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Private Gay Friendly Tour Guides

To fully appreciate Santiago you need to book a Holiday Houseboy, your gay friendly tour guide. He will be able to show you around like a local. Whether you want to see the tourist sites, places off the beaten track or discover new experiences, the Holiday Houseboy is there to help you. He looks after your safety and welfare at all times.


Cris studied sociology and dance. All his work has been customer service orientated. For example he had a vegan street stall for many years. It was in one of the most popular tourist areas called “lastarrias”. When it comes to his own interests, Cris is passionate about art, fashion, cinema and nature. He trains daily and through dance he has performed in shows such as the Santiago a Mil festival. Cris likes to show other people his city and make people feel comfortable, tweaking an itinerary to give the guest what he wants and to have the best possible experience of Santiago. Not only the major attractions but quirky places off the beaten track. Alternatively if you want a night gay bar tour, Cris will be delighted to help and guide you. Book Cris for an intriguing insight into Santiago and see what it has to offer.

Cris is not covid vaccinated, does not smoke and speaks English and Spanish.

Total cost for the guide services of Cris for one day (8 hours) = a non refundable deposit of USD 45 by Paypal or major credit card (Visa, Mastercard, American Express) PLUS USD 50 in cash to Cris after his services. Total 95 US dollars.

Alternatively the total cost for the guide services of Cris for half a day (4 hours) = a non refundable deposit of USD 25 by Paypal or major credit card (Visa, Mastercard, American Express) PLUS USD 30 in cash to Cris after his services. Total 55 US dollars.

This does not include transport, entrance fees or any food & beverage costs.


Cris was a fun, flexible guide who brought the cities alive where he had lived taking me to see those things I expressed interest in. This is my second time with the Holiday Houseboy guide service. I am delighted.” – Steven, USA.

How To Book A Holiday Houseboy

To book any of our Holiday Houseboys please go to the enquiry form.

Or send an email to

Alternatively WhatsApp +94-76-630-1069.

Remember a Holiday Houseboy is your gay friendly tour guide who looks after your safety and welfare at all times.

Please note these are guide services and not sexual services.


Highlights of Santiago

Santiago, Chile

Santiago, Chile

Santiago is the capital of Chile. Its metropolitan region in which it resides has a population of 7 million. It is truly the hub of this long elongated country. Chile itself has more than 6,000 kms of Pacific coast line. Ranging from the Atacama desert in the north to the fjords of the Magallenes region in the south. A country full of diversity from snow capped mountains, volcanoes, rich grazing pasture to sandy beaches. From Santiago you are one hour from the mountains, and one hour from the beach.

The main plaza is the Plaza de Armas. It hosts the neoclassical Metropolitan Cathedral of Santiago and the Palace where the local government resides. In addition there is the Central Post Office building.

A popular activity is to visit Cerro San Cristobal. Cerro means hill. There is a 860 metre hill on which sits a statue of the virgin mary. Half way up you can visit the zoo and a wine museum. Then take a gondola ride to the top, and admire the view of the city below. On the other hand you could chose to visit Cerro Santa Lucia. A mere 230 foot hill. Likewise you will have outstanding views in a natural setting.

Another way to see the views is to go to the Sky Costanera. Moreover it is at the top of the tallest building in Latin America. Besides having a panoramic view at 300 metres high, you have the full 360 degree view. Basically you can have a bird’s eye view of the city at every angle.
One place to head out to is the Patio Bellavista. Here you can do many activities. Visit a gallery, dine in style, buy souvenirs. Enjoy the range of food on offer and listen to the great music. There is also an area for entertainment which many street entertainers take advantage of. Nevertheless it all has a trendy vibe, and draws many locals and tourists alike.

Chile is famous for wine and there are plenty of opportunities to discover this side of the city. At Santa Carolina you can take a tour of the facilities. This includes the park, the colonial manor house, the old winery and the large cellar. Of course do some wine tasting to make the tour complete. At the end you have the opportunity to see their shop to buy a momento or two. Other wineries include the Santa Rita winery, and  a little further afield the Vina Aquitania.

Albeit other attractions include visiting some influential churches. Iglesia de San Agustin, San Francisco Church, Basilica de Lourdes and the Capilla Medalla Milagrosa Virgen De Los Rayos  to name a few. On the other hand you can always go on one day tours to explore the surrounding area. For example try the Cajon del Maipo wine valley, Valparaiso Port or the popular Vina del Mar. For nature you can do a day tour to El Tatio Geysers or the Torres del Paine National Park.

But don’t forget the city itself. Santiago has a lot to offer, especially with its street markets.

Book a Holiday Houseboy, your local gay friendly guide, to truly discover the city and all its wonders.

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