Delicious wines, untouched countryside, traditional life, and hidden cultures all make this former Soviet country ooze with intrigue for travellers seeking that next off-beat destination.
Wedged between Romania and Ukraine, eat and drink your way through this remote and obscure nation before venturing into the breakaway republic of Transnistria where life under Soviet rule continues. From minority ethnic groups to unheard-of world-class wineries, monastic life and monasteries hunkered in caves, the entwinement of culture, raw nature and former regime life make this journey fascinating for the traveller looking the last corner of Europe to discover.
Download this tour’s PDF brochure and start your planning offline!
Signature Tour 
Welcome to Moldova! Upon arrival at Chisinau International Airport, you will be met by your guide and transfer to Chisinau city (12km, 20min approx.) for your first taste of Moldova. A city dating back over six centuries which has been rebuilt many a time from WWII conflicts, through to earthquakes, absorb the soviet style architecture squeezed in alongside modern skyscrapers and trendy cafes.
Be acquainted with the city’s history as you explore the historical part of the capital. Pause at the monument of a great Moldova Ruler Stefan the Great and Saint, the Bell Tower, Lord Nativity Cathedral, the Triumph Arch followed by the Parliament, the Central Square “Stefan cel Mare”, and City Hall. This evening, enjoy a welcome dinner at a local restaurant serving traditional Moldovan cuisine. (D)
Overnight Bristol Central Park hotel Chisinau or similar
Distance and Journey Time: 30 minutes’ drive from the airport
Walking Distance: Approximately 4km
Walking Time: Approximately 2hours
Difficulty: Moderate, with no shade and a steady incline
Following breakfast, set off to explore the Cricova Wine cellars – a must-see when in Moldova (16km approx. 30min drive). Venture into the underground tunnels of the wine cellars and see a large collection of exclusive wines. Here you will become acquainted with the process of wine and sparkling wine production. The oldest wine to be stored at Cricova is a Jerusalem Wine (bottled in 1902). Cricova is a unique place housing historic wines among which Goering’s collection holds pride of place. Head into the winery tasting hall for wine tasting and lunch with dishes paired to match the wines.
This afternoon, visit the monastic complex of Curchi (46km, approx. 45 min drive), located in one of the most picturesque areas in the centre of Moldova, the Codrii forests. Here you will talk with a local monk about their daily life in the monastery.
Continue to an open-air museum complex Orhei Vechi (Old Orhei) that presents the remains of different civilizations established between the nearby Nistru and Prut rivers(40km, approx. 40 min drive). The complex comprises of caves, grottos, churches, hermitages, and a Geto-Dacian fortress. The open-air museum represents a true natural fortress inhabited since ancient times. Walk into the Orthodox Cave Monastery and feel the spirit of ancient times. Learn the way of life of the villagers of the past and visit a typical 19th century Moldavian house-museum.
Your destination for the night is the Moldavian village of Butuceni (5km, approx. 12 min drive)where the style and traditions of the Moldavian architecture of the 19th century are preserved and carefully maintained – ornamentally decorated houses, gates, fences, wells with potable water, old cellars and more certainly provide character to traditional life here. Check-in to your local accommodation in the village of Butuceni where you will spend the night in the spectacular countryside, surrounded by huge rocky hills. Dinner this evening will be in house and combination of traditional dishes and home-made wine. (B,L,D)
Overnight Eco-Resort Butuceni or similar
Distance and Journey Time: 3hr drive, 30 minutes by local electric car in Cricova
Walking Distance: Approximately 5km
Walking Time: Approximately 3-4hours in total
Difficulty: Moderate, underground winery walking, deepest point 100m, 12 degrees Celsius, to have jackets on. Open-air museum complex, rocks and cliffs, cave monastery, recommended stable shoes.
Departing the countryside, travel north-east through rural Moldova to the secluded Saharna Monastery. Set against a backdrop of forested cliffs and cascading streams, Saharna is known for its tranquil cave monastery and the 22 waterfalls formed by the Saharna River. Climb to the summit of Grimidon Hill to find a small chapel, where local legend claims the Mother of God appeared before Saint Varfolomei, leaving a footprint embedded in the stone.
Continue to Tipova, home to the largest cave monastery complex in Moldova. Carved directly into limestone cliffs along the Nistru River, the Tipova monastery dates back to the 11th century. The caves offer insight into early Orthodox Christian practices and monastic life in isolation.
Stop in the riverside village of Lalova for a traditional Moldovan lunch hosted by a local family. The warm hospitality and home-cooked meal provide a genuine connection to village life along the Nistru.
