Vina del Mar
There's beyond frequent coach bus service between Santiago and Viña. Numerous operators, abundant seating, about a 90 minute ride for approx 3000-4000 pesos one way. In holidays, however, the prices can go up twice or thrice the normal standard.
The buses depart from Santiago at Pajaritos or Universidad de Santiago Station, both parts of Line 1 of the Metro. It's recommendable to do it from Pajaritos Station if you want to avoid the stop over from Universidad de Santiago and the ride within the City, which is especially desirable if you come directly from the Airport - but you have to be in Pajaritos right on time since the bus will stop for less than 20 minutes and you may buy a ticket one minute, then have to hop aboard at the following. The 2 main lines that travel to Viña del Mar are Turbus and Pullman Bus.
The bus will drop you at Viña del Mar Station, which is 3 blocks east of DownTown and the Plaza de Armas (Central Square). Taxis are available at this point, but if you want to save some money, walk east to Plaza de Viña, and ask for transportation to your destination.
If you come from Santiago, there may be a shortage of coach bus tickets sometimes, specially in national holidays and summer vacation. In that case, take a coach bus to the city of Quilpue and then take a taxi or the Merval metro.
Merval has frequent service to/from Valparaiso and from/to other destinations in the country side of Viña del Mar such as: Quilpue, Villa Alemana and Limache. For using Metro/Train Services you have to purchased a Metro/Train Card, available at the Kiosk in the Stations. Once you get the card you have to slide it when you get in and when you get out to station (destination), there is not flat rate, each route has a different price. In Vina del Mar you will find 5 Stations. From Valparaiso to the Country Side are: Recreo (main residential area), Ecuador (Southern DownTown), DOWNTOWN close to Quinta Vergara, Hospital Station and El Salto (Industrial area)
Valparaiso Metro (Merval) is a good way to go to Valparaiso downtown, or move around Greater Valparaiso. Fares are comparable to buses. It's a great transportation method for tourists as it's clean, fast and safe. Adult fares range from 204 pesos and 1080 pesos depending on the time of day and the distance travelled. Please keep in mind that there is only one metro line, and it doesn't serve coastal sectors north Recreo. You'll need an RFID card to use metro, which can be recharged at each station as many times as needed.
There are also shared taxi cabs called Colectivos, that run routes throughout the city charge around 500 pesos (arround 1 US Dollar) for a ride. They are quicker and more comfortable than bus.
Regular Taxicabs are more expensive, but are useful if you are in a hurry. Keep in mind that taxis in Viña have one of the most expensive fees in the country, as it's a tourist destination. Also some drivers are know for trying to cheat foreigners not using or displaying taximeters, or even multiplying it's value by 10. This doesn't mean all drivers are dishonest, as most of them are helpful and friendly with tourists. Just be advised.
Colloqualy called Micro, it's the most popular public transportation method in the city. Buses vary their fare from 350 pesos to 450 pesos depending on the distance. Fares are published in the front window of the bus, and display Plan (Local) and Cerro fees. Plan is the way locals refer to the flat areas of the city, essentially the downtown area. The Regional Public Transport guide for Viña del Mar (2014) is published here. It is recomended you carry cash to pay the exact amount of the fare as bus drivers are known for not giving change back, unless you insist.
Spend time on the numerous beaches found along the coast. They are quite pretty but not very friendly for swimming.
The local football team Everton de Viña play their home matches in Estadio Sausalito. The fans are really passionate about their team and less problems are reported from Evertons matches than from the bigger clubs of Colo-Colo and Universidad de Chile. A ticket can cost 3.500 pesos or more if bigger teams will play.
Mall Marina Arauco is the biggest mall of the city, and it's also the main shopping destination. It's connected to the Espacio Urbano shopping mall, and the Boulevard Marina shopping mall by bridges. Fast fashion brands like Gap, Zara and Adolfo Dominguez have stores in this mall, and shopping in Viña del Mar is one of the main attractions for tourists and locals alike. A hidden gem of this shopping mall is the Marina Design floor, where there are great independent designer stores that carry great and unique stuff. Not for the budget conscious buyer.
Muelle Vergara is a great place where you can buy some souvenirs and exclusive items, you'll probably won't find anywhere else. Keep in mind you must carry cash as they don't take credit cards. Don't be shy to haggle.
Viña downtown is famous by its shopping galleries, that take up entire blocks and are hidden from the person that only goes by sidewalks. You may need an entire day to visit all these stores.
A very popular treat in Viña del Mar is the alfajor, a typical argentinean/uruguayan type of cookie that is also popular in Chile and specially in Viña. They can be purchased in several small pastry shops around the downtown area. Usually, alfajores are filled with caramel, manjar/dulce de leche (sweet milk confectionery), fruit jam (preferently berries), or other sweets and then covered in chocolate. They are a delight for the visitor. Boxes with large quantities make memorable souvenirs, if they make it home.
An excellent seafood restaurant, located in Camino Costero, is "La Gatita" ("The Kitten"). It specialises in such typical dishes as Machas a la parmesana y Reineta (Clams with cheese plus fried Reineta - a local fish).
Los Roldán is an artisanal empanada shop (located at 4 poniente, 6 norte) with over twenty different types of empanadas to choose from, including vegetarian options and dessert empanadas. Made by hand as you order them, cheap and tasty. It is not an inside sit-down restaurant - there is an outdoor patio where you can eat, or take it to go and sit on the beach a few blocks away.
Good and cheap accommodation is available throughout the city in residenciales (the local B & B). Early reservations are highly recommended during the summer months when the city gets flooded with holiday makers from Argentina and Santiago.
If you want to use a toilet there are some public ones on the streets and near the beaches but also in restaurants. They charge a fee but most of them are dirty. If you can, ask the staff in the casino if you can use the toilet. Being a foreign tourist will make it easier.