Hawaii Travel Guide: Planning a Trip to Hawaii? Start Here

Hawaii sits at the top of nearly every traveler’s vacation dream board, and once you’ve experienced it, it’s easy to understand why. From beaches framed by volcanic rock to lush valleys, cascading waterfalls, and warm, impossibly clear water, each island offers something entirely its own. But that’s also what makes planning a trip to Hawaii feel more complex than expected. With multiple islands to choose from, each with a distinct personality, the key isn’t just going to Hawaii, but choosing the right islands and experiences for the kind of vacation you truly want.

In this guide, I’ll walk you through how to think about planning your Hawaii trip, from when to visit and how to get there, to which islands are the best fit for your travel style, and what not to miss once you arrive. After eight visits to the islands and ongoing relationships with top resorts and local partners, I bring both firsthand experience and on-the-ground insight to help you plan a trip that feels seamless, personalized, and exceptionally well done.

Getting to Hawaii: Flights, Routes, and What to Expect

Before we get into the details of each island, let's talk about how to survive that flight to Traveling to Hawaii from the Midwest or East Coast is a long journey—typically 9+ hours from cities like Chicago and 11+ hours from the East Coast. Flights to Kaua‘i tend to be even longer with fewer nonstop options, as it’s the furthest and least developed island.

Expect airfare to start around $1,000 per person, though booking early and avoiding peak travel seasons can help reduce costs.

Each island has its own airport:

• Maui (OGG)

• Kaua‘i (LIH)

• O‘ahu (HNL)

• Big Island (KOA, with a smaller option in Hilo – ITO)

  
  

If you’re visiting multiple islands, booking a “multi-city” itinerary is often the most efficient and cost-effective option. Compare routes to determine the best order of islands based on price and flight timing.

When choosing flights:

• Prioritize shorter travel times and minimal layovers

• On the way to Hawaii, choose routes that take you as far west as possible first

• On the return, overnight flights are common, helping you maximize your last day and sleep on the journey home

For late departures, consider booking a hotel day pass for a place to relax, shower, and recharge before your flight.

Getting between islands is easy, with frequent, affordable nonstop flights (typically $60–$80) on Hawaiian Airlines or Southwest.

When Is the Best Time to Visit Hawaii?

Hawaii is a year-round destination with sunshine and summer temperatures no matter when you visit. However, prices and rainfall vary by season. Let's talk price first.

Price point

Just like anywhere tropical, winter is high season in Hawaii, with Christmas break or Festive as the peak of the high season. Prices over Christmas can be 2-3 times the norm. Booking 9-12 months out will give you the best price and availability. In addition, other school breaks in the winter, like President's Day week and Spring Break, price high as well.

Hawaii doesn't have an off season, but you can secure better pricing outside of school breaks - September and May are typically the best months price-wise.

Weather

Hawaii offers warm temperatures and sun year-round, but you will find more rain and wind in the winter months. Typically, rain showers are brief, but some islands (like Kaua'i) and some areas of the islands (north and east windward sides) see more rainfall overall. Think about it this way: Hawaii's lushness is part of its beauty. You need rain to make all that green! You also need rain for Hawaii's famous rainbows!

Which Hawaiian Island Is Right for You?

Read on for a dive into all that each island has to offer. Choose from:

• The variety and beauty of Maui’s miles of swimmable beaches, lush green valleys, rainforests, and waterfalls

• The dramatic yet peaceful natural beauty of Kaua'i, the movie star of Hawaii

• The energy, nightlife, history, and culture of O'ahu

• The diversity, power, and size of Hawaii or the Big Island, and the home of the largest active volcano on our planet

Maui: Best for Swimmable Beaches, Culinary, and Luxury

Each island is special, but Maui is my favorite. It has the best of everything Hawaii has to offer - beautiful beaches (the most miles of swimmable beaches in Hawaii), calm and warm waters for watersports and whale watching, lush valleys and rainforests, volcanic landscapes, rich culture, and culinary delights - all packaged into a sophisticated tropical paradise with down-home appeal. The island is easy to navigate and offers plenty of resorts to choose from. Contrast that with Oahu's Vegas vibe in Waikiki, Kauai's limited roads and resorts, and the Big Island's scale and drive times, and you'll appreciate Maui's "just right" size and development. That’s why most first-time visitors to Hawaii have Maui at the top of their list. And it’s why Show Them the World’s #1 destination is Maui! 

