Discover a more remote, culturally diverse and scenic India. Home to the third highest mountain in the world, Kanchenjunga at 8586m, lush forests, deep valleys and terraced hillsides, Sikkim is one of the most beautiful states of India.
Paired with the well known cities of Kolkata and Darjeeling on the tea trail, you will also dip your toe into West Bengal.
Explore unspoiled towns, wild landscapes of exotic flora and fauna as well a homestay experience in a traditional Lepcha village of Dzongu. Embrace the stark natural beauty of the Yumthang Valley, with its sacred lakes and ornate Buddhist monasteries. Take a train through the hustle and bustle of Kolkata where you will then join the Durga Puja festival, the largest and most vibrant festival of Bengal.
The lanes and parks of Kolkata transform into an open art exhibition as various groups compete to set up lavish and innovative pandals (makeshift prayer arrangements), each displaying an interpretation of the Goddess Durga. The ten-armed Goddess saved the world from evil when she slayed the demon, Mahishasur.
Be guided through this mesmerising spectacle of living tradition, participating in the festivities alongside the devout. Be prepared for an amazing journey of discovery, cultural experiences, local life, cuisine and explore the meaning and forms of spirituality, all mixed with unsurpassed scenery.
Download this tour’s PDF brochure and start your planning offline!
Signature Tour 
Welcome to India! Upon arrival into Kolkata, you will be met and transferred to your hotel. The remainder of the day is yours at leisure.
The city of Kolkata’s name is derived from the Bengali term Kolkata, the name of one of three villages that predated the arrival of the British, in the area where the city eventually was to be established. Located on the east bank of River Hooghly, Kolkata is the capital of the Indian state of West Bengal. It is also the commercial, cultural, and educational centre of East India, while the Port of Kolkata is India’s oldest port as well as its sole major riverine port. The city’s documented history begins with the arrival of the English East India Company in 1690, when the Company was consolidating its trade business in Bengal. Under the East India Company and later under the British Raj, Kolkata served as the capital of India until 1911, when its perceived geographical disadvantages, combined with growing nationalism in Bengal, led to a shift of the capital to New Delhi. The people of Kolkata tend to have a special appreciation for art and literature; its tradition of welcoming new talent has made it a ‘city of furious creative energy’. For these reasons, Kolkata has often been dubbed as the Cultural Capital of India or the Literary Capital of India.
Overnight – Hotel Astor or similar
Following breakfast this morning, you will be transferred to the airport for your flight to Bagdogra. Upon arrival you will be met and transferred to Kurseong. This evening, enjoy a scenic walk along the military road built by the British in the 1770’s. (B,D)
Overnight – Cochrane Palace or similar
Enjoy breakfast at your hotel this morning before enjoying a half day visit to the Tea Garden. Here you can observe the processing and manufacturing of the world-renowned Darjeeling tea. Early this afternoon, board the Darjeeling Toy Train from Kurseong and enjoy a ride of a lifetime in this World Heritage Site and let the scenic views mesmerise you. A journey on the Toy Train is considered the most romantic approach to the Himalayas, as this small steam locomotive slowly meanders its way through the landscape. Once you disembark the train at Ghoom, enjoy a walk to Darjeeling. (B,D)
Overnight – Dekeling Resort or similar
Rise early this morning to enjoy a one hour walk to Tiger Hill, where you will witness sunrise over the snowy peak of Kanchenjunga – the world’s third highest mountain. Enjoy a tea break before returning to your hotel for breakfast.
Following breakfast, head out to explore Darjeeling. Your first visit is to the Himalayan Mountaineering Institute, which as well as conducting training courses, also houses a wonderful collection of equipment used in various mountaineering expeditions. From here, continue onto the Zoological Gardens. Home to some of the rarest species of animals and birds, it is the only zoo in India to have Siberian Tigers and Red Pandas.
Your next stop is the Tibetan Refugee Camp, established as a centre for those who had fled Tibet with the Dalai Lama after the Chinese invasion. This self-help centre has been developed as a workshop for the manufacture of handicrafts. (B,D)
Overnight – Dekeling Resort or similar
This morning you will embark on a scenic drive (approx. 4 hours) from Darjeeling to Pelling. In the afternoon, enjoy a visit to the Pemayangtse Monastery. Planned, designed and founded by Lama Lhatsun Chempo in 1705, it is one of the oldest and premier monasteries of Sikkim, and the most famous in west Sikkim.
