spectacular – a place where misty mornings give way to golden afternoons, and every turn down a country lane feels like stepping into a storybook.

In the Southern Highlands, grand experiences await you around every turn. Meander through rolling green hills, picture-perfect pastures and timeless stone walls on one of the region’s many scenic Tourist Drives. One of our favourite routes? Start with a coffee in Bowral, then wind your way east to Robertson along the tourism road. With breathtaking views and countryside charm that feels straight out of a dream, you’ll be tempted to leave the city behind for good. Cap off your drive with a hearty meal at the historic Robertson Public House or the ever-charming Moonacres.

If your idea of bliss is fireside comfort, you’ve come to the right place. The Highlands is home to more Fireside Escapes than anywhere else in NSW – from boutique stays with crackling hearths to cosy galleries and retail spaces offering glowing refuge from the winter chill. Book a country cottage or stylish hotel, pour a glass of Pinot, and let the fire do the rest. For a more adventurous twist, dine under the stars at a fire feast experience at Osborn House or Eschalot, or join the magic of Midwinter Festival this July.

Looking for a fireside chat with locals over a soul-warming drink? Try the historic charm of Surveyor General Inn in Berrima, or sip and stay at much-loved venues like Taylor’s Inn, Berida Hotel, Peppers Craigieburn, Centennial Vineyards, Robertson Hotel, and Burrawang Hotel.

And what’s winter without red wine? Discover the Southern Highlands Wine Trail – a full day (or weekend!) journey through award-winning vineyards, boutique cellar doors, and spirited distilleries. From crisp whites to bold reds and local liqueurs, it’s an experience that’ll warm your heart and tempt your palate at every stop.

 

So, there you have it – a road trip bursting with grand experiences from coast to country. Whether you’re free-falling over Wollongong’s coastline, whale watching in Shellharbour, exploring rainforests in Kiama, connecting to culture in Shoalhaven, or soaking up the crisp, creative charm of the Southern Highlands, winter is anything but sleepy on the Grand Pacific Drive. 

So, pack the beanie, charge the camera, and hit the road – your grandest winter yet is waiting.

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Where Nature Puts on a Show

Where Nature Puts on a Show (Even in Winter)

If you thought nature hit pause in the colder months, think again. Winter is when the Grand Pacific Drive truly shines – crisp air, dramatic coastlines, misty valleys, and wide-open skies that feel like they go on forever. 

It’s the season for soul-stirring hikes, tranquil waterfalls, whale sightings from rugged clifftops, and rainforest walks that smell like eucalyptus and adventure. Whether you’re chasing sunrise over the ocean or wrapping your hands around a warm drink after a mountaintop view, this is where nature invites you to slow down, breathe deep, and Go Grand.

Wollongong: Clifftop Walks, Rainforest Trails & Coastal Wonders

Wollongong’s natural beauty doesn’t shy away in winter – in fact, the cool, clear air makes it one of the best times to explore. With less humidity, fewer crowds, and the kind of crisp light that makes every view feel a little more epic, it’s all about getting outside and going grand.

Start with a hike along the Wodi Wodi Track, a lush and peaceful bushwalk tucked beneath the escarpment in Stanwell Park. This moderately challenging loop winds through dense forest and sandstone overhangs, with pockets of quiet that make you feel worlds away. Keep an eye out for lyrebirds and native wildflowers as you make your way through Dharawal Country, rich in both beauty and cultural significance.

Next, take in one of the South Coast’s most iconic views on the Sea Cliff Bridge Walk. Suspended between cliff and sea, this sweeping bridge seems to float above the waves – and yes, it’s every bit as magical as it sounds. Whether you’re walking the full stretch or simply pulling over to take in the view, this is one of those ‘you’ve got to see it to believe it’ moments that winter makes even more cinematic.

