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How to Plan Your First Trip to Hawaii (with an expert!)

Vacation Mavens Travel Podcast

Release Date: 05/06/2025

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More Episodes

If Hawai'i is on your bucket list, you need to listen to this episode with Hawaii travel expert Marcie Cheung. Marcie is a family travel blogger and mom of two who's been to Hawaii more than 40 times, staying everywhere from luxury resorts to budget-friendly condos. She helps parents plan unforgettable Hawaii vacations with kids by sharing expert tips, honest reviews, and stress-free itineraries. You can learn more on her website hawaiitravelwithkids.com or follow Marcie on Facebook and Instagram. You can also listen to her podcast, Hawaii Travel Made Easy.

Episode Highlights:

  • The most popular tourist islands are: Oahu, Maui, Kauai, and Hawaii (The Big Island)
  • Oahu is best if you can only visit one island and are looking for a mix of experiences and attractions from Pearl Harbor to the Dole Plantation and also city life, nightlife and beaches on the North Shore or Waikiki
  • Maui is also popular for luxury resorts, a quieter vacation, the famous Road to Hana, and also great restaurants and activities
  • Kauai is even more laid back
  • The Big Island is good for those that are looking to be adventurous and take road trips, plus this is where you will find Volcanoes National Park
  • A first time visitor coming from the U.S. should look at least one week and spend it on Oahu because it has such a range of experiences. If you have two weeks, then you can island hop from Oahu to Maui or Kauai. Be active on Oahu and then relax on Maui or Kauai.
  • Keep in mind that when you island hop you still need to fly and deal with all of the airport security, rental car lines, etc. that eats up a lot of a day in travel.
  • The Big Island is really large and you need at least five to seven days. It takes several hours to drive from the beach area to the Hawaii Volcanoes National Park.
  • Expect to spend about $12,000 or more for a family vacation to Hawaii. Airfare from the West Coast is about $500 and closer to $900 from the East Coast. You can use a Southwest Companion Pass or Alaska Companion Pass if you have them.
  • Accommodations keep getting more and more expensive. Midrange hotels are $350-500 and luxury resorts can easily go over $1000 per night.
  • You need to beware about vacation rentals because they are being closely regulated in Honolulu and often they will be cancelled last minute as there are a lot of illegal vacation rentals. If you go with a vacation rental, go with something reputable.
  • Food is also expensive because so much needs to be shipped in on the islands. Plan on spending about $100 a day on food if you are able to mix up going to restaurants and buying groceries or eating at food trucks.
  • Rental car prices are high and you need a rental car for at least a few days on each island. Keep in mind that hotel parking can be $40-60 per night.
  • Activities are also quite pricey, at $300-500 per person. Luaus are at least $200-350 per person. Narrow down your wish list to 2-3 activities and have beach or pool days or exploring on your own for the rest of the time.
  • Minimum stays during winter break can be 7-14 days and this is the most expensive time to visit.
  • When planning road trips or hikes, be sure to map them out to see how far they are and how long it will take to get there.
  • Don't overpack your itinerary.

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