Next, you will explore Rabdentse, the second capital of the former kingdom of Sikkim, from 1670 to 1814. The invading Gurkha army destroyed the capital city, leaving only ruins of the palace and chortens that once stood here. (B,D)
Overnight – Norbughang Resort or similar
This morning following breakfast, you will visit Pelling, stopping en route at Khechiopalri Lake. Originally known as Kha-Chot-Palri, this lake is sacred to both Buddhists and Hindus, it is believed to be a wish-fulfilling lake. From here, enjoy a leisurely walk through the woodland trails to Yuksom. (B,D)
Overnight – Yuksum Residency or similar
Another morning drive today as you head towards Gangtok, visiting Tashiding Monastery on the way. Located on top of a hill, rising between the Rathong chu and the Rangeet River, the views from this Buddhist monastery are truly spectacular. (B,D)
Overnight – Netuk House or similar
This morning following breakfast we drive approx. 3hrs to Lachung. Upon arrival the rest of the day is yours at leisure to relax and take in this special part of India. (B,L,D)
Overnight – Yarlam Resort or similar
Today you will explore the stark natural landscapes of the Yumthang Valley. Popularly known as the ‘Valley of Flowers’, it is home to the Shingba Rhododendron Sanctuary, which has over twenty-four species of the rhododendron, the state flower. Make the most of the Yumthang Hot Spring which is perched at an altitude of over 11,800 feet above sea level. Lying close to the course of the Lachung River, this hot water spring can be accessed after a short five-minute walk from Yumthang village. (B,L,D)
Overnight – Yarlam Resort or similar
This morning you drive from Lachung to Dzongu. Dzongu is an official reserve for the Lepcha community and is largely untouched by tourism. Colourful Buddhist flags float in the mountain breeze, carrying the prayers of the Lepchas to their Gods. The contoured paddy fields add more colours to the picture-perfect scenery. The beauty of Dzongu is complimented by the weight and depth of its heritage carried by the Lepcha people.
This evening, spend the night with a local family in a traditional homestay. (B,L,D)
Overnight – Homestay
This morning, make the most of experiencing the local lifestyle and culture of the Lepcha Community before it time to farewell your host family and depart for Gangtok. (B,D)
Overnight – Netuk House or similar.
Following breakfast, enjoy a half-day excursion to Rumtek Monastery. Rumtek Monastery is the largest monastery in Sikkim and is home to the monk’s community, the place where they perform the sacred rituals and practices of the Karma Kagyu lineage.
This afternoon, visit Tashi Ling which provides an astounding view of the Kanchenjunga range. Here lies the Tashi Ling monastery mostly known for its ‘Bumchu’ (Sacred Pot). This pot contains holy water which has never run dry for last 300 years.
You will also visit the Namgyal Institute which was built to promote research in Mahayan Buddhism and Tibetan language and traditions. From here, continue onto Tsuk La Khang – a depository of a large collection of scriptures, this is the principal place of worship and assembly for the local Buddhists. (B,D)
Overnight – Netuk House or similar.
This morning drive from Gangtok to New Jalpaiguri. Enjoy some time to explore before you board the train this evening. Depart New Jalpaiguri by train ‘Kanchan kanya’ Express to Kolkata. (B)
Overnight – Overnight train
Arriving early in the morning, you will be met at the station and transferred to your hotel. After breakfast, you will depart to visit Kumartuli which is a traditional potters’ quarter. This Kolkata neighbourhood not only supplies clay idols of Hindu gods and goddesses to barowari pujas in Kolkata and its neighbourhoods, but also exports a number of idols.
Later, enjoy Pandal Hopping. The highlight of Durga Puja in Kolkata is no doubt visiting the many different displays (pandals) of Goddess Durga, each with a unique theme. There are thousands of pandals in Kolkata so it’s only possible to visit a fraction of them.
The streets are over-flowing with men dressed in their dhoti’s (unstitched garment for lower body) and women in their distinctive white and red saris. The nights are a glittering affair with light shows, elaborate arrangements and crowds that throng the cityscape. (B)
Overnight – Astor Hotel or similar
Early this morning, at the base of the Howrah Bridge, on the Calcutta side, is the city’s bustling wholesale flower market. Flowers are an essential part of life in the city, they are bought not just for temple prayers but also for wedding decorations, events and festivals. Each god or goddess has their own favourite flowers and leaves. Walking through the flower market is a colourful, fragrant experience.
This afternoon. see the immersion of the Durga Idol. On the last day of Durga Puja, known as Dashami, the festivities commence with married women placing red sindoor (powder) on the idols of Goddess Durga. They then smear it on each other. In the evening, the idols are immersed in the water. (B)
Overnight – Astor Hotel or similar
The day is yours at leisure following breakfast 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.
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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:
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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.
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:
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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.
Why travellers love our Partner Tours:
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