5 Best Hawaii Travel Planning Tips

Waikiki Beach
Just another sunny day at Waikiki Beach.

Aloooooooohaaaa! I get to talk about my favorite place in the world! HAWAII!!!

I was born in a border town in Mexico. (Stay with me.) I grew up in the southwest, mainly in El Paso, TX. All I knew was the Rio Grande, which I played in as a child and the dusty, poverty ridden sierras of Juarez, Mexico.

At my grandmother’s house in Juarez Mexico. circa 1975

I grew up translating for my mom when we would go grocery shopping or at a teacher conference meeting. I didn’t speak Spanish well but I could translate, weird, I know (it’s a long story). Years later, I got hired as a travel agent in a small agency in El Paso immediately after completing my travel and tourism certification. This was before the internet in 1990. I confess that I lied and said I knew Spanish but I didn’t know it very well.  It didn’t take long to learn real fast after starting. (Sorry Mr. and Mrs. Oaxaca)

I found myself with an opportunity to go on a travel agent familiarization trip to Hawaii. I hadn’t traveled anywhere that couldn’t be driven to. My family took many road trips but I never flew anywhere. Anyways, when I stepped of the plane in Oahu, I was blown away! I really felt like I had walked into a postcard! My group was greeted with a lei greeting and we were treated so warmly. I fell in love with the culture and people instantly! This was a life changing moment for me.

Hawaii 1990
My first trip to Hawaii, circa 1990.

I am proud to say that I’m a Hawaii Destination specialist. Hawaii is my favorite destination in the world! It’s one of those destinations that you can go back many times and see a different side of Hawaii.

Here are some tips that will help you in your research about making Hawaii your next vacation destination.

1.) When is the Best time to visit Hawaii?

The best time depends on a couple of things. First of all, why are you going there? Is it for a festival or special event? Or are you going to just getaway and check out the culture, landscape, attractions, etc?

As far as the weather in general, it is usually mild year round. They do have a rainy season and that’s springtime between Mar-May. Their summers are warmer but my favorite time of year there is the fall and winter. Between October-November is when their most comfortable time starts and December – February is their coolest time of year.

As far as the crowds and cost goes, their most crowded time is the summer of course, when school age kids are on their summer vacation. Their high-season is December -February because it’s the coolest temps and that’s when you can see amazing whales breeching all around the islands. (The same whales that head back home for the summer to Alaska.) You can take special boating tours to go out and catch wondrous sightings of these great beasts or you can even catch them breeching from your hotel room during the winter there.

Jurassic Park Movie Location at Kualoa Ranch Oahu
Jurassic Park Movie Location at Kualoa Ranch Oahu 2016

2.) Which island or islands are the best to visit?

I must recommend that you speak to a travel advisor if you really want the best advice for you. Each island offers something so unique that in order for you to be happiest and get the most out of your travel dollars, it’s the smartest thing to do.

However, I’ll give you a brief description on some of the main differences.

If you have 3-5 days, then I recommend just seeing one island. If you have 6-7 days, you can catch 2 islands and if you have more time then maybe a third island can fit into your itinerary.
If you want to see them all in a week, I recommend a cruise that visits all the islands and you don’t have to pack and unpack everyday.

Kualoa Ranch dock to Private Island in Oahu
Kualoa Ranch dock to Private Island in Oahu

Oahu is the most popular mainly because of Hollywood. You may recognize the world famous Waikiki Beach that is featured in shows and movies. Well, you’ll find it in Oahu. Oahu is also where the city of Honolulu is which is also the capital of the state. Honolulu is where you’ll see the skyscrapers set against the very recognizable Diamond Head mountain nearby.

This is a place where you can walk the Waikiki Beach area, take public transportation to some places and rent a car for a day to explore the other side of the island. Some main attractions are Pearl Harbor, USS Arizona Memorial, Hanauma Bay Nature Preserve, see the surfer’s paradise called the North Shore, and so much more!

