Crossing the Atlantic Ocean has its schedule. From Europe, the crossing usually takes place in late autumn-winter. The trade winds and currents are the factors that settle the best time for going. There are actually other times of departure too, you just need to stay away from the hurricane season, June through October. Leaving the US, you´ll probably go in the summer.
The spring or atumn will then be spent in the balmy waters of the Caribbean or Mediterrian respectively.
The voyage down to the point of crossing - Canary Islands or Bermuda most often, is an excellent training in itself for the oceans. You will get months of training and get to know your boat in all kinds of situations and will also have the chance to service or add parts in harbors along the way.
Best time for a westward-passage via the Canaries is between November and December. Leave too early and there is a risk of hurricanes. Leave too late, and the winds might be too weak.
Crossing eastwards you will be better of leaving mid-May to mid-August, when the chances of gale are lower.
You'll need charts but not for the Atlantic ocean crossing obviously (it´s pretty much straight forward). Get the charts before you set out, depending on the harbours and waters you´ll cruise before and after the Atlantic. Charts are usually easily obtained in harbours and Marinas, but the most popular can be out of stock. The Atlantic Crossing Guide provides information on harbours, crossing deadlines, distances and a whole lot more for the typical Atlantic crossing.
This route usually starts in late July, because the Bay of Biscay and Gibraltar are difficult to cross past September and October respectively. We started out late, so we shipped the boat to the Canaries from Amsterdam, and took her by truck over parts of Europe to avoid the Bay of Biscay in November.
There is not much in the Cap Verde’s and the islands are not very popular among sailors, so the islands are usually just bypassed on the crossing.