Winter walking tour through Tbilisi’s terraced Old Town, Narikala Fortress & sulphur baths
Snow-framed views of the Caucasus Mountains from Sighnaghi & the Alazani Valley
Private family lunch and traditional qvevri wine experience in Kakheti
Visit to ancient Uplistsikhe Cave Town along the historic Silk Road
Exploration of medieval monasteries including Bodbe & Alaverdi Cathedral
Winter in Georgia carries a quiet, reflective beauty. Snow settles lightly across vineyard valleys, church domes rise through crisp mountain air, and ancient fortresses overlook towns wrapped in stillness.
This journey through Tbilisi, Kakheti, and the historic heartland of Kartli reveals a country where early Christianity, Silk Road trade routes, and centuries-old winemaking traditions remain woven into everyday life. From terraced old towns and rock-hewn cave cities to monasteries framed by the Caucasus Mountains, the season lends clarity, calm, and intimacy to each place. Warm hospitality, family-hosted meals, and traditional wine cellars offer contrast to the cool air outside, creating a balanced winter exploration of Georgia’s cultural depth and landscape.
Download this tour’s PDF brochure and start your planning offline!
Signature Tour 
Tbilisi rests along the Mtkvari River, where old districts rise in gentle terraces beneath ancient fortresses and church domes. In winter, the city feels hushed and reflective. Steam rises from bathhouse rooftops, balconies frost at their edges, and the air carries the quiet clarity of the season.
On arrival at Tbilisi International Airport, transfer to your hotel in the city. The remainder of the day is at leisure to settle in and rest after your journey.
Overnight – Stamba Hotel (or similar)
Explore Tbilisi’s historic heart today, where neighbourhoods rise in terraces above the river and wooden balconies pattern the lanes with carved detail. Winter sharpens the city’s lines and colours. Pale sunlight catches tiled roofs, the air stays crisp and clear, and steam from the bathhouses hangs lightly above the old quarter.
Begin at Metekhi Church (13th century), set high above the Mtkvari River with sweeping views across Old Tbilisi. Continue on foot through winding streets and narrow lanes, passing colourful houses, ornate balconies, and pockets of striking modern architecture woven into the older city fabric.
Make your way up to Narikala Fortress (4th century) for panoramic views across the city, then descend into the historic domed sulphur bath district, the atmospheric quarter associated with Tbilisi’s origins. Dinner is arranged at a local restaurant this evening. (B,D)
Overnight – Stamba Hotel (or similar)
Begin the day with a drive east into the Kakheti region, widely regarded as the homeland of Georgian wine. In winter, the vineyards lie bare beneath a pale sky, and the distant Caucasus Mountains appear sharply defined above the Alazani Valley.
Arrive in the fortified town of Sighnaghi, known for its cobbled streets, pastel-coloured houses, and defensive walls overlooking the valley. Walk through the quiet lanes and take in expansive views across the snow-capped Caucasus range and the winter landscape below. Continue to Bodbe Monastery (4th century), the resting place of St. Nino, who introduced Christianity to Georgia in 337 AD. The monastery grounds offer sweeping views over the valley, particularly striking in the clarity of the winter air.
A visit to Kakheti includes a traditional lunch hosted by a local family, offering regional dishes and insight into everyday life in this wine-producing region. Later, visit the Gremi Architectural Complex (16th century), once the political and cultural centre of Kakheti for several centuries. The stone structures stand prominently against the open landscape. Continue to Telavi for the evening. (B,L)
Overnight – Kviria Hotel (or similar)
Begin the morning at the local farmers’ market in Telavi, where winter produce, preserved fruits, churchkhela, spices, and homemade cheeses are displayed in colourful rows. The slower winter pace allows time to observe daily life in this regional centre. Continue to Alaverdi Cathedral (11th century), which for many centuries was the tallest church in the Caucasus. Its stone walls rise prominently against the open valley landscape, often framed by snow-dusted fields and distant mountain ridges.
Drive onward to the village of Vardisubani, where a local master crafts traditional clay vessels known as qvevri. These large earthen jars have been used for centuries in Georgian winemaking, buried underground to ferment and store wine according to ancient methods. Observe the process and learn about this UNESCO-recognised tradition.
In the village of Kondoli, visit a traditional Georgian wine cellar. The host’s dedication to natural winemaking is reflected in the wines produced here. Taste “Zhghia,” a distinctive natural wine made from rare, high-quality Kakhetian grapes, with limited annual production. This wine has gradually found its place in select European markets while remaining rooted in traditional methods.
Return to Tbilisi in the evening. (B)
Overnight – Stamba Hotel (or similar)
Drive west into the Kartli region, where open plains and low winter hills stretch beneath a pale sky.
Begin at Uplistsikhe Cave Town (1st millennium BC), an ancient rock-hewn complex that once stood along the Great Silk Road. Carved directly into sandstone cliffs, the site includes dwellings, wine cellars, bakeries, a three-nave basilica church, and even an ancient theatre. In winter, the quiet atmosphere and clear air bring a particular stillness to the site, allowing the scale and ingenuity of this early urban settlement to stand out against the surrounding landscape.
Continue to Gori, birthplace of Joseph Stalin. Visit his preserved childhood house and the Stalin Museum, which presents artifacts and exhibits connected to his life and political legacy.
Return to Tbilisi in the late afternoon. (B)
Overnight – Stamba Hotel (or similar)
Today is at leisure in Tbilisi without guide or driver services. Winter lends the city a quieter rhythm. Spend time exploring neighbourhood cafés, galleries, and bookshops tucked into the old town’s narrow streets. Walk along Rustaveli Avenue, visit museums, or return to the sulphur bath district for a traditional thermal experience. The clear winter light offers excellent views from the hilltop viewpoints, while evenings invite warm meals and local wine in intimate restaurants.
The day is open to explore independently at your own pace. (B)
Overnight – Stamba Hotel (or similar)
This morning is yours at leisure until it is time for you to be transferred 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 2 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.
Stay up to date with the latest travel trends and new destinations opening up. To be the first to go, you need to be the first to know.
Travel professionals are welcome. For partnerships or agent enquiries, we recommend contacting us directly.
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:
More about our Tour Styles.
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:
More about our Tour Styles.
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:
More about out Tour Styles.
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.
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