by Ucman Scher
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Solo Gay Trip Guide to Valparaiso in Chile

Valparaiso is a coastal town famous for its artistic expression, murals and graffiti scene throughout the world and a visit to Chile warrants a visit to Valparaiso. The moment I mentioned my trip to Chile to anyone who’d been I was told not to skip Valparaiso and only when I went, I realised why. Valparaiso is full of life; the city expresses itself like no other.

Read my country guide about Chile to find answers to all your questions for a comfortable trip.

It is not just an important city in terms of art and culture, Valparaiso is also the judicial and legislative capital with Chile’s parliament located in the city.

Fun Fact: The old name of Valparaiso is Alimapo. When the Spaniards came the name slowly changed to Valparaiso. There are two stories behind this name; Valparaiso was named after the city of Valparaiso in Spain and second less accepted but more fun explanation is that it derives from Va – Al – Paraiso (Going to paradise). This was the port city and famous for its red lights area, nightlife and prostitution, hence the sailors named the port city ‘going to paradise’.

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Live Stories and Food Suggestions

Check out my Instagram stories to see Live stories as well as food suggestions here.

Getting to Valparaiso

The nearest airport is Santiago and there are direct shuttles buses from the airport if you are using LAN airline to get to Vina del Mar and then cross over to Valparaiso. Otherwise, you have to go to Santiago to take a 2-hour bus to Valparaiso bus terminal.

I’d love to drive this around…

From Santiago the buses to Valparaiso go from out three metro stations; Central station, Santiago University and Pajaritos station. They are all on the red line and it is best to take the bus from Pajaraitos station because if you start from Central station, you will pay extra and end up stopping at all three stations anyway. If you are coming from the airport, Pajaraitos is 15 minutes bus ride away from the airport.

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Where to Stay in Valparaiso

I actually do not know honestly because I stayed in Vina del Mar and commuted between two almost inseparable cities geographically. The only thing I will say is that the close you are to the plan or flat area the better public transport will be. Alternatively, stay close to an Ascensor to go up and down because the city is quite hilly and the slopes are steep. The farther you are high up the more time it will take you to go between two spots because the city is divided between 42 hills.

Valparaiso is genuinely colourful

Fun Fact: Valparaiso is located on 42 different hills and not all of them have good connectivity to the flat area; the plan. The plan is the welcome area with public institutes and city admin buildings as well as Victoria square, Arc of Britain and other squares and some murals.

Check the guide to find the best accommodation in a new city.

Truly colourful!

Vina del Mar or Valparaiso?

Hostels are an active part of the artistic movement here

This is more straightforward than I thought and has everything to do with what you prefer. Valparaiso is full of mainly hostels and has a quirky character but it isn’t the cleanest of places. The city beaches leave a lot to be desired. If you prefer a quieter, cleaner coastal town with beaches and city lined with apartment blocks, Vina del Mar is your place. On the other hand, if you enjoy a more student-ish environment with a bit of adventure, Valparaiso is the perfect city for you, it has a lot more of an individual character.

It was the last leg of my month leg trip and I needed to relax which is why I chose to stay in Vina del Mar. It doesn’t really make much of a difference practically because to go between the two neighbouring cities, it doesn’t take more than 15-20 minutes maximum.

When to Visit Valparaiso

Beach at Caleta

Summer is the short answer. This is a summer town definitely. I am not sure there’d be much to do here in winter or during rain. I visited at the beginning of January with perfect weather.

Want to plan your perfect trip? Read this guide.

How long to stay in Valparaiso

It depends on you but generally 2-3 days are enough for Valparaiso. I spent 4 days here with 2 days dedicated to Valparaiso and 2 days in Viña del Mar; one day to walk around and explore and 1 day at the beach and spa to wind down before my departure.

Arrival at the top

Travelling between Valparaiso and Viña del Mar

It is very easy to travel between the two cities. There are three options:

also truly multicultural…

Metro – I bought a metro Valparaiso card and took the metro from Miramar station to Valparaiso Puerto station to get to Sotomayor square. The ride was 10 minutes long and trains run every 10 minutes. On Vina side, the lines are underground but you ride along the coast over ground throughout the remainder of the line.

Buses There’s plenty of buses that run between the two cities and are very cheap as well. Google maps helped massively. Usually, the buses stop when you signal them and bus stops aren’t marked much or maybe the protestors and rioting rip them out but it was not hard to stop the buses. The journey times depend on traffic but in the evenings, it was around 10-15 minutes.

