How Far in Advance Should You Plan a Hawaii Trip?

If you’re traveling to Hawaii for the first time, planning the trip can seem quite daunting–especially when you’re working with a limited budget. Some people like being spontaneous and doing things last minute, while others prefer to plan way ahead. But how early should you actually start planning?

It’s ideal to plan your Hawaii trip 6 to 12 months in advance for you to create an itinerary, book cheap flights, and reserve accommodations. Due to the volume of tourists, hotels can get fully booked a year ahead. Moreover, planning early is a great way to avail promos, discounts, and packages.

In the rest of this article, you will find a guide on how to plan a trip to Hawaii to make sure that you get to stretch your budget and make the most of your vacation.

How To Plan a Trip to Hawaii

Congratulations–you’re going on a vacation in Hawaii! Time to feel the sand between your toes, soak up the sun, and eat tons of seafood! But wait, before you get to enjoy this fantastic adventure, there’s one very important thing that you need to do: plan.

Most people get overwhelmed when planning a big trip like this, precisely because there are so many things to consider and arrange. If you’re feeling a bit overwhelmed already, don’t worry. Here are some tips on how you can plan your trip like a pro.

Reserve Your Accommodation 6 to 12 Months Ahead

The first thing to take care of when planning a Hawaii trip is the accommodation. Hotels and resorts tend to get fully booked up to a year ahead, which means that if you don’t book early, you may not be able to stay where you want.

There will still be places for you to stay, of course, but they may not be in prime locations or accessible in terms of transportation. The best time to book accommodations is 6 to 12 months ahead. If you already have a budget a year before your trip, go ahead and book your accommodation already!

Just like airfare, accommodation rates vary depending on the time of the year and the volume of tourists. Booking your accommodations a year in advance means you don’t have to worry about fluctuating rates or fully-booked hotels.

Do’s and Don’ts When Choosing Accommodations

However, other than reserving a place (or places) to stay early, there are other important considerations to keep in mind when choosing your accommodation. Here are some do’s and don’ts to bear in mind when looking for a hotel, resort, or Airbnb in Hawaii.

Do’s

Choose hotels or resorts within downtown areas. It might be tempting to choose accommodations that are quite remote (especially if you want a quiet place or are feeling adventurous), but doing so may only make things more challenging for you. A hotel within the downtown area is definitely more convenient in many aspects.
Check nearby transportation options. It’s not just the accommodation itself that you need to check, but also the availability of transportation options nearby. Are you close to the bus route? Are there taxis around? Does the hotel have partner transportation services or car rentals? These are questions that you should ask.
Check for nearby restaurants and shops. You can’t beat the convenience of having good restaurants and shops nearby when you want a quick bite or catch up on some shopping. Also, when you’re too tired from going hiking or swimming, you probably would prefer to eat somewhere close.

Research about security. A safe location is a good location. While Hawaii is a pretty safe place for tourists, there will always be spots that are better not visited, just like in other countries. Choose hotels or resorts that are in safe locations and that have security precautions in place. Like they say, better safe than sorry.
Learn hotel or resort regulations. You will also want to check the rules and regulations that are in place in your chosen hotel, such as check-in and out times, to make sure that they agree with your preferred schedule and activities.

Don’ts

Miss out on other resorts on other islands. It’s recommended to spend at least a week per island in Hawaii, so when reserving accommodations, don’t forget that you’re not supposed to stay in one place the entire time, or you will be missing out on a lot.

Stay in your hotel. By all means, book a nice hotel. Get a room with a nice view or that has an amazing pool. However, don’t make your hotel the place where you spend most of your time in. You’ll want to experience the amazing surroundings.

Avail of Travel Packages or Discounts 6 to 12 Months Ahead

Another great way to enjoy a hassle-free and more affordable Hawaiian vacation is to avail of a travel package or promos. You can find these from travel agencies like Expedia or TripAdvisor, as well as hotels and airlines.

Some hotels may offer travel packages that include roundtrip fares, while big international chains may have loyalty rewards or discounts that you can avail of. Don’t forget to check these out at least 6 to 12 months ahead of your desired travel schedule by going to their websites or calling their offices. Some discounts, such as those included in rewards programs, are seldom posted, so you might want to ask yourself.

Pros and Cons of Travel Packages

Travel companies are able to offer packages because they book or purchase in bulk, allowing them to cut significant costs and offering travelers like you the opportunity to access airfare, accommodations, tours, and more for a significantly lower price. Sounds perfect, right?

Well, they do have their pros and cons, and depending on the kind of experience that you like, investing in a travel package may or may not work for you. Here are the pros and cons of travel packages to help you weigh whether they’re the right choice.

Pros

Ready itinerary. Don’t like the nitty-gritty of planning? Or simply don’t know where to start with activities or where best to go? Then having a travel package is great for you. You will have a ready-made itinerary, and all you have to do is show up and have fun!

