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In this episode we’ll talk about:

  • What summer vacation means to me
  • We are getting creative with finding summer destinations around the world 
  • How to choose the best Hawaiian island for your vacation so you can avoid FOMO
  • My favorite beaches and places to explore on each Hawaiian island
  • An interactive quiz that you can take with the entire family to help you choose the right island for your next trip

Summer is always in season somewhere in the world. So the summer vacation doesn’t actually have to happen between the months of June and August and this year the summer vacation can actually take place in December.

So if that’s the case, where can we find summer in December? Some of my favorite places to look would be Costa Rica, Galapagos Islands and Hawaii. And today I want to talk about Hawaii, how to choose the best island for your family vacation and how to make the most out of your trip. 

If you are worried about traveling internationally and getting stuck abroad, then Hawaii is perfect, it is part of the US, so even if the international borders will close, that should not apply to Hawaii.

There are 8 main islands, which make up the state of Hawaii (Hawaii, Maui, Oahu, Kahoolawe, Lanai, Molokai, Kauai and Niihau).

We will look at the 4 main islands.– Big Island of Hawaii, Maui, Oahu, Kauai, which are the most visited ones. 

The other 4 islands are also open to visitors but you may only be able to do a day trip to most of them since they don’t have many options of lodgings, if any.

One of the most popular questions that my clients ask is – Which is the best Hawaiian island for my family vacation? 

Confusing, I admit. It is very confusing. With the five main Hawaiian Islands available for selection, determining which one best. suits you can be difficult, and the FOMO is real!

There is no best island. It’s simple. All of the major islands of Hawaii have just about everything that gives an island its appeal.– calming beaches, soft white sand, lush vegetation, lots of cultural sites, and lots of fun in the sun for families. 

But they also offer different things. Your choice of a Hawaiian island would depend on what you hope to get out of your trip and how your family would want to spend their time there.

Let’s start with Oahu, Hawaii

If you have never been to Hawaii and only have one week, I recommend that you go to Oahu and stay only on this island. 

By spending time on a single island, you immerse yourself in its culture and its people. On your next visit, explore yet another. The difference is stunning. The beaches, history, and people are sure to keep you entertained. Every island has something for everyone.

Coming from NY/NJ airports it will take you 12 hours on a direct flight to get to the main city of Oahu, Honolulu. 

I like to joke that it takes 4 good movies, 6-hour time difference and I am in Hawaii. After such a long flight I doubt you would want to wait for a layover to get to another island and there is plenty to do on the island of Oahu, so don’t waste your time and start exploring right away.

Home to Hawaii’s largest city, the capital city of Honolulu, Oahu is one of the most vibrant islands in the Hawaiian chain. Honolulu has just about everything you’d expect from a modern city. A vibrant nightlife, plenty of natural wonders, historic feel, and bustling entertainment industry.

With all of its high-rise buildings, luxury shops, restaurants, and nightclubs, you’d simply be enjoying a vacation in seemingly familiar surroundings. It’s impossible to miss a visit to the iconic Waikiki, one of the world’s most famous beaches.

But Oahu is so much more than just Waikiki and Honolulu. And to be 100% transparent, Honolulu is my least favorite part of the island. I’ll share with you my experience with the island.

A few years ago my husband, Oleg, and I went to Hawaii. It was a spontaneous trip, the type of trip that you take when you are desperately in need of a getaway and you jump on the first good deal that you see. We had a crazy year and we were burnt out. We really needed to stop and smell the roses.

And we did. We bought our tickets two weeks before departure and I hurriedly planned out our itinerary. Having had limited time to prepare for the trip (usually, I book 4-6 months in advance), I only made a quick list of places we wanted to see. I also planned to have half of each day free, so we could explore the beaches of Oahu.

