All Fifty States Club

Hawaii Five 0 – Planning and Preparation

July 3, 2024



Although every state has its unique food, culture, and history - Hawaii is definitely one of a kind. As All Fifty Club President, I am excited to share the details of my family of 6 Hawaiian trip as we travelled to 3 islands in December 2023. This is Part 1 - Planning and Preparation.

Part 1 - Hawaii Planning and Preparation

Part 2 - Maui (2 nights)

Part 3 - Hawaii (4 nights)

Part 4 - Oahu (3 nights)

Part 5 - Completion of All 50 in Hawaii!

Part 6 - Hawaii Packing List



Planning and Preparation

Hawaii is often the last state for many travelers on their journey to all 50 states. In fact, Hawaii is the last state for over 25% of 50 staters. It is a GREAT state to go to last; it feels like the grand finale!

It is a big trip because of:

  • Planning – so many things to choose from
  • Time – it will likely be more than a quick trip
  • Cost – it is expensive (relative to other US travel)

Should this stop you?  No. Make the trip happen! As with planning any trip, there are ways to minimize cost and maximize the overall experience.

PLANNING - Don't plan like this will be your ONLY trip to Hawaii!

There is SO much to do in Hawaii. Regardless of what you do, you will experience Hawaii by just being there. Just landing at a Hawaiian airport will make you feel like you have arrived in another country, not another U.S. state. If you are like me and read EVERYTHING you can about a destination, you will be quickly overwhelmed. You will have to make choices, it just isn't possible to do all that Hawaii has to offer in one trip - no matter how long the trip is. Select a few must-do activities or places and work what else you can around it. Get in what you can, then later hope you can go back!


Hawaii trip planning can be time-consuming and overwhelming. Even if you don't typically use a travel agent, Hawaii may be the trip to use one! Most agents have relationships with Hawaiian resorts, but some charge a flat planning rate and book at Airbnbs.


Again, figure out what your "must-do" activity is. For us, it was visiting Hawaii Volcanoes National Park on the Big Island, so going to the Big Island was built into the itinerary first. We visited three islands - Maui, Hawaii, and Oahu and loved them all. It was ambitious to go to three islands for a 10-day trip; Two would be preferable, and definitely not four unless you have more time. Even though flights are short between islands, the time adds up with getting to the airport, renting another vehicle, grocery shopping etc. Each island transfer will require at least 5 hours.


Flights to Hawaii are about 5 ½ hours from Los Angeles, so it is already almost a full day, even if you don't have a connecting flight.  Our total trip was 10 days, but it was really only 8 Hawaii days since two days were travel days there and back.  2 nights in Maui, 4 nights in Hawaii, and 3 nights in Oahu. This is significantly under the recommended time of 4-5 nights on each island.


When you can go! Our family traveled to Hawaii at the peak time of the year – December, right before Christmas due to our work and school schedules. Sometimes you have to travel when you are able to travel! We were still able to get a deal on flights, but lower-cost accommodations were more challenging to come by. March through September is generally the best for weather and early spring and fall for best pricing.


Hawaiian Airlines is the best if the flights are comparable to other airlines, because you are going to Hawaii!  The flight attendants set the mood with an "Aloha" as you step on the plane. There is Hawaiian-focused online entertainment, a Hawaiian meal choice, and pineapple juice for mid-flight drinks.

Use Google Flights and the Hopper App to find the best flights.  Search for each leg separately, as there is rarely a better round-trip price. This will give you flexibility to pick the best cost and timing for each leg and SO much less confusing should you decide to change a leg. Once you find the best flight, book directly with the airline. Always keep in mind baggage charges. For our last leg, we flew Southwest, which enabled us to check a bag of souvenirs. Do the main legs first, then the interisland. There are many interisland flight options with Southwest Airlines and Hawaiian Airlines, and neither have change fees.

For example, here are some deals we found

LAX to Maui (American, $99)

Maui to Big Island (Southwest, $54 or 2.930)

Big Island to Oahu  (Southwest, $49 or 2,930 points)

Oahu to Phoenix (Hawaiian, $150)

Get a Hawaiian Airlines credit card at least four months before your trip. Keep your eye out for the promotion that will give you the most bonus miles at sign-up. This will give you enough time to meet any minimum spending thresholds to get the maximum bonus miles. You could get almost all of your flights covered and no checked bags fees.

Get a Capital One Venture X credit card. Again, look for a sign-up promotion to give you the most bonus points.  A perk with this card is Priority Pass airport lounge access for two people. On our trip, Honolulu was the only airport with an eligible club. The lounges I have been to have been pretty busy, but free drinks and snacks are great!  A more significant benefit to Capital One is booking hotels and rental cars through Capital One Travel. You earn more points for money spent. You also can earn or redeem points for AirBnb and Turo.  It is easy to purchase a credit card, but after signing into your account, the purchases are flagged as a travel purchase, which you can select to pay with points. Considering I don't like complicated point schemes, this ended up great. I should have listened to the commercials a long time ago. However, my timing was perfect for using miles for this trip!

Unique Lodging

Many beautiful resorts in Hawaii will go beyond all your needs. Refer to other trusted travelers or a travel agent for their recommendations. We prefer to stay in unique, budget places as we travel. I say "budget," but sometimes the unique can be more expensive. Google unique lodging in Hawaii, unique airbnb or vrbo Hawaii and see what comes up!

Airbnb pro - kitchen, laundry
Airbnb con: condo clean-up. Although we try to leave any place clean, Airbnb hosts have a higher expectation of how the property is left. Six people going to the beach are going to track in some sand.

Maui—We prioritized an Airbnb with an ocean view since it was the beginning of whale season. Although we were prepared with binoculars, we didn't see any whales but other sea life!

