Design Milk Travels to… Honolulu, Hawaii

There’s little need to ever sell the idea of a getaway to any of the islands of Hawaii. The epitome of an ideal vacation destination, Hawaii is rest and relaxation manifested as an archipelago of eight major islands. The mix of tropical landscape, picturesque warm waters, luxury resorts, and the ever present aloha spirit permeating Hawaiian culture makes visiting Hawaii the Shift-Control-Option of vacation destinations. Although my own heart always longs to return to the lush island of Kauai, it’s Oahu’s Honolulu – the capital and largest city of the U.S. state of Hawaii – which admittedly offers the greatest balance between luxe resort amenities, city life, a diverse dining landscape, laid-back island vibes, and a surprising amount of design culture and history dotting its city limits. The following Design Milk guide is here to help you make your first or tenth visit to Oahu your best one yet.


The Surfjack Hotel & Swim Club: Tucked amongst the towering and impersonal resorts lining Waikiki Beach in the heart of Honolulu is the surprisingly intimate, yet always lively Surfjack Hotel & Swim Club. The Surfjack is like finding your very own private party; guests are young and beautiful, and there’s a fair chance some sort of festivities will be happening during your stay (in our case, a magazine launch in the evening, a local designers’ craft fare in the morning). The rooms are modest, but decorated in a sophisticated island-midcentury modern style that makes returning to the room after a long day under the sun a welcome refuge. Look out your balcony and a highly Instagrammable pool presents a clear reminder your stay is likely to elicit a high degree of FOMO amongst others once shared. On the ground level the hotel’s own Mahina & Sun’s serves up a delicious menu of organic cuisine and cocktails, while the adjacent Olive and Oliver boutique sells a mix of island-tinged modern design wares, clothing, and small carry-on friendly gifts made by Hawaiian designers to bring back home.

Photo: The Modern Honolulu

The Modern Honolulu: If you’re looking for more of a traditional large scale island resort to bask around the pool, but one catering to a modern aesthetic, The Modern Honolulu is a fitting hotel destination decorated with enough thoughtful graphical and textural finishes to keep your stay playfully personal. Every guest is welcomed by “Wrecktangle”, an art installation by artist Herbie Fletcher capturing the broken jagged remnants of genuine surfboards broken while riding atop and within the massive tubes at Pipeline.

Despite the dramatic introduction, your stay will undoubtedly be more relaxing. Rooms here are minimalist and mostly white, sparse in a good way that allows for swimwear to be thoughtlessly tossed off after a long day basking at the beach and exchanged for casual evening wear before heading back out into Honolulu’s nightlife. Every room is accessorized with its very own ukelele to help guests strum their own rendition of island vibes.

Photo: The Laylow

Other notable hotels: The Laylow \\\ Vive Hotel Waikiki \\\ Moana Surfrider, A Westin Resort & Spa (ideal if you want to spill out from your room right onto Waikiki Beach) \\\ Stay Hotel Waikiki \\\ Ritz-Carlton Residences Waikiki (the luxe option) \\\ Halekulani (especially recommended for their half-day Art and Architecture tour)


Let’s be realistic, when in Hawaii most of your time is going to be spent along the beach swimming, snorkeling, and basking in the glorious warmth of the tropical sun. That said, there are few spots where design, art, and architecture might pull you away from the beach towel lifestyle.

Photos: Interior stairway and living room of Liljestrand House, included on the National Register of Historic Places.

The Liljestrand House Honolulu Hawaii: Honolulu isn’t necessarily the first place that comes to mind as an architectural destination, but that’s what makes a visit to the Liljestrand House the sort of special surprise that delights the design-minded into recognizing the time capsule of residential gems dotting the island. Designed by architect Vladimir Ossipoff in 1952, the elegant harmonization between landscape and structure have earned the home praise within the pages of Atomic Ranch, Western Interiors and Design, on the cover of Metropolis, and in the book The Hawaiian House Now.

Both sides shown of Baba’s Door, side door of Spalding House, by Tony Berlant, collaged metal, 1988.

The Spalding House: The Honolulu Museum of Art’s secondary site features galleries of art, a permanent installation of David Hockney’s L’Enfant et les sortilèges, a café, pop-up gift shop, and sculpture-filled gardens overlooking Diamond Head and Honolulu. Admission is a great deal since it permits entry into both locations.