I have customers say, “Oh I don’t want to go there, it’s so touristy.” I have to disagree. There is so much more to Oahu. I love to see the different perspectives and if you don’t want to hang out in the city, you can hang out at a ranch on the other side of the island. Kualoa Ranch is where many movies have been filmed and even Hollywood can’t deny the majestic beauty of the landscape there. It’s worth visiting! Here is a link to a more detailed description of what to do there: https://www.gohawaii.com/islands/oahu

Wailea Beach Resort Marriott Maui Entertainment
Wailea Beach Resort Marriott Maui Hula Dancer

Maui is the second most popular because of the many condo choices available to larger families. You can’t find many options in Oahu as you can in Maui when it comes to accommodating larger families. One of the concerns is the price of meals anywhere in Hawaii. It can be expensive but there are ways to get around that. For example, if you don’t mind stocking your kitchen with light snacks, drinks, and easy meal ingredients in order to avoid going out every night. Some resorts even have outdoor grills! Some properties will even stock your kitchen for you for a small fee of $5. Just give them a list of things you’d like.

Maui is more of quaint small towns, farms and beautiful beaches. You will not see any skyscrapers on this island. There are several ideal beach areas that you want to look at such as Kaanapali near the town of Lahaina. Wailea area is not as popular but still amazingly beautiful.

Popular activities are hiking or biking such places as the Haleakala Crater, exploring local farm such as the Surfing Goat Dairy Farm http://www.surfinggoatdairy.com/ or tour the Ocean Vodka Farm http://oceanvodka.com/.

Don’t worry if you’re a shopper. There are some fun small shops to browse and even some upscale boutiques.

The food has morphed in the past several years with the growing popularity of the farm to table movement. I have experienced it myself here and I can’t describe the true enjoyment of tasting such amazing meals. Meals that I will never be able to duplicate anywhere else.

While there are many wonderful roadside food establishments along the highways of Maui, there is one place that you should definitely visit while here called the Maui Tropical Plantation https://mauitropicalplantation.com/. It’s not near the beach but the views will make you forget about the beach while you’re there!

Kauai Waterfall
Gorgeous waterfall in Kauai.

Kauai is probably the most beautiful place in all the earth! (Okay, so maybe that’s just my opinion.) But you won’t be so quick to disagree once you visit there.

Again, no cities here. This is even less populated than Maui. You have to really enjoy more outdoorsy type activities here.

Your overall experience really depends on which side of the island you want to stay at. I recommend a car for the full time that you’re staying here, by the way. The North Shore is popular for the rugged mountains, cliffs and beautiful beaches. It’s the rainiest side too which means it’s very green! The south side of the island is very popular for more economical accommodations and the sunnier side of the island.

Kauai is where the Napali Coast is located, you know, the Jurassic movie looking mountainside! Other than hiking it, the only way to see it is by sea or air. (So no driving there.) The hike is about 11 miles and is considered one of the most beautiful and most dangerous hikes in the world.

And of course, you have to see Waimea Canyon, known as the “Grand Canyon of the Pacific”. While you can drive there and checkout the lookout, I have to recommend seeing this via a helicopter tour. It’s a chance of a lifetime thing!

Kilauea Iki Crater on the Island of Hawaii
Kilauea Iki Crater on the Island of Hawaii

Island of Hawaii refers to the “Big Island”. Apparently we shan’t call it that anymore. The Island of Hawaii is the biggest island of all Hawaiian islands. Two of the most popular places to stay is Hilo and Kona. There are some wonderful places to stay again depending on if you’re traveling with your family or not. This is also another island where you’ll need a car in order to get around.

Have you ever wanted to dive or snorkel with the manta rays at night? You can do that here on this island! As with any activity, subject to meeting minimum physical requirements.

You may remember the great volcanic eruption that happened in 2018. While it was dramatic, the news media really added so much more drama that was very unnecessary. This did indeed hurt the travel economy of the state of Hawaii but things are getting back to normal.  Although, the flooding in Kauai in April of 2018 didn’t help.  Be sure to get the latest updates on road, hike closures and anything else that may affect the area you plan to visit.

