Dedicated to providing travel tips, insight, and advice for travel to Hawaii from the mainland.
There are eight main Hawaiian Islands. Out of the eight - Maui, O’ahu, The Big Island (Island of Hawaii), and Kauai are the easiest to visit and have the most to do.
Disclaimer: Views expressed are my own and do not necessarily reflect those of my employer or anyone else.
I'm Aaron and I've visited Hawaii five times, traveling each time from the mainland. I've visited Maui, Kauai, The Big Island (Island of Hawaii), O'ahu, and Lanai.
On each trip, my wife and I traveled with our two sons (13 and 5). On several of these trips, we experienced Hawaii with parents/in-laws.
On my first trip to Maui, I remember thinking this is a once-in-a-lifetime vacation. After several additional trips I still can't wait to go back again!
All photographs are original and taken by me (or a family member).
While you probably already know this, Hawaii is expensive - really, really expensive!!! I don't know anyone who enjoys throwing tens-of-thousands of dollars around, massively overpaying for something they could purchase much more affordably.
In my experience round trip airfare with reasonable duration times at reasonable hours (not red-eye/overnight flights) for four people from the East Coast to the West Coast is generally around $2k. Round trip airfare from the West Coast to Hawaii is another $2k. The average AirBnB or VRBO seems to generally be around $300/per day (plus additional taxes). A rental vehicle in Hawaii can range anywhere between $600/week to $1k or more per week. Everything varies during the time of year, days of travel (flying on a Wednesday may be cheaper than a Friday) and customer demand at a given time. A good rule of thumb is to presume a trip for four from the East Coast to Hawaii is going to be at least $7k for airfare, rental vehicle, and lodging.
Southwest's Credit Card gives you bonus points (miles) and an annual companion travel pass. The annual companion travel pass enables you to fly a designated companion with you for one trip per year. Clicking this link will give me a referral bonus (something like 15k miles) and will give you a sign up bonus of miles of something like 50k miles (with some requirements). This means that if you sign up for the Southwest Credit Card, assign a designated travel companion, and book your ticket using Southwest's low fare Calendar you can get to Hawaii much cheaper!!!
Outside of using Southwest's Credit Card, use Google Flights to find the most affordable flights. If you’re willing to travel during the middle of the week (Wed/Thurs) you may be able to save hundreds, perhaps thousands, of dollars - depending on how many people are traveling with you.
Comparing AirBnB, VRBO, and Hotels.com to match lodging with your flights can make the trip much more affordable. I periodically check pricing for flights, lodging, and vehicles months before I plan on traveling. Over the course of this time I’ll gauge pricing and am
often able to find travel windows where prices are lower.
This process has enabled me to book AirBnB’s for $300/night (4-6 people) and the next week the same AirBnB was $800/night - this is obviously SIGNIFICANT! The same goes for flights - finding flights which are $80-$120 per ticket cheaper adds up.
If you're traveling from the East Coast I recommend staying in Hawaii for at least 8 days. Furthermore, I recommend a West Coast layover (San Diego, LA, Seattle, Phoenix, Vegas, etc). This breaks up 12+ hours of flying and gives travelers an opportunity to gradually adjust to time zone differences (I cannot overstate this). It’s terrific if you can arrive on the West Coast in the evening, spend the night in a hotel, then fly to Hawaii the next morning (or the following morning) on an early flight, depending on whether you want a down day on the West Coast or not. This can put you in Hawaii around noon HA time (Hawaii Time Zone).
Hotel Shuttle Services
While this seems super obvious, it's easy to overlook if you don't usually use hotel shuttle services. Selecting a hotel on the West Coast near an airport for shuttle services to the airport does not mean shuttle service operates when you'll need it (leaving the hotel at 5:30 AM, for example). Furthermore, offering shuttle service doesn't mean the hotel has dedicated shuttle service. Some hotels contract shuttle services which may pick up guests at other hotels before and/or after they pick you up (potentially adding additional travel time). Some hotels have an on demand shuttle service, which in my experience means, it may take around a half hour for the shuttle to arrive at the hotel. You want to be cognitive of this when planning your trip. I recommend calling hotel guest services to get clarification before booking.
The worst part of your trip, hopefully, will be returning from Hawaii. Getting an early-to-mid morning return flight from Hawaii to the West Coast is highly recommended. I would avoid a red-eye (overnight flight, leaving after 5 PM) at just about all costs. You're going to be flying something like five hours and will lose two-to-three hours due to the time-zone change (depending on daylight savings). You'll get to the West Coast late and will be hungry. By the time you grab your luggage and head to the hotel it may be 7:30 PM or later. Even if you ate during the flight you'll probably be hungry (you ate what seems like 3 hours ago) and won't believe how late it is.
If you have an early morning flight the next day, you'll want to head straight to the hotel, get food there (which is usually more expensive) and get ready for bed pretty soon (along with potentially being jet lagged). You've been on Hawaii Time, perhaps waking up at 6/7 AM. 7 AM on the West Coast may feel like 4 AM now, though. An 8 AM flight may mean you have to get up by 6 AM West Coast time, which feels like 4 AM to you.
