Planning a Hawaiian Vacation: Oahu vs Maui

Beach sunset at The Kahala

Last updated: September 30, 2019

Hawaii is one of those destinations that tops the bucket list of many travelers and most first-time visitors end up going to Oahu or Maui. While you can’t really go wrong with either island, they each have pros and cons depending on your expectations. In this post, we will compare each island and share considerations to help you decide which one you will enjoy visiting the most.

On a budget: Oahu

With the most number of flights and inventory of accommodations from hotels to short-term rentals, Oahu tends to be more affordable than Maui. In addition, once you arrive in Oahu, you can get by without a car rental because Uber/Lyft are available, there is a public bus service and if you’re staying in Waikiki, most things are walkable or you can bike.  Waikiki also feels like a large enough city and has a variety of dining options so that you’re not forced to eat the expensive food at the hotel.

Landing at OGG - Kahului Airport
Landing at OGG – Kahului Airport

There are a number of domestic and international airlines that service Maui and so flight deals are easy enough to come by but to see and make the most of Maui, you will need to rent a car and unless you’re staying at a vacation rental, you’ll need to spend more on meals as there are less cheap food options available. There are lots of hotels and short-term vacation rentals available and you can find deals but Maui tends to be more exclusive and so the prices tend to be higher. Kihei is the budget friendly area on the island of Maui.

Tip: If you are booking a hotel, consider that most charge a $20+ resort fee above and beyond the room rate. Sometimes, the resort fee doesn’t always include parking so you can end up paying $80 extra per day at some resorts. Find out about the resort fee and cost of parking (if renting a car).

The Hawaiian Experience: Maui

The Honolulu/Waikiki area is a large urban area with tall skyscrapers and tends to get crowded and have an almost Miami Beach/Las Vegas vibe and this can be off-putting to people who have a different image of Hawaii. Homelessness and graffiti are also more common than one might expect and this is also not part of the picture perfect Hawaiian postcard people imagine.  It is possible to escape this scene and have a more Hawaiian experience but many don’t and complain about how terrible Hawaii is.

Max on Waikiki Beach
Max on Waikiki Beach

Maui on the other hand doesn’t have a major urban area and has coastline dotted with palm trees and views of mountains and nature. With pockets of resort areas that are primarily low-rise buildings that cannot be higher than 170 feet. For comparison, the tallest building on Oahu is 450 feet tall and many large hotels are close to 400 feet tall. The roads are also smaller on Maui as there are no freeways which is good and bad as there are also traffic problems at times. In Maui, it feels as though you are exploring and connecting with the island as opposed to just walking down busy streets filled with designer stores and tacky shops in Waikiki. Again, there are gems in Waikiki/Honolulu but they’re not as accessible and it’s definitely not as pristine as Maui.

Tip: To escape the more crowded parts of Waikiki Beach, head to Sans Souci beach where you won’t hear the horns of catamarans ushering you out their way every 10 minutes.

Beaches: Both Islands

Each island has really nice beaches for activities all types. Lanikai Beach on Oahu is in our top 10 favorite beaches of all times, and its neighbor beach Kailua, is a good place to kayak. On Maui, our favorite beach is Wailea as the waves at Ka’anapali Beach and Big Beach can be too big for leisurely swims. Even if it is crowded, it is enjoyable to swim, surf, and stand-up paddle board on Waikiki Beach and the lagoons in the Ko’Olina resort area are perfect for young children and beginner swimmers.

Floating at Lanikai Beach
Floating at Lanikai Beach
Jason on Wailea Beach at sunset
Jason on Wailea Beach at sunset

Tip: It can be difficult to find parking at Wailea beach so message us to find out about our secret parking spot.

Culture and Activities: Both Islands

History buffs will want to visit Oahu due to the Pearl Harbor Memorial, Diamond Head, and the Polynesian Centre and those looking for more nature related activities will want to visit Maui’s Haleakalā National Park to see the volcano, drive down the road to Hana, and hike and snorkel near La Perouse Bay to name a few suggestions. You can also experience nature on Oahu by hiking the Lanikai Pill Box and the Makapuu Lighthouse.

View from the top of Diamond Head
View from the top of Diamond Head

Tip: If you are not renting a car on Oahu, consider buying tickets for the Waikiki Trolley to get away from Waikiki.

Surfing: Both Islands

There are beginner surfing options on both islands. We found it easy and more accessible to rent on Waikiki Beach on Oahu because you can just walk by the beach and chose a company. In Maui, you may need to pre-book and carry your gear to the beach.

View from our room at the Sheraton Waikiki
View from our room at the Sheraton Waikiki

While it does get crowded, beginners and those who want easier waves to ride will enjoy the soft and gentle rolling waves on Waikiki Beach. Those who want to watch professional surfing, will want to visit the North Shore where waves often hit 20+ feet.

Beginners looking to surf will want to head to Lahaina or Kihei on the island of Maui. “The Breakwall” in Lahaina and “The Cove” in Kihei are two popular spots where you can rent gear and take lessons pretty easily.

Tip: Depending on the location, surfing can be better during low or high tide, so ask around and plan to surf when conditions are optimal.

