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Help me Choose an Island!

This post is all about deciding on what Hawaiian Island(s) is/are right for your vacation!

So you’ve decided your honeymoon/vacation will be in Hawaii – YAY!! But there are 4 major islands and 2 minor ones to choose from…how will you ever decide which one(s) to go to?

Well, I can help with the 4 major islands because I have been to them: Oahu, Maui, Kauai and the Big Island (also known officially as Hawaii). For tips on the two smaller islands, Lanai and Molokai, well you’ll have to wait until I get there myself, but I would probably try Google if all else fails. 🙂

Map of the Hawaiian Islands from

I don’t have a favorite island; in fact, I love all the islands I’ve visited for different reasons. Pick an island based on what you love to do at the moment. A good rule of thumb is 1 week = 1 island. Don’t try to cram all 4 islands into a trip less than 3 weeks. It is doable, but with the hassle of packing up checking out, renting and returning a car, traveling from island to island…you will use up precious vacation time dealing with the logistics. Better to just save it for another trip (and you will be back!). There’s plenty to do on each island, and you will also want to factor in time to relax as well…I mean, it’s a vacation after all!

If you are traveling with kids…kids love all islands because they love the water, and being at the beach. Each island has spectacular beaches. Even though we don’t have kids now, we still see a plenty of them on every island and they look like they are having a blast.

Here’s my take on the different islands, what are YOUR thoughts?




  • # of times visited: 7 (twice as a kid, 4 during adult years)
  • most recent visit: 1-week in November 2015
  • next visit: unknown

View of Waikiki and downtown Honolulu from the top of Diamond Head. The pink structure in the middle is the iconic Royal Hawaiian Hotel

Oahu is the pulse of Hawaii – a vibrant city vibe mixed with beautiful beaches, mountains, and a boatload of activities. Oahu is also where world-famous Waikiki Beach is located. It’s the easiest island to get to because most airlines will fly from the mainland into Honolulu International Airport and then travelers can make their connection to other islands from there. It’s fantastic for people-watching, history buffs, dining out, beginners surfing, and just having a great time in general. Oahu is a good place to come with friends in addition to a significant other. There is nightlife, plenty of celebrity-chef restaurants, spas, and scenic drives. If you are a foodie, Oahu is where you want to be. The most diversity in terms of restaurants and food culture are found on Oahu. A visit to Pearl Harbor is a must. The beaches of Lanikai and Kailua are amazingly beautiful. We love to eat all over the island, from 5-star dining at Alan Wong’s to searching out a tiny okazuya in Kalihi. We love the food in Honolulu and consider it part of the adventure. Oahu is also known for its beautiful and laid-back North Shore – the town of Haleiwa has a classic beach-gal/surfer-dude vibe and the beaches are a great place to watch them in action. If you are a city-person who still loves to get away from it all, Oahu is the place for you.

The beautiful North Shore…completely different from downtown Honolulu and less than an hour away

Some things to note: Waikiki beach does get crowded and the hotel rooms a bit small – you will not find sprawling resorts here (unless you venture west to Ko Olina or north to Turtle Bay), but the history surrounding this area is evident in classic hotels such as the Royal Hawaiian, the Westin Moana Surfrider, and the Halekulani. I mean, DON DRAPER vacationed on Waikiki beach.

Mad Men’s  fictional Don Draper and wife on Waikiki Beach – pic from

Best Island for: foodies, history buffs, visiting historic landmarks such as Pearl Harbor and Iolani palace, high-end shopping, changing scenery, famous beaches, people-watching, vacationers on a budget,  lots of local and diverse food.

Known for: Pearl Harbor, Waikiki Beach, North Shore, Diamond Head crater, Honauma Bay, Leonard’s malasadas (portugese doughnuts), Rainbow Drive-In, the Dole Plantation, Polynesian Cultural Center, food trucks, and the worst traffic in all of Hawaii.

