Experience Georgia’s 8,000-year-old wine heritage, including traditional Qvevri tastings.
Join hands-on cooking experiences with local families across multiple regions.
Explore the vineyards and historic towns of the Kakheti wine region.
Travel the Georgian Military Highway into the Greater Caucasus Mountains.
Discover ancient sites from Old Tbilisi to the rock-hewn city of Uplistsikhe.
Georgia sits at the crossroads of Europe and Asia, where mountain landscapes, ancient monasteries, and fertile valleys shape both culture and cuisine. With an 8,000-year-old winemaking tradition and a table defined by regional diversity, the country offers one of the world’s most distinctive culinary journeys.
This immersive eight-day experience explores Georgia through its food, wine, and local communities. From the cobbled streets of Tbilisi to the vineyards of Kakheti and the dramatic peaks of the Greater Caucasus, each day combines cultural heritage with hands-on culinary encounters. Visit family-run wineries, learn the UNESCO-listed Qvevri winemaking method, prepare traditional dishes alongside local hosts, and discover regions rarely included in conventional itineraries.
Blending historic architecture, mountain scenery, and authentic hospitality, this journey offers a comprehensive introduction to Georgia’s enduring traditions and contemporary revival, one shared meal and one glass at a time.
Download this tour’s PDF brochure and start your planning offline!
Signature Tour 
Welcome to Georgia! Upon arrival in Tbilisi, you will be met at the airport and transferred to your hotel. The remainder of the day is yours at leisure.
Tbilisi’s cobblestoned old town reflects a long, complicated history, with periods under Persian and Russian rule. Its diverse architecture encompasses Eastern Orthodox churches, art nouveau buildings, and Soviet Modernist structures. Looming over the city are Narikala Fortress, a reconstructed 4th-century citadel, and Kartlis Deda, the iconic “Mother of Georgia” statue.
Overnight – Stamba Hotel or similar
This morning after breakfast, set off on foot to explore Tbilisi, starting at the 13th-century Metekhi Church and taking in magnificent views over the old city.
Wander the narrow streets of the historic districts, where colourful terrace houses with carved wooden balconies stand alongside examples of modern architecture. Learn how Tbilisi has long been home to Georgians, Armenians, and Azerbaijanis living side by side, and discover a city where mosques, cathedrals, Russian Orthodox churches, synagogues, and Zoroastrian temples coexist within the same neighbourhoods.
Continue through the ancient 4th-century Narikala Fortress, taking in panoramic views over the town below, before walking down to the historic domed sulphur bath area. Lunch will be served at a local restaurant. (B,L)
Overnight – Stamba Hotel or similar
Depart Tbilisi this morning and travel east into the Kakheti region, Georgia’s principal wine-producing area, known for its hospitality and culinary heritage. Arrive in the 18th-century hilltop town of Sighnaghi, enclosed by defensive walls and distinguished by tile-roofed houses and carved wooden balconies. From its elevated position, enjoy views across the Alazani Valley toward the Greater Caucasus Mountains.
Continue to a local farmer’s home for lunch featuring homemade regional dishes. Take part in a cooking experience, learning how to prepare Churchkhela, the traditional walnut and grape confection, and observe Georgian bread baking in a clay oven.
Continue to the Gremi Complex (16th century) for a photo stop before visiting the renowned Kindzmarauli Winery in Kvareli. Taste Georgian wines paired with local cheeses, guided by sommeliers who have carefully developed complementary flavour profiles. Continue to Telavi for the evening. (B,L)
Overnight – Kviria Hotel or similar
Begin with a walk through Telavi, a town known for its relaxed atmosphere, historic buildings, and longstanding hospitality traditions. Continue to Alaverdi Cathedral (11th century), which stood for centuries as the tallest church in the Caucasus. Nearby, sample traditional Georgian sour milk in a variety of flavours.
Travel onward to Pankisi Gorge, an area rarely included in standard itineraries and often described as a hidden valley of the Caucasus. Experience the distinct culinary traditions of the Kist community and take part in preparing the local dish Jijig-Galnash. Lunch will feature Kist-Georgian specialities.
In the afternoon, visit the 19th-century estate of Duke Alexander Chavchavadze in Tsinandali. The landscaped garden and residence once served as a cultural gathering place for poets and artists.
Continue to Kondoli to visit a traditional Georgian wine cellar, where you will taste wine produced in Qvevri, the ancient clay vessel method of winemaking recognised on UNESCO’s Intangible Cultural heritage list. Return to Telavi for the evening. (B,L)
Overnight – Kviria Hotel or similar
Depart Telavi and visit Vardisubani, where generations of artisans continue the tradition of crafting Qvevri clay vessels. Meet a local family of Qvevri makers and learn about the detailed, multi-stage process behind these vessels, central to Georgia’s distinctive winemaking heritage.
Continue through Akhmeta and the scenic landscapes of Tianeti before joining the historic Georgian Military Highway, which leads north toward the Russian border. En route, stop at the Ananuri Architectural Complex (17th century). The fortress and its two churches overlook the turquoise Zhinvali Reservoir, and the intricate stone carvings represent some of the finest examples of Georgian ecclesiastical art. Drive onward through dramatic Caucasus Mountain landscapes to Stepantsminda, the principal town of the Kazbegi region. (B,L)
Overnight – Rooms Hotel Kazbegi – Mountain View Room or similar
Visit Gergeti Trinity Church, the defining landmark of the Kazbegi region. Drive through forested valleys to 2,170 metres above sea level, where the 14th-century church stands against the backdrop of the Greater Caucasus. On clear days, Mt Kazbegi (5,054 m) and its glacier dominate the horizon.
In the afternoon, continue through the dramatic Dariali Gorge, which leads toward the Russian border. The steep rock faces and river valley create one of the most striking landscapes in the region.
Return to Stepantsminda and visit a local family home for lunch featuring Khinkali, the iconic Georgian dumpling originating from the mountain regions of Mtiuleti, Pshavi, and Khevsureti. Take part in preparing your own Khinkali during a hands-on masterclass. Afterwards, observe traditional felt-making techniques and sample a variety of homemade jams. (B,L)
Overnight – Rooms Hotel Kazbegi – Mountain View Room or similar
Depart the Caucasus Mountains and travel south into the Kartli region, often considered the historical heart of Georgia. Stop in Kaspi to visit a local wine cellar where younger generations continue Georgia’s winemaking traditions. Taste natural wines, including Tavkveri, produced from rare grape varieties that were once close to extinction. Lunch will be served at the family home. Take part in a traditional Khachapuri masterclass, learning to prepare Georgia’s celebrated cheese-filled bread.
Continue to the ancient rock-hewn city of Uplistsikhe, once a key point on historic trade routes. Explore preserved halls, caves and passageways carved into the rock, including remnants of an ancient theatre, pharmacy and wine cellar. In the late afternoon, return to Tbilisi. (B,L)
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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