Step into a winter storybook as Romania reveals itself through candlelit streets, snow-dusted castles, and traditions that have endured for centuries.
Our immersive 10-day journey ventures beyond the Christmas markets to uncover the soul of the country, beginning in Bucharest where layers of history and resilience shape the capital’s character. From here, travel into the heart of Transylvania, where Craiova’s vibrant market sets the tone before Sibiu’s glowing squares draw you into a world of festive charm and quiet magic.
Wander through medieval towns where time slows, from the cobbled lanes of Sighișoara to the imposing presence of Corvin Castle, where Gothic legends linger in stone. Share in local traditions, explore Saxon villages, and pause for a wine interlude in Jidvei, where Romania’s lesser-known flavours come to life.
In Brașov, framed by the Carpathian Mountains, experience winter in a region where rural life and heritage remain deeply connected. Conclude with the iconic Bran Castle and the refined elegance of Peleș, before returning to Bucharest.
Download this tour’s PDF brochure and start your planning offline!
Welcome to Romania! Bucharest sits at the crossroads of Eastern and Central Europe, where wide boulevards, Belle Époque facades, and monumental communist-era architecture define the cityscape. In early December, festive lights begin to illuminate the capital, and Christmas markets bring seasonal activity to its historic squares.
On arrival at Bucharest airport, you will met and transferred to your hotel. Check in and settle into your accommodation. The remainder of the afternoon and evening is at leisure to rest or begin exploring the city at your own pace.
Overnight – Epoch Belle Hotel or similar
Begin in Bucharest with a guided exploration of the capital’s layered architecture, where late 19th-century boulevards sit alongside monumental communist-era structures. Visit the Palace of the Parliament for a guided tour, providing direct insight into one of the defining projects of the Ceaușescu period.
Continue to the Village Museum, an open-air collection of traditional Romanian buildings relocated from across the country, representing regional construction styles and rural life.
In the evening, visit the Bucharest Christmas Market, set in the square before the Palace of the Parliament. The space is defined by rows of wooden chalets, lit façades, and a central Christmas tree anchoring the square. Stalls focus on regional craft traditions, from carved wood and woven textiles to ceramics, alongside seasonal food including grilled meats, pastries, and mulled wine. The atmosphere builds as locals gather through the evening, with live performances and light installations shaping the setting. (B)
Overnight – Epoch Belle Hotel or similar
Depart Bucharest and travel south to Craiova by private vehicle, with a journey time of approximately three and a half hours.
In the late afternoon and evening, explore the Craiova Christmas Market, widely regarded as one of Romania’s most elaborate seasonal markets. The central squares are transformed with large-scale themed installations, illuminated structures, and distinct zones that shift in design and atmosphere as you move through them. Seasonal stalls offer regional food, sweets, and hot drinks alongside artisan crafts, while light displays and staged settings define the experience after dark. (B)
Overnight – Prestige Boutique Hotel Craiova or similar
Depart Craiova and travel north into Transylvania. Arrive in Sibiu, a former Saxon stronghold defined by its upper and lower towns, pastel façades, and steeply pitched roofs overlooking a series of interconnected squares.
As evening falls, visit the Sibiu Christmas Market in the Grand Square. The setting is anchored by the surrounding medieval architecture, where softly lit façades and arcaded buildings frame the market below. Wooden chalets line the square, arranged around a central tree, with the scent of spiced wine and baked pastries carrying through the open space. Light installations are integrated into the architecture rather than dominating it, creating a more composed and immersive atmosphere as the square fills with visitors. (B)
Overnight – Art Hotel Sibiu or similar
Begin with a full-day journey west from Sibiu into the deeper landscapes of Transylvania, where you will see the winter light across open valleys and forested hills. Arrive at Corvin Castle in Hunedoara, a vast Gothic-Renaissance stronghold rising above the surrounding plain. Timber bridges, defensive towers, and enclosed courtyards create a layered interior that feels both fortified and ceremonial. The scale and verticality of the structure, combined with its setting, give it a distinctly dramatic presence in winter.
Continue to Alba Iulia and explore the Alba Carolina Citadel, a grand Vauban-style fortress defined by symmetry, wide avenues, and formal gates. Wander through its geometric layout at a slower pace, with its open sightlines across the ramparts and the surrounding town. Return to Sibiu in the late afternoon.
