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This information is offered for those who are planning a trip to Hawai`i for the first time. These are my opinions — others may disagree — but that is the beauty of opinions.
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Anytime is fine but I prefer Fall (September to mid-December) and Spring (Easter to Memorial Day) because there are fewer tourists during these times. “Snow birds” from the colder climes prefer to escape their frigid homelands during the winter months — and families tend to visit during the summer months because schools are generally not in session then. As a result, flights and ground accommodations are easier to book and often less expensive during the off-peak times — plus once you arrive, you will find everything is a bit less crowded.
Note that the Christmas holidays (and to a lesser extent, the Thanksgiving holidays) are very popular and you may need to book well in advance.
The weather is generally fine all year long. It does tend to rain a bit more during the winter and it is a bit warmer during the summer. However, typically the weather varies more due to location than the calendar. This is true both regarding the choice of island and where you are on that island. For instance, it may be raining at Kapalua but Lahaina or Wailea may be dry.
Plan to visit for at least ten days (longer is better). Many people plan a one-week visit but find, to their dismay, that one week just flies by and they are not ready to return home. I cannot tell you how many people have said to me, “You were right, we should have stayed longer.” Remember that your travel days will be full of, well travel — not much time (or energy) for the beach or sightseeing.
As you plan, consider how expensive the airfare is (whether using dollars or frequent flier miles) versus extending your trip by a few extra days. Remember that it is difficult (maybe impossible) and expensive (change fees, higher fares) to change your itinerary at the last minute prior to your trip or after you arrive in the islands.
Plan to visit only one or two islands. Hawaii requires the visitor to settle down and relax — get in touch with "Hawaii time" — and just let the world flow by.
Note that changing islands can take the better part of a day. Think about how long it takes to pack, check out of your hotel or condo, drive to the airport, return your rental car, check in your luggage, go through security, the flight itself, wait on your luggage at your destination, pick up your rental car, drive to your next hotel or condo, check in, unpack, quick trip to the grocery store (if staying in a condo) and finally, relax. Plus you have to pad those expected times in case of delays in any part of the process.
Some of the major airlines offer non-stop flights between certain cities on the mainland and the neighbor islands. There are frequent flights between the islands — although things are a bit more confusing since Aloha Airlines ceased operations. Hawaiian Airlines, Island Air, Go (Mesa) Airlines, Molulele and a few small carriers with smaller aircraft provide service.
Pay attention to the details of any prospective itinerary. If you are traveling between neighbor islands (for example, Maui to Kaua`i), many flights now require that you first fly to Honolulu then change planes for the flight to the second island. Considering that you can often see the neighbor island from the island you are on, it seems like a waste of time. Look for non-stop flights or direct (no change of plane) flights.
You might also consider the possibility of using alternate airports — for instance, flying to Kapalua West Maui airport can save quite a bit of time if you are staying in the West Maui area compared to the main airport at Kahului. The same is true with the two airports on the Big Island (Hilo and Kona). Do pay attention to any difference in fares.
It depends on which island you are on and which you are traveling to. There is ferry (people only, no cars) service between Maui and Lana`i as well as between Maui and Moloka‘i. It is less expensive than air fares and certainly less hassle with luggage and security. However, some days the sea may provide swells that some folks cannot stomach.
O‘ahu - this is the most populous island — as a result, there are many people and lots of traffic. Accommodations and food tend to be cheaper plus there is lots of shopping and a good bus system. You can escape the crowds to some extent by heading to the North Shore. There are some very nice beaches, great surfing, interesting museums, etc. and the Arizona Memorial.
Maui - this is my favorite island for a vacation. It is a nice compromise between too much civilization and too little. Maui has a dormant volcano, waterfalls, great beaches and beautiful scenery. During the winter months, you can see the humpback whales. Locals say “Maui no ka oi” — “Maui is the best”.
Kaua‘i - for many people this is their favorite island. It is very green and lush but tends to have a bit more rain (Mt. Waialeale is the wettest spot on earth). All that water has carved out the spectacular Waimea Canyon, dubbed “the Grand Canyon of the Pacific”.