Favorite Memory: In 2003 I visited Oahu with my then-boyfriend- now-hubby, Steve. It was one of our first “real” vacations as a couple and we had a blast. We were on a budget but it didn’t matter – we ate splendidly over the course of a week because we sought out the local-style places where plate lunches were only 7 bucks and oftentimes we would share because the portions were so big. We splurged at the end of that vacation with a dinner at the 5-star restaurant, Alan Wong’s. It was because of that restaurant that I fell in love with Hawaiian Regional Cuisine and now consider it one of my favorite restaurants ever.

Visit my Yelp list for our Oahu restaurant and activity reviews.

Visit our Oahu trip reports here (2012), here (2013), and here (2015)




  • # of times visited: 4 (once as a kid, and three times in the past 5 years)
  • most recent visit: 10 days over Oct-Nov 2013 to celebrate our 5th anniversary
  • next visit: unknown

At the Marriott Wailea…take a picture with your phone…post on facebook or other social media…instantly make everyone jealous

Maui is probably the ideal honeymoon location. By far, I have gotten the most questions about Maui because EVERYONE I know wants to or has honeymooned/vacationed there over the years. I think it’s because Maui has a nice blend of things people want on their honeymoon/vacation – luxurious beach-front resorts, great restaurants, curated activities, fabulous beaches, some shopping, a little nightlife, and a lot of romance. In addition to all the honeymooners, you will also find a lot of families here. 2 of my sisters, 4 co-workers, countless friends, and friends of friends have asked me about Maui and for good reason – Maui is just a really great overall introduction to Hawaii. There are activities which everyone does – The exciting Road to Hana, sunrise or sunset at the summit of Haleakala, visits to Blackrock at Kaanapali Beach and Big Beach in Makena, a luau, a ton of fantastic snorkeling, whale-watching (seasonal), walking down Front Street in Lahaina, and eating all over the island!

The black sand beach on the Road to Hana

Best Island for: honeymooners, romantic getaways, biking down a volcano, family trips, scenic drives, luxury resorts, fine dining including a handful of celebrity chefs (Sheldon Simeon of Top Chef can i buy propecia online fame is one of the latest to open a restaurant there)

Known for: Haleakala for sunrise or sunset, beautiful sun-drenched beaches, the adventurous Road to Hana with waterfalls and lush tropical scenery, scenic Upcountry with several farms (the farm-to-table foodie movement is big here), Mama’s Fish House restaurant (consistently voted one of the best restaurants in the USA), fantastic snorkeling, watching the windsurfers in Paia, the posh landscaped Wailea area, and bountiful beach-y resort area of Kaanapali.

Favorite Memory: The day after we arrived on Maui in 2009, we did the Road to Hana in a convertible. It was both scary and exhilarating at the same time to drive next to cliffs with a steep drop and no guard rail, over one-lane bridges…a wrong turn and we’d be plunging down…luckily we did not and had a very lovely vacation instead.

Some things to note: There are a few differing opinions that Maui is considered the “least” Hawaiian island because of the huge influx of expensive hotels, restaurants, and tourist-culture. You will see this happening on every island to an extent but Maui tends to cater to the luxury crowd hence the over-development of some of the beach-front areas like Kaanapali and Kihei/Wailea. I do agree with this somewhat but I also feel that Maui is a place where hidden gems are prevalent and there is a strong local culture filled with delicious (and cheap!) local foods if you know where to look! Even if you’re on a budget I think Maui is very doable.

It’s not only fancy hotel restaurants here, visit my list on some of the best Cheap Eats on Maui Part 1, Part 2, Part 3.

Visit our Maui Yelp list to see our restaurant reviews and activities.

Visit our Maui Trip reports here (2009) and here (2013).




  • # of times visited: 2
  • most recent visit: February 2015
  • next visit: unknown

I was utterly spellbound by Kauai’s natural beauty. Many people LOVE Kauai and only visit Kauai out of all the Hawaiian Islands because it really resonates with people looking to get away from it all and experience nature at its finest.

