Structure
Most place names of Hawaii are a combination of Hawaiian words. The names can be noun groups such as "Hanauma" hana “bay” + uma “curved”, verb groups like "Nānākuli" nānā “look at” + kuli “knee”, or single words like "Mānoa" “vast”.""
Some noun groups include articles: "Kalihi" ka “the" + lihi “edge”, or "Napali" na “the, plural” + pali “cliffs”. Others contain reduplications of words like "Waikiki" wai “water” + ki “spout forth” (x2). Reduplication typically conveys the meaning of "continuing a state or activity".
Some places are named after people. Alexander ʻIolani Liholiho gave his name to a palace and a school, while the Kamehameha dynasty is referenced in the names of countless buildings, institutions, and roads. Western names can be Hawaiianised: Emekua is the Hawaiian version of "Emerson", for a famous physician who recorded the folk tales of Hawaii. "ʻĀina Haina" is a mix of ʻāina "land" + Haina "Hind", after the Hind family that used to own the area.
Sources
Most names predate the arrival of the Europeans to the Hawaiian islands. They tend to describe geographic features, but there are also names coming from plants, events, people, and even legendary animals. "Mōʻiliʻili", for instance, means Mō "legendary lizard destroyed by Pele's sister" + ʻili "pebble" (x2).
After the different waves of immigrants settled in the islands (originating, in chronological order, from Western Europe, China, Portugal, Japan, and the Phililppines), names from foreign languages came into existence. These names typically come from discoverers, missionaries, and business or political figures. There are exceptions, like "Yokahoma bay", which has a Japanese name simply because it was the last station of the Oʻahu railway that sent Japanese fishermen off.
Now, new names for hotels, streets, and developments typically combine English words or simple Hawaiian words that newcomers can easily pronounce. A few of them contain mistakes. The most famous example is certainly "Lanikai", which reads lani "heavenly" + kai "ocean". This name coined in the 1930s should have been "Kailani", as the adjective follows the noun in Hawaiian.
Difficulties
Polysemy is common in Hawaiian. When several words have the same exact pronunciation, modern translators must choose the most probable meaning based on the topography or context. For instance, it makes more sense to parse "Kailua" as kai “sea” + lua “two” (due to the currents, especially on the Big Island) than as kai “sea” + lua “pit, hole”.
In some cases, several interpretations coexist. "Nānākuli" can be either understood as Nānā “look at” + kuli “knee” (in the honor of the tattooed knee of a chief) or Nānā “look” + kuli “deaf” (local inhabitants may have been said not to give enough food to the strangers passing by).
Some words are too old or too obscure to be clearly translated. This is the case of the names of the islands. Oʻahu has been translated as “gathering place”, however such an explanation would make sense only if the ʻokina was before the initial, as in ʻOahu. Equally hazardous to parse are the translations of Molokaʻi, Kauaʻi, or even Hawaiʻi.
A few names are only documented in Western maps without the accentuation and the ʻokina. The pronuciation has been lost. It is then impossible to know exactly how to parse them. The meaning has been lost.
A Useful Glossary
The top ten words used in Hawaii place names are:
wai "stream, river, fresh water"
kai "sea"
puʻu "hill, mount"
moku "district, island"
hale "house"
lani "sky, royal chief"
lae "cape, point, forehead"
manuma "mountain"
pali "cliff"
ana "cave"
Here are a few qualifiers too:
loa "long"
nui "large"
iki "small"
ʻula "red"
kea "white"
Why?
Learn the language! You already know the words. Once you have heard that "Waimānolo" means wai "water" + mānolo "potable", you have already memorized two very useful Hawaiian words that you will probably never forget.
Learn the history! Did you ever wonder who was Keʻeaumoku? He was a Hawaiian chief, father of Kaʻahumanu. Explore the map to know who Bishop, Dilingham, or Likelike were!
There is a lot more to Hawaii place names than their literal translation. Place names appear at length in Hawaiian sayings and chants - there are tales, histories, and meanings attached to them. Some specialists of Hawaiian culture can describe with precision the multiple layered meanings of a single place name. This map is only an introduction.