Family Travel Guide to Hawaii

Hawaii is Paradise

We’ve traveled to Hawaii a number of times as a couple and family and are sharing our guides to the islands of Maui, Kauai & Oahu in a series of separate posts for your family vacation to Hawaii! Read on for our general Hawaii tips and about the islands below.

We first went to Hawaii during Christmas and New Years before we had kids. Unfortunately, it poured during our stays at Kauai and Maui. Almost 5 years later, we returned to Maui in the springtime with our two toddlers, my parents and sister and fell in love with Maui. We celebrated our 10th anniversary in the fall at the St. Regis in Princeville where it rained a lot. A few years later we celebrated a big birthday in Kauai at the Grand Hyatt with our three kids. We ventured to Oahu a few years later and stayed at the Royal Hawaiian for an anniversary trip. We wanted the kids to experience Pearl Harbor on Oahu and spent spring break 2017 on Oahu and Maui. Most recently, we enjoyed spring break 2019 on Maui and Kauai. Can you tell that we love Hawaii and are excited to share our tips for your family vacation to Hawaii!

The Good and the Bad about Hawaii

Hawaii is without a doubt my favorite family vacation destination.  We love the sheer natural beauty and spectacular waterfalls, the abundance of activities, the gorgeous hotels, all of the beautiful beaches, the friendly people, and that its part of the U.S. (no passport, US dollar). 

The only cons are the distance and expense. If you’re lucky enough to book a direct flight, go for it! A direct flight from Chicago to Maui is just under 10 hours and you’ll need to factor in the time difference which is 5 hours from Chicago. Everything in Hawaii is expensive — but hey, it’s an island in the middle of the Pacific Ocean! Read on for our tips to get the biggest bang for your buck!

General Tips for Your Family Vacation to Hawaii

• Consider redeeming your airline miles and hotel points for a Hawaii vacation to defray the costs.  When is a good value to use your points?  IF you can find a saver ticket (valued at 45,000 miles) and the roundtrip cost is greater than $630, then use those miles!  At the time of this post, thanks to The Points Guy, a United mile has a cash value of $.014, so if the cost of a roundtrip ticket is more than $630, redeem those miles ($.014 * 45,000 miles = $630).  Click here for our tips on earning airline and travel points. Hawaii is also a great value to redeem hotel points. According to The Points Guy, the value of a Marriott Bonvoy point is .08 and Hawaiian value is usually higher than this (even with the category changes)
• Recommend at least a week vacation as the flights are far and you may need time to adjust to the time zone difference (-5 hours from Chicago) and there’s just so much to do and see (and that includes relaxing on the beach).  Suggest spending 2-3 days on one island to acclimate to the time zone, visit the “musts” for the island and then soak in the aloha on the 2^nd island for the duration of your vacation.
• Shop at the grocery stores (Target, Costco, Walmart) on the islands for snacks, breakfast and lunch food to defray the costs.  Many of these stores are near the airports, so consider stopping on your way to your hotel/condo.
• PLAN ahead! There are some phenomenal restaurants that you’ll want to eat at as the sun is setting (and so does everyone else) so make reservations.  Check out our island posts for the restaurants NOT to be missed.

Our Guide to the Islands

• Maui: “Valley Isle” and has been voted the Best Island in the U.S. for 20 years by Conde Nast.  The island is home to some of the most famous beaches, migrating humpback whales and the infamous Road to Hana (a must!). 
• Kauai: “Garden Island” that has so much natural beauty with amazing waterfalls, jagged cliffs, tropical rainforests.  Some parts of Kauai are only accessible by sea or air.  The Waimea Canyon and Napali coast are both in Kauai.      A lot of movies (i.e. Jurassic World, The Descendants) were filmed in Kauai). 
• Oahu: “Heart of Hawaii” is where you’ll find Honolulu, Capital of Hawaii and the famous Waikiki Beach (and lots of shopping).  Pearl Harbor and Diamond Head are both on Waikiki. 
• Big Island (aka the Island of Hawaii):  Nearly twice as big as all of the other islands combined, hence its name as the BIG Island.  Hawaii’s Volcanoes National Park and a black sand beach are in the Big Island.  While we haven’t been to the Big Island, it seems to have the most moderate climate.  Family Galavant has not yet been to the Big Island. 
• Lanai:  Luxury and rugged nature blend on this enticing island”.  It’s the smallest inhabited Hawaiian island and only nine miles from Maui.  The Four Seasons and award-winning golf course are home to Lanai.  Family Galavant has not been to Lanai.
• Molokai: “Remains true to its roots” meaning that much of its population are Native Hawaiian ancestry who continue to preserve their rural lifestyle.  There is not a major resort on Molokai, which many people love.  Family Galavant has not been here.

If you have dreamed about a family vacation to Hawaii, read on!

Happy Travels

Bridget, Family Galavant

This family travel guide to Hawaii is part of our Hawaii posts. Be sure to check out our family travel guides to Maui, Kauai and Oahu for your next vacation to Hawaii!