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  • 19 N Pauahi St, Honolulu, HI 96817, USA
    Big baggy aloha shirts—that could double as canoe sails—goodbye. Instead head to this Chinatown boutique, featuring the sharp, tapered designs of the eponymous Roberta Oaks. She draws on her hippie, farmhouse childhood and mid-century modern Hawai‘ian flair to create prints, which she then combines with a more fitted and form-flattering modern silhouette. These fabrics also take a star turn on graceful day dresses and even doggie bandanas. Open since 2009, this alluring boutique goes beyond attire, selling jewelry, candles, surf photography, and scents like Sándalo (a moody meditation on the islands’ vulcanism with ash, patchouli, and Royal Hawai‘ian sandalwood).
  • 65-1279 Kawaihae Road
    In The Gallery of Great Things, visitors will find much more than “things” to experience when they walk in the shop. The actual building was a nurses’ quarters during WWII serving an estimated 50,000 soldiers who passed through during the war. Maria, the shopkeeper who founded the gallery, has filled her store with art, antiques, and curiosities that reflect the Pacific culture, history of the Islands, and Hawai‘ian lifestyle. She has endeavored to preserve the culture of the Islands through her work in the store and sells the work from more than 200 local artisans, including the best known Hawai‘ian artists. One walk through her crowded shop guarantees everyone will find a treasure—whether it’s a wind chime, koa wood sculpture, painting, or just postcard.
  • 624 Front St, Lahaina, HI 96761, USA
    In the native Hawaiian language, the word “Lahaina” literally translates as “cruel, merciless sun.” Given the name, it should come as little surprise that not only is Lahaina the hottest place on the island, but it can be five degrees warmer than neighboring Ka’anapali, just three miles down the road. When walking around town, one of the best ways to beat the heat is to cool off with a syrupy shave ice. This sweet treat has become synonymous with Hawaii, and its origins date to Japanese plantation workers who would combat the heat by shaving ice off of blocks. Today, no visit to Maui is complete without enjoying a refreshing shave ice, and the best shave ice on the west side of the island can be found at Local Boys West. Conveniently situated across from the Banyan Tree, Local Boys is an island favorite for all of the free add-ons which accompany each serving. In addition to the soft, melt-in-your-mouth ice flakes that can be flavored with multiple syrups, Local Boys includes ice cream on the bottom and Kauaʽi Cream on top, completely free of charge. For those traveling with kids, you can even top the treat with gummy bears for exactly the same price. While waiting in line for your syrupy treat, take a moment to watch the surf films or shop for locally-made merchandise. This store was opened by a man and his young son who humbly sold snacks on the street, and it’s grown into arguably the best place in Lahaina to enjoy the island flavor.
  • 585 Hinano St. Hilo, HI. 96720
    Very few people have the willpower to resist a candy shop. Anyone with curiosity about the candy making process will be drawn to Big Island Candies with the big picture windows into their production room. Their small batches ensure fresh shortbread cookies and chocolate truffles are distributed to their resellers and customers. The shortbread comes in several Hawaiian flavors like macadamia nut, pineapple, and kona mocha. There are so many chocolates to choose from, but my pick is the Hawaiian macadamia nut caramel cluster, with a side of milk chocolate macadamia nut toffee, and a last course of dark chocolate covered whole Kona coffee beans. If your candies make it home, they will be the perfect gift for friends and family.
  • 74-4968 Queen Kaahumanu Highway
    Hawaiians once lived in harmony with the land: farming, fishing, and harvesting fruit. Today, the state imports 80 to 90 percent of its food. Visit Kaloko-Honokōhau to catch a glimpse of the Big Island’s ancient agricultural traditions, which residents are working hard to revitalize. The park’s landscape of rugged rock contains more than 200 archaeological sites, ranging from fishponds and elevated planters to petroglyphs, lava-tube shelters, and hōlua (toboggan-like slides). Watch for native species like the fragrant pua pilo flower and the endangered Hawaiian stilt, a subspecies of the black-necked stilt. A sugar-white beach stretches north from Honokōhau’s boat harbor and often attracts sea turtles.