Pre-arranged activities. Hawaii can be overwhelming for a first-time traveler because there are just so many things that you can do and places that you can go. With a travel package, you’ll be able to visit some of the most popular tourist destinations.
Logistics are taken care of. No need to rent a car yourself or know where to ride a bus or how to get a taxi. Everything, including the logistics of your travel, will be taken care of for you.
Cheaper. This is the best choice for those who are looking to travel on a budget. You can explore and experience the best of Hawaii at a fraction of the cost of traveling on your own.

Safer for lone travelers. You will most likely be touring with a group, which means that if you’re traveling alone, you’ll have instant travel buddies when you choose a travel package.

Cons

Less flexibility. A ready-made itinerary is great if you don’t like planning, but it also makes for less flexibility. You won’t be able to change plans last minute, or you’ll miss out on the activities set for the day, for example.
You may mix with other groups. If you’re a family or a couple that wants to enjoy your vacation by yourselves and do as you please, you might not appreciate having to be around other people the entire time.

Activities may feel rushed. Pre-arranged activities follow a set timeline and schedule, which can mean that you may end up not being able to linger longer somewhere you really like, or having to finish things quickly so you don’t get behind schedule.

Create a Detailed Itinerary 3 to 4 Months Ahead

How Far in Advance Should You Plan a Hawaii Trip

If you’re planning to stay in Hawaii for two weeks or more (It’s recommended, by the way, to stay at least a week so that you can enjoy the different islands), you can’t underestimate the importance of a good itinerary.

It can spell the difference between a nightmare and a great time. Seriously. The better planned and the more detailed your itinerary is, the greater the chances that you’ll be able actually to have fun when you’re there.

How To Create the Best Travel Itinerary

To make sure that you don’t leave out anything, it’s best to create an itinerary 3 or four months ahead. This will give you ample time to make adjustments when necessary in a way that doesn’t affect your budget and other arrangements.

To create the best itinerary for you, here are some tips to bear in mind:

Plan daily activities. List your activities per day, including what time you expect to get started and finish. You don’t have to follow your schedule strictly, but having a guide will help you make the most of your vacation.
Be as detailed as possible. It’s better to have too many details than to leave out things that appear small but are important. So be as detailed as you can be: Include where you will eat, transportation choices, and more.
Prepare a Plan B. On any vacation, things don’t always go according to plan. So always come up with a Plan B for activities or places to go, so that you don’t waste time figuring out what to do instead.

Book Flights Two Months Ahead

If you’ve been saving up for this vacation, you probably already know that the flights make up a huge chunk of the vacation budget. That’s because traveling to Hawaii is never cheap. So if you’re planning a family vacation, you better get ready to pay the big bucks.

Round-trip plane tickets to Hawaii cost anywhere from $350 to $900, and that’s if you’re flying coach in the off-season. If you want to travel first-class or during the peak seasons, the costs could double.

Thankfully for the budget traveler, there are ways to book a flight without having to spend a thousand dollars on one ticket. And one of the most common (and easiest) to do so is to simply book flights early.

If you checked travel agencies for promos, discounts, and packages but have not found airfares that fit your budget, you might want to check airline websites about two months prior to your desired schedule. The best time to book to get really cheap flights is about two months ahead, or more or less 54 days.

In some cases, you may find cheaper flights earlier, and other times you will do so later. Still, the earlier you are able to check for the best flights, the better your chances of making your budget work.

You can even travel to Hawaii without booking a flight. It may be less common, but you can reduce your expenses. Learn how in my complete guide. [How to Travel to Hawaii Without Flying (Traveler’s Guide)]

How To Choose the Best Time to Go

When you decide to go to Hawaii is also a huge factor in how expensive your vacation will be and even how much fun you will have. Hawaii is a famous tourist destination, and while it’s great for the tourism industry it’s not quite as great for the tourists themselves who don’t know when to schedule their vacation.

Here are some tips on how to decide on the best time to go so (experience and budget-wise):

Go during the off-season. If you want to avoid very crowded streets and sky-high prices, you might want to go during the off-season. There are typically fewer tourists from April to June and from September to December.

Consider the weather. Hawaii is always sunny, even in the winter. However, it does experience a lot of rain, especially from November to March.
Avoid hurricane season. You definitely wouldn’t want to get caught in a huge storm during your vacation. To make sure that doesn’t happen, avoid scheduling your trip from June to November.
Don’t go on major holidays. Major holidays like Thanksgiving are also a no-no when scheduling your trip because Hawaii usually sees a huge influx of tourists around these dates. If you go on a holiday, you might end up wasting a lot of time in traffic or fail to enjoy some peace and quiet even on so-called secluded beaches.

Conclusion

Vacations are a major logistical and planning challenge. Often, what we think about when planning a vacation is the fun we’ll be having, and we forget that in order to have fun, there is a good amount of planning that needs to be done and done well.

I hope that this article has helped you plan your best vacation yet.

Sources

Women on the Road: The Pros and Cons of Package Tours: What Solo Travelers Should Know