Nestled at the crossroads of Europe and the Balkans, Bulgaria beckons with an irresistible blend of ancient history, vibrant culture, and awe-inspiring landscapes. This Eastern European gem, often overlooked, unfolds a narrative that spans millennia – from Thracian civilisations to the medieval splendours of the Bulgarian Empire.
Wander through charming cobblestone streets in Sofia, the dynamic capital, where modernity harmonises with historic treasures. Explore picturesque villages like Melnik, perched against sand pyramids, and experience the warmth of Bulgarian hospitality. Traverse the Rhodope Mountains, where folklore intertwines with stunning vistas, and indulge in the culinary artistry of local wineries. Bulgaria’s heritage is etched in the walls of Rila Monastery, a UNESCO World Heritage Site, and the architectural wonders of Kovachevitsa. Whether you’re captivated by cultural immersion, mountain escapades, or gastronomic delights, Bulgaria invites you to unravel its secrets.
Download this tour’s PDF brochure and start your planning offline!
Signature Tour 
Welcome to Bulgaria and the capital city of Sofia! Upon arrival at the airport, you will be met and transferred to your hotel. The remainder of the day is yours at leisure.
Nestled at the foothills of Vitosha Mountain, Sofia exudes an alluring charm with its diverse architectural landmarks, from the iconic Alexander Nevsky Cathedral to the ancient Roman ruins scattered throughout the city. As a dynamic European hub, Sofia captivates visitors with its lively atmosphere, bustling markets, and a burgeoning culinary scene, making it a captivating destination that harmoniously embraces its past while embracing the promise of the future.
Overnight – Hotel Sense or similar
Embark on an immersive walking tour through Sofia, a city that effortlessly intertwines its historical significance with modern vibrancy. Starting near the iconic St. Alexander Nevsky Cathedral, the largest church in Bulgaria, your journey navigates through the renowned Yellow Pavements, a symbol of Sofia’s core and a pathway to key landmarks like the National Assembly, Council of Ministers, and the National Theatre. Strolling along these cobblestones, you’ll encounter architectural gems such as the Sofia city bath, Banya Bashi Mosque, Central Sofia halls, the synagogue, and the National Palace of Culture, each revealing a unique facet of the city’s heritage. To truly absorb the contemporary spirit of Sofia, your exploration concludes with a delightful break at Vitoshka for a coffee.
Lunch today is all about Soviet nostalgia in a retro communist themed restaurant. Dine amongst the communist memorabilia and bask in the mid-century minimalism of bare bulbs and blocky, modernist propaganda posters. Indulge in the rich falvours of Bulgarian cuisine while basking in the eclectic soviet atmosphere. The menu, thoughtfully curated, showcases an array of dishes, from hearty mezes to expertly crafted mains, all complemented by an extensive selection of Rakia, the iconic Bulgarian fruit brandy, making every bite a delightful celebration of local culinary artistry.
You will then Transfer to Plovdiv (150km, approx. 2hr). Steeped in over 6,000 years of continuous habitation, Plovdiv proudly boasts the title of Europe’s oldest continuously inhabited city. Stroll through its enchanting, cobbled streets, where well-preserved Roman ruins harmonize with vibrant art scenes and lively cafes, creating an ambiance that seamlessly bridges the gap between the past and the present.
Dinner this evening is a short stroll from your hotel in an exclusive and private venue. Perched on top of an ancient Roman defence wall from around 2nd century, the house of Philipopolis is a gem of beauty and elegance. This mansion is declared a national monument of culture. Dine in this restored historic residence amongst a collection of art from 19th century to the present day. Sit amongst the history of the Bulgarian people after the Liberation from Ottoman dominance to modern times, embodying legends, stories, artists fortunes and events. A truly enchanting experience and a venue exclusive to Crooked Compass. (B,L,D)
Overnight – Hotel Vizualiza Residence or similar
Begin your journey through the charming, cobbled streets, where the enticing aroma of traditional Bulgarian delicacies fills the air. Our expert local guide will lead you to hidden gems, from bustling markets to tucked-away eateries, unveiling the diverse flavours that define Plovdiv’s culinary identity.
Savour mouthwatering banitsa pastries, aromatic kufte kebabs, and the famed Plovdivian specialty, Kapama, a rich and savory slow-cooked meat stew. Immerse yourself in the vibrant atmosphere of the Kapana district, and discover the city’s passion for wine as you sample local varieties and learn about the rich winemaking heritage of the region.
