The artist's technical knowledge around watercolor grew organically, starting off as a boy under the tutoring of his mother who was an amateur artist herself. She made copies of still life items from books, which may not have inspired the young Winslow especially, but it did intrigue him regarding these techniques. His time as an illustrator, prior to making it an independant artist, taught him about the use of clear outlines to create form, and this method has some similarities with how one puts together a watercolour painting. In this case, one might construct the composition with lines of pencil or chalk before then starting to add the washes of colour. He also worked in a lithography store during the 1850s which further opened his eyes to alternative materials that he might consider experimenting with. This early stage of an artist's career tends to be when they are at their most experimental and curious, and though many of these efforts are not fruitful, their enthusiasm continues to drive them ever onwards.
Some of the mediums that he worked with could then aid his work with others. For example, Homer is known to have produced many simple watercolours, sometimes referred to as wash drawings, which provided the basis to later engravings that were completed on wood. In fact, he would sometimes apply them directly onto the block itself before cutting across the lines with his tools. These preparatory studies would normally be destroyed at the time and so we do not have the luxury of being able to study them in order to understand more about his working practises on these artworks. Despite all these different experiments across a number of years, it was not until his professional career had been in full swing for around two decades before he started to truly devote time exclusively to this art form for the purposes of producing presentable watercolour artworks. One must also consider that the formative years were all about establishing an artistic reputation and that the market for watercolours in the United States was pretty small at that time. He would not have been encouraged from a financial perspective to have pursued this art form any earlier, because it would have done little to raise interest in his career.
The methods used with watercolour painting is much better suited to travelling around and this would be a major factor in why Homer preferred to work on his oil paintings whilst in the comfort of his own studio. The artist found that he could enjoy the beauty of the American countryside whilst carrying just some notebooks with his box of colours and some other instruments. This has been the case for a number of other artists who have worked across different mediums, such as Claude Monet, Paul Klee, Albrecht Durer and also William Turner. An American artist who worked extensively in watercolours and on similar topics to Homer was John Singer Sargent. The collections of artworks found in notepads are sometimes sold on in bulk, whilst artists have sometimes pulled out individual sleeves when they were particularly happy about a particular painting. Researchers have found these notebooks to be invaluable in tracking and understanding the production processes of various artists, displaying both their study pieces and also the chronological order of different compositions.
Homer loved the spontaneous nature of watercolour painting, where decisions would have to be made quickly and were difficult to then reverse. This provided a contrast to the techniques of oil painting, where layer upon layer of paint is added over time and minor adjustments to detail can be made as often as one chooses. Watercolours are also very suitable for landscape and seascape painting, because of the importance of light within them, and these were the genres in which this artist was most interested. The speed at which the artist would have to work, because of the quick drying nature of this medium, he would produce an extraordinary amount of work during each trip, even though they may have been as short as a week long. Others did last for several months. The destinations that feature within his notebooks of watercolours include the New England seaside, in the Adirondacks, Quebec and also Florida, the UK and the Caribbean.