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When in Tagaytay, an important thing you need to research is the place you're going to stay overnight. Check out if its near the highway because the noise of cars coming in and out of your hotel area where you stay may be overwhelming especially the trucks going down on midnight. In the end, it is better to choose a lodging place AWAY from the highway for a better R&R.
Some hotels are charging rip-off rates especially peak months of Oct to Dec., always ask if its tax and service inclusive, to save you the disappointment if the room is not what you expected, stay away from places that offers overlooking the volcano as these are the selling points of higher rates.
Avoid being attacked by walking vendors of items when you're travelling by foot, they came in groups and you might be robbed of your belongings without knowing it. Also avoid being attacked by "agents" offering boat ride to Taal for 1500 pesos, chances are they are just getting their commissions from the real entities below along the Talisay area.
Make sure to bring along extra rubber shoes or pair of flipflops when you feel like doing a walking tour like Palace in the Sky or Picnic Grove.
Ask people how much is the tricycle fare if going in a certain place, chances are if you are a traveller as you look like, they charge double.
Always be ready with smaller bills when buying or paying tricycles for the two of you, or if you travel in groups(they could give a better discount)
If you need to change your foreign currency, two money changing shops available at The Tagaytay Robinsons area vicinity. Some little shops and markets do not accept credit cards.
If buying things in a local market or tiny shops, its best to haggle a little with the price as they do not have price tags on it.