My first trip to Maui was with my husband and 6-month-old baby. We stayed in budget-friendly Kihei (south Maui) at the Mana Kai Maui and took Brady with us everywhere! We even traveled the Road to Hana with him, pulling over at the easy stops like the black sand beach and blowholes. I remember Brady squealing with delight when the blowholes would blow! I also remember him screaming like crazy on the ride home from Hana because he had suddenly decided breastfeeding was not enough for him, and we made a frantic pit stop for baby food. We also took a trip to the Iao Valley where the scenery is breathtakingly beautiful. Beyond that, it was mostly beach, pool, repeat for us, but we were all happy to be lazy and enjoy the views.

Since that first trip back in 2008, I've become a Maui expert, with stays in Wailea and Ka'anapali and tours of all the best resorts. Baby Brady is now all grown up and has been to Maui multiple times as well as to O'ahu, Kaua'i (twice!), and the Big Island. Maui is still his favorite.

Snorkeling excursion to Lana'i, surf lessons, and outrigger canoe.

Where to Stay on Maui

Best Activities on Maui

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Kaua‘i: Best for Lush Landscapes, and a Slower Pace

The lush tropical paradise of Kaua'i is what most people dream of when they think of Hawaii, because it’s the landscape most featured in iconic movies like Jurassic Park, Avatar, Soul Surfer, and Raiders of the Lost Ark. With four trips to Kaua'i, this island holds a close second to Maui for me because of its jaw-dropping natural beauty, relaxed pace, and small-town charm. The only reason Kaua'i isn’t my top recommendation for visitors is because it’s not as easy to navigate as Maui given that 80% of the island is only accessible by water, air, or on foot. But I love that about Kaua'i, because it challenges you to be adventurous.

On my first trip to Hawaii in 2000, my childhood friend and I kayaked the Na Pali Coast – 17 miles of open ocean, majestic cliffs, and sea caves to explore. Other than the Chicago marathon and childbirth, it was the most physical activity I’ve done in my life - but it certainly was more fun than the other two! We also toured the island by helicopter, saw the red canyons of Waimea, bought a coconut on the side of the road on the way to Opaeka’a Falls, and hung out in Hanalei Bay where we stayed in a B&B. On our last day, we hiked the first two miles of the Na Pali coast. (The rest of the 11-mile hike is for experienced backpackers and requires a permit). On the hike back to our car, I decided to speed ahead of my friend to get more of a workout. I must have been entranced by the view, because next thing I knew, I was sliding off a cliff on my bum. Luckily, another hiker saw me go over and pulled me up to the path before I could slide too far. The lesson here is to watch where you’re going and stop when admiring the view, because falling off a cliff is a real thing here!

I visited Kaua'i a second time on our babymoon, so I wasn’t quite as adventurous that go around. We stayed at the Princeville Resort (now it's 1 Hotel Hanalei Bay and still just as amazing), and we hiked the Na Pali coast again. Luckily, I did not fall down the cliff this time!

We took the kids in 2023 and stayed on the south shore for the first time and did all the adventures. Mountain tubing was a hit! I didn't get my fill of the north shore, though, so we came back in 2025 and stayed at the spectacular 1 Hotel Hanalei Bay.