When we got to the Waikiki Beach, I almost cried. I was longing for peace and quiet, a secluded beach, drink and a book in hand. Instead, I found myself in a place that reminded me of both the Las Vegas Boulevard strip and Miami’s  South Beach. Don’t get me wrong, there is nothing wrong with either of those places and there are times when I wish I was there, but this was not that type of trip. Needless to say, we did not spend much time at the Waikiki Beach and ventured outside of Honolulu as much as we could.

The first beach outside of Honolulu that we visited was Kailua. It was much quieter than Waikiki. It still had a lot of people, but it did not feel crowded. However, it was not the beach of my dreams. Kailua beach is part of Kailua Beach Park, so the beach is at the end of the park and feels like a typical city beach. I could not point out what was wrong there (there really wasn’t anything wrong, it was just all in my head), but I wasn’t happy. Luckily, Hawaii is in the US, so I had perfect cell phone service. I started looking at the map on my phone to see what was near us because I was getting bored and was not feeling the Kailua beach vibes.

And there it was, a tiny dot on the map – Lanikai Beach. I don’t even know how I noticed it, because if you Google it, you will see the name of the beach, but the terrain does not look yellow, like in typical beaches on Google maps. Lanikai Beach was a 3-minute drive from Kailua, so we decided to give it a try. 

We entered the coordinates into the GPS and a few minutes later found ourselves in the middle of the residential street. Moreover, this was a residential street that did not have any sidewalks. All the cars were parked back-to-back on the side of the road, which didn’t even look like a road where you could park. Great! Where to next? 

I didn’t see a beach and we were risking getting our car towed. I started losing hope. 

Then I saw a family emerge from a narrow pathway between two houses; they were carrying towels and a cooler and clearly coming from the beach.

I think the universe felt bad for us, because this family happened to get into the parked car right in front of us and leave. We took their parking spot and strolled down the narrow path. At the end of that path there it was – a little piece of paradise on Earth. That beach from my dreams, that secluded piece of white powdery sand without another human in sight. Oh heaven, here I come!

It was everything I dreamed of and more. The beach sat in front of multi-million dollar mansions, but because all the beaches in Hawaii are public, anyone could enjoy it. The water was turquoise, but not as warm as it usually is in the Caribbean. Well, keep in mind the Caribbean beaches are in the middle of the sea, while Hawaii is in the middle of the ocean, so the water is cooler. But honestly, I did not care. I just wanted to sit there and stare at nothing. It was a non-peak season afternoon in Oahu, so the beach was empty. We ran back to the car, took our floating chairs and parked on the beach for the next 3 hours until it got dark.

We explored a few more beaches on Oahu in the next few days, but still kept coming back to Lanikai Beach, because for me it was truly a little piece of paradise. So, venture out to see it next time you are hanging out on Oahu.

And we are off to Maui, Hawaii

Maui is your ideal resting place. If your vacation is meant to be a peaceful, relaxing time, visit Maui. 

It offers everything that makes Hawaii so special. Golden sunny beaches, majestic whales in the winter, Haleakala National Park, and relaxing luxury resorts, some that cater to families and others that cater to couples and honeymooners. There is also no shortage of things to do from snorkeling and swimming with the turtles, to hiking to the volcanoes and experiencing the luau.

One of the most incredible things you can do in Maui is see the sunrise from the top of Haleakala National Park. 

For most people, the chance to sleep in late is one of the perks of going on vacation. But on Maui, you definitely want to get up early at least once.

A Maui sunrise is extra special when viewed from way up above the island shores, Haleakala Summit. From here you can view the incredible views east of the morning sun, and watch as the morning light spreads dramatically across the volcano’s crater floor.

So if waking up early is not an issue and then spending the rest of the vacation exploring different beaches with your family is the definition of your perfect vacation, then Maui is your choice!

Let’s talk about Kauai, Hawaii

Kauai, the Garden Isle, is the oldest island of the Hawaiian chain. If you wish to enjoy nature in its pure, romantic form, Kauai is the island for you. The grand waterfalls, remarkable coastal trails of Napali Coast, unblemished beaches, lush green cliffs, and colorful gardens combine to make Kauai a place to love. Throw in a hiking visit to the Grand Canyon of the Pacific, and your Hawaii vacation is complete.  