  • 1151 Punchbowl Street, Honolulu, Hawaii 96813
    One of the most recognizable sites in Hawaii, this volcanic ash cone overlooks Waikiki’s coastline—a tectonic memory from an explosion half a million years ago, measuring almost 3,500 feet across. British sailors named it Diamond Head in the 1800s, mistaking calcite crystals in the crater’s soil for jewels. Despite its volcanic grandeur, the ascent takes most hikers an hour or so, clocking in at 560 feet of elevation gain and 1.6 miles round-trip. At the top, on a clear day, you can see all of Oahu’s south shore, from Koko Crater and Waikiki to the mountains of the Wai’anae Range.
  • 1913-J S Kihei Rd, Kihei, HI 96753, USA
    With its thatched roof, bamboo bar, and surfboard decor, this beloved watering hole—often voted Maui’s best bar by locals—checks all the tiki boxes. Head here for live music, lanai seating, and late-night dancing, plus fun and fruity rum cocktails like mai tais, zombies, daiquiris, and piña coladas. Beyond its drinks, South Shore Tiki Lounge was recognized by the state of Hawaii as an outstanding business for its regular fund-raising efforts, which benefit local organizations like the Keiki Cupboard, Hawaii Wildlife Fund, Maui Humane Society, and Hawaii Animal Rescue Foundation. All that to say, you can feel good coming here to wash down a massive chili-cheese hot dog with a lychee-watermelon martini.
  • 2335 Kalakaua Avenue
    The vibe in Waikiki is the most frenetic of all the spots in the islands, but there is an escape. The scene at the current iteration of the classic Hawaiian hangout, Duke’s, is a step back even by Oahu standards. Best approached via the beach to enhance the original feel and avoid the mall-like carnival from the street entrance, this is the kind of bar that welcomes sand on your flips. Slip in for happy hour and be prepared to jockey for a spot. Even with the crowd, the music, the food, the drinks are all designed draw you back to a simpler time when Duke was still riding the longboard. I’m partial to the beers and french fries, but will never refuse a fish taco. With a long relationship with the Kona Brewing brand, I opt for the Longboard larger or Fire Rock Pale ale. The umbrella drinks don’t disappoint, but neither do the gin and tonics. The local musical talent that ply the stage at Duke’s are traditional Hawaiian in style and like to keep the island theme front and center. There is a family vibe to the musical community, much like the rest of Hawaiian culture, and it’s not unusual to get a sibling or cousin to come up on stage and do some traditional Hawaiian dance or help out on a song or two. There was an 8 year old girl that got asked to come up on one of our visits and she blew the crowd away! The strip a Waikiki can be a bit daunting in terms of relaxation, but Duke’s remains my refuge from the madness. Aloha.
  • 2199 Kalia Rd, Honolulu, HI 96815, USA
    The most enviable address in Waikiki, the beachfront Halekulani is all about restrained elegance and pitch-perfect service. The hotel dates back a century, though it was entirely rebuilt in the 1980s—and the room decor—fifty shades of white and plantation shutters framing the turquoise sea—complements the scene outside. The beach itself is small and usually mobbed, but the pool is a dream—a giant oval big enough for laps, and quiet enough (few kids here) for a long doze under your chaise’s umbrella. The grassy courtyards and seaside restaurants are just as improbably serene; some might say stuffy, but for others, the reliably hushed atmosphere is a welcome tonic to the hubbub of Waikiki, just outside the Halekulani’s marbled entrance.
  • 10 Wailea Gateway Pl, Kihei, HI 96753, USA
    Belly up to this Wailea bar, which dazzles with a display of blue-glass Japanese fishing floats, for Hawaii’s best mai tai. Here, chef Peter Merriman, a pioneer of Hawaii Regional Cuisine, brings his genius to the classic cocktail, adding a thick head of honey-lilikoi (passion fruit) foam. Be sure to also score a table for later, as Monkeypod Kitchen does double duty as one of Maui’s top restaurants. Menu standouts include such seasonal dishes as kiawe-roasted squash ravioli, coconut-corn chowder, Hamakua wild mushroom pizza drizzled with truffle oil, and bulgogi pork tacos with Asian pear and house-made kimchi.
