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Image by Sean O.


The islands of Hawaii are on everyone's vacation dream board for good reason - miles of white (and black!) sand beaches, 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. 

With all that Hawaii has to offer, planning a vacation there can be overwhelming. That's where I come in. As a Certified Hawaii Destination Specialist and frequent visitor myself, I can help you determine which islands to visit, secure the best lodging to meet your needs (at the best price!), and work with my local experts to curate top adventures as well as "off-the-beaten-path" gems to help you build the Hawaii vacation of your dreams!

Any time of year is a great time to visit, but winter is high season (and whale watching and surfing season!) and will be significantly more expensive. April-September is considered the secondary season while prices (and waves) drop considerably during the fall. My family and several clients will be taking advantage of the deals this October!

COVID update:

To bypass the 10-day quarantine, all travelers to Hawaii must show proof of negative COVID test results before beginning the last leg of their trip to Hawaii. Click here for more information

If you're visiting multiple islands, you may require a second test. I can help you navigate the ever-changing requirements! You can read about the additional restrictions for Kaua'i below.


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, maybe two. 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. No matter which island you visit, you'll want a rental car (book ahead!) so you can explore!

Choose from:

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

  • The variety and beauty of Maui's 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, the home of the largest active volcano on our planet

On any of the islands, you should get out on the water - surfing, kayaking, snorkeling, sunset sail, outrigger canoe, standup paddleboard, sportfishing. Read on for specific recommendations for each island!

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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 ("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 island experience, try the Ko'Olina coast or North Shore.



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, 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, go early to Hanauma Bay, a protected nature preserve, and checkout Halona Blow Hole. 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.

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. Across the street is Waimea Valley, a beautiful botanical garden for afternoon strolls.

You can't leave Hawaii without experiencing a luau, and you have several options to choose from on O'ahu. My favorite is Paradise Cove at the Ko'Olina Resort or the Chief's Firedance Luau in Kapolei.

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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. 

Maui 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 vacation with beautiful beaches, the Wailea area is right for you. If you like things more lively, Ka'anapali Beach and Lahaina are great choices.

Read on for favorite Maui adventures!



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 2am, but given the time change, that won't be a problem on day one! If you're adventurous, you can do an exhilarating bike down the mountain afterward (ages 12+). After your adventure at Haleakala, head to beautiful UpCountry or spend the rest of the day napping by the pool or at one of Maui's beautiful beaches before you grab dinner in Lahaina town.  

A snorkeling cruise is a must on Maui - choose from the ever-popular Molikini Crater (it will be crowded!) or Lanai's Hulopoe Beach. Book with Trilogy my favorite snorkel group on Maui. And if you're on Maui during the winter, you gotta go whale-watching, too!

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 from Kahului depending on stops. And stop you must because that's 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 with a tour group. Download the GyPSy Guide app either way! And if you can't imagine doing the drive there and back, Temptation Tours will drive you and then helicopter you back! 

Last on my list are water adventures: rappelling the waterfalls, an outrigger canoe paddle experience, and kayaking or SUP! And you can't leave Hawaii without experiencing a luau, and the one with the prettiest view on Maui is the Old Lahaina Luau

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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, 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! Kauai has less swimmable beaches but more than makes up for it in beauty and adventure!

Most visitors stay in the Po'ipu Beach area where the weather is more predictable, but Lihue and the Coconut Coast have good options, too. If you want to be near the Na Pali coast and want to get away from it all, then gorgeous Princeville will suit you just fine.



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 coves​ is not to be missed! For boat tours, go with Capt. Andy or if you're ready for a big workout, you can even kayak the whole coast, an amazing adventure I did in my younger days.

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!

If that's not enough adventure for you, try mountain tubing down sugar plantation chutes, a zip 'n dip (zipline and waterfall swim), or an ATV waterfall tour through Jurassic Park! End your visit with an oceanfront luau at the Kaua'i Sheraton.

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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, 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 couple nights in Hilo or even in Volcano Village so you're closer to Volcanoes National Park - and the rest of your time on the Kona 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 (Hilo east side, Kona west side). Drive time between the two sides is 1.5 hours for the shortest route, 3 hours for the scenic route.



Volcanoes National Park is the biggest draw to the Big Island. Follow the lava flow by car and on foot, see the lava flow into the ocean by boat, and experience the glow at night from above in a helicopter. And don't forget about the lava tubes and black sand beaches, especially Punaluu Beach Park! Consider a guided tour with Hawaii Forest & Trail to make sure you see it all!

North of Hilo sits the lush Waipi’o Valley – book a ride on the valley shuttle or tour by horseback or ATV to the black sand beach. You’ll also want to spend an afternoon in quaint Hilo town including Hilo Bay and Banyan Drive. This side of the island has botanical gardens and waterfalls to keep you here a bit longer – Liliuokalana Gardens, Akaka Falls, and Rainbow Falls top the list.

Once you make your way over to the Kona side, you’ll want to get out on the water for snorkeling, kayaking, whale watching, or sportfishing. Try a kayak and snorkel cruise to Kealakekua during the day and swim with the manta rays at night. And if the black sand beaches aren’t enough for you, you can even find a green sand beach on the southern-most tip of the island, but you have to hike to find it!

The Big Island has a wealth of experiences for to expand your mind as well – Mauna Kea summit stargazing; Puuhonua O Honaunau Historical Park, a sacred historic site of carved idols protected by a huge rock wall; and Puako Petroglyph Preserve.  And there’s no shortage of adventure opportunities either! Try the Kohala Zipline Canopy tour or the Zip ‘n Dip (canopy + waterfall) or go on a scenic horseback ride from the valley to the coast. Kids and animal lovers will delight in the Ocean Rider Seahorse Farm and the Mokupapapa Discovery Center, a free aquarium.


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