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Small mom-and-pop Hawaiian shops sit nestled between restaurants on the vintage sidewalks of Kapahulu Avenue. After perusing impressive collections of aloha shirts at the antique shops, stop by Diamond Head Grill for delicious island confections, Uncle Bo’s for kalua pork and dumplings, Leonard’s Bakery for a warm malasada pastry, or – if it’s a Saturday – the Waikiki Specialty Farmers’ Market for fresh island produce.

Eat: Rainbow Drive Inn, Leonard's Bakery, Side Street Inn

Drink: Growler Hawaii, Uncle Bo's, Hula's Bar & Lei Stand

Built on the side of Oahu’s Diamond Head volcanic ridge, quirky Kaimuki is marked by historic hillside homes, indie coffee shops, and specialty boutiques. Eateries such as Town offer delicious farm-to-table fare, while Kaimuki Superette’s menu features specialty salads and sandwiches, and Koko Head Cafe gives comfort food a Hawaiian flare. Check out Juicy Brew for environmentally-sustainable coffees, juices, and vegan treats, or swing by da Shop. for the community’s favorite independent book store.

Eat: Okata Bento, Aloha Crepes, Koko Head Cafe

Drink: Talk Kaimuki, The Surfing Pig Hawaii, Blind Ox

The up-and-coming Kakaako art district has been named “Honolulu’s hippest neighborhood”, and an outing there will surely clarify how it earned that title. What used to be an industrial block of abandoned warehouses was transformed by local street artists, using the walls of Kakaako’s buildings as a canvas to create the open-air POW! WOW! Mural Art gallery. Stylish enterprises soon appeared, including the gourmet food stalls, urban retail stores, and juice bars of SALT at Our Kakaako.

Eat: Moku Kitchen, Highway Inn Kakaako, Piggy Smalls

Drink: Bevy, Waikiki Brewing Company

Wellness: The Hang Out AntiGravity Fitness & Yoga

Located on the North Shore of Oahu, Haleiwa is a must-visit destination for anyone traveling to the island. This charming surf town offers a unique blend of Hawaiian culture, laid-back vibes, and breathtaking natural scenery. Visitors can explore the boutique shops, local art galleries, and restaurants that offer delicious multicultural cuisine. Haleiwa is also known for its world-class surf breaks, attracting surfers from all over the globe.

Eat: Haleiwa Joe's, Rajanee Thai Haleiwa, Banzai Sushi Bar

Drink: Uncle Bo's Haleiwa, Maya's Tapas and Wine