Sunrise from Kapa’a – amazing

If you were to do a helicopter tour in Hawaii I suggest saving it for Kauai. It is spectacular, and easily one of my most favorite things I’ve ever done in my life. The Napali coast is one of Nat Geo’s natural wonders of the world and it is easy to see why:

Kauai coastline from a helicopter – breathtaking

Kauai also has it’s share of luxury resorts…the St. Regis Princeville and the Grand Hyatt Poipu are on my wishlist of splurge resorts. Kauai also has some of the most beautiful beaches ever. Everyone loves the lush and beautiful north shore (including the quaint town of Hanalei) – and the sunny and fun south Poipu area. There are some parts of Kauai which are not accessible by car – so helicopter or boat are ideal. However, you can attempt the 11-mile Kalalau trail along the Napali coast…something which I may never do since I don’t like to hike. Helicopter please!

Kauai also has it’s share of good eats, with Hawaii restaurants, Roy’s and Merriman’s having outposts there. Hamura’s Saimin is an old-time James Beard historical landmark of tasty noodle soups, and there are lots of restaurants which look like they haven’t changed in decades (and I hope it stays that way). Although we’ve had good food on our trip to Kauai, there is definitely less selection than on other islands like Oahu.

Best Island for: honeymooners, romantic getaways, taking it easy, getting away from it all, nature-seekers, hikers, rustic adventurers, scenic lookouts, old Hawaii feel.

Known for: Napali Coast, Waimea Canyon, north shore, beaches such as the lovely “Tunnels”, the towns of Hanalei and Poipu, nature at it’s best!

Favorite Memory: The helicopter tour of a lifetime on Blue Hawaiian helicopter’s A-Star choppers. Also spotting a monk seal during sunrise on the beach in Kapa’a, it was just lying there sleeping, with no one around! In fact, we saw several of them on Kauai and we haven’t seen them on any other island.

Visit our Kauai Yelp list for restaurant reviews and activities.

Visit some photo trip reports from 2010 here and here. Visit my most recent trip report to Kauai in February 2015.




  • # of times visited: 2
  • most recent visit: 1 week with my family in June 2012
  • next visit: unknown

The Big Island or, Hawai’i, is an adventure-seeker’s delight. There are so many things to do on the Big Island, and with all but 2 of the world’s climate zones on one island, there is definitely something to do for everyone. The Big Island is b-i-g, hence the name,, it sometimes takes a few hours to drive to your destination which can be on the other side of the island, so be prepared for a lot of time spent in the car. A must-do is a visit to the active Kilauea Volcano at Hawaii Volcanoes National Park. It is amazing and probably the only time I’ll ever be that close to an active volcano!

Kilauea as seen from a helicopter

The Big Island also has some fantastic snorkeling and beaches. I love visiting the Punalu’u Black Sand beach because you’re almost guaranteed a giant turtle sighting on it’s ebony-colored sand. The food on the Big Island is also really great because a lot of the produce you’re eating was grown right on the island! Also Big Island beef is sourced from the cattle ranches up in Waimea, and it has great flavor. The resorts on the Kohala Coast are world-renown. The Four Seasons Hualalai is on my luxury hotel bucket list. For now though, I definitely enjoy renting a condo so we can cook and eat the fresh produce we buy at the farmers’ markets! Oh and don’t forget to get a taste and a tour from one of the fabulous Kona coffee farms!

The posh looking sunset from the Fairmont Orchid on the sunny and dry Kohala Coast

Best Island for: adventurers. nature-seekers, sprawling resorts, snorkeling, scenic drives, those in search of farm-fresh food, night snorkeling with Manta Rays

Known for: Kilauea Volcano, Waipio Valley, lush green local feel of Hilo, dry and sunny Kohala coast, farm-to-table foods, snorkeling around Captain cook monument, Kona coffee, South point (Ka Le) – southernmost point of the USA

Favorite Memory: Visiting the volcano and having my mom all freaked out that it was going to erupt at any second!

Visit our Yelp List for the Big Island for restaurant reviews and activities.

Visit our family trip report to Oahu and the Big Island here.


I’ve only covered a few things on this page, but I hope that gives you a slight flavor of the islands. If you have any helpful advice, please leave them in the comments section. Mahalo!!


February 15, 2014 - 4:47 pm

Josh - Thank you for all of this great information!!

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