“Which Hawaiian island should I visit?” is one of my most frequently asked questions! I get it from clients, friends, and strangers on social media! As a resident of Oahu, Hawaii since 2018, and a frequent island hopper (I’ve traveled to the outer islands more times than I can count, both for work and pleasure), I’m not a definitive expert by any means, but I can certainly share my knowledge as a resident and traveler!

Hawaii is comprised of hundreds of islands, but there are 8 major islands, and you may have only heard of 4. I’ll cover those four most frequently-visited here: Oahu, Maui, Hawai’i Island (commonly referred to as the Big Island) and Kauai.

OAHU – THE GATHERING PLACE

Oahu is the busiest and most populated island – by far. Home to nearly a million people, including myself! Oahu is bustling and busy, with the capital of Honolulu, and the busy tourist hub (and neighborhood within the city of Honolulu), Waikiki. Waikiki Beach is world famous with endless hotels, restaurants, and shops, bordering arguably one of the world’s most famous beaches, with Diamond Head towering in the backdrop. I’ve heard many visitors lament that they’re taken aback upon landing at the Honolulu airport, grabbing their luggage, and exiting onto an 8 lane freeway. Don’t expect a sleepy little island right out the gate. Honolulu may not be nearly as big as NYC or LA, but it’s an urban city, nonetheless.

That’s not to be said you can’t find laid-back island style here on Oahu. Once you venture out of the urban areas, Oahu has plenty of hidden nooks and crannies and is also home to the North Shore – famous for it’s winter surf breaks, attracting surfers and enthusiasts from around the world. Disagree if you want, but I also believe Oahu has the best and most diverse beaches of all the islands! And the best hiking! Waikiki is not to be missed, but if that’s all you see, you’ve definitely missed the best parts of Oahu.

I love Oahu for the diversity. You can belly up to a late night bar in Waikiki or Chinatown, but you can also find miles long strips of white sand beaches, nearly all to yourself.

Oahu highlights:

Airport code: HNL
My fav restaurants: The Pig and the Lady, Hau Tree, Monkeypod Waikiki
Best beaches: Lanikai, Sunset Beach, Waimea Bay, Waikiki (yeah, yeah, it’s touristy, but it’s worth seeing!)
Don’t miss: hike up Diamond Head (reservations required), snorkel at Hanauma Bay (reservations required), drive the north shore, take a surf lesson, book a tour at Kualoa Ranch, sunset catamaran along the coast of Waikiki

All of my clients receive my Oahu travel guide, jam packed with pages of pages of my all my favorites – restaurants, bars, places to grab shave ice, hikes, beaches, and much, much more!

MAUI – THE VALLEY ISLE

Maui is far less busy than Oahu, but not as sleepy as the Big Island or Kauai. When I think of Maui, I think of bougie resorts and restaurants – plenty to keep you (and everyone you’re traveling with) entertained. I think Maui has the best (and arguably, most expensive) restaurants, and definitely more of a resort vibe, vs hotels, which are more common on Oahu (though there are a handful of resorts there too). Maui just feels like paradise.

You could chill at a resort for a solid seven days straight, but Maui also has plenty to do. There are endless waterfalls, and the Road to Hana and Haleakala National Park could keep you occupied for days. There’s snorkeling and whale watching and you can even take a ferry to the island of Lanai! Not to mention exploring all the gorgeous beaches.

I love Maui for the bougie resort vibe mixed with endless natural beauty!

Maui highlights:

Airport code: OGG
My fav restaurants: Merriman’s, Mama’s Fish House (I recommend making a reservation as soon as you know you’ll be on Maui), Maui Brewing (Kihei brewery location), The Birdcage
Best beaches: Big Beach (and adjacent Little Beach), Napili Bay, Ho’okipa
Don’t miss: The Road to Hana, sunrise or sunset at the summit of Haleakala (reservations required for sunrise), cliff jump and snorkel at black rock at Ka’anapali Beach, whale watch (winter only)

Click here for my Maui travel guide!

HAWAI’I – THE BIG ISLAND

The Big Island is, well… big. Even though I’ve been there dozens of times, it’s the island I feel like I know the least, because it always seems there is something new to discover. It’s really too large to even cover in a 7-10 day trip, so if you come here, I recommend doing your research and having an idea of what you want to see and do. And possibly planning long distances to get there.

Upon landing, you’ll notice right away that the Big Island is so different than the other islands. It doesn’t have the jagged green mountains you’ll find on the other islands, but rather two massive volcanic peaks – so massive in fact, it’s hard to comprehend the scale.  Mauna Kea, the highest point of all the islands at 13,000′ + is the tallest base-to-summit mountain in the entire world – taller than Everest by more than a mile! Beyond Mauna Kea you’ll see endless miles and miles of black lava fields, and what appears to be very little vegetation. But there’s really so much diversity and so much to see on this island.

I love the Big Island for its sense of adventure and the feeling of endless discovery! There are also some bougie resorts here.

Big Island highlights:

Airport code: KOA (or ITO; Hilo, but most tourists will fly into Kona, especially if it’s your first trip)
My fav restaurants: The Coffee Shack, Canoe House, Kona Brewing
Best beaches: Kua Bay, Old Airport Beach, Punalu’u Black Sand Beach, Papakolea Green Sand Beach
Don’t miss: Volcanoes National Park, night snorkeling with manta rays, drive to the summit of Mauna Kea

Click here for my Big Island travel guide!

KAUAI – THE GARDEN ISLE

Kauai. Dare I say this is my favorite island?! I don’t know if I’m bold enough to make that claim, but I will say, I think Kauai is the prettiest of the islands. It’s the oldest (hence the extra millennia to grow vegetation), the wettest, and the landscape here is pretty much guaranteed to blow your mind! Kauai is also the quietest, least developed, and has the most what one could call, “island vibe.” Single lane roads, everything closes by 8 or 9 pm, super laid back. What you may compromise in dining quality and/or options, Kauai will make up for it with less crowds and pristine beaches.

I love Kauai for the vivacious, rugged beauty and the incomparable Napali Coast!

Kauai highlights:

Airport code: LIH
My fav restaurants: Postcards, Tahiti Nui, Beach House
Best beaches: Shipwreck, Hanalei Bay, Tunnels, Poipu
Don’t miss: Waimea Canyon, take a boat/catamaran/zodiac on a Napali coast tour, take a doors-off helicopter tour (I think this is beautiful on any island, but especially Kauai with the stunning Napali coast), Wailua Falls, hike to Queen’s Bath

Click here for my Kauai travel guide!

To paraphrase, I’d sum up each island with some key words:
Oahu: bustling, diverse, biggest array of dining/bar options, Waikiki, north shore
Maui: white sand beaches, romantic, whale watching, road to hana, fancy resorts and five star dining
Big Island: volcanoes, lava fields, vast, fancy resorts, secluded
Kauai: traditional island vibes, green and verdant, stunning landscapes, Waimea Canyon, Napali coast

Have you visited any of the Hawaiian islands? Do you agree with my assessment? DM me on Instagram and lmk!!