Hawaii: Which Island to Visit For First-Timers

Hawaii is my happy place.  Just hearing Hawaiian music makes me smile.  My husband and I have been the 5 past years and we can't get enough of it.  We've spent countless  hours reading guidebooks and blog posts to find the best beaches, hikes, fun activities and places to stay!   A lot of our friends ask us for our recommendations about Hawaii so I thought it was time to put together a post of our recommendations!  These recommendations are based on our trips that we've had.   Planning a Hawaii trip can be a little overwhelming.  I hope this helps you a little with your decision based on what you're looking for in a Hawaiian getaway.   Every trip we've had has been a little different and amazing in a really cool way!  

If you're looking for:

Oahu:Classic hawaiian Adventure 

Oahu (The Gathering Place) has a little bit of everything, the beautiful Hawaiian mountains, a little urban vibe in Waikiki, a little country.  History and culture.  The breathtaking North Shore,  the stunning Windward side of the island.  Many people think of Honolulu and Waikiki Beach when they think of Oahu.  Personally, this is not what I think of at all, but for some people it's exactly what they're looking for!  My favorite spots are the North Shore and the East side!  Check out Kuoaloa Ranch for some stunning scenery and famous movie settings (Jumanji, Jurassic Park, King Kong)!  Don't miss the beautiful drive on the East side of the island and Lanakai Beach/Kailea!  Laei Point is also a beautiful lookout!  


Turtle Bay-North SHore

We have stayed at Turtle Bay twice and it's lovely! I love the property because it's so close to the water and the waves are so big!  They also have some great trails on the property for running, walking or biking!  They also offer a free yoga class by the water, which is awesome!  There's also stables nearby and you can book a horse back riding tour!  The golf course is pretty nice, so if that's your cup of tea, you can enjoy!

The Royal Hawaiian - Waikiki



Haleiwa Town and Waimea Bay

Sunset beach/Banzai pipeline  

If you are going between November and January there are a couple of major surfing tournaments that are really fun to check out!  We have been to the Vans World Cup of Surfing and it's so much fun! This is not the place to try surfing for the first time! 

Surf/paddle board

Waikiki or Lanakai

Hike to Diamond Head

Lanakai Beach

You're welcome.  One of the prettiest beaches I think in all of Hawaii!  

Kualoa Mountains/Visit Kualoa Ranch

The mountains of Oahu are gorgeous. one of my favorite things is just to enjoy the scenic drive up to the North Shore.  At Kuoloa Ranch you can take the movie tour, do a horse back ride or do an ATV tour.  Be aware the ATVS max out about 20 mph. Not very exciting. Horse back riding would be my recommendation! 

Makapuu Lighthouse/Trail and Lookout


Kauai: Natural Wonders/Authentic Hawaii:

Kauai is the oldest Hawaiian Island, and it's become quite gorgeous in the past thousand years or so.   Kauai has definitely become the "popular kid"  in the island chain in recent years, yet it still maintains its authentic, rustic and peaceful vibe.  Just go.  You won't regret it.   I fall more in love with Kauai each time I go!   It's no secret this is my favorite island!  Read Complete Kauai Guide



For Romantics, OR peace and quiet Koa Kea (Poipu)

I loved this place, so much!  It was understated, but still so luxurious. We had a room right by the water and could hear the waves all night.  Heaven!

For families and fun: The Grand Hyatt Kauai

I say it's great for families, but Rob and I loved it (no kids yet)!!  The property is absolutely gorgeous.  Tons of pools, a lazy river and most importantly: a super fun WATERSLIDE!  This might be my favorite resort in all of Hawaii.  The beach by the property is really nice to

Ultimate Luxury: St. Regis Princeville

Get ready to be feel like a celebrity.  The views for are epic in the heart of the North Shore!  Don't worry if you can't drop that kind of money to stay here, just visit the property for drinks and sunset! 


Cruise and snorkel along the Na Pali Coast 


Kalalau Trail - first 2 miles no permit needed, beyond that, you will need a permit because you have to camp overnight!

Maha'ulepu Heritage Trail- easy coastal trail by the Grand Hyatt.  

Helicopter Ride

Read about our tour

Visit Waimea Canyon and the West Coast

North Shore (Hanalei and Princeville)


Maui:Pristine Beaches and Ultimate Luxury  

When it comes to stunning beaches, Maui (at least in my opinion) totally wins.   Maui offers a lot of variety. If you want Adventure AND Luxury you can have your fill of it here!  Wailea and Kapalua are my favorite areas.   Kapalua is ideal for those who want a quieter vibe with less crowds.  Wailea offers many high end resorts, including the Grand Wailea and The Four Seasons.  Hmm, Mai Tai's anyone?!