During your walking tour, you’ll discover the Roman ruins of Plovdiv, a city built atop remnants of the Roman Empire still being excavated today. Highlights include the Ancient Theatre of Philippopolis, a 2nd-century AD marvel of Roman engineering that once hosted grand performances and now offers panoramic views of the city. Beneath Plovdiv’s bustling streets lies the Roman Stadium, a well-preserved structure that once hosted athletic contests. As you wander the cobblestone streets of the Old Town, you’ll encounter Roman walls, gates, and buildings, all showcasing the enduring legacy of Roman civilization.
Next, we have arranged an exclusive meeting with a fascinating iconographer, an artist specializing in the creation of icons – religious images typically used in Eastern Orthodox Christian worship. This sacred vocation transcends artistic expression, blending symbolism, theology, and techniques passed down through generations. Our host, one of the few practicing this rare trade, showcases incredible skill, and you can witness works she is restoring dating back to 800 years old from various churches around Bulgaria.
You will then transfer to Dragomir Winery in the heart of the Thracian valley which is famous for its traditions in winemaking that date back to ancient times. The Thracians are known to be among the best winemakers in the Antiquity and their strong, aromatic wine is world famous, with even Homer writing about its qualities. Explore the intricate process of wine production, from grape to bottle. Led by a knowledgeable oenologist, delve into the vineyard’s terroir, witness the meticulous winemaking techniques, and conclude the tour with an exclusive private tasting of Dragomir’s exquisite wines, each sip revealing the nuanced flavours that define the region’s viticultural excellence. (B,L)
Overnight – Hotel Vizualiza Residence or similar
This morning, you will transfer to Gela (100km, approx. 2.5hrs). Legend has it that Gela, nestled in the enchanting Rhodope Mountains, is the mythical birthplace of Orpheus, who ventured into the nearby Devil’s Throat Cave in search of Eurydice. Steeped in ancient history, the village’s name derives from the Thracian Bes tribe, revered as the Priests. Founded by the Thracians, Gela boasts remnants of a Thracian fortress near its borders, echoing tales of times long past. Perched high in the mountains, Gela feels like a secluded haven, inviting you to embrace its timeless charm. Renowned as one of Bulgaria’s three major energy centres, Gela is blessed with crisp mountain air and the rejuvenating Fion wind from the Aegean Sea offers a haven for respiratory health. Gela’s charm shines each summer as it hosts the National Bagpipe Festival, drawing over 10,000 attendees to the Rhodope Mountains, a global hub for this iconic instrument.
Visit Bachkovo Monastery, the second largest and profoundly significant Bulgarian monastery, which stands as a cultural crossroads, blending influences from Byzantine, Old Georgian, and Bulgarian traditions. Established in 1083 by Georgian brothers, the monastery houses the oldest carved wooden iconostases in the region, alongside a treasure trove of original icons, frescoes, church artifacts, and manuscript book covers. A jewel within its walls is the revered icon of Our Lady of Vlaherna, shrouded in silver and revered for its miraculous aura, although its origin remains shrouded in mystery since its appearance in the early 19th century. The monastery’s extensive library, with its wealth of books and manuscripts dating back to the 1930s.
This afternoon, enjoy a walking tour through Gela. As you walk the charming, cobbled streets, your guide will unveil the village’s Thracian origins, showcasing remnants of a bygone era, including the legendary Thracian fortress.
Next, delve into the rich flora of the Rhodope Mountains as part of a unique foraging experience for wild mushrooms. Led by a local expert, you will learn to identify an array of edible fungi hidden beneath the forest canopy. Your foraging adventure will be infused with insights into traditional mushroom-picking practices passed down through generations. (B,D)
Overnight – Hotel Gela and Spa or similar
Today you will drive to Kovachevitsa, stopping enroute at a mountain village where you will meet Maria Jekova, the winner of Bulgarian Masterchef, who now has her own TV show called The Taste of Bulgaria. Maria’s culinary journey extends beyond the screen – she has transformed an abandoned hamlet into a charming guesthouse and kitchen, using her Masterchef winnings. Witness the revival of this once-forgotten mountain village as Maria gradually lures locals back by providing employment in this remote and rejuvenated location. Enjoy a hands-on cooking class with Maria, utilising ingredients sourced from the surrounding forests and mountains. This is more than a cooking class; it’s a mountain-to-plate odyssey, where you’ll not only learn the art of crafting authentic Bulgarian dishes but also partake in a culinary narrative that breathes life back into an abandoned village.
Continue to Kovachevitsa, a village with well-preserved 18th and 19th-century architecture featuring traditional stone houses adorned with wooden details before returning to your hotel. (B,L,D)
Overnight – Hotel Gela and Spa or similar
This morning, depart for the captivating villages of Leshten. Leshten welcomes you with the timeless beauty of Kovachev architectural style, where houses perch gracefully on the mountain’s steep slopes, preserving the authentic spirit of Bulgarian village life.