And for those ready to earn their view, lace up your hiking boots for the Sublime Point Walking Tracka steep, invigorating climb through rainforest gullies, sandstone outcrops, and towering eucalypts. This trail is not for the faint-hearted, with a series of ladders and steep stairs adding to the adventure (and the leg burn), but the payoff is absolutely worth it. At the top, you’ll arrive at the Sublime Point Lookout, where sweeping views of the Illawarra coastline open up beneath you like a living postcard. On a clear winter day, you can see for miles – it’s the kind of view that makes every step feel well worth it.

Shellharbour: Untamed Coastlines, Hidden Bays & Serene Waters

Shellharbour is where nature goes wild – in the best possible way. Here, winter brings a quieter kind of magic to the coast: sea mist at sunrise, crisp ocean air, and unspoiled landscapes that invite you to wander, slow down, and connect with the outdoors.

Start at Bass Point Reserve, one of the region’s most ecologically significant coastal headlands. Rich in Aboriginal heritage and natural beauty, the reserve is home to Bushrangers Bay, a calm, protected aquatic sanctuary abundant with marine life. Here, snorkelling is still on the cards even in winter, simply hire a wetsuit from the local dive shop. Wander the walking tracks along the rugged coastline, watch the waves crash against volcanic rock, and breathe in that unmistakable salty air — it’s wild, grounding, and incredibly beautiful.

Next, venture to Killalea Beach, affectionately known as ‘The Farm.’ Part of the Killalea Regional Park, this untouched beach is famous among surfers, but it’s just as inviting for walkers, wildlife-spotters and anyone in need of a scenic escape. With rolling green hills, native vegetation and a long stretch of golden sand, it’s the kind of spot where time slows down – and so should you.

For a gentler outdoor experience, head to the foreshore of Lake Illawarra, a peaceful haven for kayaking, stand-up paddleboarding, fishing or simply enjoying a walk along the foreshore path – including the captivating Lake Illawarra Art Trail. The lake mirrors the winter sky in the calmest of ways, especially at sunrise or sunset, and is perfect for a family outing or a quiet solo stroll. Bring binoculars – you’re likely to spot pelicans, black swans, and maybe even a sea eagle or resident seal. For those with families, the Red Lamp Playground and Ninja Park is a must visit for kids.

Kiama: Thundering Blowholes, Coastal Trails & Rainforest Escapes

Kiama knows how to put on a show – from salt-sprayed clifftops to ancient rainforest valleys, this stretch of the Grand Pacific Drive is bursting with natural moments that’ll stop you in your tracks (sometimes quite literally, thanks to the sheer power of a blowhole).

Start with a visit to the iconic Kiama Blowhole, where seawater shoots skyward through a natural rock formation with dramatic force. When the swell is right, it’s nature’s version of a fireworks show – loud, unpredictable, and totally exhilarating. For a quieter (but still impressive) alternative, check out the nearby Little Blowhole, a smaller but more consistent performer with fewer crowds and equally epic ocean views.

If you’re keen to stretch your legs, the Kiama Coast Walk is an absolute must. This stunning 20-kilometre trail hugs the coastline from Minnamurra to Gerringong, winding past beaches, headlands, grassy farmland and dramatic cliffs. You don’t need to do the whole thing – shorter sections are perfect for a morning wander – but if you’re up for it, the full trail delivers a grand sense of scale and connection to the land and sea.

For a total change of pace, step into the cool, green world of the Minnamurra Rainforest. This pocket of pristine subtropical rainforest is home to towering fig trees, tranquil creeks, and the breathtaking Minnamurra Falls, best viewed from a scenic elevated walkway. The loop track is well maintained and family-friendly, making it ideal for a peaceful stroll that still feels like an adventure – especially when the winter mist drifts through the canopy.

Shoalhaven: Sacred Peaks, Snow-White Sands & Coastal Wilderness

Shoalhaven is where nature and culture meet in unforgettable ways. From challenging hikes with panoramic payoffs to peaceful beaches and ancient bushland, this region invites you to explore slowly, deeply, and with wonder – especially in the cooler months when the air is crisp and the crowds are few.

