There is a ton of debate raging on the internet and in tattoo shops everywhere about the symbolism and meaning of these popular tattoos. There are tons of articles on this site explaining it and on many other sites on the internet you can find people debating and arguing about the exact symbolism behind things like the nautical star tattoo or the anchor tattoo. You see these are three of the most popular and famous of the old school tattoo designs. They are also pieces that can easily be combined to make a much larger design such as a chest tattoo that features two swallows flying between an anchor.
Well to make it really simple and so as to not mislead you there are no clear cut meanings nor symbolism for these tattoos. The problem is tattoos grow in popularity organically in multiple places at a time. The reason behind one person getting a tattoo is different then another person getting that same tattoo. The symbolism behind a certain tattoo might be agreed upon by a group of people for example sailors on the East Coast. That does not mean Sailors in England would agree. Couple that confusion fact with history and time and in the end you have multiple versions of what the tattoo might have symbolized in the past and no clear cut answer which is the right one. So stop the debate once and for all, enjoy your tattoo and feel confident that you won and it means whatever you want it to me for you.
With that said the bulk of evidence and conglomeration of facts, lies and fiction one can make out a shady idea of what the symbols probably meant back in time and are a good indicator of what they can symbolism today. That way you are not ascribing a meaning to a certain design that is way different then it was meant to be.
All three of these tattoo designs are old school tattoo designs that were worn by sailors originally. Just look at Sailor Jerry's tattoos or a little more contemporary Ed Hardy and you will see anchors, nautical stars and swallow throughout their designs. In the past few years their has been a real rebirth and celebration of the art of tattooing and many of the designs from these greats have come back into fashion be it Ed Hardy Clothing or the website and possible movie dedicated to Sailor Jerry.