Upon arriving on a Hawaiian island it’s wise to pick up your rental vehicle immediately after deboarding your flight. I head straight to the vehicle rental center while my family deboards and gets luggage. In my experience, there can be long lines at the vehicle rental counters and the lines may not move as quickly as on the mainland - you’re on island time and you may need to exercise a little extra patience. Even though it may not seem
like it initially, the lines at the rental agencies do move relatively quickly.
You paid an obnoxious amount of money for this vacation. You'll probably be very excited to get your dream vacation going. I strongly urge you to be polite to others, exercise a little extra patience, and invest conscious effort to smile at others - will yourself into a good mood even though you're jet lagged and a bit tired. Getting your vehicle won't take as long as you may expect, even if the line is 30 people deep! Using this time to search Google Maps for a nearby restaurant could be a good use of time.
Once you get your rental vehicle, go grab a bite to eat and THEN make a Costco run. Costco’s are located near most of the airports. There may be a grocery store near your hotel/AirBnB, however, you’ll be paying 20%-40% more for some items, so Costco can easily save you several hundred dollars.
You’ll be super excited to be in Hawaii and WILL NOT want to do the Costco stop. This extra 45 mins of grocery shopping will pay HUGE dividends during your vacation - especially when you don’t feel like driving to a restaurant or waiting for a meal after returning from the beach. If you arrive in Hawaii at noon(ish) you’ll probably have several hours before you can access your hotel/AirBnB, so grabbing lunch and groceries is a great use of time before you can unpack.
As a side note, it's amazingly refreshing to shower the sand off and get some food after spending several hours at the beach. The sun’s been beating down on you, wearing you out, you’re exhausted from swimming/snorkeling and walking to and from your vehicle while carrying beach equipment! Being able to return to your hotel/AirBnB, get a shower, and eat some food feels like a God-send!
Traveling + varying sleep + sunshine beating down on you at the beach = tired & cranky!
I’ve heard vacationers who return from Hawaii proclaim that it rained during their whole trip. That hasn’t been my experience! I don’t know whether they were locked at a resort without a vehicle or it was just bad timing, but, I’ve done five trips to the Hawaiian islands (Feb once, Apr once, Sept twice, Nov once) and have had spectacular weather EVERY time with minimal rain. Since I’ve heard stories of it raining during others’ entire trip, I prioritize beaches and snorkeling early in our vacations! If it rains later, we already did the beaches and are OK with indoor activities. You’re paying a lot to go to Hawaii, and it takes a lot of vacation time away from work to do this trip. While it may sound surprising, it can be tough to get motivated to get out the door and get good parking at the beach. Again, jet lag and erratic sleep can interfere with motivation to get out the door early.
Whatever budget you elect to set for Hawaii, consider it as a theoretical goal and be flexible. This is difficult to wrap one’s head around. However, after returning from Hawaii, you don’t want to regret not doing something that could have been amazing for a few additional shekels (taking a tour, eating at a restaurant, upgrading to a convertible or renting an additional convertible for a day on Turo). You traveled a long distance to visit Hawaii and spent a lot of money to be there. Pinching pennies and/or griping about the prices and trying to not spend money will tremendously limit your enjoyment (as well as the enjoyment of others traveling with you). If you solely enjoy NOT spending money, DO NOT VISIT HAWAII - even if it’s a free non-transferable trip!
Maui. Actually, the good news is that each Hawaiian island is amazing! So, you can’t make a poor choice. Depending on what you enjoy doing (or think you’ll enjoy doing) you may be motivated to visit a certain island (or islands) on your first trip.
In my experience, every Hawaiian island has phenomenal beaches, amazing food, spectacular scenery, and interesting things to do. While all the islands are similar, they’re all much different also (I wish I could explain this better). Furthermore, if Hawaii’s “your thing”, you’ll be scheming of ways to return and visit other islands as soon as reasonable (or possible). Being in Hawaii, staring at the ocean as the sun sets makes one genuinely feel an appreciation for being in
that place at that moment. You’ll feel present - not trying to rush anything or slow it down, just enjoying the moment and intrinsically appreciate being where you are. It’s an amazingly relaxing and peaceful feeling unlike anywhere else I’ve been.
Regardless of the island, rent a vehicle and use Google Maps to explore! Go out of your way to see different things and try different foods. Drive along the coast, visit the small towns, drive around and enjoy the scenery. Take pictures and make sure you (whoever usually takes pictures of others) are in pictures too.
Maui: When driving on the north-west side of the island, don’t drive past the Nakalele Blowhole (blue circle) TURN AROUND at the Nakalele Blowhole. The road becomes very narrow (red circle) turning into one lane without a way of turning around.
The Big Island: If planning on visiting the southernmost beach (whatever that’s called) ensure that your rental agreement doesn’t explicitly prohibit you from visiting that location - apparently there are many break ins and theft at that location.
The Big Island | O'ahu | Kauai | Lanai