When Lisa Pagotto founded Crooked Compass in 2014, her goal was not to build another large tour company. At the time, much of the travel industry focused on scale, fixed itineraries, and high passenger numbers. Lisa chose a different direction.
From the beginning, Crooked Compass focused on boutique curation rather than mass tourism. Small group journeys, carefully researched destinations, and meaningful local partnerships became the foundation of the company’s travel philosophy.
Instead of designing itineraries around the most visited landmarks, Lisa built journeys around cultural access and deeper context. This often meant travelling to places that required greater planning, stronger local relationships, and a commitment to understanding communities rather than simply passing through them.
Since launching, Crooked Compass has grown from a niche concept into a globally respected travel company offering over 300 itineraries across more than 70 countries. Despite this growth, the company has remained committed to its original model of small‑group travel designed to foster authentic cultural engagement.
Crooked Compass journeys are structured around long‑term local partnerships, allowing travellers to spend time with historians, guides, artisans, and community members who shape the stories of each destination. This approach reflects a broader belief that immersive travel should prioritise participation, conversation, and cultural understanding rather than observation alone.
This philosophy also extends beyond itineraries into tourism development projects that create tangible benefits for host communities.
In Papua New Guinea, Lisa led the creation of Crooked Compass Lodge in the Highlands, a culturally immersive lodge developed in partnership with local communities. Built in one of the most logistically challenging regions in the world, the project required sourcing local materials, navigating cross‑cultural design decisions, and working closely with village leaders. The lodge now provides year‑round employment and direct economic benefits for the surrounding community, while offering travellers deeper insight into the cultural traditions of the region.
Similarly, in Mongolia, Lisa led the development of a private ger village for our 2025 Golden Eagle Festival, created in collaboration with more than 50 Kazakh families who had never previously participated in tourism. The initiative created a 60‑ger village where every element from traditional furnishings to food preparation, was sourced through the local community.
The project transformed a cultural event into a temporary micro‑economy, demonstrating how tourism can support communities while preserving traditional practices. It also showed how carefully designed travel experiences can create lasting economic and cultural impact.
Through projects like these, Crooked Compass has continued to push the boundaries of what experiential travel can achieve. Rather than extracting value from destinations, the company focuses on building partnerships that support cultural preservation, local employment, and meaningful exchange between travellers and host communities.
Over the years, Lisa Pagotto’s leadership in experiential travel has been recognised within the global business and tourism industry. Her work through Crooked Compass has helped highlight the value of boutique travel design, cultural access, and carefully curated small-group journeys.
A major milestone came in 2017 and again in 2025, when Lisa Pagotto won Entrepreneur of the Year at the Women in Travel Awards, recognising her leadership and innovation in the travel industry.
These recognitions reflect the impact of a business model that prioritises depth over scale. Instead of following a mass tourism model built around large tour groups and standardised itineraries, Crooked Compass focuses on research-driven journeys, cultural collaboration, and immersive travel experiences.
The company’s growth reflects this philosophy. In recent years, Crooked Compass has expanded its destination portfolio while maintaining its commitment to small-group travel and strong local partnerships. Notably, a significant portion of bookings now come from returning travellers and direct referrals, demonstrating strong guest loyalty and the value travellers place on meaningful, carefully curated journeys.
Industry recognition also highlights the role Crooked Compass has played in promoting experiential travel as a meaningful alternative to conventional tourism. Through small-group exploration, long-standing partnerships with local experts, and a commitment to storytelling through travel, the company demonstrates how tourism can create deeper understanding between travellers and the places they visit.
For Lisa Pagotto, this recognition reflects more than individual achievement. It represents the continued growth of a travel philosophy that values authentic engagement, curiosity, and respect for the communities that make each journey possible.
The philosophy behind Crooked Compass began with a simple belief: travel should reveal deeper stories about the world and the people who live in it.
For more than a decade, Lisa Pagotto has shaped journeys that prioritise small group exploration, cultural understanding, and carefully curated destinations. This approach continues to guide every itinerary created by Crooked Compass.
Travellers who join a Crooked Compass journey are not simply visiting a destination. They are participating in experiences designed to provide context, conversation, and meaningful connection with the places and communities they encounter.
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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:
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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