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  • 770 Auloa Road
    Visible from anywhere in Kailua-Kaneohe are the three peaks of Mount Olomana. The majestic peaks are named after a mythical Hawaiian warrior and offers more than spectacular views from all angles. To reach your destination from Honolulu you take the Pali through the Kalanionaole Highway and look out for the Luana Hills Country Club. You can park right outside of the club as the entrance to the hike is just a quarter mile from the entrance. The peaks are challenging, with steep drop-offs and some rock climbing, and are only for experienced hikers. The first peak offers the highest views and the third is the most dangerous of all the peaks. Make sure you do your research and talk to locals about likely conditions. That said, it’s been my favorite hike on Oahu so far and it offers unforgettable views of the city. Bring some snack and water with you to sit atop one of the peaks and have a quick picnic.
  • 310 W Kaahumanu Ave, Kahului, HI 96732, USA
    Every Saturday from 7 a.m. to 1 p.m., the island’s largest open-air market sprawls across the University of Hawai‘i Maui College campus, creating a lively scene with more than 200 vendors. Many of Maui’s best boutiques sell their wares here, but for much cheaper prices than at their brick-and-mortar locations. Browse for muumuus, wood carvings, and other handmade crafts like bone and shell jewelry, or treat yourself to a shave ice while perusing piles of leis, local fruit, and homemade baked goods. The market is especially strong when it comes to street food—don’t miss the spam kebabs, banana bread, and goji kombucha.
  • If you’re looking for a great snorkel experience accessible to Waikiki, I found Hanauma Bay a great spot. Turtles and fish galore.
  • 1 Bay Dr, Lahaina, HI 96761, USA
    Set within the 24-acre oasis of Montage Kapalua Bay, this pop-up bar and lounge pairs Veuve Clicquot Champagne with Maui’s world-class sunsets. Open Thursday through Sunday from 3:30 p.m. to 7 p.m., the Champagne Hale (pronounced HAH-leh, which is the Hawaiian word for house) serves a range of bubbly, from Veuve’s signature Yellow Label, Rosé, and La Grande Dame labels to special Rich and Rich Rosé offerings, available for the first time on the island. Pair your sips with light bites like Kualoa Ranch oysters, bigeye tuna tartare, and burrata toast with pickled strawberries and pistachio pesto, then take in the views as the sun goes down over the Pacific. From the bar’s clifftop perch above Namalu Bay, you’ll enjoy stunning vistas of the ocean as well as Molokai and Lanai islands in the distance.
  • Lower Saki Mana Rd, Waimea, HI 96796, USA
    Spectacular sands—making up the longest stretch of beach in Hawaii—sweep for 15 miles starting here, fringed by postcard-perfect turquoise water. This patch of ocean is rough, rowdy, and perilous: Watch for sneaker waves as you stroll along the coast. Swimmers should stick to the Queen’s Pond, an area girdled by a protecting reef. But the big attraction at Polihale Beach remains the dunes, which can pile up to 100 feet high. In summer, hot sand can slip into your shoes, causing burns; savvy beachgoers wear only wool socks, according to Andrew Doughty, author of the excellent Ultimate Kauai Guidebook. Make sure to pack plenty of water—and also an umbrella, if you plan to linger.
  • 3550 Wailea Alanui Dr, Wailea, HI 96753, USA
    Opened in 2013, Andaz’s first and only Hawaiian property has four cascading infinity pools (plus many more private plunge pools) and an enviable location on Mokapu Beach, meaning guests are never more than a few steps from water.

    The 290 rooms and suites are decked out in stylish, contemporary furnishings—some even come with Viking grills on private lanais—and 10 luxurious villas feature up to four bedrooms, with the largest maxing out at a sprawling 4,000 square feet.

    The resort’s full calendar of activities offers everything from coconut leaf weaving to kayaking, outrigger canoeing, and stand-up paddleboarding—plus GoPro shooting and editing lessons to best capture it all. At Morimoto Maui, one of four restaurants on the property, renowned chef Masaharu Morimoto combines Japanese and Western influences in inspired dishes like yellowtail “pastrami,” served with a gin-spiked crème fraîche.

