Venture well and truly off-the-beaten track and explore this spectacular path through the Palestinian Territories. Many of the villages here have not seen western travellers for a long time, an untouched and exotic aura of tradition encompasses this region. Understand both sides of the Israel-Palestine conflict and witness a unique and diverse culture. Hike alongside shepherds herding their flocks, camp with the Bedouins who retain their old worldly traditions against the pushes of the modern world. Discover historical biblical sites of the Holy Land, meet local people and hear their narratives and stories and float in the Dead Sea!
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Welcome to Israel! Touch down at Ben Gurion Airport, where you’ll be met and transferred to Bethlehem. Settle in before an insightful orientation on the complex history of the Holy Land and what lies ahead on your journey. The rest of the day is yours to unwind and explore at your own pace. (D)
Overnight – Sunrise Hotel or similar
After breakfast at your hotel, travel to Jerusalem. Jerusalem occupies a unique place in the world. It is holy to Judaism, Christianity, and Islam. Start your day at Mt. Scopus, which offers an impressive panoramic view of the city from the east. Mount Scopus is part of a ridge of mountains taking in the Mount of Olives and is the perfect location for an overview of the city. Visit the Mount of Olives, one of three hills on a long ridge to the east of Jerusalem, which is the location of many biblical events. Rising to more than 800 metres, it offers an unrivalled vista of the Old City and its surrounds. Continue to Garden of Gethsemane, near the foot of the Mount of Olives. This site was named in the New Testament where Jesus went with his disciples to pray the night before he was crucified.
In the afternoon, explore the Old City on foot, where you will have the opportunity to see and touch the Western Wall (Wailing Wall), the only remnant of the Second Temple. Walk along the Way of the Cross, the Via Dolorosa, to Calvary and the Church of the Holy Sepulcher, which houses both the traditional site of the Crucifixion and the Tomb of the Resurrection. Just outside the Old City, visit Mount Zion, with the traditional tomb of King David and the Room of the Last Supper. Return to your hotel. (B,D)
Overnight – Sunrise Hotel or similar
After breakfast, visit the old city of Bethlehem, then walk through the Manger Square to visit the Church of the Nativity, the Grotto of the Nativity and Chapel of Saint Jerome. The Church of the Nativity is the most important landmark in Bethlehem and marks the site where the nativity took place. It was in Bethlehem just over 2,000 years ago that Mary gave birth to baby Jesus. Today, Bethlehem is a thriving city in the Palestinian Authority West Bank, approximately 10 km south of Jerusalem, and the Nativity Church is the city’s top attraction.
Next you will observe the exterior of The Walled Off Hotel, designed by the anonymous London-based artist known as Banksy. The hotel is not currently open, however previously has served as not only a place to stay but also serves as a powerful art installation and a platform for political commentary on the Israeli-Palestinian conflict.
In the afternoon, transfer to Battir. The Battir hill landscape comprises a series of farmed valleys, known as widian, with characteristic stone terraces, some of which are irrigated for market garden production, while others are dry and planted with grapevines and olive trees. This is considered one of the last farming villages in Palestine that still uses a unique irrigation system from the Roman times.
Upon arrival in Battir, meet the local farmers, enjoy the view, and savour a traditional lunch. Then, commence your hike to Beit Jala, a distance of 5.08 km. Situated on a hill adjacent to Bethlehem, the city of Beit Jala has existed for thousands of years, and its Christian community is one of the oldest in the world. The name ‘Beit Jala’ comes from Aramaic (the language of Jesus) and means, “Grass Carpet”. Anthropological evidence shows that humans have lived in the Bethlehem area since prehistoric times, even as far back as the Stone Age, 200,000 years ago. Afterwards, transfer back to Bethlehem for the night. (B,L,D)
Overnight – Sunrise Hotel or similar
After breakfast, travel toward Wadi Qelt, a valley that runs from the northwestern slopes of the Jerusalem Wilderness just outside Jerusalem and down to the city of Jericho to the east. Today’s trail starts just above Saint George Monastery and continues through the mini canyon of Wadi Qelt down to Jericho. The hike takes 2-3 hours (7 kilometres) and includes a stop at the Monastery of St. George of Ghoziba, known as Deir al-Qilt, which is located on the old road that connects Jerusalem and Jericho, and another stop at the old ruins of Herod’s winter palace. The site was known in the Greco-Roman era as the City of Gardens. King Herod used it as a winter resort for himself and his family.
From here, transfer to Jericho for lunch before exploring the old city of Jericho. Reputed to be the oldest town on earth, visit the sycamore tree mentioned in the Biblical tale of Zacchaeus. Stop at Elisha’s Spring that supplied Jericho with fresh water for centuries. View the Mount of Temptation.
Continue to visit the Dead Sea. At 400m below sea level, the Dead Sea is the lowest point on Earth, the area characterised by high annual temperatures, low humidity and high atmospheric pressure, while the air is extremely oxygen-rich. With the highest content of minerals and salts in the world, the waters of the Dead Sea possess anti-inflammatory properties, while the dark mud found at its shores has been used for therapeutic purposes for more than 2000 years. Return to Bethlehem. (B,L,D)
Overnight – Sunrise Hotel or similar
This morning, after a short transfer, you will head through the desert landscape that rises to the west of the Dead Sea. The path brings you to the edge of the Kidron Valley or Wadi al-Joz, a deep limestone canyon, from where you can see the even more remote and spectacular desert monastery of Mar Saba, built into the cliff face on the opposite side of the ravine. Mar Saba is one of the oldest continuously inhabited monasteries in the world. Part of the Mar Saba visit is the exclusion of female visitors. Whilst men can enter, ladies can only overlook the complex from a vantage point called the Women’s Tower. Enjoy a moderate hike of the Mar Saba Monastery Loop, following the shepherds’ tracks deep into the canyon, across the riverbed, and back up towards the monastery, covering a distance of 12 kilometres. Afterwards, transfer to the Rashaydeh area for an overnight with a local Bedouin community who now find themselves forced to the very margins of society.
Learn about their cultures and traditions as you have the unique opportunity to spend the night here in the black goat hair tents. Your stay as guests here is helping these families to find new ways to maintain old traditions. The Bedouin people have also retained their ancestral knowledge of desert plants, and it may be possible to have a guided walk through the herbal and medicinal plants around the camp. (B,L,D)
Overnight – with the Bedouin community
Enjoy an early morning walk and watch the beautiful sunrise with the Dead Sea in the foreground and the mountains of Jordan in the background. You will be transferred back to your hotel in Bethlehem to have a shower and a short rest. After resting, travel to the al-Taybeh village, 32km north of Jerusalem. Tyabeh is the only Christian village left in Palestine, holding on to its memory of Jesus seeking refuge here shortly before his crucifixion.
Visit the Beer Factory, home to Taybeh—Palestine’s only beer, brewed in four varieties: Golden, Amber, Dark, and Zero (non-alcoholic). Proudly promoted as ‘The Finest in the Middle East,’ this locally crafted beer carries the name of its village. If you’re here in October, you might catch Taybeh Oktoberfest, a vibrant village festival celebrating not just the beer but local produce and culture. Continue to Ramallah to visit the Yasser Arafat Mausoleum and Museum before returning to Bethlehem. This evening, immerse yourself in tradition with a folklore night at a local restaurant in Beit Sahour. (B,L,D)
Overnight – Sunrise Hotel or similar
This morning is yours at leisure until it is time to be transferred to Ben Gurion 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:
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:
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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.