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Planning a trip to Hawaii? Start here!

Updated: Aug 4

The Islands of Hawaii are on everyone’s vacation dream board for good reason – miles of white (and black!) sand beaches; clear blue water and all the beauty and adventure it provides; “perfect” weather all year round; a welcoming and laid back culture that helps you unwind and feel right at home; and diversity of landscape that allows you to experience multiple vacations in one – majestic sea cliffs, lush rainforests, active lava flows, towering waterfalls, green mountains, red canyons, and flowers beyond your wildest dreams. With Hawaii, you get a unique, exotic, and “foreign” vacation with all the convenience of U.S. travel. When planning a trip to Hawaii, your first decision is which island or islands to visit. If you have a week, I suggest one or two islands. If you have two weeks, I suggest two or three islands. Remember, the flight to Hawaii is a long one (about 12-14 hours from the East coast), so you want to maximize your stay by seeing as much of Hawaii as possible. The good news is inter-island flights in Hawaii are a short hop and inexpensive.

Choose from:

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

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

  • The serene luxury and seclusion of Lana'i

  • The leisurely pace and jaw-dropping scenery of quiet Moloka'i

As a certified Hawaii Destination Specialist and a frequent visitor myself (trip #6 planned for 2023!), I can offer fantastic deals on luxury resort packages plus expert guidance on top adventures as well as “off-the-beaten-path” gems to help you create the vacation of your dreams. I work with all the best tour suppliers recommended to me by local experts, so you'll get the "best of the best" for each activity! Read on for a dive into what each island has to offer. Contact me to start planning! Here's a great resource, too!


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. Better yet, split your time between Waikiki and the west 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 five-hour time change. On our way out of the city, we snorkeled Hanauma Bay (go early before the crowds!) 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! After O'ahu, we headed to Kaua'i – more on that when we talk about the Garden Isle!

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 over Thanksgiving. 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.

Later this year, I will visit O'ahu again with my whole family – my daughter’s first trip! We’re staying at Disney Aulani on the Ko’Olina Coast, an area of O'ahu I have yet to see! I imagine we’ll spend a lot of our time at the resort, but we plan to hit Waikiki to see the sites and ride an outrigger canoe, Waimea Bay to watch the surfers or swim if the water is calm, Hanauma Bay for snorkeling, and I’d love to explore the Kualoa Ranch, too. I wish we had time for Pearl Harbor, but with only three days on O'ahu and none of us being history buffs, it didn’t make the cut.

Ko'Olina Coast, Pearl Harbor, Hanauma Bay


Maui: The Valley Isle

Maui is probably my favorite island, although I’ve only visited once and I had a 6-month-old baby in tow, so I’m sure there’s a lot of the island I missed! What I love about Maui is it has the best of everything Hawaii has to offer – beautiful beaches (the most miles of swimmable beaches in Hawaii!), lush valleys and rainforests, volcanic landscapes, rich culture and culinary delights - all packaged into a sophisticated tropical paradise with downhome appeal.

When we visited with my baby, we stayed the whole week at the Mana Kai Maui in Kihei on the central west coast. My mom traveled with us and stayed with her cousin and babysat Brady when we could bear to be away from him. We took advantage of her babysitting offer for a snorkel excursion for the two of us, but otherwise, we brought him with us! We 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 Up Country where the scenery is breathtakingly beautiful. Beyond that, it was mostly beach, pool, repeat for us, but we were all happy to be lazy.

Later this year, we’ll head to Maui after we leave O'ahu where we’ll get to spend eight amazing days on Ka’aanapaali Beach at the Hyatt Regency. My list of activities is so long that we booked more time in Maui vs. splitting the time evenly between O'ahu and Maui. So far my list includes:

  • Road to Hana again but with all the best stops since we won’t have a baby!

  • Haleakala sunrise hike

  • Snorkel cruise to Lana'i

  • Old Lahaina Luau - the best on Maui

  • Rappel waterfalls and rainforest cliffs - it will be terrifying but amazing!