Top: 2023 mountain tubing and ATV

Middle and bottom: 2025 1 Hotel Hanalei Bay, doors-off helicopter, shelter dog field trip

Learn About Kauai

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O‘ahu: Best for History, Dining, and Shopping

O'ahu offers big-city fun in a small island setting. As the most populated and most developed Hawaiian island, O'ahu has many iconic Hawaii activities in a compact area, making it ideal for first-timers. If you want to be in the heart of it all, stay in Waikiki Beach, two miles of oceanfront resorts, restaurants, nightlife, and shopping. Accommodations are plentiful, but if you want quintessential Hawaii, The Royal Hawaiian and the Moana Surfrider are the two most historic Waikiki resorts. If crowds are not your thing and you’d prefer a more island experience, try the Ko’Olina coast or North Shore.

On my first trip to Hawaii with a childhood friend, we stayed in Waikiki at the Hilton Hawaiian Village and on the North Shore, which allowed us to experience the best of both worlds in O'ahu. We thoroughly enjoyed the waters of Waikiki, strolled the promenade, and partied as late as we could at Duke’s - which was not late at all given the six-hour time change. On our way out of the city, we snorkeled Hanauma Bay (reserve a permit!) and explored quieter beaches like Lanikai, Kailua, and Waimea Bay (my favorite!). We spent the afternoon at Waimea Falls Park enjoying its botanical gardens, waterfalls, and peacocks before heading to see a friend who lived on the North Shore with her kite-surfing champion boyfriend. What luck getting to experience surf culture and quaint Hale’iwa town firsthand!

Waikiki Beach, Waimea Falls, Waimea Bay

Ten years later on my second visit to O'ahu, my husband and I took our 2½-year-old and stayed on the North Shore at the Turtle Bay Resort, which is now a Ritz-Carlton property. Normally, I would say visit more than one island or location, but when you’re traveling with a baby or toddler, it’s easiest to stay put! We explored the North Shore, including a luau at the Polynesian Cultural Center. We drove down toward Waikiki, stopping at Waimea Falls and Diamond Head where Brady rode piggyback up the trail. But most of our vacation was spent entertaining a toddler, and all he really cared about was the beach, pool, and playgrounds.

Most of my clients want to experience Pearl Harbor but prefer to spend most of their vacation on one of the other Hawaiian islands because of the busyness and city feel of Honolulu. I suggest two ways of doing Pearl Harbor:

1. On the day clients are heading home - If clients are visiting Maui, for example, they fly to O'ahu early morning on their departure day. They spend the day seeing Pearl Harbor and checking out Waikiki. Then they fly home that night from O'ahu.

2. Spend three days on O'ahu - In those three days, you can do Pearl Harbor, experience Waikiki, and tour the island. If clients choose not to overnight on O'ahu, then I have them fly from whatever island they're visiting to O'ahu early morning of their departure day.

Ko'Olina Coast, Pearl Harbor, Hanauma Bay

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The Big Island (Hawai‘i Island): Best for Adventure & Diverse Landscapes

The Big Island is just that – big – bigger than all the other islands of Hawaii combined. With the most ecologically diverse landscape – multi-colored beaches, lush rainforests, waterfalls, lava fields and a very active volcano, plus a snow-topped mountain – the Big Island has a lot to offer! Be prepared for A LOT of driving if you want to see it all.

The west side of the island (Kona, Waikoloa, Kohala coast) offers luxury resorts and the best beaches, weather, and nightlife, so you'll want to spend most of your time on this side. However, Hawaii Volcanoes National Park and the natural beauty on the east side are not to be missed. If you want to stay put on the Kona side, plan on a full 12-hour day of driving to circle the island and see most of the top spots. Or you can spend a night or two near the volcano.

I visited the Big Island on our Babymoon when I wasn’t feeling so hot. With all the driving required to see the sights, plus a helicopter tour and the fumes from the volcano, I don’t have the best memories from this part of our trip.

2007 trip: Hawaii Volcanoes National Park, helicopter tour, Lava Tube

My husband and I went back in 2024 on an invite from Fairmont Orchid for their Rediscover Hawaii Experience, and I now have a new appreciation for the lunar landscapes and the peaceful vibe of this lovely island. With all that space, the resorts have plenty of room to spread out, so nothing feels crowded or touristy.

