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  • 417 South King Street
    Known today as the Hawaii Five-O headquarters façade, Aliiolani Hale means “house of the heavenly king” in the Hawaiian language. The building was designed under King Kamehameha V and served as a palace with government offices for the Kingdom of Hawaii until the monarchy was overthrown in 1893 and the Republic of Hawaii was established. Shortly after Hawaii became a US state, the building was renovated. However, as the government grew, various departments moved out of Aliiolani Hale and now the Hawaii State Supreme Court makes use of this historic building along with a museum about the Hawaii judiciary and a law library. In front of the iconic building, there is a statue of King Kamehameha I, who founded the Kingdom of Hawaii.
  • 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.
  • Keanae Rd, Hawaii 96708, USA
    The world-famous Road to Hana hugs a jagged black lava shore. Just past mile marker 16 lies the Keanae Peninsula, where visitors can explore a traditional village, a stone church from 1856, and vast taro fields. The peninsula itself was formed by a massive lava flow from Haleakala, then softened by native Hawaiians, who carried soil down basket by basket to blanket the young rock. Today, the area is covered in lush greenery, which makes for an impressive sight against the turquoise sea and Maui’s famous North Shore waves. Before getting back on the road, be sure to stop at Aunty Sandy’s, one of the best banana bread stands along the Hana Highway, for a slice, a shaved ice, or a pork sandwich if you’re hungrier.
  • 2169 Kalia Rd, Honolulu, HI 96815, USA
    Both of Waikiki’s Outrigger hotels are a good value, but this one is a little bigger and a little quieter. It’s right on the beach, just north of the main resort cluster, and though a short walk to the middle of the action, far enough to feel out of the fray. The hotel itself is a quintessential Hawaiian family resort—big and friendly, with an unmistakable good-time vibe, old-school Polynesian decor throughout, and any number of activities on offer. The pool is set back from the beach and nothing fancy (no waterslides, no swim-up bar, and up against a giant wall), but it’s large enough for a serious game of Marco Polo, and there are plenty of lounge chairs to go around. Perhaps the best reason to stay here is the beach—a fairly narrow but sparkling white strand with more elbow room than its sister beaches; the rocky bottom may have something to do with that, but it’s a good place to learn to surf and a great place to catnap in the sun. One warning: the hotel lobby may feel overly commercial to some, what with a row of gift shops and a hard-to-miss timeshare desk, but it’s easy enough to ignore, if you wish.
  • 4100 Wailea Alanui Dr, Wailea, HI 96753, USA
    Of all the accommodations in Maui’s tony Wailea resort community, the 22-acre, waterfront Fairmont Kea Lani may be the most family-friendly of the bunch thanks in large part to its all-suite-and-villa setup. The property’s 450 guest rooms are some of the biggest on the island—the smallest suites start at a generous 860 square feet, while the two- and three-bedroom beachfront villas weigh in at 1,800 square feet and up. All cater to families, with separate sleeping and living areas, entertainment systems, furnished outdoor space (for lounging and dining), sleeper sofas, and some type of kitchen facilities, while villas encourage group gatherings with plunge pools and BBQ grills. Both adults and kids will love the deep-soaking tubs, too. Elsewhere, three indoor and three outdoor pools provide space for fun when kids’ club activities (among them volcano building, hula lessons, and tide pool excursions) aren’t on the agenda. Grown-ups can also amuse themselves with activities like outrigger canoe journeys, cultural programs, tee times at three nearby championship golf courses, and locally inspired treatments at the Willow Stream Spa, which offers dedicated fitness and wellness programs. Fuel your adventures at the five on-site restaurants, including the seafood-focused Nick’s Fishmarket Maui (with its 2,000-bottle-strong wine cellar) and the award-winning Kō, where the flavors are inspired by Hawaii, the Philippines, Korea, and beyond.