Haleakala at sunrise, Waterfall rappel, Lana'i island


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 two trips to Kaua'i under my belt, this island holds a close second to Maui for me because of its 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 when I visited O'ahu and Kaua'i 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! I will do this again when my kids are a bit older! 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 actually stop to admire the view, because falling off a cliff is a real thing here!

Na Pali Coast, Waimea Canyon

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, which is crazy beautiful, and we hiked the Na Pali coast again. Luckily, I did not fall down the cliff this time!

On my next trip to Kaua'i (which isn’t planned yet but I’m ready!), I want to spend a whole week there with my family so we can do all the adventures: kayak the Na Pali coast again, hike Waimea Canyon, go mountain tubing, do the movie tour to see all the waterfalls and beautiful vistas of Kaua'i, and zip and dip (zipline + waterfall swim) because my kids are big lovers of ziplining. I think we’ll stay in Po’ipu Beach this time, an area I’ve never even seen!

Kauai kayaking, ziplining, and mountain tubing


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! 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. However, I’m ready for another go! Next time we will stay on both sides of the island – Kohala or Kona on the west side and Hilo on the east side – so that we aren’t spending so much time in the car. You can even fly into one side and fly out the other (Kona west airport, Hilo east airport). Drive time between the two airports is 1.5-3 hours. Kona/Kohala offers luxury resorts, the best beaches, more sun, and nightlife so you'll probably spend more time on this side. However, the drive from Kona to Volcanoes National Park - the major attraction on this island and where you'll spend a day or two - is at least 2 hours whereas the Park is only a half hour from the Hilo area.

The volcano experience (including lava tubes, cloud forest, black sand beach, and waterfalls) will top our list and I plan to hire one of the private tour guides to make it easier than last time. My stomach decided I will skip the helicopter tour this time, even if my family chooses to go. Also on the east side is exploring quaint Hilo town, stargazing at the Maunakea Summit, and relaxing at Lili’uokalani Gardens.

Hawaii Volcanoes National Park, Lava Tube, Lili'uokalani Gardens, Maunakea Summit

On the west side, my #1 pick for our next visit is the night-time manta ray snorkel excursion. The whole thing sounds freaky and amazing all at the same time! I also think my kids would love daytime snorkeling, experiencing cowboy culture at a rodeo in Waimea, and the canopy tours and zip and dip in Kohala. If I want a week in Kauai and want to experience both sides of the Big Island, I think we’re going to need a good 10 days!

Nighttime snorkeling with manta rays plus daytime snorkeling, too!


Lana'i: The Secluded Isle and Molaka'i: The Friendly Isle

Lana'i and Molaka'i are technically part of Maui Nui (greater Maui) and are the smallest and least developed of the Hawaii islands. Both islands can be reached by ferry from Maui, so are potential day trips from there or you can stay on either island.

Lana'i offers serene luxury and seclusion with quiet, upscale resorts and a pristine reef. Bill Gates was married on Lana'i at the Four Seasons to give you perspective on what I mean by serene luxury. Moloka'i offers a rugged yet leisurely pace, the world’s highest sea cliffs, and longest coral reef in the U.S. However, Moloka'i is probably best known for its leprosy colony. I haven't visited either island but plan a snorkeling trip to Lana'i when we’re on Maui this year.


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 lodging to meet your needs, and fill your vacation with amazing activities you and your family will never forget! As a partner with TPI and Signature Travel Network, I have access to inventory, special deals and experts that will save you money, time and peace of mind! Hawaii is waiting for you! Aloha!


Heather Vergara is a former PepsiCo marketing executive who left the corporate world to be a Mom and never looked back. In addition to travel and adventure, Heather is passionate about kindness, community, whole food, and sweating every day. Heather has an MBA from Indiana University, a Digital Marketing Exec Ed certificate from Columbia University, and a BA in Journalism from the University of North Carolina. She lives with her husband, two kids and two furry dogs in Zionsville, Indiana.

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