As evening settles, step back into the Old Town and the Christmas Market. The square feels more intimate on a second visit, with familiar paths through the chalets. (B)
Overnight – Art Hotel Sibiu or similar
Depart Sibiu and continue deeper into Transylvania, where vineyard-covered hills and quiet rural roads define the landscape. Begin at Jidvei, one of Romania’s leading wine estates, set among rolling countryside. A guided visit introduces the estate and its production, followed by a tasting and lunch featuring regional wines and local dishes.
Continue to Sighișoara, a UNESCO-listed medieval citadel still inhabited today. Enter through its preserved walls and walk the cobbled streets, where coloured houses, narrow lanes, and defensive towers remain largely unchanged. The compact scale and elevated position give the town a distinct sense of continuity and enclosure.
By late afternoon, arrive in Brașov, set dramatically at the foot of the Carpathian Mountains, where forested slopes rise directly behind the town. The medieval centre is anchored by Council Square and framed by tightly ordered streets, with the Black Church standing as a defining Gothic landmark. In winter, the surrounding peaks and dark pine forests make for a spectacular backdrop behind the town. (B,L)
Overnight – Schuster Boarding House Brașov or similar
After breakfast, set out to explore the historic city of Brașov, one of Transylvania’s most charming medieval towns. Walk through the beautifully preserved Old Town, where cobbled streets lead to Council Square (Piața Sfatului), framed by colourful baroque buildings. Visit the Black Church, the largest Gothic church in Eastern Europe, and stroll along Rope Street, one of the narrowest streets in Europe.
Later, spend time at the Brașov Christmas Market, set within Council Square. Wooden chalets gather around a central tree, with the surrounding façades and mountain backdrop enclosing the square. As evening approaches, lights come into focus across the buildings and market stalls, shaping a more atmospheric setting. Time is allocated to explore at your own pace.
In the evening, head beyond the town into the Carpathian forests for a wildlife observation experience with local rangers. Travel into dense woodland areas where sightings may include deer, wild boar, and, with luck, bear, depending on conditions. Return to Brașov later in the evening. (B)
Overnight – Schuster Boarding House Brașov or similar
After breakfast, set out into the rural heart of Transylvania, where Saxon villages remain largely unchanged, with fortified churches, whitewashed houses, and open countryside shaping the landscape.
Begin in Viscri, a UNESCO-listed village known for its preserved character and traditional way of life. Walk through the village and visit the fortified church, set on a small hill overlooking the surrounding fields. The simplicity of the setting and its continuity offer a clear contrast to the region’s larger towns.
Continue with a traditional lunch hosted locally, reflecting regional dishes and seasonal ingredients.
In the afternoon, travel to Saschiz, a village with a long-standing craft tradition. Take part in a pottery workshop inspired by Saxon designs, with time to engage directly with the techniques and materials used in the region.
In the evening, arrive at Bran Castle for a private after-hours visit. Explore the castle interiors exclusively by lamplight, where narrow passages, timber staircases, and enclosed rooms create a more atmospheric experience after dark. The visit concludes with a tasting of local wines and cheeses within the castle. Return to Brașov later in the evening. (B,L)
Overnight – Schuster Boarding House Brașov or similar
After breakfast, depart Brașov and travel through the Carpathian Mountains toward Bucharest, following one of Romania’s most scenic routes. Stop in Sinaia, a former royal retreat set in the forested foothills of the mountains. Visit Peleș Castle, the former summer residence of Romania’s royal family and one of the finest examples of Neo-Renaissance architecture in Europe. Explore the richly decorated interiors, where carved wood, stained glass, and detailed craftsmanship define each room. Continue to Bucharest in the afternoon. On arrival, check in to your hotel and enjoy the remainder of the evening at leisure. (B)
Overnight – Belle Epoch Hotel or similar
The morning is yours at leisure until it is time to transfer to the airport for your onward flight. (B)
Download this tour’s PDF brochure and start your planning offline!
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**Please note that this tour can be organised on request for private departures.
* Pricing is subject to change at anytime until full payment has been received.