  • Chain of Craters Rd, Pāhoa, HI 96778, USA
    There are several hidden treasures among the volcanoes on the Big Island of Hawaii. The one that I found most fascinating was a short (0.7 mile) hike from the Chain of Craters road to the Pu’u Loa Petroglyphs. I was most fascinated that this land has been lava coated—and recoated—for ages and yet these petroglyphs still managed to escape centuries of fresh molten lava. I also thought this image, etched in the rock, was the likeness of a couple and imagined some ancient Hawaiian man carefully carving out the images and comically telling his wife: “I lava you a lot.”
  • 133 Prison St, Lahaina, HI 96761, USA
    Sister restaurant to local favorite Serpico’s in Upcountry, this sweet, welcoming spot serves New Jersey–style pizza in an old plantation-style house in West Maui. Tourists dine here, sure, but Prison Street isn’t overrun with overpriced rum cocktails or macadamia-crusted everything. Instead, the pizzeria keeps things simple with subtle nautical decor—a nod to Lahaina’s past as a whaling port—and thin-crust pies in variations like barbecue chicken, Philly cheesesteak, and the Windmills, a curiously named mix of Italian ingredients like pesto, mozzarella, and roasted red peppers. Also available are subs, salads, and calzones, all of which can be delivered if you need a break from dining out one night.
  • 78-128 Ehukai St, Kailua-Kona, HI 96740, USA
    The newly refurbished Sheraton Kona Keauhou Bay Resort is stylish, with a large pool and water slide. But it was the history and the view from the hotel (located off the famous Ali’i Drive) that won me over. The hotel gives you an excellent vantage point to the bay around which King Kamehameha III was born (stillborn, as legend has it). He grew up to become Hawai’i’s powerful and benevolent ruler, and sought to unite the people. He called The Big Island his home and is beloved by many. The hotel offers several notable cultural markers, including two heiau (Hawaiian temple) replicas.
  • 78-6740 Alii Dr, Kailua-Kona, HI 96740, USA
    One of the more relaxing evenings away from home was spent at the Outrigger Hotel in Kailua-Kona on the Big Island of Hawaii. I checked in with no problems and was even upgraded to a partial ocean view room! I had enough time to mosey on through town to grab some dinner and watch the sun sink to the ocean (complete with a green flash). The hotel was comfortable and situated next to a beach filled with a all sorts of fish and sea turtles. Snorkeling at Kahaluu Bay Beach Park, right next door to the hotel in the morning was one of the best snorkeling experiences I have had in Hawaii. The water was clear and the marine life was over-abundant! Sitting at the beach bar in the evening with live music and the sound of the surf was enough to relax the body and soothe the soul for a great night of sleep! If you are local, make sure to book their Kamaaina rate. **Unfortunately, the Keauhou property has closed. However, the Outrigger has several other properties on the Big Island.
  • 658 Wharf St, Lahaina, HI 96761, USA
    Lahaina, with its many Victorian flourishes, may look picturesque today, but the port town teemed with sailors, gamblers, and prostitutes in the 19th century. The Pioneer Inn changed all that when it opened for business in 1901, foreshadowing the tourist industry that would ultimately replace whaling, sugar, and pineapples. Step through the swinging doors of this vintage bar, which now bizarrely anchors the courtyard of a Best Western, and you’ll be transported back in time. Oars, harpoons, and a ship’s figurehead still adorn the space, looking down on platters of coconut shrimp, Parmesan-crusted fish over coconut rice, and margaritas made with POG (a mix of passion fruit, orange, and guava juices). Come during happy hour, which runs daily from 3 p.m. to 6 p.m., for discounted beers and cocktails.
  • 92-1001 Olani Street
    This Four Seasons Resort offers guests plenty of ways to relax and get to know Hawai’i.

    First, you can push beyond the protected cove and explore the coastline of Lanikuhonua, a sacred spot that served as a retreat for ancient Hawaiian chiefs and royalty. Part of the Four Seasons Resort Oʻahu curator program, this serene early morning experience blends exercise, education and meditation, thanks to its leader Anu, a kahuna (shaman), and his band of merry watermen. “Too often modern life drowns out engagement with nature,” he explains. “We give too much time to our gizmos and forget the ocean can bring health and peace of mind.” Suitable for all levels of paddlers.