Take on the legendary Didthul (Pigeon House Mountain) hike in Morton National Park, a rewarding climb that’s as rich in cultural significance as it is in views. Known to the local First Nations people as ‘Didthul,’ this striking mountain rises proudly from the landscape and offers a moderately challenging trail through forest and heath, finishing with a series of ladders to the summit. At the top, you’ll be treated to sweeping views over cliffs, valleys and the rugged coastline – it’s wild, beautiful, and deeply grounding.

For something a little gentler but no less grand, spend a day exploring Booderee National Park, a place of immense natural and cultural importance on Wreck Bay Aboriginal land. Here, you’ll find white sand beaches, bush tracks brimming with wildlife, and spiritual connections that run deep through the land. Visit Green Patch for a peaceful picnic among the trees, walk the tranquil trails to Cape St George Lighthouse, or simply breathe in the salty air and take in the ever-changing colours of the bay.

And for coastal beauty that looks straight out of a postcard, set off on the White Sands Walk in Jervis Bay. This short and stunning trail links some of the area’s most pristine beaches – think Blenhiem, Chinamans, and Greenfield – with impossibly soft sand and water so clear it sparkles, even in winter. It’s an easy, family-friendly walk with the kind of views that make you stop, smile, and take that deep, happy sigh.

Southern Highlands: Misty Falls & Garden Escapes

Start your adventure at Belmore Falls, a true showstopper in Morton National Park. After a scenic drive through Kangaroo Valley or from Robertson, you’ll find yourself gazing over the edge of an escarpment where twin streams plunge dramatically into the valley below. The surrounding lookout walks are short but oh-so-sweet, offering perfect vantage points for misty morning views and golden-hour photo ops.

Not far away is the equally spectacular Fitzroy Falls, where the falls thunder 80 metres into a deep, forested gorge. The main lookout is just steps from the visitor centre and The Burrow Cafe, but those with a little more energy can follow the rim trails for a longer walk with panoramic cliff-edge views and peaceful forest detours. Interpretive signage shares the area’s deep cultural significance, adding richness to every step.

To round things out with a touch of elegance, wander the grounds of Retford Park in Bowral – a National Trust estate that pairs manicured gardens with natural beauty. The gardens change with the seasons, and in winter they’re full of quiet charm: mossy pathways, sculptural trees, and views framed by bare branches. It’s the perfect place to slow down, reflect, and let nature do what it does best – make you feel calm, grounded, and totally inspired. An added bonus is that Ngununggula Regional Art Gallery is just down the garden path, offering a rotating exhibition and coffee and a warm meal at Hearth by Moonacres.

 

From thundering waterfalls to whispering rainforests, wild coastlines to serene lakes, winter on the South Coast & Southern Highlands is anything but quiet. It’s a season of crisp air, wide open views, and unexpected beauty – where nature doesn’t slow down, it simply changes pace. 

So, take the scenic route, breathe in the fresh air, and let the grandness of it all completely sweep you away.

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A Winter Feast of Flavour

A Winter Feast of Flavour on the Grand Pacific Drive

If your ideal road trip includes cosy cafés, long lunches, and discovering local gems one bite at a time – this one’s for you. Winter is when the South Coast and Southern Highlands really turn up the flavour, with hearty seasonal menus, steaming mugs by the fire, and vineyards and distilleries that invite you to sip and stay a while. 

From ocean-fresh seafood to slow-cooked paddock-to-plate feasts, every stop along the Grand Pacific Drive is serving something worth pulling over for. 

Hungry yet? Let’s Go Grand.

Wollongong: Coastal Feasts & Comfort With a Twist

Wollongong is serving up big flavour energy this winter – from modern Italian soul food to nostalgic Aussie classics reimagined with a coastal flair.