I want to talk a little bit more about the Grand Canyon of the Pacific, which is a huge gorge named Waimea Canyon that’s 14 miles long and 3,000 feet deep. Although small in comparison to the real Grand Canyon, which is 277 miles long and 6,000 feet deep.

“Waimea” is Hawaiian for “reddish water,” no doubt referencing the color of the canyon and the tint the water takes on as it runs through. 

If you are going to be looking for summer in Kauai, during the winter rainy season, those red walls will be green with new growth and provide a beautiful contrast.

One of the first things a first-time visitor to the canyon should do is take a drive through it. Waimea Canyon Drive begins in the small town of Waimea and goes north, merging with Kokee Road as it enters Waimea Canyon State Park and the Puu Ka Pele Forest Reserve.

There are several overlook points perfect for stopping and taking in the jaw-dropping views of the sprawling canyon. Two additional spots to check out are the Kalalau Lookout and the Puu O Kila Lookout for vantage points over the Kalalau coast and its tall, green ridges.

Helicopter Fly Over is one of the coolest ways to check out the canyon. Nowhere can you get a more comprehensive understanding of its massive size than from above.

And with that comes the adventure of being in a helicopter, zipping over the forests and the canyon and gaining access to remote areas that would otherwise be unreachable by car or on foot.

I recommend going on a tour that combines a flyover of Waimea Canyon with the nearby, world famous Na Pali Coast to get the most bang for your buck. 

Now let’s explore The Big Island, Hawaii

The last of Hawaii’s biggest, most popular islands. The Big Island is the largest of the Hawaiian island chain.  It is big, literally, bigger than all of Hawaii’s other islands when combined. The Big Island is twice the size of as Delaware and almost four times as large as RhodeIsland

A vacation on the Big Island is one you wouldn’t forget in a hurry. And there is no shortage of activities to keep you busy. It is an island with history. Stories of kings, gods, and traditions are sure to grace your stay. 

Stunning waterfalls, untouched rainforests, silvery beaches, an active volcano, and snow-capped mountains. What’s not to love? The Big Island also has incredible sunsets, so I recommend a sunset cruise or dinner outdoors with a view. 

The Big Island is the largest and most volcanically active of all Hawaiian islands. The island still grows every day because of its #1 tourist attraction (which also happens to be one of the most active volcanoes in the world): the Kilauea volcano.

If you like beaches you are in luck. The island has quite some amazing white, black, and green sand beaches!

Hāpuna beach, which is consistently voted among the best beaches of the world. It also is one of my favorite beaches in. Hawaii because of the long white sand beach, easy parking and good facilities. Great for swimming and snorkeling, some hikes available.

Mauna Kea beach with white sand, a family beach good for sunbathing and snorkeling.

Punalu’u beach with black sand, It is easily accessible and great for swimming, seeing turtles, and snorkeling and Papakōlea with green sand, that is made out of lava from the volcano and crystals.

Another question that I get asked a lot is, when is the best time to go to Hawaii? Does Hawaii have a hurricane season?

Officially yes, Hawaii does have the same hurricane season that the Caribbean has, which is summertime into mid-fall. But but Hawaii hasn’t had a hurricane in almost 30 years, since 1992. And, considering that a Busy Atlantic Hurricane Season Predicted For 2020; Pacific Near Normal, I would look to visit Hawaii this year over Caribbean islands especially during the official hurricane season, June 1 marks the beginning of hurricane season, which will continue through November.

I promised an interactive family quiz at the beginning of the episode so gather your family, grab a bag of M&Ms and take a quiz to figure out which is the best island for your family!

