Welcome to your checklist

Knowing how much you have to work with will make a huge difference as you undergo your planning. I’ve seen plans as low as a couple thousand, and I’ve seen plans as high as tens of thousands. Your budget, even if it’s just an estimate or guess at this point will help guide your plans.

Your plans will change dramatically depending on who is going. If you have a romantic getaway for 2, a family trip, or a large group of friends. Each will have a wide difference in planning.

There are benefits and drawbacks depending on the season that you are going. You can’t go wrong here, but if you want to see whales, go between December and April, but you’ll be likely to get some rain (there are certain areas you can reduce this risk). If you want to avoid the crowds you can choose certain islands or avoid certain dates. Wondering about the weather? Check out our article Catch the Best Hawaiian Weather

We recommend no more than 1 island per 7 day period of your trip (you can easily spend more than this on each island).

Each island has areas where there are lots of people and with that, lots of things to do, as well as out of the way areas, with less to do. At this point you just need to have a general idea of where you’d like to spend the majority of your time on the island(s). There’s also places that are on the beach, ocean view, and up country. Beach locations will be more expensive.

I’ve seen flights as low as $298 round trip from California (through Alaska and United), and as high as several thousand. Your costs will depend on where you are coming from, when you are going, and at what point you buy your tickets. We recommend buying tickets about 1 1/2 to 2 months before you go. For now, at this point in your plans, we do not recommend purchasing your flight, but simply narrowing down your choices and getting an idea of what it will cost. Don’t forget about baggage fees, taxes, etc. as they can add quite a bit to your total.

Get information about Hawaiian Flights here.

We recommend that upon your arrival that you purchase a lei greeting. While it is an additional expense, it starts your vacation out right. You don’t want to be one of those arriving that is not greeted, you will feel left out. So put your lei greeting on your plans. They are normally about $25 per person but can go much higher if a more elaborate lei is desired.

See available Hawaiian Lei Packages here.

You’ll need to figure out where you want to stay while on vacation. You can rent a hotel room or condo for an average cost of about $200 a night, a little more for ocean views and on the beach. You can rent a home with services like HomeAway. You could even camp out if you’re very adventurous. If you have a larger group and want to all stay together we recommend renting a home, you can usually find a place for under $200 a night (per couple) depending on location. We have seen some luxury homes that are available for several thousand a night if you want to go all out, perhaps for a wedding.

You can check out our recommended hotels here

We personally recommend renting a car in Hawaii. While there are other options like public transportation if staying in Waikiki (and if you only plan on going to that beach and nothing else, this may be sufficient), most of the fun activities require getting around. Your options vary when considering rental cars. Depending upon the size of your group will determine what vehicle you want. If there are 4 or less people in your group, consider a convertible or jeep as a way to have a little more fun. You can even go all out and rent a luxury car like a Porsche or Lamborghini if your budget allows.

You can check out our recommended local car rental here

There are many options of what to eat in Hawaii.

While exploring the islands, you'll certainly need to refuel. As part of your trip planning, we highly recommend dining at local eateries to fully experience the best of Hawaii's culinary delights. Local dishes are not just meals; they're a journey through the rich tapestry of Hawaiian culture and flavors.

If local cuisine isn't on your palate or you're craving something familiar, don't worry – national chain restaurants are available on every island. However, to truly embrace the spirit of the islands, trying local food is a must.

We have created a list of many local Hawaiian restaurants for you to try.

At this point you should have most of the basics taken care of. This is where you’ll list all the things you want to do while on your vacation. The list of things to do vary widely by island, by athletic type, and by your desired vacation experience. Here’s a list of potential activities to get your started, but each island has their own unique things as well. It is not a complete list, but should be good to get you starting thinking about your plans.

The best activities sell out faster, so don't expect to reserve the best activities when you get there. If you don't have things booked you can still find things to do, but you will miss out on some of the best activities.

There are several apps that you might want to have with you on your trip. For travel guides consider the Gypsy Guides or the Shaka Guides.

Make sure you have reserved all the necessary steps: Flights, Hotel, Car, Activities

See above for details on each of these steps.

You don’t want to get down to the final days and realize that you need something from Amazon only to find it’ll take 2 weeks. Plan your packing list early so you can order any of the things necessary with plenty of time to spare.

I’ve been known to pack the night before, and in one case the morning of a trip, but this trip is supposed to be relaxing. Don’t put extra stress on yourself trying to remember if you have everything in the last minute. If you need to run to the store for something, it’s better done the day before.

We recommend taking a printed copy of your itinerary in addition to any digital copies you may have. You never know when you won’t have wifi. I lost it once when I was going through the airport security and my only boarding pass was still on my text and wouldn’t download. I’ve also had a time when I got into a cab and couldn’t access the address of the hotel I was going to. Avoid the stress and have it printed out in case you need it.

You’re done planning, now is the time to let the islands flow through you and fill you with peace. Go and have a great vacation knowing that you’ve planned it out well. Stay safe by checking out our article Staying Safe in Hawaii

Oh, and don’t forget to come back here and let us know how it went. What did you really like, did you have any problems along the way (we hope not)? Your experiences will help others along the way, and in turn theirs will help you the next time you go (is it already time to start planning our return trip?).