Start your culinary stroll at Restaurant Santino, where warm lighting, big-hearted hospitality, and rich, soulful flavours create the ultimate winter comfort zone. Their take on Italian fare is anything but ordinary – the mafaldine pasta with lamb, sugar snaps, anchovies, pecorino, and herbs is a hug in a bowl, layered with savoury depth and just the right amount of zing. Cap it off with an affogato biscotti for dessert – the kind of sweet, strong, crunchy-soft combination that lingers long after the last spoonful. This is slow food made with love, and worth every bite.

For something a little more laid-back but no less flavour-packed, head to South Sailor in Thirroul. A modern take on the classic Aussie fish shop, this beachy hangout brings sustainably sourced seafood to the table with serious style. From tempura prawns and poke bowls to fish tacos and local wines, it’s all the seaside nostalgia – minus the paper-wrapped chips and seagulls.

And for a meal with a view that’s just as grand as the flavours, book a table at The Imperial at Clifton. Perched dramatically on the escarpment edge, this beautifully restored pub pairs panoramic ocean views with a locally inspired menu that heroes Southern Highlands beef, fresh South Coast seafood, and seasonally crafted cocktails. Come for the vistas, stay for the dessert.

Shellharbour: Marina Views, Seafood Feasts & Easy Going Elegance

Shellharbour is where coastal charm meets refined flavour, and winter is the perfect time to settle in for long lunches, seafood spreads, and cocktails by the marina.

Start your tasting tour at Relish on Addison, an intimate, modern Australian restaurant nestled in the heart of Shellharbour Village. With a menu that’s all about fresh local produce and creative flair, you’ll want to come hungry. Start with South Coast oysters, dive into the melt-in-your-mouth confit crispy pork belly, and don’t skip the blue swimmer crab linguine – it’s rich, silky, and packed with flavour. Pair it all with something from the cocktail list and settle in – this is refined dining without the fuss.

Just down the road at the stunning new Waterfront Precinct Shell Cove, The Waterfront Tavern brings a whole new level of coastal cool. Overlooking Shellharbour Marina and buzzing with atmosphere, this is the spot for a long, leisurely meal that turns into evening drinks. Executive Chef George Sideris has created a menu that reimagines classic bistro favourites – don’t miss the signature seafood platter or the cold seafood bar, where freshly shucked NSW oysters and delicate sashimi steal the show. With sparkling water views and bold, bright flavours, it’s a feast for all the senses.

Round out your visit at Georgia Rose Shell Cove, a café by day and cocktail bar by night that nails the laid-back-luxe vibe. Whether you’re fuelling up with a big brekky, dropping in for a lazy lunch, or soaking up the marina atmosphere with a signature cocktail at golden hour, Georgia Rose brings colour, creativity, and chilled-out charm to every visit.

Kiama: Vineyard Views, Brunch Bliss & Farm-Fresh Feasting

From sunrise brunches to vineyard lunches and everything in between, Kiama plates up a seriously tasty slice of the South Coast – with views to match.

Set against a backdrop of rolling vines and sweeping valley views, Crooked River Estate is the kind of place that makes you want to linger. This award-winning winery and restaurant blends elegant paddock-to-plate dining with a laid-back country charm that feels just right for a winter road trip. Head Chef Dane Tobias and his team are serving up a menu full of local flavour – don’t miss the crispy zucchini flowers or the sous-vide lamb rump, both bursting with bold, seasonal ingredients. And of course, no visit is complete without a swirl and sip of their house-made wines – go on, treat yourself to a tasting.

If brunch by the sea is more your pace, Diggies Kiama has you covered. This breezy, sun-soaked spot is where locals grab their morning coffee, tuck into a wholesome all-day brunch, or cool off with a cheeky afternoon cocktail. With ocean views and salty air as your side dish, it’s the perfect place to pause, refresh, and soak up that effortless coastal vibe.