Snorkeling/Scuba: Both islands but Maui for Scuba

If you’re looking to snorkel, both Oahu and Maui have options: from the famous Hanauma Bay in Oahu to Molokini in Maui, there are options for everyone. That being said, Maui has a slight advantage because you can snorkel easy from Wailea Beach and Black Rock on Ka’napali. On Oahu, snorkeling from a beach is not as easy.

As for scuba, Maui has more options according to this website:

View of Hanauma Bay from the top of Koko Crater
View of Hanauma Bay from the top of Koko Crater

Dining Scene: Both Islands

It really depends what you’re looking for here. We have favorite places to eat on both islands but there are definitely more options on Oahu in Waikiki/Honolulu than on Maui. Maui’s dining scene tends to be more concentrated in the resort areas for dining on site so unless you have a car and seek out things, they’re not as accessible. Since we always rent a car and don’t often on resort, we visit our favorite spots on Maui:

With a little bit of research, you will be able to find good options at various price points on both islands if you’re not planning on cooking your entire vacation.

Food hall in Waikiki
Food hall in Waikiki

In Waikiki, various food halls/food courts have recently opened offering cheaper options for lunch and early dinner.

Banan in a papaya boat with toppings
Banan on Oahu in a papaya boat with toppings
Happy hour at Monkeypod in Wailea; 1/2 appies
Happy hour at Monkeypod in Wailea; 1/2 appies
The Mopsy's kahlua pork pizza at Flatbread Co in Paia
The Mopsy’s kahlua pork pizza at Flatbread Co in Paia

Tip: For local and budget-friendly dining options on Oahu, check out our blog post – Where to Eat and Drink on Oahu in Hawaii.

Best Weather: Kihei/Wailea on Maui and Waikiki and Kapolei on Oahu

The further north-west you go in Maui, the higher the probability of precipitation is. We’ve stayed in Ka’anapali, just north of Lahaina numerous times and have experienced rain more often than we would like, especially during rainier season. Since we rent a car, it’s easy for us to drive south to Kihei and Wailea, where it’s often sunny when it’s raining up north.

Ka'anapali Beach on a rainy day
Ka’anapali Beach on a rainy day

On Oahu, it’s easy to fall in love with the scenic beaches and less busy atmosphere on the east side of the island in Kailua, Lanikai, and Kaneohe but it tends to rain a lot more here than on the West side where Waikiki/Honolulu and Kapolei are located. If you rent a car, it’s easy to visit each coast when the weather is optimal.

Compared to Caribbean destinations, the Hawaiian Islands are less predictable when it comes to weather. Once, during our April visit, it rained every day and it was too cold to enjoy the beach in Kailua. If there is room in your suitcase, pack a sweater and rain jacket!

Tip: For the best chances of good weather, plan your visit outside of rainy season and choose the less rainy parts of the island.

For Family Vacations – Maui

You can find options suitable options on both islands for family vacations but Maui’s resort setting is definitely more appealing. If you can afford it, the Grand Wailea, A Waldorf Astoria resort on Maui is a great place to stay due to the extensive water park on site. We stayed at the Grand Wailea as part of our honeymoon and had a blast going down the water slides and appreciated the easy access to Wailea Beach.  On Oahu, the Hilton Hawaiian Village is a good resort choice for families.

Saying goodbye to my welcome lei in Lahaina as we leave
Saying goodbye to my welcome lei in Lahaina as we leave

Tip: For ideas on where to stay on Oahu, have a look at our blog post – Where to Stay on Oahu: Waikiki and Beyond.

For a Wedding – Maui

Depending on what type of wedding you want and your budget, Maui would offer a nicer setting. It just seems that Oahu is a wedding factory with brides everywhere all the time taking photos with visitors like us accidentally photobombing. When we decided to invite our immediate family to celebrate our wedding and anniversary, we ended up choosing Maui because we felt they would enjoy it the most and to this day, they still talk about how much of a beautiful and unique place it was. As much as we enjoy Oahu, we don’t think it would have provided the same experience and atmosphere for our family, most of whom were first-time visitors to Hawaii.

Hawaiian Sunset
Sunset at Monkeypod in Wailea at our anniversary/wedding dinner

Tip: Plan your wedding during shoulder season in mid-November or early December for better deals, more availability, and decent weather. 


As you can see, both Oahu and Maui offer similar things but in a very different setting. There is so much more we could share in this post as we’ve barely scratched the surface when it comes to each islands pros and cons. We’ve had so much throughout the years visiting Oahu and Maui and appreciate each trip and place for very different reasons as we have come to know what to expect and what to seek out. If you can visit both islands or more on your trip, that would be the best otherwise we recommend that first-time visitors go to Maui first for a more picturesque Hawaiian experience. If you plan on visiting Oahu and Maui, go to Oahu first due to how much busier it is and then spend the last few days relaxing in Maui where the pace of things is a lot slower and less crowded.

View from the Four Season Ko'olina
View from the Four Seasons Ko’olina

You really can’t go wrong when you visit Hawaii because it’s a beautiful place, it’s clean, the infrastructure is good, the people are friendly, and it truly is, the closest to paradise on earth, at least to us! For more information, message us directly as we love to talk about Hawaii and our love of these islands with others.

Have you been to either island? If so, which one did you enjoy more? Did your visit meet your expectations? If you haven’t visited either island, which one do you want to visit after reading this post?

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