    At the ‘Awili spa, where guests can choose locally sourced ingredients for a custom body treatment.
  • 217 Johnson St, Santa Fe, NM 87501, USA
    Located in downtown Santa Fe, this perfectly sized museum is dedicated to the artistic life of Georgia O’Keeffe (1887–1986) and houses the single largest collection of the artist’s work in the world. Rotating exhibits often include O’Keeffe’s iconic desert landscape paintings alongside lesser-known gems painted in Lake George and Hawaii (where she was commissioned by the Dole pineapple company). Often, notable pieces from established peers and contemporaries like Ansel Adams, Jackson Pollock, and Andy Warhol join hers on the walls.
  • Often described as the Grand Canyon of the Pacific, this 10-mile-long Kauai valley is a kaleidoscopic array of scarlet earth, verdant valleys, and raw volcanic crags. Bands of color streak the corrugated landscape, each representing a different eruption and layer of lava. Waimea Canyon Drive has a series of lookouts; among the most popular is Waimea Canyon (past the Mile 10 marker on Highway 550), where a number of rivers once cascaded down the gently sloping shield volcano. When part of its flank collapsed, the rivers combined with dramatic results. Continue into the mountains to explore Koke’e State Park beyond. Its small, free museum contains a 3-D map, which sheds light on the canyon’s wild beauty, while the gift shop specializes in local art, crafts, and Niihau shell jewelry.
  • 79-7251 Hawaii Belt Rd, Kealakekua, HI 96750, USA
    Teshima’s Restaurant is a historic Japanese diner on the west coast of Hawaii Island in Kealakekua. Welcoming and reasonably priced, the diner serves Hawaiian Japanese comfort food. The set meals are the best value, a sampling of small dishes that might include sashimi, sukiyaki, fried fish, rice, and sides of cucumber, cabbage, and miso soup. The ahi is excellent (and the wasabi so soft and fresh), but the restaurant is really known for its shrimp tempura: Every local we asked about Japanese food told us to try it here. You can get it on its own, or as part of the “deep sea trio” of shrimp tempura, fried fish, and sashimi.
  • 2435 Kaanapali Pkwy, Lahaina, HI 96761, USA
    Located in the heart of Whalers Village on Kāʻanapali Beach, Hula Grill is a busy hangout with live music seven days a week. You can sit for a meal in the open-air dining room, but the real party happens at the restaurant’s Barefoot Bar, right on the water’s edge. Kick off your shoes and sink your feet in the sand, then order a Barefoot Brew (made specially for the bar by Maui Brewing Co.) or cocktails like piña coladas, mojitos, and Maui Mules with organic vodka. Also on offer are a range of non-alcoholic drinks, from house-made sodas and fresh-squeezed juices to local kombucha and pure coconut water, as well as a solid food menu that highlights Hawaiian farmers and fishers. For a great deal, head here for Aloha Hour, which takes place daily from 2:30 p.m. to 5 p.m. and includes special prices on pupus and drinks.
  • 1354 Kuhio Highway
    In the heart of old town Kapaa, the Olympic overlooks Main Street with laid-back Hawaiian style. Upstairs in an old building that’s been converted into a collection of ragtag shops, the cafe has a commanding presence. Park and wander along the street to make your way to the stairs leading up to the bar and cafe. No pretense upon arrival. The tables lining the open windows in front are choice for people watching and catching the breeze from the prevailing trades. Late afternoon sun streams in and heats things up but is a welcomed delight. There’s always something cold close by to help with the temperature regulation. The bar is a mix of locals and tourists. Happy hour is a draw from four to six with discounts on drinks and select appetizers. I’m a big fish fan when near the source and the fish tacos at the Olympic take the gold. Dressed with a mango salsa and sides of beans and rice, they use two kinds of fish to keep your tastebuds guessing. There is a good selection of island beers and all the fruity umbrella drinks you can imagine. It’s right on the Kapaa multi-use path, so you can cruise in on your beach bomber for a refreshing break. Staff are friendly and service is casually good. Worth a stop when trolling around Kauai for someplace to take a break from vacation.