    After a day on the water, head to their restaurant. This surf-style restaurant elevates Hawaii’s food truck fare at the Four Seasons Resort Oʻahu at Ko Olina. Expect ahi poké, wild boar hot dogs and the coolest French fry innovation out there: a heaping platter of slender spuds topped with parmesan, cherry tomatoes and wilted arugula for that “it’s healthy, really” feeling! Wash it all down with kombucha on draft – with flavors like lychee or lilikoi (passionfruit) – or cocktails such as the Castaway, featuring melon vodka, coconut water and lime juice. Come prepared to lounge outside, as the Waterman wraps around the family pool and also serves its exclusive beach. Open 11am to 6pm.
  • 412 Lewers St, Honolulu, HI 96815, USA
    The 112-room Surfjack Hotel channels 1960’s Hawaii, with vintage upholstery on the headboards, reed ceilings, and midcentury modern furnishings. The onsite Swim Club, with its outdoor pool bar, hosts music events and movie nights. Don’t miss a meal at Mahina & Sun from celebrated Honolulu-born chef Ed Kenney, whose menu showcases island cuisine and ingredients, or a trip to the Olive & Oliver boutique, whose clothing and accessories line are inspired by Hawaiian culture.
  • 5900 Lower Honoapiilani Rd, Lahaina, HI 96761, USA
    When eating at the Sea House Restaurant, it’s hard to decide what is actually better: the view of Molokaʽi across the water, or the Molokaʽi sweet potatoes used in the frittata. Either way, both combine for a memorable breakfast on the island’s northwestern corner. Opened in 1963 when tourists were just discovering Maui, the Sea House restaurant celebrated its 50th anniversary in 2013—thereby making it one of the oldest restaurants in West Maui. Even with the history, fame, and ocean views, it’s one of the island’s most affordable restaurants. Most items on the breakfast menu will cost you $12 or less, and when you’re done with your meal, you can splash in the waters of protected Napili Bay. The Sea House sources many of their ingredients from local Hawaiian farmers (such as the Molokaʽi sweet potatoes), and they also follow traditional fishing calendars when choosing their fish for the menu. This is a great option for beginning the day on the island’s northwestern coastline and is a filling starting point for later adventures toward Honolua Bay and beyond. Or, just relax on the sands of Napili beneath the shade of a rustling palm. After all, there are only three hours between the end of breakfast and the start of the Sea House happy hour—an affordable menu that starts at 2 p.m. and has been voted one of the best on Maui.
  • Waialua, HI 96791, USA
    Ancient Hawaiians believed their souls would leap into the spirit world from this lava shoreline on the western tip of Oahu. These days, people jump off here in gliders instead, soaking up views of the Waiʻanae coast to the south, Mokuleʻia to the north—and the glorious, denim-blue Pacific stretching from here to eternity. Take a 5.4-mile round-trip hike and check out the albatross sanctuary on Kaʻena’s wild coastal acreage (free to visit). Keep an eye out for monk seals, one of the world’s most endangered species, found only in Hawaii. Watch for their silvery-gray sausage shapes as they lounge on the beach, but give them space. Always retreat if a seal awakes, vocalizes, shies away, or tries to shield a pup.
  • Paia, HI 96779, USA
    The final stop before the Hana Highway, Pā’ia was once a plantation town; today it’s a boho enclave full of galleries, independent boutiques, lazy cafés, and a Tibetan Buddhist stupa (place of meditation). Stock up on fuel for exploring at Mana Foods: Like Doctor Who‘s TARDIS, this indie health-food store is bigger on the inside than it looks from the outside. (It also has a shockingly vast selection at reasonable prices.) Other highlights include Mahina, often voted Maui’s best boutique, and the funky soaps, jewelry, clothes, and Hawaiiana of Alice in Hulaland. Downshift at Baldwin Beach Park, the best for bodyboarding and swimming. Then drive out to Ho’okipa Lookout (before the Mile 9 marker) to marvel at the massive breakers in winter or advanced windsurfers streaking across the sea almost all year round.