Viazul  buses have a twice daily service from Havana stopping at Cienfuegos, and a daily service from Santiago de Cuba stopping at Holguin, Camagüey, and Sancti Spiritus. It costs 25CUC as of January 2016. There is also a service to/from Varadero stopping at Santa Clara and Cienfuegos that is not listed on the Viazul website. It leaves Varadero at 7:30AM and returns from Trinidad at 2:25PM. Viazul and Cubanacan offer direct buses to/from Viñales as well. You buy Viazul tickets from the air conditioned office right in front of where the buses park, not from the Astro or local bus counters. Check the viazul website for up to date schedules.
Travel via taxi, specifically, unofficial taxis is also an effective way to travel to Trinidad, typically costing the same or slightly more than the price of a Viazul ticket per person if travelling in a full taxi e.g. 30CUC per person in Jan 2016. It is straightforward to find other travellers to share the taxi with, just go to the Plaza Vieja, find a driver, and try to ask other people hanging around in the area if they are looking to travel to the same destination as you. The taxi driver will also help. It shouldn't take you too long to find someone. You'll get there in less than half the time, and in much greater comfort. When traveling with children, you might find this the preferred method of travel.
Trinidad has not been connected to the rest of Cuba by train since a hurricane destroyed an essential bridge in 1992. There is a local train running to the Valle de los Ingenios.
Street names may be difficult to find, although the town is very small. Once you wander around you can find every thing easily. The central part of the town is small enough to explore on foot.
The waterfalls just outside of the town in Topes de Collantes are beautiful. These are accessible either by car or by taking one of the day tours offered by Cubatur. (The local bus service to Topes de Collantes hasn't run in years.)
There is also salsa dancing in the square at night. Check out the colonial homes and furniture too. The houses are open and some of the antiquities are visible from the streets. Check out Casa de la Música: It is an open air location where there is a small platform from which groups perform at night. Usually, there is salsa musica and great salsa dancers there enjoy the music and dance and perform with foreigners. It is great to enjoy a few drinks there as well.
Walk around in the old colonial center.
Go to the beach on the Ancón peninsula, a 5-10 minute taxiride outside the city center. It is well within biking distance from Trinidad; there may also be a local bus running (check at the local bus counter at the bus terminal, located on the left as you enter before the Astro counter). The peninsula is one of the few places in Cuba where you can access a great beach without staying at a resort hotel. Make sure you have mosquito repellent, especially if you intend to stay on the beach in the evening.
The Museum of the War Against the Bandits (Lucha Contra Bandidos) is in a former convent close to the cathedral near the Plaza Mayor in the old colonial center. The War Against the Bandits was the 1961-1969 fight against U.S.-sponsored counterrevolutionaries, who hid out in the nearby mountains. If you don't read Spanish the displays may be difficult to understand, but the piece of the American U-2 spy plane shot down speaks for itself. Also well worth the entrance fee is the mirador (view) from the convent's tower, reached by several flights of wooden stairs, which has superb views across the whole town. The cathedral is beautiful inside.
Also the market in the old colonial center which is nice to walk around and look at the handicrafts - drawn thread tableclothes and linens seem to be a speciality. The vendors are refreshingly laid back, you can look around and get virtually no hassle or pressure to buy.
The streets are cobble stones and very irregular and walking could be difficult for older folks. Wear runners for sure. Do not even think about wearing high heels. Your ankles will pay.
Climb the hill behind the town to get a great view. To get there, continue up the hill northeast from the Plaza Mayor. As you walk up the hill you go through poorer neighbourhoods. You may be asked for clothes or trinkets by the local kids. Seems pretty safe during the day but be careful at night. A lovely older lady named Felicity sells trivets she makes herself.
There's a very atmospheric discotheque in a cave near the top of this hill (Las Cuevas). There is no sign or indication that it is there, just a steps leading into a hole in the ground behind a bush. It is in a huge cave with stalagmites and statactites. More tunnels and caves can be seen near the bathrooms. This is where young Cubans go to party, the music is mainly reggaton and techno. Fun starts after 11 pm. Very much worth checking it out. Cover charge for foreigners was 3 CUC [2012-09] including one drink (cocktail or beer). Beers were overcharged for foreigners (3.0 CUC asked) but could be paid for at the price for Cubans by flatly paying 1.5 CUC at the counter [2012-09].
Take one of the day tours offered by Cubatur. These include several options to Topes de Collantes.
If you want to learn Spanish during your stay in Trinidad you can take an Intensive Spanish course from one week up to four weeks. The classes are held 4 hours per day and give you the opportunity to improve your Spanish quickly during a short time period.
Learning to dance
Take cheap, private and professional Salsa lessons for men or women.
There is a lovely old ceramics factory called El Alfarero, where you can see people working and buy finished pottery. It's on Lirio Blanco at Andres Berro, east of town about 15 minute walk. The building is turquoise.
Before you go:
There is a pizzeria, which is refreshing due to the lack of variety of vegetarian food in Trinidad. There are many other amazing places to eat with much fish and chicken cooked in imaginative ways. One restaurant far more affordable than other touristic spots is El Bucanero on Calle Real del Jigüe a couple blocks northwest of Plaza Mayor.
Many casa particulares offer dinner, for a fee, which are usually authentic dishes and very well prepared and well worth checking out.
There are quite a few Paladars in the town, which offer quality home cooked style food which is usually served at the back of the hosts Casa or House. Its quite hard to find Paladars if you havent first been taken there by a tout or you have friends that could recommend one. If taken to a Paladar by a tout, be prepared to have their commission added to the bill.
There are several 'so called' peso pizza establishments in the town which allow tourists to purchase pizza for the national peso price. This usually works out at around 10 national pesos. This is a good idea for travellers on a budget. One good place is on Maceo near Bolivar.
In the square at night, there are often events and there is a very good club open until the early hours. It is a lovely town with amazing visitors and inhabitants, and small enough for you to wander and choose your drinking hole. The Mojito's and rum cocktails are great.
There are also places where the locals hang-out and which serve quite decent beer at a very reasonable price. These places usually serve draught beer and stay open just as long as there is beer to serve. When the beer from one place has been drunk, then it's off to the next place or not. Many of the locals drink their beer outside on the street and Trinidad is so small so these places are easy to spot.
There is a beautiful colonial hotel on the main causeway up to the square. It is a little expensive, but worth it as it has colonial rocking chairs and 2 four poster beds.
There are many casas particulares in Trinidad due to high levels of tourists. Rooms are very easy to find upon arrival so no need to book and lose some bargaining edge by doing so. The most expensive colonial rooms will cost at most 25 CUC in high season but you can bargain a standard room down to 10 CUC for two (breakfast included) in low season if your nationality plays in favour of a low price, and in any case less than 15 CUC with nearly no negotiating.