Even though we were only there for two nights, we checked swimming with manta rays off our list, an extraordinary experience you must do! You don a mask and snorkel and lie face down in the water, holding onto a lighted float. The manta rays swim up to the lights to feed on plankton. They came close to us, doing barrel rolls right by our faces. You could hear everyone squealing through their snorkels!

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We loved the Big Island so much that we brought the kids in 2025 for their first visit. We rented a pool cabana our first day to recover from jet lag, enjoyed the Fairmont's cove beach, and experienced the manta rays with the kids - this time from the beach, a much more intimate experience vs. the boat option we did last time! While the boys golfed, I toured the top resorts (new blog story coming soon!), and we did an island tour, including the volcano. When it comes to the volcano, I suggest keeping your plans flexible and only doing that long drive if there's active lava flow. Otherwise, it's just a big rocky crater.

How to Plan the Perfect Hawaii Itinerary

With so many islands, resorts, and experiences to choose from, planning a trip to Hawaii can quickly become more complex than expected. The difference between a good trip and an exceptional one often comes down to choosing the right islands, the right accommodations, and a thoughtfully-paced itinerary.

As a certified Hawaii Destination Specialist who has visited the islands multiple times, I bring both firsthand experience and trusted local relationships to every itinerary I design. I spend time on the ground touring top resorts and experiencing excursions, so I can offer guidance that goes well beyond what you’ll find online.

If you’re starting to think about a trip to Hawaii and want it to feel seamless, personalized, and truly well-planned, I’d love to help you design an itinerary tailored specifically to your family and travel style. Schedule a call to get started.

Schedule a Call

If you’d prefer to learn more about how I work before scheduling, you can explore my Start Planning page.

Hawaii FAQs

Which Hawaiian island is best for my trip?

Each island offers a completely different experience. Maui is ideal for beaches and luxury, Kaua‘i for lush scenery and a slower pace, O‘ahu for nightlife and culture, and the Big Island for diverse landscapes and volcanoes. The best choice depends on your travel style and priorities.

How many days do I need in Hawaii?

At minimum, plan for 7 days. If you want to visit multiple islands, 10–14 days is ideal to avoid feeling rushed and allow time to adjust to the long travel distance.

Should I visit more than one island?

If you have a week, it’s best to stay on one island. For longer trips, you can visit two islands, but careful planning is important to maximize your time and minimize travel days.

When is the best time to visit Hawaii?

Hawaii is considered an expensive destination. Flights alone can start around $1,000 per person, and overall trip costs vary based on accommodations, activities, and travel style. Planning ahead can help manage costs.

What makes Hawaii special compared to other beach destinations?

Hawaii offers more than just beaches - you’ll find volcanoes, waterfalls, rainforests, rich culture, and a wide range of activities like snorkeling, hiking, and surfing all in one destination.

Explore Hawaii

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Heather Vergara is a former PepsiCo marketing executive who left the corporate world to be a Mom and never found her way back. Instead, she focused on her passion for travel and adventure and created Show Them the World, a travel concierge service for busy families longing to reconnect and see the world together. She's now a Top Producer and Multi-Million Dollar Advisor with Gifted Travel Network, a boutique luxury host agency partnered with Virtuoso. Heather has helped hundreds of families experience Hawaii, Alaska, Costa Rica, the Caribbean, Italy, France, Greece, England, Ireland, Croatia, Spain, Portugal, Switzerland, Iceland, Africa, Australia, New Zealand, the Maldives, National Parks, and more to come!

Heather has an MBA in marketing from Indiana University, a Digital Marketing Executive Education certificate from Columbia University, and a BA in Journalism from the University of North Carolina at Chapel Hill. She lives with her husband, two kids, and two furry dogs in Zionsville, Indiana.