Return to Butuceni in the Orheiul Vechi region for an evening culinary experience. Join a local cook for a hands-on masterclass preparing plăcinte, traditional round pastries filled with seasonal ingredients such as cottage cheese, potatoes, pumpkin or apples. Share your creations over dinner, paired with a glass of Moldovan wine. (B,L,D)
Overnight Eco-Resort Butuceni or similar
Distance and Journey Time: 4hr drive
Walking Distance: Approximately 4km
Walking Time: Approximately 2hours
Difficulty: Moderate, sometimes shaky hills in Saharna area when getting to Saharna cascades, there are rocky hills, recommended stable shoes.
Following a countryside breakfast, depart for northern Moldova. Your first stop is the historic town of Soroca, strategically positioned on the Nistru River. Visit the 15th-century Soroca Fortress, originally built in 1499 by Stephen the Great as a wooden fortification. It was later reconstructed in stone and has since withstood Tatar invasions, Cossack sieges, the campaigns of Polish King Jan Sobieski, and military actions led by Bogdan Khmelnytsky and Peter the Great. The guide will provide insight into the fortress’s military history and its role in regional power struggles.
Continue through Soroca to the Gypsy Quarter, known for its flamboyant mansions built by the local Roma community. These elaborate homes are inspired by iconic buildings, including a replica of Moscow’s Bolshoi Theatre. A short stop at Gypsy Hill offers a photo opportunity overlooking the area.
After lunch in Soroca, travel to the nearby village of Pocrovca, home to Moldova’s Old Believers. This conservative Russian Orthodox community lives in relative isolation, and while you will not meet the villagers directly, your guide will explain their traditions and way of life. You will visit their distinctive wooden church, an important part of their spiritual practice.
Nearby lies Moldova’s sole UNESCO-listed site, the Struve Geodetic Arc. This 19th-century chain of survey triangulations helped establish the size and shape of the Earth, and a preserved marker sits just outside Pocrovca.
On the return journey to Chisinau, stop at Clisova Noua to explore the Arta Rustica handicrafts museum. Housed in a traditional village setting, the collection showcases Moldovan folk art and heritage. View traditional carpets, handwoven garments, pottery, and functioning wooden looms that reflect generations of rural craftsmanship. Arrive in Chisinau for hotel check-in and dinner. (B,L,D)
Overnight Bristol Central Park Hotel Chisinau or similar
Distance and Journey Time: 5.5hr drive
Walking Distance: Approximately 3km
Walking Time: Approximately 1.5hours
Difficulty: Moderate, with no shade and a steady incline
Transnistria – officially called the Pridnestrovian Moldavian Republic by Moldova – is a narrow strip of land between Moldova and western Ukraine that is home to about 500,000 people. It is an unrecognized breakaway state that left Moldova after the collapse of the Soviet Union in 1990. The Transnistrian government has de facto independence, but it is recognized by other countries and the United Nations as part of Moldova.
Today you will have a full day trip to Transnistria (68km, approx. 1hr drive), diving into the history of this self-proclaimed independent and unrecognized Pridnestrovian Moldavian Republic that has its own currency, border guards and policy.
You will explore the 16th century Tighina fortress and visit the on-site museum. The first documented mention of ‘Tighina Fortress’ was in 1408. Its walls have survived to the present time and offer an example of classic Moldavian defensive construction. Tour the city Bendery with lots of Soviet relics, visit a Soviet style café ‘Stolovka SSSR’ and feel the atmosphere of Communism.
While in the capital of Transnistria, Tiraspol (11.9km, approx. 18min drive), you’ll see the Drama and Comedy Theatre, the Lenin and Suvorov Monuments, the Parliament, the House of Soviets and have a walking tour along the river Dniestr. It was founded by the Russian general Alexandr Suvorov in 1792, whose statue is rising on the central square in Tiraspol.
Enjoy lunch at a local restaurant, sampling several Soviet-style dishes.
After lunch, you’ll find yourself at KVINT, a distinguished cognac distillery. The KVINT brand produces excellent spirits like cognacs, whisky, liquors, vodka, wine and more. Tour the factory and taste some of their locally produced spirits.
In the evening, visit a Sturgeon Fish Farm in Tiraspol. Sturgeon Caviar is considered to be the gold standard in caviar, and this farm is one of the largest producers of Sturgeon caviar in the world. You will learn how sturgeon fish are farmed, and the process of producing black caviar. You will also try some of the black gold for yourself! Check in to your hotel in Tiraspol for dinner and overnight. (B,L,D)
Overnight Rossia Hotel or similar
Distance and Journey Time: 3.5hr drive
Walking Distance: Approximately 3-4km
Walking Time: Approximately 3hours
Difficulty: Moderate, with no shade and a steady incline
Following breakfast at your hotel, head to the South of Moldova to experience the history, culture, and traditions of the Gagauzian people. The Gagauz, a Turkic-Orthodox Christian people, have lived in the Balkans for hundreds of years, managing to preserve their language and culture.
