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The Islands of Hawaii
Breathtaking backdrops and that warm aloha spirit
Aloha!
Traveling the world fills me with joy, and Hawaii holds a special place in my heart. It was my first love, and it's the place I keep going back to again and again. My kids feel the same way. Even though they've been multiple times, when I ask them where we should go next, Hawaii is always on their list.
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What makes Hawaii so special?
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Miles of white (and black!) sand beaches framed by black rock and groves of palm, almond, and pine trees
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Perfect weather year-round
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A welcoming and rich culture that gives meaning to your vacation and helps you feel right at home
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Breathtaking and diverse landscapes that allow you to experience multiple vacations in one - beaches, active volcanoes, snow-capped mountains, waterfalls, lush rainforestsā
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A wide range of natural adventures to keep everyone engaged - surfing, snorkeling, SUP, kayaking, whale watching, hiking, biking, ATV, ziplining, helicopter tours, farm tours, and more!
I've visited Hawaii eight times (and counting!), experiencing all the islands and many of the activities. I take time during each stay to tour all the top resorts, so I have personal knowledge and strong relationships across all the islands. With all that Hawaii has to offer, I understand that planning a vacation there 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 perks!), 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!ā
Which Island(s) Should I Visit?
Your first decision is which island or islands to visit. If you have a week, I suggest one island. If you have 10-14 days, then definitely two islands! Remember, the flight to Hawaii is a long one, so you want to maximize your stay by seeing as much of Hawaii as possible. The good news is inter-island flights are short and inexpensive. Other than Oahu, you'll want a rental car so you can explore the island. Choose from:
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The variety and beauty of Maui's swimmable beaches, lush green valleys, rainforests and waterfalls
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The dramatic yet peaceful natural beauty of Kaua'i, the movie star of Hawaii
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The energy, nightlife, history and culture of O'ahu
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The diversity, power and size of the Big Island, the home of the largest active volcano on our planet
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Read on for specific recommendations on each island!
MAUI: The Valley Isle
Maui 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 down-home appeal.
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Maui is my favorite island for first-time visitors, because it's easy to get around and it has no shortage of beautiful oceanfront resorts with amazing amenities to keep you entertained when you aren't out exploring. If you like a more peaceful and luxurious vacation with beautiful beaches, the Wailea area is right for you. If you're on a budget and like things more lively, Ka'anapali Beach is a great choice.
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Read on for favorite Maui adventures!
MAUI Favorites
If your vacation begins in Maui, then your first full day should start with a sunrise tour of Haleakala Crater, what many people describe as a life-changing experience. You'll have to get up at 2:30am, but given the time change, that won't be as difficult on day one! If you're adventurous, you can do an exhilarating bike down the mountain afterward (ages 12+). If you don't want to get up that early, you can always see sunset on Haleakala instead.
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A snorkeling cruise is a must on Maui - choose from the ever-popular Molikini Crater (it will be crowded!) or the island of Lana'i. And if you're on Maui during the winter, look out for whales! You can spot them from the shore, but you'll definitely see them on your cruise!
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The Road to Hana may be one of the most beautiful yet difficult drives you'll ever take - 64 miles of narrow, winding cliff-hanging roads that will take you 7-9 hours roundtrip. The stops are where the real beauty lies - waterfalls for pictures and for swimming, blowholes, black sand beaches, surfer lookouts, a lava tube and garden maze, botanical gardens, beach caves, and the Seven Sacred Pools. You can do the drive on your own or on a guided tour. And if you can't imagine doing the drive there and back, Hana SkyTrek will drive you and then helicopter you back! If being in and out of the car all day isn't appealing, try the Rainforest Waterfall Hike with Hike Maui or waterfall rappel at Halfway to Hana!
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Last on my list are water adventures: surf lessons (yes that's me surfing - it wasn't pretty, but I did it!), outrigger canoe, and kayaking or SUP! And you can't leave Hawaii without experiencing a luau!
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, and Raiders of the Lost Ark. Kaua'i holds a close second to Maui for me because of its jaw-dropping beauty, relaxed pace, and small-town charm. However, Kaua'i is more difficult to navigate 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! Kaua'i has less swimmable beaches but more than makes up for it in beauty and adventure!
