New Settlements
When you first start the game, your absolute first priority is to build new settlements. Since each settlement has to be at least two spaces apart, this means you will generally need to build two new roads whenever you want to build a settlement. Spend your wood and brick on roads early on, and create a new settlement as soon as you can. The extra resources you get from having 50 percent more settlements than before make your first settlement the best investment of your time and effort.
Expansion
Move to a port early, if possible. The 2-to-1 ports are great if you have a high production of the associated resource. This means that you will not have to rely on other players to get what you need. Ideally, you want to have lots of room to play new settlements and possibly establish the longest road. Try to expand by building roads towards underpopulated areas. If you are competing with someone else for the same area, move to block them if you can. However, do not waste your time building roads to go to a spot on the board that you can anticipate you will be blocked from going to.
Upgrade to Cities
Aside from building new settlements, upgrading your settlements to cities is the only way to increase your resource production. Generally speaking, the best spots available on the board are chosen during the initial settlement placement, so your starting settlements will probably be the ones you want to upgrade into cities first. But, if you can afford to upgrade a settlement, it is almost always worth it.
Development Cards
If you started with some ore and wheat production but not enough to upgrade a settlement, get a few sheep and buy some development cards. At worst, these are a soldier, sometimes a victory point, and sometimes a special card that will allow you to swing the game in your favor later. Holding lots of soldiers leaves you in a good position to keep a robber off of your property, and sets you up to gain the largest army bonus later in the game.
Trading
Although not as reliable as using the ports, a large part of Settlers is trading with other players. Most people will not trade with you unless they gain a boost to their position, so be sure that any time you trade, you are gaining a boost to your position as well. Trade on your turn to get resources you can use immediately. You’ll improve your board position faster with extra roads and increased resource production and may avoid the robber.
The Robber
The robber will strike whenever anyone rolls a seven. This is the most common number to roll on two six-sided dice and will happen on average every six turns. For this reason, sitting around with more than seven cards in your hand is a bad idea. In most cases, the goal is to spend resources whenever possible. Obviously, this means building new cities and settlements whenever you can or even building extra roads and buying extra development cards. Do not be afraid to use the ports if you have a large hand of cards. Shipping three sheep for a brick may seem like a bad deal, but it can help keep your hand under the robber limit while simultaneously giving you the resources you need.