Continue to Zornitza Family Estate, your home for the next 3 nights. Start with a tour of the property, beginning with a stroll through the lush vineyards, where the estate’s exquisite wines take root. Learn about the winemaking process, from the meticulous cultivation of vines to the artistry of crafting fine wines, as you visit the state-of-the-art winery. Walk through the olive groves, where the estate produces its exceptional olive oil. Witness the harvest and pressing of olives, gaining insights into the estate’s dedication to quality and sustainability.
The tour extends to the exquisite culinary realm with a visit to the estate’s kitchens. Here, indulge your senses as talented chefs transform locally sourced, seasonal ingredients into culinary masterpieces. Discover the secrets behind the estate’s farm-to-table philosophy, celebrating the richness of the region’s flavours. As the tour unfolds, immerse yourself in the luxurious ambiance of the estate’s boutique hotel and spa. Marvel at the seamless integration of modern elegance with the natural surroundings, offering a retreat where relaxation and sophistication harmonise.
This evening, experience a culinary delight with a BBQ Dinner in a secret location. An enchanting evening that combines the rustic charm of a barbecue with the sophistication of the estate’s luxurious surroundings. As the sun sets, guests are invited to a specially curated outdoor setting, where the enticing aroma of grilled delicacies fills the air. BBQ Dinner unfolds with a selection of premium meats and fresh, locally sourced ingredients expertly prepared by skilled chefs. Indulge in a feast that showcases the rich flavours of the region, with succulent meats grilled to perfection and accompanied by an array of delectable side dishes. (B,D)
Overnight – Zornitza Family Estate or similar
After breakfast, start your day with a scenic drive to Melnik, the smallest town in Bulgaria but abundant in cultural and historical charm. Wander through the cobbled streets lined with traditional Bulgarian houses, many of which are national monuments. You may wish to visit the Kordopulov House (not included/paid locally), a well-preserved 18th-century mansion showcasing the region’s architectural heritage.
Continue to the Sand Pyramids, a natural wonder formed by erosion, creating whimsical sand formations. Take a leisurely walk around the pyramids, marvelling at the unique shapes sculpted by wind and water over time. Capture stunning panoramic views of the surrounding landscapes from the elevated viewpoints.
Relish a delightful lunch at a local restaurant in Melnik, offering traditional Bulgarian cuisine with a modern twist. Savor regional specialties, including local cheeses, grilled meats, and fresh salads, paired with renowned Melnik wine.
After lunch, travel to Rozhen Monastery, a significant cultural and religious site. Explore the monastery complex, featuring the Nativity of the Mother of God Church, adorned with remarkable frescoes and icons. Take in the serene atmosphere of the monastery’s surroundings and enjoy panoramic views of the Pirin Mountains.
You will then return to your accommodation. The afternoon is yours at leisure to relax and enjoy some of Zonrnitza’s spa treatments and facilities.
As the sun sets over the picturesque Melnik region, you are welcomed to a charming pre-dinner reception drink at Aya Estate. Sip on a glass of the finest wine or enjoy a refreshing cocktail amidst the lush vineyards and scenic beauty that surrounds the estate. For dinner, return to Zornitza and enjoy the Chef’s Tasting Menu, curated by the estate’s talented chefs, and showcasing a symphony of flavours, artfully presented in a sequence of courses. Each dish is a masterpiece, highlighting the freshness of locally sourced ingredients and the creativity of the culinary team. Complementing the gastronomic delights, Zornitza’s knowledgeable sommeliers guide guests through a thoughtfully curated wine pairing experience. (B,L,D)
Overnight – Zornitza Family Estate or similar
Today is yours at leisure to relax and enjoy some of Zornitza’s spa treatments (not included, paid locally) and facilities. (B)
Overnight – Zornitza Family Estate or similar
Enjoy a morning at leisure before departing for Rila Monastery. Founded in the 10th century by the revered hermit St. Ivan of Rila, the UNESCO listed monastery has undergone expansions and renovations over the years, now revealing a harmonious blend of architectural styles that include elements of the Bulgarian Renaissance. The main church, adorned with vibrant frescoes depicting biblical scenes, captures the attention of visitors with its stunning iconostasis and gilded altar.
Continue to Sofia (175km, 2.5hrs) and check into your hotel. (B,L)
Overnight – Juno Hotel or similar
Enjoy breakfast at your hotel and time at leisure until you transfer to the airport for your onwards flight (flight not included). (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.
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:
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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.
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