Listen, I will always pass on any and all information that will help you make the most informed decisions as I would want someone to do for me.

3.) Is it best to use vacation packages or not?

The majority of my clients have traveled with packages because the supplier is able to either get a break on the air cost or hotel rate. Also, some packages will feature a free excurison, or breakfast included. It’s just a matter of shopping around and seeing what is available not only for the time you’re going but during the time that you’re shopping.

Airbnb is very popular for bigger families but know that I personally will never recommend or book this for any of my clients. They may have their use in this world but please know that I cannot due to some of the following reasons.

Illegal sub-letting practices, guests can have a negative impact on the locals quality of life (I can explain more in another blog article), there’s no local services offered or locals to employ, you’re at the mercy of your host where they can cancel your booking at the last minute, (that’s scary), and the most unnerving is the lack of security and safety.

Travel advisors have options for these but you know that ol’ saying, “You get what you pay for.”

4.) What options are there for families, couples & solo travelers?

There are some great condos in Maui for families, as stated before. You can opt for a 1, 2 or 3 bedroom villa complete with kitchen, lanai and all the amenities and services that you’ll need. Of course, price ranges from luxury to low budget.

Here are a few of my favorites for families:

Montage Kapalua Bay is a luxurious residential style resort on Kapalua Bay Beach in
Maui. It’s perfect for multigenerational families as well as those looking for something more secluded. This is a very laid back property and perfect for those that want to avoid the more “touristy” areas of the island.

Montage Kapalua Bay
Montage Kapalua Bay is a great for families and couples.
Montage Kapalua Bay Kids Club
Take nature walks and daily crafts at the Montage Kapalua Bay Kids Club.

The Westin Kaanapali Ocean Resort Villas is just north of Kaanapali Beach but so close to shopping, dining, town of Lahaina and more. The resort itself is great for kids of all ages, gorgeous grounds, outdoor grills, kids pools with pirate ship and a waterslide, beautiful serene rooms and just lovely.

The Westin Kaanapali Ocean Resort Villas

The Aston Kaanapali Shores is a property you will want to look at if you’re on a little bit more of a tight budget. Make no mistake, this property is moderate and one of the original properties built in 1980 but has been renovated since. I was there in 2016 and was getting a soft update which means a lot of their furniture and accessories were being updated.

I have to say that the people are particularly warm and friendly or maybe it was just more noticeable because the property is smaller than the bigger resorts. Every condo has a view of the ocean pretty much and you are directly on the beach! I love this place!

Here are a few of my favorites for couples:

The Moana Surfrider, A Westin Resort Waikiki Beach on the island of Oahu. It’s historic, stunning, and just so romantic. Even though it sits in the heart of Waikiki Beach area, you wouldn’t know it once you stepped into the resort itself. It has an open air lobby where you can see all the way through to the Pacific Ocean. The beach isn’t big but at least you have your own area. This property has so much to offer!

Maui Sunset
Maui Sunset

The Andaz Maui at Wailea Resort is super chic and very intimate, meaning it’s not near the more popular Kaanapali area. It is complete with a private adult pool area where you can literally feel the stress melt away from your body the moment you walk in. (It took great effort for me to leave this area, I admit.) They should just sell the cabana beds and forget the rooms, because this area alone was worth it! Pardon me while I take a moment to reflect on the memory of being here…sigh.

Andaz Maui at Wailea Resort Lobby
Andaz Maui at Wailea Resort Lobby


Andaz Maui at Wailea pools
Andaz Maui at Wailea pools

The Fairmont Orchid in Kohala Coast, on the Island of Hawaii is breathtaking. This is actually family friendly but also great for couples. What makes it special is the attention to detail and level of service there. When you go on vacation or want to celebrate something special, this property will fulfill your dreams.

5.) How much can you expect to spend on a vacation to Hawaii?

Well, well, now we’re getting down to the nitty-gritty. Let’s start with airfare. One of the tools I use to get a range for flights is Google Flights. You can see the price by date but remember there’s always a reason for what these prices consist of.