Photo: Exotic pool at Doris Duke’s estate Shangri La.

Shangri La Museum of Islamic Art, Culture & Design: Hopefully by the time of your visit this gem currently going through renovations will be reopened for public tours. The home of American heiress and philanthropist Doris Duke (1912-1993), the residence was transformed into a museum in 2002, displaying Duke’s collection of art and design pieces collected over the years of her extensive travels throughout North Africa, the Middle East, and South Asia and reflects architectural traditions from India, Iran, Morocco and Syria. The permanent collection features over 4,000 objects that include more than 2,500 objects from Spain, Morocco, Egypt, Syria, Iran, Central Asia, India and parts of Southeast Asia.

Photo: Sean Connelly, Thatch Assembly with Rocks (2060s), 2017 ; Honolulu Biennial Foundation

Honolulu Biennial: Schedule your visit accordingly (in 2019, so you have some time to plan ahead of time) and you can be amongst only the second group to attend the second Honolulu Biennial. The inaugural 2017 Biennial was curated by Fukui Nanjo, Director of the Mori Art Museum in Tokyo and former commissioner of the Japan Pavilion at the Venice Biennale (1997) and commissioner at the Taipei Biennale, with artists from Hawaii, the Pacific Islands, Asia, North America, Australia, and New Zealand put at the forefront. We expect the followup to improve upon the foundation set by 2017’s show.



IN4MATION: The spot to get outfitted with streetwear, skate and surfwear appropriate for island living. Their in-house brand of tees and hats sporting the “HI” logo beat out any other touristy-themed island wear in our book.

Photo: Olive & Oliver

Olive & Oliver: The Surfjack Hotel & Swim Club’s very own aforementioned boutique proved to be one of our the friendliest and best stocked boutiques for gifts. With two additional locations – one for men (Oliver), another for women (Olive) – fashionable local brands are complemented by some keen curated homewares and accessories from the mainland, like ceramics from LA’s Kat Hutter & Roger Lee.

Photo: Roberta Oaks, Honolulu

Roberta Oaks: No visit to Honolulu is truly complete without a visit to Roberta Oaks, a boutique decorated with vintage and midcentury decorative pieces that has become synonymous with the revitalization of the Hawaiian shirts as truly modern and stylish pieces worthy of integrating into your everyday wardrobe upon returning to wherever you call home. Designed and handmade in Honolulu, Roberta Oaks is a wonderfully welcoming hostess of her namesake shop; she’ll do everything to help you find the perfect shirt or dress that will undoubtedly result in envious and knowing glances amongst the growing number of Roberta Oaks converts.

Photo: Owens & Co

Owens & Co: The ampersand in the shop’s name makes it clear this shop is of the trendy variety. And indeed it’s wares reflect a contemporary eye for the beautiful, particularly their stock of most gift-worthy graphical Cultivate Hawaii MAKAI Tea Towels, each design inspired by the very forces that shaped the islands.

Sig on Smith: Imagine Undefeated, but with sandals switched out for sneakers, colorful aloha shirts instead of streetwear. Sig Zane Designs has been around since 1985, but they’ve remained defiantly relevant with modern interpretations of island motifs that honor the past while represent the present.


Honolulu is often denigrated in comparison to more groomed resort-styled destinations across the various islands. But what I’ve learned during my numerous visits to Oahu and the other islands is that Honolulu is a remarkable city currently bubbling with young creatives and diversity uniquely its own. Its brimming with energy, but only a few minutes away from the laid-back life attributed to Hawaii. If you simply leave the bounds of the cookie-cutter resorts, there are memorable friends and memories to be made amongst locals and visitors alike at spots like The Pig and the Lady and Piggy Smalls, cultural events like the Honolulu Biennial, and even gazing under a monumental sculpture serving celestial purposes. We hope to see some of your own Hawaii adventures off the beaten path tagged on Instagram with #designmilktravels so we can add to this abbreviated list of Honolulu favorites.

What else am I missing? Comment below with your favorite sites to stay, visit and shop and I’ll check them out!

Gregory Han is a Senior Editor at Design Milk. A Los Angeles native with a profound love and curiosity for design, hiking, tide pools, and road trips, a selection of his adventures and musings can be found at