  • Kailua, HI, USA
    Kailua Beach is always named one of the best beaches in the world. It has the most deliciously soft sand, gentle surf, and maybe a turtle ( honu) to swim with. Kailua Beach is actually many beaches. For a fascinating study on ancient beach names, take a look at the historical Hawaiian names in John R.K. Clark’s book “The Beaches of Oahu.” In modern times the beach names are three. Oneawa ( AKA Castles), lies to the north near the house the President favors for holidays. Kalama sits in the middle of the crescent named to honor Queen Kalama the wife of King Kamehameha III, former owner of the entire Kailua district. Kailua Beach Park is thirty acres with parking, picnic facilities, lifeguard and restrooms. Kayak rentals are close by and you may pull the boats across the street, stopping for a custom made sandwich at Kalapawai Market, and paddle out to one of the Mokulua islands. If you want a quieter experience albeit with no facilities or life guard, try Kalama Beach via any marked public right-of-way along Kalaheo Avenue beginning in 300 block and proceeding north. Pay attention to no-parking signs; find parking down a side street off Kalaheo Avenue TOWARDS the mountains. Leave nothing of value in your car, take chairs, towels, sunscreen, hats, a cooler of water and perhaps lunch. If winds pick up, pack up and head to docile Waikiki.
  • Old Road, Antigua and Barbuda
    All across Antigua you can find what may, at first glance, appear to be regular pineapples, but if you pass up on sampling the Antigua Black Pineapples, or just Antigua Blacks for short, you’d be missing what many call the sweetest pineapple on the planet. It’s said that Arawak Indians brought the first pineapples to Antigua’s shores more than 1,000 years ago. Upon cultivation in the island’s unique environment, these early pineapples soon adopted the distinctive flavor, appearance, and make-up of the Antigua Black we know today. The flavor being crisply sweet, not cloying, thanks in part to the Antigua Black’s low acidity. The appearance is so diminutive that you may think these pygmy pineapples aren’t ready for primetime compared to their oversized cousins from Hawaii, but one taste and you’ll change your tune. Check out Cades Bay Agricultural Station down south on Old Road to learn the history and explore the Antigua Black’s cultivation first hand.
  • 555 Kaukahi St Wailea, Kihei, HI 96753, USA
    Perched 300 feet above the Pacific on 15 verdant acres, Hotel Wailea is a former members’ club that still feels like a hidden enclave of cool. In 2014, new owners invested $15 million in a redesign that left 72 one-bedroom suites with white oak floors, Sub-Zero appliances, and Hawaii-inspired art. Still, it’s the pool that really wins over guests—it’s calm and quiet (thanks to the hotel’s no-kids policy); there are umbrella-shaded loungers and bungalows with fans for when you’ve had too much sun; and the beyond-gracious staff are always at the ready with water, cocktails, kombucha, and coconut water. The hotel lounge offers free wine and appetizers at 5 p.m. on Friday nights, while the farm-to-fork restaurant highlights produce grown in the resort’s own garden. Complimentary on-site activities include yoga, outrigger canoeing, and mixology classes, but guests can take the hotel’s Tesla Model X house vehicles anywhere in Wailea or rent an electric bike and cruise the South Maui coast if they want to get off property.
  • Hahaione St, Honolulu, HI, USA
    Escape the hubbub of Honolulu and stretch your legs on this 4.4-mile, moderate, out-and-back path. Somewhat steep, this serious glute workout attracts a lot of trail runners, especially on the weekends. The hike begins among rocks and small shrubs, then snakes among massive tree roots, before the dirt stairs near the top. The ridge unfurls gorgeous views of Waimanalo and the Nā Mokulua Islands, as well as Rabbit Island and Koko Crater. Note: drivers have to park in a residential neighborhood, then walk up an access road. Start early to avoid the heat and crowds, and make sure to bring plenty of water.