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

The Islands of Hawaii are on everyone’s vacation dream board for good reason – miles of picture-perfect beaches framed by black rock and groves of palm and almond trees; clear blue water and all the beauty and adventure it provides; “perfect” weather all year round; a welcoming and rich culture that gives meaning to your vacation and helps you feel right at home; and diversity of landscape that allows you to experience multiple vacations in one. With all that Hawaii has to offer, planning a holiday here can be overwhelming. I can help! Read on for my Hawaii Travel Guide, including the best islands for your vacation, getting to Hawaii, when to visit, where to stay, and the top activities on each island.

As a certified Hawaii Destination Specialist and a frequent visitor myself with eight visits to the islands (and counting!), I can offer expert guidance and local connections. I take time during each visit to tour the top resorts and experience the best excursions, so I have personal knowledge and strong relationships. With all that Hawaii has to offer, I understand that planning a vacation here can be overwhelming. That's where I come in. I can help you determine which islands to visit, secure the best lodging to meet your needs (with the best price and exclusive VIP amenities), and work with my local experts to curate top adventures as well as "off-the-beaten-path" gems to build the vacation of your dreams!​

When planning a trip here, your first decision is which island or islands to visit. The four main islands - Maui, Kaua'i, O'ahu and the Big Island - are very different, so my first step is matching your time, travel style, and wishlist to the best island(s) for you. If you have a week, I suggest one island. If you have 10-14 days, I suggest two or three islands.

Getting to Hawaii: Tips for Your Flight

Before we get into the details of each island, let's talk about how to survive that flight to Hawaii. If you're coming from the East Coast or the Midwest like me, you know it's a long haul. From Chicago, it's 9 hours of flying, while the East Coast is 11 hours or more. If Kaua'i is on your agenda, know that it's the furthest west and the least developed of all the islands, so flight times are longer and you're less likely to find nonstop options.

Here are my travel tips for making your flights as easy as possible.

• Cost: Plan on flights to be at least $1k per person. If you book early and outside of peak season (Christmas, winter, Spring Break), fares can be lower.

• If you're only visiting one island, you'll fly round-trip. The airport codes are:

  • Maui: OGG

  • Kaua'i: LIH

  • Oahu: HNL

  • Big Island: KOA

    • The Big Island also has an airport in Hilo (ITO) on the east side. If you're staying by the volcano, you can investigate whether you should fly in or out of Hilo, but this airport is smaller with fewer options.

• If you're visiting multiple islands, look for a "Multi-City" itinerary on the airline's website. For example, if you're flying from Chicago and visiting Maui and Kaua'i, you will research the following multi-city itinerary on Google Flights to find your best options.

  • ORD-OGG, LIH-ORD

  • ORD-LIH, OGG-ORD

  • Compare the pricing to see which island you should visit first.

• Choose the itinerary with the best price and best schedule. Here's what "best schedule" means to me:

  • Shortest duration. In Google Flights, I always sort on shortest duration, and it puts the nonstop options at the top. Then the options with the shortest layovers will be next. I rule out any options with long layovers.

  • Outbound flight: If you aren't flying non-stop, pick an itinerary that gets you as far west as possible. For example, if there's no significant price difference, I'd pick a flight that stops in San Francisco over one that stops in Dallas or Denver. By getting as far west as possible, your second leg to Hawaii isn't as long.

  • Return flight: Your flight will most likely depart Hawaii at night, and you'll arrive home the next day in the afternoon. A night flight is good for two reasons.

    • 1) You get an extra day in Hawaii!

    • 2) It's easier to sleep when you're flying at night. Because you'll be sleeping on the way home, it's better to get as far east on that first leg, so you have more time to sleep. If you're flying roundtrip, you may not have a choice, but if you do, then I'd prefer a flight from Hawaii to Phoenix, Dallas or Denver over a flight to San Francisco.

  • If you have a very late departure, consider buying a resort daypass at your hotel or a hotel by the airport. We did that for our 11pm departure from Kaua'i and booked a daypass at the Royal Sonesta in Lihue. This allowed us to have a home base to chill, nap, and shower before our late flight. Some resorts also have departure lounges where you can shower before your flight.

• Inter-island flights: To get between islands, you'll fly Hawaiian Airlines, which has the most options, or Southwest Airlines. Inter-island flights are quick and inexpensive (normally $60-80 per person). Make sure you book nonstop flights.

Google Flights Multi-City Itinerary example: Chicago to Maui, Kaua'i to Chicago

When 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 Islands Should You Visit?

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: The Valley Isle

I adore Hawaii and feel that 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: The Garden Isle

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 More About Kauai

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O'ahu: Vibrant Mid-Pacific Hub

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 for 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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Island of Hawaii: The Big Island

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!

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.

If Hawaii is on your dream board, contact me and we'll work together to make that dream a reality! I'll help you decide which islands to visit, find the best accommodations to meet your needs, and fill your vacation with amazing activities you and your family will never forget! Through my relationships with the top Hawaii resorts and my luxury partnerships, I can offer you exclusive VIP perks and promotions you can't get on your own. My expertise and personal connections help make your vacation easy ... and spectacular!  Hawaii is waiting for you! Aloha!

Let's Get Started!

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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 Million Dollar Advisor with Gifted Travel Network, a Virtuoso agency. Heather has helped hundreds of families experience Hawaii, Alaska, Costa Rica, the Caribbean, Italy, France, Greece, England, Croatia, Spain, Portugal, Ireland, Africa, Iceland, 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.