Maui is probably the most expensive island in terms of food, lodging and activities.  You pay a premium for those epic views, but it is worth it.   Airbnb or condo rental would be a great option if you want to stretch your budget a little further! If I'm being honest paying an arm and a leg for lunch by the pool gets a little old after a few days!  





Wailea Beach Resort


Montage Kapalua Bay ($$$) There should be an exclamation point after the dollar signs. It's my dream to stay here one day!

Condo Rental via Home Away


Travaasa  Worth noting there's not a lot to do in Hana, but Hana is arguably the most beautiful spot on the island and this would be an ultimate escape!


ROad to Hana

A full day event, but in my opinion it is a must do on Maui!  The Black Sand beach at Wai'anapanapa State Park was one of those places that makes you stop and say, am I really seeing this?  

Sail Trilogy Discover Lanai Tour

Just the best day ever! Seriously.  You can read about our experience here.  


Snorkel and Paddle Board at Wailea and Kapalua

Iao Valley

Sunrise or Sunset at Haleakala

Old Lahaina Luau

Paia Town


Big Island: Awe inspiring Views  

The Big Island is so much more than Volcanoes!   The youngest Hawaiian island definitely stands out (in a good way) among the other islands.  It's so different, yet no less breathtaking.    A few of my favorite spots on the island were, Hilo, Akaka Falls State Park and Volcanoes National Park.  Unfortunately, when we went to the park is was pouring rain and there was no lava flow visible from land so we were a little bit disappointed, but it's a good excuse to go back again!   One of my most memorable experiences  was doing a summit tour of Mauna Kea!  You ascend to the summit (almost 14,000 ft up), above the clouds to watch the sunset!  Mauna Kea is a sacred place to the Hawaiians and I can definitely see why!  Read my post about our Mauna Kea tour here.  Also don't miss the beautiful Hamakua Coast for some lush green cliffs.   As the name states, it's big, there's a lot to see!  


Mauna Lani Resort

Mauna Kea Beach Hotel


Volcanoes National Park


Such a neat surf town!

Akaka Fall State Park

Waipo Valley

Mauna Kea Summit Tour

You can read about our tour in my post here.  Be aware the altitude is almost 14,000 ft!  Do not underestimate it like I did! 

Yes, you are above the clouds to watch the sunset.  And two hours earlier you were at the beach.  Hawaii, you're such a show off!  :)


Lanai:Ultimate Seclusion

If you want to really get away from it all, Lanai is the place for you! 

I have been to Lanai and it is incredible! There are only  2 resorts, 1 of which is a Four Seasons (hello luxury).

Snorkeling at Hulopoe Beach with Sail Trilogy!

Snorkeling at Hulopoe Beach with Sail Trilogy!


Hotel Lanai

Four Seasons Resort

These are only your two hotel options!  


Snorkel Hulopoe Beach

Rent a Jeep and go off-roading

Some friends my mine did this as a day trip from Maui and said it was awesome! 

Hike to Sweetheart Rock

We did this after snorkeling!  Very cool!



Molokai: Epic seacliffs and

Molokai is the only island I have not visited yet.  Some friends I know that have been have given me their recommendations.  I can't wait to see the Sea Cliffs, some of the largest in the world.  


Hike Halawa Valley

Take a Boat Ride to see the Sea Cliffs


Planning Your Trip:

Time of Year: Winter or Summer?

The winter months get the most rainfall, but can offer some amazing whale-watching, while the summer months bring calmer waves and dryer weather.  Winter also means big waves and surf tournaments!  I've visiting the islands in August, September and November.  November was definitely the rainiest month, and September was very HUMID which is not typical of Hawaii.  I think ideal months would be March-May, October or February,  but really there is no bad time to visit Hawaii.  Even when it rains, you're still in paradise!  

If you are looking to get the most sunshine on your trip, I recommend staying on the South or West parts of the island as they are generally dryer.  The East and North areas get the most rain, but are more lush and green so they are beautiful! 

Island Hopping

If you have enough time (10 days or more) you can definitely easily hop between islands!  They islands are pretty close together so most flights are under one hour unless you are going from the Big Island to Kauai.  If you 7 days or less, I highly recommend just focusing on one island!  

Have more questions?  Feel free to ask me in the comments below or send me an email! 

Helpful Resources:



Hawaiian Airlines

Hawaii is such an extraordinary place.  You honestly can't go wrong, all the islands have something wonderful to offer.  Whether you want to play and explore, treat yourself at the spa, or soak up the sun by the pool drinking Mai Tais!  I am confident you will fall in love and I promise it's not just a fling!

Want even more resort ideas?!  Here's a list of the Best Resorts in Hawaii from Conde Nast Traveler!  


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