A rich neighbourhood…

Uber Uber is quite cheap and readily available in both the cities.

Check out all the different modes of transportation you can use in a new city.

Food in Valparaiso

There are a lot of nice restaurants in the city and most of them are Peruvian. Peruvian food is all the rage and dear lord it is delicious! The ceviches, traditios, chaufa rice; I just drooled a little bit thinking about it. I couldn’t find a nice steakhouse unfortunately but couldn’t find much. This is a seafood place anyway and variety is endless.

Peruvian trio to perfection!

I made the mistake of trying sushi, it was the worst I have ever had in my life. The rolls had a very thick coating of rice and had crème fraiche in them.

There are some amazing places on top of hills for amazing views for tea or food as well as some good restaurants. If you want to get recommendations check out my Instagram stories above.

Paila Marina

Another must-try is the seafood at Caleta Portales. It is a small fisherman village (not anymore) with a public beach and amazing seafood restaurants. Paila marina is a delicacy that includes seafood of all sorts, chicken and sausage. The portion was huge and I could barely eat half of it but it was an amazing lunch.

Things to do in Vina del Mar


Get lost to find Murals and Graffiti in Valparaiso

There is no one place, mural, graffiti, spot to see specifically. The art changes fast and you might not be able to find the same stuff on your next trip, this is what makes Valparaiso so interesting. It is very fluid and the art is always ‘up-to-date’. For the whole time I spent in this beautiful city I kept taking photos of this and that and eventually realised you just cannot document enough of them so I learnt to enjoy them instead of being a spectator and while they didn’t speak much as a spectator, they definitely woke up as a participant.

Learn about all the ways you can use to explore a new city.

Beaches of Valparaiso

There are some beaches in Valparaiso but honestly, if you are looking for good beaches you will need to move a little bit towards Vina del Mar or even Concon. The public beaches nearby are pretty alright but nowhere near as gorgeous as Renaca or dunes of Concon. The nearest nice beach is Caleta but is incredibly busy and loud. It might be a good idea for a nice lunch but definitely not a relaxed experience.

Boat Tour from the Port

The Port of Valparaiso isn’t the prettiest of ports with quite a few massive cargo and navy ships docked at all times but you can still take a boat tour for 30-40 minutes to see Valparaiso from the sea and admire its beauty. There is always a ship and people inviting you for the tour as soon as you set foot in the area. I think the ticket was CLP 4000 which was not bad. I had a dinner reservation so decided to ditch it but it seemed like good fun.

Free Walking Tour

Free Walking tour is the best way to get to grips with the craziness of Valparaiso. It is hard to pin the place down and difficult to comprehend which hill to climb first because there’s colour and art overload in each direction. It really helped understand the layout and history of this beautiful city and how it is struggling to keep up economically with the capital despite pulling a lot of money in. I also got some great food recommendations from the guide. You can check it here.

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Starting point of the tour

Chinchineros Performance

Chinchenero is a type of dance with a man dancing while beating a drum at his back while rotating at the spot. It is quite a fun thing and a speciality of Valparaiso (although you will see Chincheneros in Santiago as well). Usually, you will see some in the evenings in the squares.


Lunch at Caleta Portales

Another must-try is the seafood at Caleta Portales. It is a small fisherman village (not anymore) with a public beach and amazing seafood restaurants. Paila marina is a delicacy that includes seafood of all sorts, chicken and sausage. The portion was huge and I could barely eat half of it but it was an amazing lunch.

Nearest Metro Station:  Portales

Explore the Hills

Each hill offers a unique view

The second and biggest part of the city is the hills. Like I mentioned there’s 42 of them and some are more accessible than others. Most of the views, murals and art is located either on top or while climbing these hills.

Visit the Old Prison/ Parque Cultural de Valparaiso

The old prison of Valparaiso is located on top of Cerró Cárcel. The climb isn’t too bad and there are some interesting views on the way as well. It has been turned into a cultural phenomenon with outdoor space, some amazing views and some interesting indoor space. A lot of locals bring their dogs to the green space. It also makes for a fun space for an afternoon chill or even a nap (I loved it unashamedly).