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Most visitors stay on the south shore in the Po'ipu Beach area where the weather is more predictable and resorts are more plentiful. However, the north shore is what makes Kaua'i unique, so Princeville or Hanalei gets my vote. My first choice for Kaua'i will always be the spectacular 1 Hotel Hanalei Bay where I can offer Virtuoso amenities and where you're close to the Na Pali Coast and oh so charming Hanalei. The east side (Lihue, Kapa'a and the Coconut Coast) offers budget-friendly options, but that area is less picturesque.
KAUA'I Favorites
No trip to Kaua'i is complete without an adventure on the Na Pali Coast. Whether on foot, helicopter or boat - or all three! - this 17-mile stretch of sea cliffs and caves, green mountains, and sandy covesā is not to be missed! Choose from an expedition raft cruise that can get into sea caves or a catamaran that even goes to a Forbidden Island! Or if you're ready for a big workout, you can kayak the whole coast, an amazing adventure I did in my younger days.
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Travel to the other side of Kaua'i to see Waimea Canyon, the Grand Canyon of the Pacific. You can take pictures at the overlook or you can hike the Cliff and Canyon Trails and stand along a cliff edge for a 360-degree view!
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If that's not enough adventure for you, try mountain tubing down sugar plantation chutes, waterfall rappelling, ziplining, or an ATV waterfall tour!
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 high rise oceanfront resorts, restaurants, nightlife and shopping. Accommodations are plentiful, but if you want quintessential Hawaii, The Royal Hawaiian ("Pink Palace") and the Moana Surfrider are the two most historic Waikiki resorts. If crowds are not your thing and you'd prefer a more relaxed island experience, try the Ko'Olina coast or North Shore.
O'AHU Favorites
Waikiki Beach is a must-see even if you're staying in Ko'Olina or the North Shore. Stroll the beach to see the surfers then shop, dine and people watch on the Waikiki Beach Walk. Hike Diamond Head for gorgeous views (you need a permit), then grab dinner at Duke's and stay for the Friday night fireworks!
Spend the day or a few hours at Pearl Harbor. History buffs can set up a tour with a veteran and see the USS Arizona and Missouri, the USS Bowfin Submarine Museum, Pacific Aviation Museum, and Punchbowl Cemetery. For easy snorkeling, get reservations at Hanauma Bay, a protected nature preserve. Keep going toward the Windward Coast and check out the beautiful Lanikai and Waimanalo Beaches and Kailua Town. If the mountains are calling you, head to Kualoa Ranch for horseback riding, ATV, or zipline tours.
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On the North Shore, check out Waimea Bay, my favorite swimming spot when the water is calm or watch the surfers when the waves are crashing. The Polynesian Cultural Center and Dole Pineapple Plantation are both great for kids!
HAWAII: The Big Island
The Big Island is just that - big - bigger than all the other islands of Hawaii combined. Because of all that space, the vibe is chill and the crowds are few, but you can expect to spend some time in the car. With the most ecologically diverse landscape - multi-colored beaches, lush rainforests, waterfalls, lava fields, a very active volcano, plus a snow-topped mountain - the Big Island has a lot to offer!
Given its size, consider staying on both sides of the island - a night or two near Volcanoes National Park - and the rest of your time on the west side where you'll find luxury resorts and the beaches, sun and nightlife that go with them. You can even fly into one side and fly out the other. Drive time between the two sides is 3 hours. Trust me: you can spend A LOT of time in the car on the Big Island.
BIG ISLAND Favorites
While Volcanoes National Park is the biggest draw to the Big Island, if there's no active lava flow, a visit to the volcano can be a tad underwhelming. The lava tube, Punalu'u black sand beach, and Akaka Falls were the favorites from our island tour, but it was a full day of driving to see it all. The lush Waipi’o Valley tops the list as well.ā
You'll be happy to spend the majority of your time on the west side where the sunsets are as spectacular as the luxury beachfront resorts. Choose from Kona Village, a Rosewood Resort, Four Seasons Hulalali, Mauna Lani, Fairmont Orchid, and Mauna Kea. I toured them all and it's hard to pick my favorite as they're all so unique.
When it comes to excursions, my all-time favorite by far is the nighttime swim with manta rays, the butterflies of the sea. We've done it twice now - once from a boat and once from the beach, and the intimate beach excursion wins my vote, hands down! ā The snorkel cruise to Kealakekua, hiking the petroglyph preserves, and Mauna Kea summit stargazing are also must dos.