Hawai’i Dreamin’ | Travel Guide to Oahu

TRAVEL GUIDE TO OAHU, HAWAI’I: 


Now, granted, we squeezed exploring all of Oahu into just shy of a week! So, we still have a bunch of places we want to see but this was a great start. Since our last trip about five years ago, we haven’t had the chance to explore Oahu but since moving to the Big Island, our interest has sparked again! Sure enough, this trip was so much better than our first! We were able to both adventure and relax! Totally worth an extended weekend stay. We loved every moment + I wanted to share my insight on how to plan your next trip!

Arvo + Paiko | Coffee Shop + Plant Store

This was the cutest place! We stopped here right when we got off our early morning flight. The coffee was yummy (and much needed), the toasts were all scrumptious – but the vibe of the place – that’s what got me! It was 50% plant shop, 50% coffee shop and 100% rad. Plus, what better way to get your day started than a smiley face on your latte?!

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Royal Hawaiian | Honolulu Hotel

We stayed the first two nights at The Royal Hawaiian aka The Pink Palace of the Pacific! It was absolutely fantastic and everything I had dreamed of.  Thank you to Royal Hawaiian for graciously hosting us – you can see more of their property at @royal_hawaiian! If you’re into old hawaiian charm, this historic hotel is the one for you. It had expansive views of Waikiki Beach, delicious food + cocktails and the best atmosphere around! Their staff was accommodating to boot + we loved our stay here.

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Lanikai Pillbox Hike | Oahu Hike

100% worth the beeping alarm clock at 5AM! This gorgeous, scenic hike is ranked intermediate because of the steady steep incline right from the start of the trail head. But c’mon! LOOK AT THAT VIEW!

Throughout the climb, you’ll be rewarded with striking views of the Mokulua Islands, Kailua Beach + Lanikai Beach! In the distance, you can also see Kaneohe Bay, Chinaman’s Hat, Waimanalo Bay + the Makapu’u Lighthouse. It’s truly a bird’s eye view!

The Lanikai Pillbox Hike is a moderate 1 hour (possibly 90 minute, depending how far you decide to go) round trip. You can easily reach the first old military bunker (aka ‘pillbox’) in about 20-30 minutes. From that point, it’s another 10 minute walk along the top ridge to the second pillbox (less crowded, definitely go here!).  Most hikers turn around at this point + travel back down the Kaiwa Ridge Trail although there is a third pillbox beyond the first two if you’re feeling adventurous!

For directions + specifics, click here.

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Paddle Boarding on North Shore | Oahu Activities

If you go to Oahu, you MUST explore the North Shore. Haleiwa is the most darling surf town that gives you a more authentic dose of the ‘Hawaii Life’ – we felt much more at home on this side of the island! After poking around the town a bit + getting some early dinner, we rented some paddle boards from Salt N Sea in Haleiwa. We spent about an hour taking in the sunset with my mom on the beautiful water! It was a gorgeous, peaceful way to spend the evening and I definitely recommend it!

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The Modern Honolulu | Honolulu Hotel

The Modern Honolulu is the definition of luxury! Wow-o-wow. No detail was forgotten at this Waikiki Resort + the entire property was pristine. We were greeted with complimentary beverages and taken up to our dreamy, calming room!

We loved their Friends with Benefits Program – by booking direct through the hotel, you receive great perks like free valet for 1 car, welcome amenity, discounts on spa treatments, discounts on daybed experience, etc. on top of a daily hotel credit (up to $150 per day) to be spent anywhere on-property. You don’t have to have a prior stay and the benefits begin when you arrive! It’s a great program.

The rooms + bathrooms were AMAZING and totally had my minimalist, interior-design-loving heart booming! We had a delightful dinner at their restaurant, Passageway, and spent the following day lounging in one of their day beds.
Glorious, much-needed R+R. (P.S. you must try the Frozen Coconut Mojito – heavenly!)

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Lanikai Beach + Kailua Beach + Waimanalo Beach | Oahu Beaches

These beaches are stunning! Absolutely beautiful white sands, talcum powder soft + clear, sparkling aqua waters. They tend to be tourist hot spots (but locals also love them) so make sure to get there early if you want a bit less busy of a scene.

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(and yes, of course we brought MANGO along with us to the beach! More on this vintage VW Bus below!☟)

Sunset Sail | Oahu Activity 

We loved sailing off of Waikiki and getting a whole different perspective of the city! We went out with Manakai Catamaran via the Activiter App! Read more about our experience here. 

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The Surfjack Hotel + Swim Club (Snag a Coffee at Olive & Oliver) | Oahu Hotels + Coffee Shops

We stopped into The Surfjack and loved how well curated everything was! The pool’s floor reads “Wish You Were Here!” (which right now, I do!) and the coffee was so yummy at Olive & Oliver. I totally recommend a stop in here (or to stay here)!

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Hana Hou Campers + Maelekahana Beach Camping | Off The Beaten Path Oahu Lodging

Since we enjoyed every part of this trip, it’s really hard to say that any individual part was “the highlight” BUT touring the island and camping on the beach in a vintage VW bus . . . It might have taken the cake! (If you ask Aaron, he would definitely say it took the cake)

This beauty is named MANGO (as seen on the license plate) because the owner totally redid the interior of the bus in reclaimed wood from an old mango tree! It was such a stellar experience driving this bus around the island together, taking backroads + going the slower route to simply just explore.We chose to camp on the beach of Maelekahana, steps from the waves, thanks to the recommendation of Brett (the owner of Hana Hou Campers) who was more than helpful when it came to finding beaches to camp on, etc.

We would ABSOLUTELY recommend staying with Hana Hou Campers if you go to Oahu!

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Lai’e Beach Swing | Must-Sees on Oahu

This darling little spot on the side of the road is the perfect place to stop, be still + soak in the moment. It’s kind of an island secret + we just had to keep a sharp eye out when looking for it! In keeping with tradition, I will just tell you to closely watch your right side as you head up Kamehameha Highway as you’re approaching Lai’e! If you find this spot from my blogpost, be sure to post on IG + tag me!! Happy hunting ;)

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Crouching Lion Hike | Oahu Hike

When you google “Crouching Lion Hike” you may see that it’s on the Top 5 Most Dangerous list on Oahu. . . At least, that’s what the locals we ran into told us. BUT don’t let that make you scroll past this! Instead, think about going on the Crouching Lion MINI Hike! This hike is difficult at points but the view from the top are SO WORTH IT!

Here’s a blogpost about how to make it to the top: Crouching Lion MINI Hike

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All in all, our second go of Oahu was AWESOME (and so much better)! It goes to show you, with a little research and some local insider knowledge – you truly do get a better experience when you travel!

What are YOUR favorite spots on Oahu?

Keep an eye out for my upcoming post about how to plan your next vacation entirely from Instagram!
Until then, happy wanderlusting! xoxo 

Author: elanaloo

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