  • 68-1400 Mauna Lani Dr, Waimea, HI 96743, USA
    (Note: Google insists this is Kamuela, it is Kohala) The lava coast of Kohala on the Big Island is dramatic. Waves dash against the black rocks relentlessly until eons from now they will be sand. True, there are fewer white-sand beaches per square foot of land on the Big Island than others in the Hawaiian chain, but the island is huge. Beaches here often hold secrets, are the sources of legends, and are part of the circle of life for creatures indigenous to Hawaii. There have been lava flows since the ahapua’a land divisions were formed, but from the very tops of the mountains running to the sea, most beaches remain intact. One of my favorites is in a little inlets fronting the Mauna Lani Bay Hotel on Makaiwa Bay called Keiki Beach. Not for much swimming, it is a sandy-bottomed dipper’s delight or, as the name states, a place for children (keiki) to play in. A tree for shade, sand, tide pools to explore, a canoe house (hale) covering a koa canoe nearby, and a friendly turtle (honu) who feeds here are all part of what could be a perfect day. There is surf off the point in winter and snorkeling in other seasons. You might even want to rinse off and have lunch at the Mauna Lani pool restaurant. Parking is a good 15 minute walk via a trail. Follow signs to public parking off Mauna Lani Drive, bring water and beach gear, and get there early. Of course you could stay at the Mauna Lani Hotel and Bungalows too. http://www.maunalani.com/
  • Kapaʻa, HI 96746, USA
    Swift streams and waterfalls continue to carve these vertiginous and rugged valleys as they pour into the sea. One of the most stunning wilderness areas on earth, it also contains ancient Hawaiian ruins of graves, temples, house platforms, and terraced fields. The fear factor increases past the initial two-mile path to Hanakāpīʻai Beach (best visited in summertime, as winter swells tend to wash it away). Only experienced hikers in good condition and with proper gear should venture further along the famous 11-mile Kalalau Trail. Check for path and park closures before making plans and don’t forget the $20/night permit to crash at a campsite. However long you trek, stay on the main path and pack out what you brought in.
  • Kapaa, HI 96746, USA
    Take a riverboat up the Wailua—which translates as the “river of the great sacred spirit"—fed by the Mount Waialeale shield volcano, one of the wettest spots on the planet. Seven temples once stood along Hawaii’s longest and only navigable freshwater passage. Today, the remains of four are still visible, alongside petroglyphs and rocks where the island’s alii (royalty) would give birth. Stretch your legs at the stunning Fern Grotto: Verdant plants blanket the roof of the volcanic-rock cave there. Smith’s offers 80-minute tours there on open-air boats, which include the songs and stories of ancient Hawai’I, plus a bonus hula lesson (smithskauai.com).
  • 3850 Wailea Alanui Dr, Wailea, HI 96753, USA
    A honeymooner’s dream, the 40-acre Grand Wailea hails from the era of the Hawaiian mega-resort. From its perch over the Pacific, the hotel offers an impressive collection of original art (much of it created by locals specially for the property), 40 acres of lush tropical gardens, and over-the-top water features among the nine swimming pools, including slides, caves, a Tarzan swing, swim-up bars, and a canyon with an enclosed “lava tube.” The resort even boasts Humuhumu, a Hawaiian-inspired restaurant set in a man-made lagoon, and 780 guest rooms, all of which include a private patio or balcony. Opt for accommodations on the Napua Club level for a more intimate “boutique hotel within a resort” feel.
  • 1775 Moana Blvd., Honolulu
    A fairly new addition to the Waikiki waterfront, the seven-year-old Modern was a dream come true for those young urbanites who never quite felt at home in the more traditional Hawaiian resorts. It’s not directly on the beach—the closest is the lagoon and expansive beach in front of the Hilton Hawaiian Village, a quick walk on the hotel’s ramp—and instead overlooks the picturesque Ala Wai Boat Harbor, where many of the island’s boating excursions depart. Designed by George Yabu and Glenn Pushelberg, celebrities in the world of fashionable hotels, the look is warmly modern, all whites and creams and luxurious wood, and some striking art pieces, including a large surfboard installation in the lobby (titled “Wreck-tangles”). There’s a fun nightclub and some seriously good restaurants, though the real scene is out on the Instagram-worthy two-tiered teak pool deck, lined with lots of cushy chaises and shady corners to curl up. Upstairs is the adults-only pool—less a pool than a shallow water prop for frequent DJ-hosted dance parties. But for as much as the Modern is a hipster haven, the service is surprisingly good at making sure guests never feel like they’re crashing someone else’s party.