And for a taste of community-powered goodness, pull up a seat at The Farmer’s Table. This warm, welcoming café champions local growers and seasonal produce in every dish – from the vibrant Brekky Bruschetta to the crowd-favourite Salty Beef Bagel. It’s about more than just good food here – it’s about connection, care, and celebrating the region from the ground up.

Shoalhaven: Gourmet Journeys & Coastal Indulgence

Shoalhaven is where flavour meets finesse – a region where paddocks, producers, and passionate chefs come together to serve food that’s thoughtful, bold, and absolutely worth the drive.

Start your foodie adventure in the charming village of Berry at South on Albany – a small, hatted restaurant tucked away on a quiet street but known far and wide for its big heart and refined flavours. Hosts John and Sonia welcome you in with a seasonal set three-course chef’s menu that changes fortnightly and puts the best of the region front and centre. Think fresh, local, and thoughtfully crafted, with optional extras like freshly shucked oysters and perfectly matched wines. It’s intimate, welcoming, and a must for those who travel with their appetite.

Next, head south to Bangalay Dining, a standout destination where luxury meets the land. This multi-award-winning restaurant is known for its clever use of native Australian ingredients and clean, elegant dishes that let the produce shine. From the delicate South Coast yellowfin tuna crudo, to the rich, earthy sauteed potato gnocchi, and the dreamy white chocolate mousse, every dish is a work of art. Stay the night in their stylish on-site accommodation and roll from table to retreat in true gourmet road-trip fashion.

And for the ultimate long lunch or sunset session, Cupitt’s Estate in Ulladulla offers something truly special. Overlooking vineyards and rolling hills, this family-owned estate blends house-made wine and beer, fresh regional produce, and a strong focus on sustainability. Choose a casual bite in the Wine Garden or go all-in with a multi-course meal in the Dining Room. Either way, you’ll be treated to warm hospitality, unforgettable flavours, and views that make you want to stay just a little longer – and lucky for you, their luxury Estate Villas are the perfect excuse to do just that.

Southern Highlands: Fireside Feasts, French Flair & Country Elegance

If ever there was a place to eat your way through winter, it’s the Southern Highlands. Here, cool-climate wines, seasonal menus, and a love for local produce create a food scene that’s as comforting as it is sophisticated.

Begin at the storybook-worthy Bendooley Estate, where meals are served with a side of literary charm. Dine beside a roaring fire inside the iconic Book Barn, surrounded by shelves of beloved reads, or opt for a sun-drenched seat among the vines and gardens. The seasonal menu champions the region’s finest ingredients, while the Cellar Door offers tastings with vineyard views, and their evening venue Leo’s by Night brings candlelit country dining to life in the most elegant way.

For a dash of European indulgence, step into the warmly lit world of Bistro Sociale at the Berida Hotel in Bowral. Here, Chef Nathan Jackson serves up modern French-inspired fare with local flair – think buttery sauces, prime cuts, and house-made mustards, all served fireside in cooler months. It’s the kind of place where every bite feels like a weekend away in Paris, without the jet lag.

And tucked in the heart of Berrima’s historic village, Eschalot Restaurant is a true destination for seasonal, paddock-to-plate dining. With an abundant kitchen garden on site and strong ties to local producers, the menu changes with the harvest – always fresh, always beautifully plated, and always deeply rooted in the land it comes from. The setting? Pure countryside charm, wrapped in heritage and hospitality.

 

From seafood by the sea to paddock-to-plate perfection and everything delicious in between, the Grand Pacific Drive is a road trip made for food lovers. Whether you’re toasting with cool-climate wines in the Southern Highlands, sharing oysters by the Shellharbour Marina, or lingering over long lunches in Shoalhaven, this journey proves that winter is the season to truly savour. 

So, bring your appetite, follow your tastebuds, and Go Grand – your next unforgettable meal is just around the bend.

road trip ideas

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Here's what your grand escape could look like...