Hawai‘i - the "Big Island" is the largest and youngest in the chain. Kilauea is the volcano which is active (but not explosive). You can see it up close — don't miss it. The Big Island is my second favorite because it is so different than any place I've ever seen. The influence of the volcanoes is everywhere — be sure to visit the black sand beaches.
Moloka‘i - a very quiet, out of the way place. There are no nightclubs or supermarkets, no high-rise buildings or bustling cities, no traffic or traffic lights — this island moves in harmony with the wind and the palm trees, the waves and the sky. The one major resort (and golf course) was closed in 2008 — although the smaller hotels, condos and B&Bs can be quite delightful.
Lana‘i - a small island which was largely a pineapple plantation until a few years ago. Pineapples have been phased out because they are cheaper to grow elsewhere. Two luxury hotels have been built that cater to the rich and famous. For the rest of us, there is the small rustic Hotel Lanai — it isn’t fancy but you have access to the beach and many of the facilities of the two luxury hotels — and the restaurant there is fabulous. Lana`i is an interesting place to visit because it is probably what all of Hawai‘i was like, perhaps early in the 1900’s. You might consider this as a shorter stay — mainlanders tend to become bored after a few days — but it will certainly be a part of the trip you would never forget.
If you asked me to recommend the best combination for a ten-day trip, I would probably say seven days on Maui followed by three days on the Big Island or Lana‘i .
O‘ahu (where Honolulu is located) has a good bus system, so it is your choice whether you wish to ride the bus or rent a car. On the neighbor islands, generally you should reserve a rental car — the public transportation is limited and you will probably prefer to have a car to get around for sightseeing, beach activities, shopping and dining.
Lana‘i is an exception because it has few paved roads and a bus service connecting the hotels — a moderate per person fee will be added to your hotel bill. If you really want to explore Lana‘i, you can rent a 4WD vehicle and travel the dirt roads to many interesting, out-of-the-way spots. Note that both the rental and gasoline are quite expensive. Further, if the weather is or has been rainy, you may find further restrictions on the unpaved roads that you can drive on.
IMPORTANT: Do not leave valuables in your rental car — they have a tendency to disappear.
I recommend condominiums over hotels. Condos typically provide you more living space plus they all have full kitchens (generally including sink, refrigerator, stove, oven, microwave, coffee maker, silverware, plates, glasses, cooking utensils, pans). Thus you can throw together a quick meal or snack rather than having to take the time and expense of visiting a restaurant every time you're hungry. You still have the option of going out to a restaurant and you can even bring home a doggie bag for the next day’s lunch. Another advantage of most condos is a common area with barbeque grills. Hotels do tend to offer mini-bars but fill them with expensive beverages and snacks, leaving little room for your use.
The space issue is even more important if you have family members who have different sleep patterns. In a condo, if someone wants to stay up late and read or watch TV, they can do so without disturbing those family members who retire early. Similarly, early risers can get in their exercise, shower and breakfast while the late sleepers catch a few more Z’s.
On the down side, condos often provide maid service on a less frequent basis — so your towels and sheets may be replaced every few days instead of every day as is typically the case in a hotel. Also, hotels will generally have more and better restaurants, shops, etc.
Bed and Breakfast places are another alternative. I have had good experiences with B&Bs in Hawai‘i — accommodations at a reasonable cost plus generally good breakfasts. Many B&Bs also will allow you a bit of space in a refrigerator for leftovers, etc.
Whether dining out or cooking in a condo, food tends to be more expensive than on the mainland. Farmer’s Markets offer great produce at better prices than the average supermarket. They are found on each of the islands: ask at your hotel or condo about the local farmer’s market. The sellers are friendly and will give you free samples and preparation tips. In addition, there are special treats that you should experience if you have the opportunity — some of my favorites...
Bananas: buy the apple or ladyfinger bananas for extra flavor that you don’t experience on the mainland (the bananas found there are picked green and gassed to turn yellow). Make sure they are Hawai‘i-grown.
Strawberry Papaya: also called "Sunrise" Papaya. It has pinker flesh and a smoother taste compared to the standard papaya.
