How to Plan a Trip to Hawaii: A Simple Guide to Get Started

Dreaming of a Hawaiian getaway but not sure where to begin? You’re not alone. Planning a trip to Hawaii can feel overwhelming – with multiple islands, endless resort options, and so many “can’t-miss” experiences. But don’t worry. I’m breaking it down step-by-step so you know exactly where to start and how to make it all come together.

Step 1: Choose Your Island (Or Two—But No More!)

The very first decision to make when planning a Hawaii vacation is which island to visit. Each island has its own personality and highlights, and choosing the right one is key to setting the tone for your trip.

• Oʻahu offers iconic sights like Waikiki Beach and Pearl Harbor, along with a bustling city-meets-surf vibe.
• Maui is known for luxury resorts, scenic drives (hello, Road to Hāna), and incredible whale watching in winter.
• Kauaʻi is lush, quiet, and a dream for nature lovers.
• The Big Island is full of adventure with its active volcano, black sand beaches, and stargazing.

I usually recommend sticking to one island unless you have at least 8 days to travel. In that case, two islands can work beautifully—just be sure to spend a minimum of four nights on each to make the most of it.

👉🏼 Which Hawaiian Island Should You Visit? Read more here: https://wheretogotravelco.com/2024/11/21/which-hawaiian-island-is-right-for-you/

Step 2: Choose Your Travel Dates (and Be Smart About Timing)

Once you’ve picked your island(s), it’s time to think about when to go. Hawaii is beautiful year-round, but there are a few things to keep in mind:

• Peak Season: Mid-December through March and June through August. Expect higher prices and more crowds.
• Shoulder Season: April–May and September–mid-November are ideal—fewer crowds, better rates, and still amazing weather.
• Winter Travel Tip: If you’re heading to Hawaii in the winter months, Maui is the place to go for whale watching (prime season is January–March).

Step 3: Work with a Travel Advisor Who Specializes in Hawaii

Here’s where things get much easier, and a lot more fun.

The next big step is choosing your accommodations, which will likely be the largest part of your trip budget. This is not the time to go down a rabbit hole of online reviews and second-guessing. This is the time to work with a Travel Advisor who knows Hawaii (hi, that’s me!).

Travel Advisors like myself travel to Hawaii often. We tour the resorts, meet with the hotel staff, stay on-site, and eat at the restaurants. We know which resorts are great for couples, which are perfect for families, and which ones to avoid if you’re not a fan of crowded pools or dated rooms.

My goal? Match you with a resort that fits your style, your needs, and your dream vacation vision.

Step 4: Plan and Pre-Book Your Must-Do Activities

Once you’ve nailed down your flights and resort, it’s time to think about how you want to spend your time in paradise.

This part takes more planning than many people realize. Here’s why:

• The best tours—like sunrise at Haleakalā or snorkeling at Molokini—sell out months in advance.
• Popular parks require timed-entry reservations, and those spots can disappear quickly.
• Even restaurants in high-demand areas book up far ahead of time.

A Hawaii specialist (like me) can help you plan and reserve your top picks in advance—before they’re gone. And yes, I make those reservations for you as part of our concierge service.

Step 5: Fill in the Gaps with Self-Guided Sightseeing + Downtime

With the essentials locked in—flights, resort, activities, dining—it’s time to think about the in-between moments. I love helping clients build in just enough to make their days exciting, without feeling overscheduled.

We’ll fill in your itinerary with scenic drives, beach hopping, short hikes, and other self-guided suggestions. And yes, we’ll carve out time for poolside cocktails and lazy beach mornings, too.

You Don’t Have to Plan It All Alone

Planning a trip to Hawaii should be exciting, not overwhelming. At Where To Go Travel Co, my goal is to make your dream vacation as seamless and stress-free as possible, from start to finish.

Whether you’re traveling as a couple, with kids in tow, or with extended family, I’ll help you choose the right island, resort, and experiences so you can focus on making memories—not logistics.

✨ Ready to start planning your Hawaii getaway?

Tell me a little about your trip, and I’ll take it from there.

Want help choosing an island? Download our Hawaii Planning Guide below to view the top attractions on each island.