In any town or city, neighbourhoods and buildings teach us about a cultures way of using space, its interactions, its identity. Over years, layers build up, layers of history that we can pick apart and use to understand cultures and traditions.
Bordered by the jagged snow-capped Andes, Santiago is an eclectic mix of old vs new. French art deco vs concrete slab buildings that lack any kind of lustre. Shanty suburbs vs sprawling mansions. As a first timer to Santiago, Chile, and with only a very short period of time up my sleeve, I was not interested in seeing the touristy cathedrals, museums and open plazas bursting with gimmicks for travellers. I wanted to discover the guts of this city. Feel its pulse and experience it like a local.
Jumping on my trusty two wheels, I set off with my local guide, Isabel, in search for the soul of Santiago. She assured me she would take me to districts that some locals didn’t even know existed.
Starting at Parque Bustamante, and making our way to the Plaza Italia, or Baquedano, I learn that locals believe if you live south of this plaza, you are deemed as poor, and north of the plaza, you are wealthy. Santiago itself is still a very financially imbalanced city.
Cycling through Parque Forestal, past stately palms, we pause to watch a handful of children swimming in the local fountain. There are not many public pools in Santiago and the heat of the city is stifling at this time of the year (December). Children frolic and splash about on the three tiers of the fountain without any cares in the world.
We veer to the left and down a narrow street. We take a breather and pause at Emporia La Rosa, a popular ice-cream store with queues down the street located at the start of the bohemian district, Barrio La Starria. Many guide books will tell you that this is the best ice creamery in Santiago. I tend to agree. The queues of local people winding down the street will also confirm this for you as well.
Barrio La Starria which has reincarnated itself over recent times, is bursting with art galleries, bookstores, music stores, cafes, theatres, bar and restaurants giving it a quaint European village ambiance. From La Starria, we circle around and pass the Museo Nacional de Bellas Artes.
Continuing once again through the Parque Forestal, the rushing brown river that divides the city runs alongside us. On the far side is the ‘poorer’ side of Santiago. Slum towns and shanty houses we are told. A few modern buildings are starting to pop up here, as locals are forced to build outside the city centre as the costs of living rises. This new area is called Patronato.
We reach the Mercardo Central. Home to the largest produce markets including a fresh seafood market where the locals will cook you up something tasty. These central markets have started to become quite touristy. For the more authentic fresh produce markets, head across the river to La Vega. This is where the locals shop!
Over the road we make a brief stop at Estacion Mapocho which is heavily French influenced. No longer serviced by trains and now used as an exhibition centre, this station looked like a mini Gare Du Nord. Here we learn of the importance of infrastructure in Santiago and the amount of engineering that has to go into every building due the cities regular shake up with seismic activity.
As we reached the cross intersection of the Pan American Highway, we swung left and headed into a grid of quiet streets. Starting off through the Cumming area, we passed clusters of pastel coloured houses, all connected to each other like duplexes mirroring the houses on the opposite of these narrow laneways. There were about four streets of these low rise dwellings and at the end of each street was the threatening development of high rise complexes. Due to Chile being such a narrow country, there is not much opportunity to span the city outwards so as its population grows, the only way is up.
These local homes we were witnessing are a dying breed. In five years, they will not exist anymore. We rode quietly through these streets, taking in the locals in their worlds. Calling out to each other across small laneways from house to house. Street BBQ’s with large chunks of meat roasted on rusty BBQ’s made from half steel barrels, the earthy aromas wafting through the air. Music pumped from one of the houses, a thick latino beat pulsed through the street as the BBQ sizzled on.
Vibrant graffiti lined the walls, the streets were dusty and almost deserted.
Continuing on, we rode through the Brazilian Quarter. An area that has always been known as a ‘slum’ but which our guide told us will soon become the next hip and trendy area in 10 years. A few outdoor cafes line the streets, but only servicing local specialities. There is not a tourist in site.
To the west of Plaza de Armas, this neighbourhood shows the different styles and stages of urbanisation in Santiago’s history. With a conserved identity and rich in cultural activity, these architectural treasures such as the Peluqueria Francesa (French Barber Shop) and the Teatro Novedades (novelty theatre) , the neo-classic and neo-gothic palaces on Concha y Toro and Brasil Streets create a strong ambiance of the wealth that once existed here in times gone past.
We weave our way to a small plaza, Plaza Libertad de Prensa in the Diecioho neighbourhood. Home to Chile’s elite during the 19th century, this area is a testimony from this era with its palaces and mansions. The typical icon of this neighbourhood is the Cousino Palace. This area has many emblematic buildings that compete with their beauty and spectacularity such as the Errazuriz Palace, the Iniguez Palace or the mansions along Republic Street, currently occupied by universities and professional institutes.
To cycle through these streets, seeing these mansions is to take a trip through history from the 19th century to the dawn of 20th century Santiago. This area of Santiago is also an area which is sure to disappear in the near future with the pressures of modernisation and the need for space, high rise complexes are sure to come in and take over this beautiful quarter soon enough.
Exploring Old Santiago, we biked through parks, along sidewalks and through narrow cobbled streets.
We reach a small gate way and turn inside. We are greeted with a stunning garden surrounded by two narrow alleys of brightly coloured colonial style terrace houses. Stunning architecture, this narrow strip is currently residential, but again, our guide tells us, that within 10 years, she feels this will become bars and restaurants.
We then arrive at the Quinta Normal Park which is Santiago’s answer to Central Park. Home to the Natural History Museum, thousands of local residents stroll through this park daily. Looking across the vast lawn, locals laze, sleep and picnic in the park. A man with a llama walks past as young men break dance to some thumping music drawing in the crowds. We chill on the grass for half an hour and take in our surrounds while sipping on a local Chilean drink of cinnamon, ginger and orange rind.
Back on our bikes, we cycle passed street vendors selling locals snacks, and make our way passed La Moneda presidential headquarters. A giant Chilean flag flaps in the breeze. Constructed at the end of the colonial period, it wasn’t until after independence that this palatial building became the seat of government. Designed by the Italian Architect, Joaquin Toesca, sadly this stunning building is most famous for being bombed during the coup d’etat in 1973. Zig-zagging through the back streets, we make our back to our starting point, as we cross through Santiago’s downtown area of pedestrian only shopping streets, bursting with the crowds of locals.
Having now witnessed the multitudes of layers that make Santiago what it is today and a glimpse into its past, I am excited to see what lies ahead as this city booms further and one of South America’s most vibrant cities starts to thrive as the economy and exposure of such a city grows.
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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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