Ultimate Old San Juan Guide for First Time Visit
Before you go...
Old San Juan is a very walkable area. However, if you would like to explore more in the Island, or are staying outside the area, I would strongly suggest renting a car since public transportation is nearly null. In the case you don't want to rent a car, you can always use Uber to get around, which works just fine in the metropolitan area.
It is most of the time a good time to travel to Puerto Rico, but my favorite season to spend at Puerto Rico is during holidays because we are very well known for having the longest holidays of the world. Our Christmas season starts with Thanksgiving in November and ends with the Fiestas de la Calle San Sebastian two weeks into January (eight days after the Three Kings Day). The Fiestas de la Calle San Sebastian are a great festival to attend to; during the day if you are more interested in cultural activities, during the night if you are a party animal. However, if you're avoiding the crowds, this season might not be the ideal for you.
Having that said, make sure to pack some comfortable shoes so you can make the most of your trip. Since it is summer all the time in the Island, shorts, tank tops, sun block and swimwear are a must during your trip. Make sure to keep hydrated, especially, if you are not used to the heat. Temperatures might vary from season.
Our lowest season is during September, October and first three weeks of November. This could be good if you would like to avoid the crowds, but make sure you purchase a good travel insurance, because it is when the Island is more prone to having hurricanes.
Summer is a great time to visit if you're looking for an in-between and for meeting local people, since most Puerto Ricans do their staycation during this time. The only downside would be that temperatures are generally higher during this time.
Where to Stay
If Old San Juan is the only area, you will be visiting, I would always suggest staying in the core of Old San Juan, especially, if you are visiting without a car. Otherwise, other great areas to stay at would be Condado area, or Isla Verde area. Both areas are filled with hotel, restaurant and even night life options. Usually, properties in Condado and Isla Verde are larger. Also, if you like gambling, there are a few hotels in the area that have Casino's.