Big Island—We wanted to visit different parts of the island, so we stayed at three different places for four nights! We spent two nights in a rainforest on the island's east side near Hilo, one night on volcanic rock near Volcanoes National Park, and one night at a Hostel in Kona.

Oahu—affordable was very hard to find in December! We stayed at a condo with a great location near Waikiki/Diamondhead. The building was pretty dated, and there were no resort amenities, but the condo was clean and convenient, and come-and-go parking was free.

Please don't kill yourself by looking for different options. Pick one and go with it. Ultimately, it is a place to lay your head, and you will spend your waking hours exploring Hawaii!

Rental Car

Rental Car rates for the same time and place vary widely, so always check multiple sources such as Expedia, Hopper, Costco Travel, Turo, and Capital One Travel. On this trip I found the best rates with Costco Travel and Turo.

Typical rental car company pro - they have an extensive fleet, they can adjust easier, and you can return the car as-is (within reason).

Typical rental car company con - you interact with company employees; with Turo, you interact with a local, and the cost is typically less.

What to do first?

Set aside a few hours to do some research and be ready to book immediately. If you see a good deal on a flight from the mainland to Hawaii, you should take it. Most airlines allow you to cancel within 24 hours of booking, so you will be able to cancel should lodging or other plans not fall into place.  Always attempt to book refundable lodging - at least until you get the details of your trip worked out. Same for rental cars, only book refundable. Costco Travel is usually refundable. On Turo, you have to read each rental's specific cancellation policy. Take a deep breath! In the end, you will have a dream vacation!


Pick your must-do experiences then work everything else around them.

Night snorkeling with the Manta Rays (Big Island)  (I found a deal on Groupon)

Whale Watching (Maui, but on other islands, winter is best)


Surf Lessons

Pearl Harbor through NPS,

Diamon Head  through Hawaii Sates Parks




Finalize your overall itinerary, then fill in the gaps as you go.

Day 1 – Flight from Nashville to LAX, LAX to Maui

Day 2 – Explore northern Maui, Haleakala Crater for sunset

Day 3 – Service project in Lahaina, Maui, flight to Big Island

Day 4 – Explore Waterfalls, Hilo, beach, snorkeling, sea turtles

Day 5 – Explore Airbnb chocolate farm/waterfall property, Waimo Valley lookout, Waimea, Hakuna Beach, Saddleback Road, Lava Temple, Uncle Robert’s

Day 6 – Volcanoes National Park, South Point, Coffee, Captain Cook, Manta Rays

Day 7 – Breakfast in Kona, flight to Oahu, Pearl Harbor, fireworks on Waikiki

Day 8 – Pick up surf boards, Dole Pineapple Plantation, Haleiwa Beach Park, Dinner at Food trucks North Shore

Day 9 – Hike Diamond Head, Leonard’s Bakery, Waikiki Beach, Rent paddle board, Christmas Eve service on the beach

Day 10 – Drive by State Capitol, Iolani Palace, Fly back to the USA



I'll be honest, I don't like dealing with insurance and never purchased any for US trips. We have AAA to cover for tow services for road trips across the country. Although we only used it a few times in 20 years, it was reassuring to know we had options. However, Hawaii is different. Yes there are medical services on the Island, but for a serious, long-term situation you are going to want to be back at home. We opted to purchase an annual travel insurance policy with Allianz Global Assistance for the family since we travel frequently. Purchasing travel insurance just for your Hawaii trip is also an option. Policies provide rental insurance coverage, so along with Capital One X rental car insurance no additional insurance is needed. The policy covers basic adventures - snorkeling, hiking, skiing, etc. It is an added cost, but if something should arise it will have saved you alot of stress and money.

Get Excited!

One of the blessings of planning a big trip in advance is the build up!

  • Movies - Watch Blue Hawaii with Elvis, Lilo and Stitch, Moana
  • Books - Read Hawaii by John Mitchner (this is a LONG book, has great reviews)
  • Podcasts - Listen or watch Haole we do it

I like to countdown before a trip and share interesting facts about whereever we are going. For our family I post destination trviia on a group text thread.

Trip Countdown Hawaii trivia and tips

30 days  Hawaii Beach picture

20  days Hawaii has 137 islands, but 6 main ones.  We are going to Maui, Oahu, Hawaii aka The Big Island.

16 days Hawaii didn't become a state until 1959.  The grandparents were around 16

14 days  The Hawaiian flag was designed in 1816 and uses the same colors as UK, USA Frankce and the Hawaiian gods - makes everyone happy.

12 days -  Hawaiian city names can be confusing because they are almost the same Kohala Kohuna, Holoa - come to find out the Hawaiian language only has 13 letters!

10 days - Download the airline apps and make sure you can log-in so getting free wi-fi on the plane will go smoother

9 days - Weather update............

8 days -  Get ready for Hawaiian food -  loco moco, siamen, poke, bbq, shaved ice, macadamia nuts, luau stew, and malasadas.

7 days - Name the 2 native land mammals on Hawaii. Hawaiian Hoary Bat and Hawaiian Monk seal.  One non-native, the mongoose brought to Hawaii to get rid of rats in the sugar fields.

6 days - Hawaii was once governed by a monoarchy - with a King and/or Queen until 1893. The capital of Hawaii is in Honolulu very close to the Iolani Palace which used to be the royal residence.

5 days - Pack your bags.  Here is your Hawaiian Trip Packing List. 

4 days - Lodging info - This is where we are staying!

3 - Weather update

2-  Volcano status

1 - Boarding Pass/Flight Confirmation of First leg of the trip




There are a few extra items to bring along to Hawaii that may not be on your regular packing list.  Waterproof backpack, Swimshoes, Binoculars, and a Full-face snorkel mask.

For a detailed packing list check out the blog post, Hawaii 5-0 Packing List




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