Bucketlist-Worthy Oahu, Hawaii

Advisor - Brit Healey
Curated By

Brit Healey

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  • USA

  • Hawai'i

  • Oahu

  • Active Travel

  • Adventure Travel

  • Beaches

  • Domestic Travel

  • Tropical Vacations

  • Hiking

  • Island

  • Shopping

Beach in Oahu, Hawaii
Curator’s statement

Modern-day Hawaii in 2022 is a heavenly destination for natural exploration, hiking and beaches. On the other hand, it is also consistently turning into a more metropolitan city, too – advancing more and more in the culinary and hospitality scene. Here you can have a cultural, adventurous and shopping experience all-in-one, making it a perfect destination for all kinds of travelers looking to disconnect in the tropical capital of Hawaii.

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Where to stay in Oahu, Hawaii

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The Beach Waikiki Boutique Hostel

It’s all about communing with your fellow traveler at this clean and comfy hostel just a block from Waikiki Beach.

Surfjack Hotel & Swim Club

From the handcrafted, mid-century-inspired coffee tables to the carefully curated artwork sourced from local artists to the historical nods woven into each room, the heritage of Waikiki comes to life in every room at the Surfjack.

The Laylow, Autograph Collection

Sunny interiors, mid-century accents and a centerpiece pool attract a hip crowd to this Waikiki favorite.

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Advisor - Brit Healey

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Things to do in Oahu, Hawaii

Hiking in Oahu, Hawaii

Hiking & Adventure

When on Oahu, hiking is an absolute must for the best views in town. Pillbox Hike at sunrise or sunset will bring some of the best views on the island. Consider hiking the Koko Crater Trail, a  challenging two mile out-and-back hike. The incline is no joke. This hike is strenuous, but breathtaking and better than Diamond Head in my opinion. Finally, Mermaid Cave is a stunning hidden gem water cave. Admire it from above or explore at your own risk. Make sure to check conditions in advance as it can be potentially dangerous. 

Are you feeling more like swimming, snorkeling and kayaking? Head out to Lanikai and Kailua Beach in Kailua. Go for the white sandy beaches. It's like a whole other world compared to Waikiki. Book a transparent kayak from Hawaiian Recreations.


The Ho’omaluhia Botanical Garden is one of the most picturesque and peaceful spots on the island and a must for any plant-lover. It's also the perfect backdrop for a new profile picture. When you’re done there, pack a picnic and spend a few hours at one of the beaches on the Ko Olina Coastline.


Stop by the Byodo-In Temple for a glimpse at local culture and a chance to reflect. The Kualoa Ranch Private Nature Reserve is another excellent destination. If you are a huge movie buff and lush landscape lover, spending a few hours at Kualoa Ranch will make your trip memorable.


Save room in your suitcase for all the stuff you want to buy and bring back home! Buy leis to take home from M.P. Lei Shop. Favorite local boutiques and shops include Paiko, Hound and Quail, MORI, GINGER13, Manuheali'i, no. 808, Olive Boutique on Kailua, HiLife, Salvage Public and FIGHTING EEL


Try a farmer's market to taste the most delicious tropical fruits and specialty snacks. The KCC Farmers Market and Kailua Farmers Market are two spots to hit up. Aloha Stadium Swap Meet & Marketplace is Hawaii’s largest open-air market. Stop by Art + Flea too for a fun spot to check out local artists, vendors and creatives that happen monthly. Great for local gifts.

Day Trips 

Rent a car and drive to the North Shore. On the way there, drive down the super scenic Pali Highway, which goes from Honolulu to Kailua.

Check out Haleiwa and eat all you can from the local food trucks: North Shore Tacos, Giovanni's Shrimp Truck, Fumi's Kahuku Shrimp Trucks, Impossibles Pizza, Leonard's Malasada Truck, Mayjah Grings, Mike's Huli-Huli Chicken, Haleiwa Bowls Truck and more!

Eat & drink in Oahu, Hawaii

Hawaiian food in Oahu

Breakfast & Brunch 

Breadshop: A craft bakery located in Kaimuki. Order online, on Tock, for pickup.

Malasadas at Leonard's Bakery. Go in the late morning on a weekday to avoid huge lines.

Podmore: Created by the same chefs behind Senia. A full English breakfast is a must here.

BAR MAZE:  Has a once in a lifetime omakase experience.


The Farm Cafe at Kahuku Farms: North Shore lunch spot. Enjoy walking around the farm. Their fried banana bread is highly recommended.

Waiahole Poi Factory: The secret is out that this spot has the best Hawaiian comfort food.

Ted's Bakery: Year after year, Ted’s Bakery makes Hawaii's Best list. Try the Chocolate Haupia Pie. 


Sushi Sho: By Renowned chef Keiji Nakazawa at The Ritz Carlton, this place requires online ordering on Tock for pick up. 

Heiho House: A 10 course prix fixe menu by Chef Aaron Lopez who is shaking up the industry. A fusion of art and food unlike any other.

Senia: Award-winning buzzy restaurant serving regional American cuisine, perfect for every occasion. 


Go bar hopping in Chinatown and hit up the following bars: Bar 35, Bar Leather Apron, Proof Social Club and Skull Crown Trading Co. It's an entirely different scene compared to Waikiki.

Brix and Stones: Hawaii's only indoor cigar lounge. It also has high-quality wine and spirits.

Advisor - Brit Healey

Travel Advisor

Brit Healey

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