* A minimum of 4 adults is required to guarantee this departure.
A non-refundable deposit of $1000 AUD per person is required to secure your place. Final payment is due no later than 60 days prior to departure. Travel insurance is mandatory for travelling with Crooked Compass. For full terms and conditions, please click here.
Small group tours providing intimate connections to gain a deeper understanding and emotional connection to the community, tribes, cultures and lands explored.
Exploring the world’s most remote reaches and challenging destinations requires a high level of expertise which can only be learned from first-hand experience. We know because we go.
In an ever-changing global landscape of rules, regulations and restrictions, rest-assured you are being looked after by those in the know. Given the remote regions that we explore, our passengers safety is our top priority.
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This category of tours involves light trekking, walking, cycling, rafting or kayaking for a few hours each day with a small amount of inclines and declines. You will require a reasonable level of fitness and good health to participate. It is important to note that due to the nature of some of our trips, they may take place in remote areas (with basic facilities) and can involve long travelling days on various modes of transport.
Suggested preparation : At least 3 months prior to departure, it is recommended that you undertake aerobic exercise (this may include jogging, cycling or fast walking) for 30 minutes, three times a week. It is also advised to walk on variable terrain and in variable weather conditions. For a cycling adventure, road cycling twice a week is recommended and for adventures which involve paddling and kayaking, it is important to gain confidence and rhythm rather than speed prior to departure.
This category of tours involve trekking, kayaking and cycling for period of 6 to 8 hours a day at a fairly consistent pace. Ideal for people looking to slightly increase the heart rate. For our moderately rated tours, you must have a good level of fitness and also be in good health. It is also important to be prepared for variable weather conditions. Altitude may also come into play. This category of tours may involve visiting remote areas where facilities can be quite basic. Accommodation may also involve camping, homestays or basic accommodation where facilities may not be considered of western standards. To enjoy this style of travel, it is suggested for travellers to have a reasonable level of fitness and health, a positive attitude, as well as a fairly active lifestyle. An open mind is also required.
Suggested preparation: At least 3 months prior to departure, it is recommended that you undertake 45mins – 1 hour of aerobic exercise, three to four times a week. Some potential exercises that could be beneficial include hill walking with a backpack on over variable terrain and weather conditions, as well as running and cycling dependent on the activity you plan on undertaking.
This category of tours involves trekking, kayaking, cycling or other adventure activities in remote areas for up to 8 to 10 hours a day. It is important to note that with the remoteness of some regions comes a variety of other challenges such as variable weather conditions, accommodation as well as facilities. You must have an excellent level of fitness and good health to be able to partake in this category of tour. You must have confidence in your own ability and be in good physical condition. Includes extended periods of endurance.
Suggested preparation: At least 3 to 4 months of strenuous exercise, four times a week. When preparing for treks it would be beneficial to participate in hill walks with a weighted day pack (approximately 5-8 kg) once a week for aerobic fitness and strengthening of leg muscles. It is also important to do this on variable terrain to prepare for challenging adventures. When preparing for cycling adventures, regular bike riding (at least 4 to 5 times a week for 1-4 hours is essential). It is also important to cycle on uneven surfaces or even participate in other aerobic exercises such as running or swimming to build up strength and stamina. Altitude may also be a factor in these tours.
This category of tour often involves extreme trekking, cycling or other extreme adventure activities. It is important to expect remote and poorly defined tracks and to be prepared for variable weather conditions for 10 to 12 hours per day (may sometimes be more depending on weather and altitude). These adventures are suitable for travellers who have prior experience in strenuous travel and activities, are extremely fit and have excellent health. It is also important to note that some of the terrain on these adventures will involve trekking in snow, at high attitude levels and may require technical equipment.
Suggested preparation: It is important to note that physical fitness should be an ongoing activity, commencing around 5-6 months prior to departure, or even before if you have no prior fitness. Exercise should focus on building maximum endurance and stamina. Four to five hard sessions of 40-60 mins per week should be completed and can include exercises such as going to the gym, running, swimming or cycling to focus on building aerobic stamina. It could also be beneficial to prepare by hiking on rough terrain, in extreme weather conditions or partake in altitude training.