Today, the Gagauz people occupy a unique position between the Turkic, European, Muslim, and Orthodox worlds. With a population of about 250,000, the Gagauz people primarily live in the Autonomous Territorial Unit of Gagauzia (ATUG) in Moldova, where Gagauz is the official language along with Russian and Moldovan.
The Gagausian capital of Comrat (126km, approx. 2hr10min drive) is situated in the southern zone of Moldova. It is known for producing delectable red wines. While touring the city, you will visit the Central Cathedral, the History and Ethnography Museum, the Turkish Library, and the Central Market. On a walking tour of the local food market, you will mingle with local producers and see the freshest and highest-quality products on offer to locals and visitors alike.
Then, visit the winery ‘Comrat-Vin’ where you will have a chance to taste Gagausian wines which have a special aroma of south region wines. Enjoy lunch in Gagauzian style at the winery restaurant. You will taste traditional dishes like ‘kavurma’ – lamb roast, ‘guzlemea‘ – salty pastry with sheep cheese stuffing and other local delicacies.
In the afternoon, drive to the nearby Besalma village (20km, approx. 22min drive) to visit the Museum of History and Ethnography featuring the story of the unique Orthodox people of Turkic origin that call Southern Moldova home. In 1966 the writer D. Cara-Ciobanu founded a museum in Besalma to preserve the culture of the Gagauzian population and their origin. Hundreds of artifacts collected from all over Gagauzia are now on display in the museum for visitors. Watch a short movie about Gagauzian nation, their traditions, and get the whole picture of their life.
A folk group performance of local Gagauzian women dancing and singing national songs will have you up and joining in too!
Continue to Congaz (10km, approx. 12min drive), which is considered to be the biggest village in Europe. You’ll visit the ethno yard “Gagauz Sofrasi” where the locals will greet you with their traditional hospitality, welcoming you with bread and salt. Of course, you will be refreshed with some local Gagausian wine.
Tour Gagauz Sofrasi, visiting the village museum and small airbrick houses with wooden furniture and natural clay walls where you’ll be spending the night experiencing authentic countryside accommodation.
Take some time to settle into your accommodation for the night and freshen up. Before a Gagausian dinner, your host will invite you to a culinary master class where you’ll make a traditional salty pastry ‘giuzlemea’ which is stuffed with sheep cheese. (B,L,D)
Overnight Congaz Guesthouse or similar
Distance and Journey Time: (approx. 155km, 3hr drive)
Walking Distance: Approximately 3km
Walking Time: Approximately 1.5hours in total
Difficulty: Moderate, with no shade and a steady incline
Today, you will explore the oldest Moldovan monastery, and the legendary wine collection of the world’s largest wine cellar at Milestii Mici winery.
Leaving the Gaugasian region to head towards Chisinau, the first stop is at Capriana Monastery. Capriana monastery is considered the oldest in Moldova and is located in the beautiful forest region of Codrii. It was founded by the great Moldovan Ruler Stefan the Great. Closed and dilapidated during the post-war period, it was only reopened again in 1989, becoming a symbol of national revival.
After breathing the fresh air of Codrii, step into one of the biggest wine cellars in the world and witness ‘the Golden Collection Milestii Mici’ which holds a place in the Guinness Book of Records for storing more than 1.5 Million bottles of wines from all types of drops including Pinot, Traminer, Muscat, Riesling, Feteasca, Codru, and Negru de Purcari.
The underground wine cellar is a maze of tunnels and you’ll be transported around the 200km of tunnels by buggy! Your wine tour is followed by wine tasting (of course) and lunch in the winery’s underground tasting hall. In the afternoon, continue to Chisinau and check into the hotel before enjoying a farewell dinner at a local restaurant. (B,L,D)
Overnight Bristol central park hotel Chisinau or similar
Distance and Journey Time: approx. 196km, 3-3.5hr drive, 20 min underground drive on electric car in the limestone wine cellars.
Walking Distance: Approximately 2km
Walking Time: Approximately 1.5hours in total
Difficulty: Moderate, with no shade and a steady incline, underground walking in Milestii Mici, 12degrees Celsius, recommended warm jacket on
This morning is yours at leisure until it is time for you to be transferred to the airport for your onward flight. (B)
Distance and Journey Time: 30 minutes’ drive to the airport
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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.
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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.
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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.
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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.
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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:
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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.
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