The bunker in the centre used to be the infirmary with (I think) 4 feet thick walls. While the building has been turned around, it also has lots of pain from the past and you can see that in the indoor spaces. There is a sense of loss in the buildings which have been turned into studios, I couldn’t bear to stay inside for too long and returned to the green space outside.

Explore the Funiculars and Hills of Valparaiso

Funiculars are an essential experience while visiting Valparaiso. There are around 10 of them left and more are planned to be built in the future or rather restored.

Fun Fact: There were around 30 ascensores in past while only 10 are left today. The cost of a ride in either direction is CLP 100 pesos except 3 long ones which cost CLP 300. Ascensor Artillería is one with CLP 300 fee.

It is definitely a great way to go up and down the hills because most of them are quite steep. My favourites are below but the views are not limited to these only because every side of this gorgeous city shows you something crazy and interesting. I have mentioned the names of hills next to the name of funicular but most of them are named after the hills they serve.

Ascensor Reina Victoria – Alegre Hill

Perhaps the most touristy one but has great views and some great cafes on top with great views and food both. Check out my Insta stories for details. Once I got to the top, it was quite easy to walk to other spots with lots of beautiful murals just when you arrive.

Reina Victoria Ascensor

When you get to the top, you will see the Concepcion House and Lutheran Church on your right-hand side. The buildings are beautiful and quite important and the views offered are also amazing. They are from the ‘German’ side of Valparaiso.

Check the nearby Piano Stairs as well, I found them cute.

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love the art, hate the stairs…

Ascensor Concepcion – Concepcion Hill

The walk between the Concepsion and Alegre hills is quite smooth and offers great views.

I loved being surrounded by colour

The funicular has an exhibition to show how these machines work. It has been recently renovated as well.

Check out Fischer stairs in a rainbow colour nearby to get down at the end.

On top of the stairs there is an interesting workshop/studio/shop with really quirky pieces, don’t miss it. It is called Manejo Taller.

Ascensor Artillería – Artillería Hill

It is one of the longest funiculars with a great viewpoint on top. I could see all the way to the boundary between Valparaiso and Vina del Mar from here. It also has a Navy museum on top which I gladly overlooked. It is another good spot with a beautiful way down.

On the way down.

Ascensor Cordillera – Cordillera Hill

Another funicular not to be missed. It has the beautiful Valparaiso stairs right next to it. The area on the top is also quite funky as expected and doesn’t disappoint.

The whole city is a viewpoint

Explore the Viewpoints of Valparaiso

Being the city of hills, there is o lack of viewpoints but my favourites are the viewpoint of Paseo Atkinson and Paseo Gervasoni. Both offer not only great views but a unique insight into the colourful architectural history of this city of culture. There are also multiple restaurants for which I’d recommend dinner time as the Plano is fairly dead at that time and if the night is clear you can see some amazing views of the port and ocean.

Equally beautiful at night

Explore The Plano

Plano is the flat area at the base of the hills hosting the port area as well as other important buildings like the parliament of Chile, the naval headquarters and Victoria square.

The main places to look out for are:

Victoria Square

This beautiful square is host to some British style statues, a garden and the main cathedral of the city. It is buzzing with life during the day and the evening with locals take a breather and kids playing around. While it hosts the main cathedral of the city, Valparaiso isn’t a very religious city and not many people including the tour guide seemed enthusiastic about the building.

Arco Británico

This arch is a ‘gift’ from British who had a special relationship with this city being a naval nation. The rest of the country was under Spanish control but the British managed to get hold on to Valparaiso.

Arch and the library

First public library – Right behind the arch is the first majestic public library of Valparaiso. The building is grand and a reminder of the rich history this city had with philanthropist patrons.

Pirámide Street

This street isn’t anything special with any landmarks but I really liked the fresh fruit I got from here with a bit of bustle from the locals. the fruit was also cheap and amazing.

nom nom nom

Naval Headquarters and Plaza Sotomayor

The plan is also host to Armada de Chile or the Naval Headquarters of Chile. It is a beautiful blue building behind the Plaza Sotomayor. This square is also the last stop on the metro and a busy spot for tourists. Most tours also start from here.

Read more tips and tools you can use during travelling.

Valparaiso is a unique experience, a city of incredible talent, people of incredible depth and a unique signature that I haven’t seen anywhere else. They truly love the culture of their city and I am very happy I got to share it with them. What do you think of Valparaiso?

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