Our Signature Tours are the cornerstone of the Crooked Compass journey: meticulously designed small-group itineraries that balance authenticity, comfort, and ease. These are destinations where travel can be complex—from navigating evolving logistics to reaching places far from the usual tourist path—yet our expertise ensures your experience feels smooth, effortless, and deeply rewarding.
From the moment you arrive, every detail is handled with care. You’re welcomed personally on arrival and met for a private transfer to your accommodation, where you’ll join the rest of your group. Your guide will walk you through an orientation, helping you understand the rhythm of the journey ahead and settling you in with clear, practical insights from the very start.
Accommodation is selected for both comfort and character, reflecting the richness of its locality through thoughtful design, creative ingenuity, and a genuine sense of place. Whether it’s a boutique property, a sustainable lodge or a homestay, each choice is made to connect you meaningfully with the destination.
Cultural integration sits at the heart of our approach. Every itinerary is crafted with respect for local communities, aligning sensitively with their values and protecting the authenticity of their culture. Through this, travellers experience a deeper connection —stories shared firsthand, traditions encountered in their true context, and moments that shift perspectives long after returning home.
With a maximum of 12 travellers and our most trusted local partners, you explore with confidence, guided by teams who combine deep regional knowledge with an intuitive understanding of Western traveller expectations. Through the powerful medium of storytelling, our journeys inspire personal reflection and spark genuine emotion, turning travel into something transformative.
For travellers seeking even more flexibility or personalisation, our Tours By Design journeys are crafted with the same care — mindfully designed around your interests for a more tailored experience.
Why travellers love our Signature Tours:
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Our Founders Tours are rare, one-of-a-kind journeys personally hosted by Crooked Compass founder, Lisa Pagotto. Designed for the traveller who seeks more than just adventure, these exclusive small-group expeditions uncover places few have ever seen – experiences not featured in our regular collection, chosen for their depth, beauty, and story.
Each itinerary is hand-crafted by Lisa to offer meaningful connection and unique access built through years of trust and collaboration with local communities. Travelling alongside her gives you an unparalleled perspective into the world of ethical exploration – from the behind-the-scenes partnerships that shape our journeys, to the human stories that inspire them.
With an intimate group size and seamless support from our expert team, a Founders Tour is less a trip, and more a masterclass in discovery.
Why travellers love Founders Tours:
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Set sail on a rare journey across remote islands, wild coastlines, and untouched ecosystems aboard a small, luxury expedition vessel. Travelling by sea unlocks access to places few travellers ever reach – from isolated villages and pristine reefs to dramatic landscapes that can’t be accessed by land – while each evening, you return to the comfort of your beautifully appointed cabin.
These voyages blend adventure with refinement. Expert-led excursions bring you face-to-face with raw nature and vibrant cultures, while exceptional onboard dining, service, and comfort allow time to unwind and reflect.
To complete your experience, Crooked Compass can seamlessly craft pre- or post-cruise land extensions, ensuring your journey flows effortlessly from sea to shore.
Why travellers love our Expedition Cruises:
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Our Tours by Design experiences are private journeys curated exclusively for you by the Crooked Compass team. Whether you’re drawn to one of our existing itineraries, wish to adapt a small-group tour for private travel, or want to design something entirely new, we’ll craft a journey that reflects your pace, passions, and sense of discovery.
Why pay for inclusions that don’t fit? With Tours by Design, every detail is intentional – from the destinations and experiences to your style of travel and choice of accommodation. Each itinerary is hand-built through our deep local partnerships and expertise, ensuring authenticity, comfort, and connection in every moment.
Why travellers love Tours by Design:
More about our Tour Styles.
Our Partner Tours are carefully chosen group journeys operated by our long-standing, in-country partners — experts who share our values of authenticity, cultural respect, and meaningful connection. These departures, averaging between 17 and 22 travellers, are designed and delivered by our partners, while Crooked Compass manages your booking and provides full support from start to finish.
Enjoy the reassurance of booking through an Australian-based company, delivering our same personalised service and attention to detail you expect from Crooked Compass. We take care of the logistics, so you can focus on what matters most – the journey itself.
Why travellers love our Partner Tours:
More about our Tour Styles.