Maui Gold Pineapples: sweeter, with less acid than the standard pineapples.
Local fish: the deep sea fishes have a firm flesh and are quite tasty (you can even barbeque if staying at a condo).
Maui Potato Chips: look for the Kitch'n Cook'd brand (red and gold packaging) from the Maui Potato Chip company. Granted, they’re not heath food but you can cheat and have a few.
Taro Chips: made from the same underground tuber that poi is made from. The chips are much tastier to the mainland palate.
Hula Pie: an ice cream pie with a crust made from crushed Oreo cookies (just the chocolate part, not the cream filling), filled with macadamia nut ice cream, topped with hot fudge, macadamia nut bits and whipped cream. It is available from any of the TS Restaurants such as Kimo's on Maui. One slice is huge and can easily be shared. Remember that counting calories will have to wait until you return home.
Hawaii is a golfer’s paradise — the foliage is lush and the views are spectacular. As is the case in most resort areas, it is also expensive. You can save by booking twilight tee times or calling Stand-By-Golf (check the phone book). There are also a few municipal courses that offer reasonable rates and a chance to mingle with the locals. If you plan to play only once, it may be less hassle and less expensive to rent clubs.
Note that some airlines are now charging exorbitant fees to carry golf clubs. DO check with your carrier before heading to the airport!
One way is to buy a good guidebook (paper book or e-book) — a $10 or $15 investment will save you from potential mistakes that could ruin your vacation. This will help you learn more about locations, properties, beaches and things to do. Remember, that if you are going to spend $1,500 or more (possibly much more) per person, a small expense up front is smart insurance.
The Internet can also provide you with useful information — although you may want to cross-check multiple web sites.
English is almost universally spoken in Hawai`i. There has been a wonderful cultural preservation effort in recent years to preserve, among other things, the Hawaiian language. You will find it useful if you learn a few words which you will encounter frequently.
Almost all place names in Hawai‘i are in the Hawaiian language. You don't have to learn the meaning but it would be helpful to learn a few pronunciation rules — even if just to ask directions. The missionaries first assembled a written equivalent of the oral Hawaiian language they encountered when they first arrived in the late 18th and early 19th century.
There are eight consonants — h, k, l, m, n, p and w. All are pronounced as in English with the exception of "w". At the beginning of a word or after an "a", it is pronounced like "w" or "v" (choose the "w" — both are acceptable and it's one less rule to remember). After an "i" or "e", it is usually pronounced like "v". After a "u" or "o", it is usually pronounced like "w".
There are five vowels — a, e, i, o and u. All are pronounced in the Latin style. Thus "a" sounds like "ah"; "e" sounds like "ay"; "i" sounds like "ee", "o" sounds like "oh" and "u" sounds like "oo". Note that you may see a dash over a vowel such as "ā" — don't fret it only makes the sound a bit longer.
Hawaiian words consist of syllables (like English) — consisting of a consonant and vowel sound or just a vowel sound (simpler than English). If you look for that pattern and sound out each syllable, you'll almost always come close — at least close enough to be understood. Additionally, note that the next to last syllable is the one that gets the emphasis — for example "ah-LOH-hah" (aloha).
The is also a pseudo consonant masquerading as a punctuation symbol — the okina "`" or backward apostrophe (the character to the left of the "1" on your keyboard"). It tells you to pause your aspiration between syllables. For example, the famous beach resort area on Maui is Ka`anapali Beach. The name is pronounced "kah-(brief pause)-ah-nah-PAH-lee".
One last gotcha — if two vowels appear together, they usually become a diphthong (unless there is an okina (‘) between them). You can memorize the combinations or do what I do —practice saying the individual vowel sounds, repeating them faster and faster until they become one. Try it with "ai" -"ah-ee, ah-ee, ah-ee, ah-ee" — did you notice it started to sound like a long "i" (eye). For example, the former royal capital (and whaling center) is Lahaina. It is pronounced "lah-HIGH-nah".
Hopefully, with these tips you can ask where Kihei (KEE-hay) is. I can't tell you how many times I've heard tourists say "KIE-hee". If you mispronounce it that badly, please don't expect any local to be able to give you directions.