To prepare for the quiz, put a bag of M&Ms into a big bowl, sit in a circle around the bowl and give an empty cup to each family member. Make sure you M&Ms have these colors – Orange, Green, Yellow and Blue.

If you don’t have M&Ms at home you can give each family member 4 markers of different color Orange, Green, Yellow and Blue and a piece of paper to mark their answers.

I will read the questions and give you multiple choices of answers. Each answer will correspond to a color which will correspond to a Hawaiian Island. You will find out which color belongs to which island at the end of the quiz. 

To answer questions either put the M&M of your color choice from the shared bowl of M&Ms into your cup or make a little mark on your paper with the marker of your color choice. 

At the end of the quiz, the color that predominates in your answers is the perfect Hawaiian island for your next trip.

 Quiz – 12 questions
  1. When you imagine Hawaii you are thinking of:
  • Romance (Orange)
  • Crowd free beaches (Green)
  • Nightlife (Yellow)
  • Volcanoes and Waterfalls (Blue)
  1. All the islands boast absolutely spectacular scenery and lush tropical vegetation. What one of the below would you hate to miss?
  •  Green is known as the Garden Island
  •  Yellow offers amazing vistas
  •  If you’re willing to take on Orange island’s twisting highways you’ll discover scenes that will stay with you forever.
  • The Blue Island offers unique contrasts – tropical forest and lava, desert and jungle, waterfalls and ranch lands. 


  1. If you love to hike, pick Green island. Hawaii has many exceptional hikes, but on the Green island many hiking trails will. present themselves without you doing any work. 


  1. If you love to snorkel pick Blue Island. The blue island tends to have the clearest water and offers the best snorkeling in Hawaii.


  1. If you would love to try your skills as the beginner surfer.– Green and Yellow islands are the best bets for beginner surfers.


  1. No island skimps on tourist activities, indeed there are many things to do in Hawaii.– helicopter rides, boat tours, luau and many more.
  • But Yellow islands infrastructure lends to some activities that are not found elsewhere.– museums, a zoo, aquariums, a water park and Pearl Harbor.
  • Green island is famous for Napali coast boat trips during the summer.
  • Orange island has the best whale watching boat trips during the winter
  • Blue Island has the best fishing and of course Volcanoes National Park.


  1. If you would like to go shopping while on vacation check out the Yellow island.


  1. If you want to see where they filmed Jurassic Park and 50 First Dates, check out the Yellow island.


  1. Hawaii has many world-class chefs and restaurants with several hotels noted for their exceptional dining.  If you are a foodie, visit Yellow and Orange islands
  1. Two islands are most likely to satisfy tourists interested in history – Yellow and the Blue Island.
  • Blue Island has several interesting landmarks that relate to the History of the Hawaiian people including the remains of old temples.
  • Yellow island features both ancient and contemporary Hawaiian history and has many landmarks relating to WWII.
  • Yellow island is also home to the Bishop Museum, Hawaii’s state museum of natural and cultural history.


  1. If you would like to have a large selection of luxury hotels for your vacation stay, the Orange island is the one for you.


12.  If you would like to have a large selection of budget hotels for your vacation stay then the Yellow island is the one for you.



Maui / Orange

Kauai / Green

Oahu / Yellow

Big Island / Blue

Hawaiian island

How many yellow islanders do we have? How many green, orange or blue?

The color that predominates in your answers is YOUR perfect Hawaiian island for your next trip. 

I would love to know which island WON in your family.

Go ahead to our Instagram page and comment with your island of choice under this episode’s post.

Thanks for listening! Don’t forget to subscribe to our podcast so you don’t miss the next episode. 

Are you planning your family vacation to Hawaii on your own?

Then you’re missing out on authentic experiences and our seamless execution of the most complex itineraries.

To plan a custom trip to Hawaii – book a time on Anna’s calendar here 

Additional Resources:

Sample itinerary for a trip to Hawaii

BLOG post – How to Pick the Right Hotel for Your Next Trip

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More about your host Anna

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