For example, they could be with a long layover in Chicago..whaaaa?, or a 15 minute connection in Los Angeles? Anyone knows, if you’ve been to LAX airport, changing planes is crazy right? I don’t think that’s even legal but you have to really look at your flight details.

Phoenix has some direct non-stop flights to and from some of these islands. At times, these flights are the least expensive because the airlines want to fill these planes. The outbound direct non-stop flights are ideal but the return options are not. That’s because they are red eye which means you fly all night and arrive in Phoenix at 6 or 7 am the next day.

I’m seeing airfares ranging from $600-$900 per person. So for 2 people, we’re already looking at $1200 – $1800 total for airfare alone.

Now, let’s look at accommodations. This is where you can start pulling your hair out! It will take some shopping and comparing. Play with dates and type of hotel rooms. Which hotels have a special going on like kids stay free or breakfast included for 2? Which hotel is renovating during your stay? (This is frightening even for us professionals.) The hotel executives still refuse to give us heads up about this but we find ways to get that information when possible.

You also have to look at surprise mandatory daily fees like self-parking fees, valet only parking fees, resort fees, amenity fees and who know what else. These fees can be annoying, not to mention, even if you’re not using the pool…you still have to pay the fees. Needless to say, your preferred travel advisor should be letting you know about all of these details so that you aren’t caught off guard.

A typical vacation package starts with flights, hotel, transportation between airport and hotel or car rental, taxes and fees. Anything else is extra like activities, tours, tickets, shows, special occasion reservations, spa treatments, food (unless all-inclusive but not available in Hawaii), shopping, etc.

Surfing Goat Dairy Farm Maui

Just like airline inventory, hotel inventory fluctuates depending on the season. Spring Break, Summer, High Season (December-February) and holidays are always more expensive. Book 8 to 10 months in advance for those high traffic times and less for low season times.

I just priced a package at the Aulani, Disney Vacation Club Villas for 2 adults and 2 kids, June 1 – 8 in a 1 bedroom villa Islands Gardens view room, direct non-stop flights for all 4 travelers, taxes, fees, travel protection insurance and transfers (no car rental) came out to be $10,739 total.

That’s $383 per person per day which I consider to be on the high end. Still not including all your tours, activities, meals, etc.

Same exact dates but at a different property is the Embassy Stuies Waikiki Beach Walk in a City View 1 bedroom suite, FREE breakfast, direct non-stop flights for all 4 travelers, taxes, fees, travel protection insurance and transfers (no car rental) came out to be $7,438 total.

That’s $265 per person per day which I consider to be on the lower end. Still not including all your tours, activities, meals, etc.

That’s a difference of $3301. Now what you have to think about is what is it worth to you be one the beach with an ocean view, breakfast included or not a big deal, wowing your kids with the world of Disney or not a fan, etc.

This is why it’s so important to find the perfect travel advisor for you. One that will ask all those important questions and put their heart and soul in the research for you and your family. You may even enjoy the research part. Talk to your travel advisor and find out how you can work together so that you get the best of both worlds. You may not want to book with he/she but he/she could let you know what her hourly rate is or flat consulting rate.

It boils down to this. Our world is everchanging. What once was may be gone tomorrow. Did you know that there are some times of the year when there is no beach at certain hotels? The tide is too high during that time and the beach is hidden temporarily.

Hotel management changes from day to day. One is buying out the other and same with the airlines.

Rules and regulations, change. You get the idea. I’ve been back recently and plan to return every chance I get. I will never know everything about everything but it’s my job to make sure I know what I need to for you.

So much of your hard earned money is spent on your vacation. Do you want to trust an 800 number to that or a local member of your own community? A big box retailer or the local small business person that’s putting their heart and soul in your travel details.

I wish you the best and really hope this helps you. My only regret is that I didn’t run into any of the cast of the TV show, Hawaii 5-O! Ugh!

If you need more information on Hawaii, please contact me at 480.290.1889 or cristina@cultivatedescapes.com.  Your Ohana will thank me!