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  • 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.
  • 3550 Wailea Alanui Dr, Wailea, HI 96753, USA
    Expect the unexpected at Ka‘ana Kitchen, set within the funky yet sophisticated Andaz Maui. Here, executive chef Isaac Bancaco draws from the best of the island’s bounty, using local ingredients in a mix of Filipino, Chinese, Japanese, French, and Native Hawaiian cuisine. Think breadfruit hush puppies, Kona clams with savory malasadas (Portuguese doughnuts), and ahi tataki with burrata and lilikoi (passion fruit), enhanced only by the restaurant’s sweeping coastal views. You don’t need to change out of casualwear to dine here, but Bancaco has a knack for turning meals into events, inspiring diners to dress up a little.
  • 3750 Wailea Alanui Dr, Wailea, HI 96753, USA
    Hilo-born Sheldon Simeon realized the appeal of his soulful, heritage-based cooking as a finalist on season 10 of Top Chef. Once back in Hawaii, he opened the upscale Lineage in Wailea, where he’s earned a loyal fan base for dishes like kimchi dip, fried turkey tail adobo, and squid luau with creamed taro leaf. Cocktails here are equally creative, ranging from a mai tai made with banana milk punch, Earl Grey tea, raisins, and coconut to a cucumber vodka number garnished with huli huli chicken skin. Whatever you order, be sure to pair it with the chili pepper water, a condiment and digestive aid that’s served in a take-home flask.
  • 3850 Wailea Alanui Dr, Wailea, HI 96753, USA
    At this stunning restaurant in the Grand Wailea Maui, Lahaina-born chef Alvin Savella wows diners with bright flavors and striking plating. Start with appetizers like Cantonese barbecue-style char siu pork belly, squid ink bao, and ulu (breadfruit) risotto with nasturtiums, then move on to impressive mains like lobster ramen in red miso–coconut broth and free-range huli huli chicken with garlic fried rice and charred pineapple relish. Set in a lagoon, the round, thatched-roof restaurant—named for Hawaii’s state fish, the humuhumunukunukuapuaa—offers spectacular sunset views, so plan your dinner accordingly.
  • 658 Front St #102, Lahaina, HI 96761, USA
    Founded in 2015 by three childhood friends from Georgia, Down the Hatch brings a Southern twist to the aloha spirit. The classic watering hole serves shrimp po’boys, chicken and waffles, and Mexican-inspired fare like seared ahi tacos, but the real draw is the cocktails, which range from tiki favorites and Moscow Mules to craft libations like the Snake Oil with gin, dragon fruit, lilikoi kombucha, and CBD oil. Featured on Guy Fieri’s Food Network show Diners, Drive-ins and Dives, Down the Hatch also boasts the longest happy hour in Maui. It takes place daily from 2 p.m. to 6 p.m. and features specials on appetizers, draft beers, and select cocktails.
  • 744 Front St, Lahaina, HI 96761, USA
    Fleetwood Mac front man Mick Fleetwood is behind this bar and restaurant, located on a third-floor rooftop in Lahaina. Here, guests sip drinks under beige umbrellas while taking in views of the dreamy blue Pacific. To pair with award-winning cocktails like the Heart of the Jungle (Cynar, Velvet Falernum, coconut rum, and lemon juice), which comes in a tiki artichoke, executive chef Eric Morrissette serves a menu of elevated bar bites, fresh local fish, and meatier dishes like filet mignon with peppercorn reduction. If you’re not a cocktail person, know that the robust drink menu also features beers from Maui Brewing Co. and Kohola Brewing as well as exclusive wines like Krug Brut from Reims, Luberri Gran Reserva rioja, and even a Chateau Musar red blend from Lebanon.
  • 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.
  • 3550 Wailea Alanui Dr, Kihei, HI 96753, USA
    This elegant bar at the Andaz Maui overlooks tiers of pools, waterfalls, and tropical foliage, all cascading down to the Wailea coast. Hotel guests and visitors alike come here to lounge under umbrellas by day and around a fire pit by night, sipping on cocktails like the Upcountry Buck (white rum, ginger, and pineapple) and the Lahaina Town Fizz (blanco tequila, strawberry, and elderflower). For something unique, try the Silversword, a cocktail designed by legendary Hawaiian mixologist Julie Reiner that features mezcal, sweet vermouth, pineapple, and chocolate bitters. Pair it with snacks like chilled shrimp summer rolls and Thai lettuce wraps, then finish with a ginger ice cream sandwich made in-house.
  • 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.
  • 820 Olowalu Village Rd, Lahaina, HI 96761, USA
    Open since 1932, this pit stop on the road to Lahaina is most famous for its Hawaiian hot dogs. They’re just standard red franks, grilled and stuffed in a bun, but Maui’s pro surfers and their fans—who usually stop here on their way to Olowalu Beach—have elevated the snack to almost cult status. If you’re not one for hot dogs, the general store also sells boiled peanuts, shave ice, and Spam musubi, along with an abbreviated Mexican menu when the kitchen’s cranking. In between bites, take time to browse the shop’s collection of locally made souvenirs and appreciate its unique decor. A late employee had a soft spot for starving artists and would often trade food for artworks, asking only that the pieces incorporated his favorite vehicle—a Volkswagen Beetle.
  • 4051 Omaopio Rd, Kula, HI 96790, USA
    Hawaii Sea Spirits is behind Ocean Organic Vodka, widely recognized for its turquoise bottle inspired by the 14th-century Japanese glass fishing net floats that used to wash ashore in Maui in abundance. At the company’s distillery on the slopes of Haleakala, entrepreneur Shay Smith desalinates deep-ocean mineral water from off the Kona Coast of Hawaii, then adds the bounty of his 80-acre organic farm, where he and his team cultivate more than 30 varieties of Polynesian sugarcane without the use of GMOs, herbicides, or pesticides. Discover the intricacies of his harvesting and distilling process on a farm tour, which takes place seven days a week, then hit the gift shop and stock up on vodka to take home.
  • 728 Front St, Lahaina, HI 96761, USA
    At Island Sole in Lahaina, the authentic, locally made gifts are designed to help shoppers “find their aloha.” Head here for shirts and flip-flops in tropical colors, home decor like jellyfish coasters and ukulele-shaped table clocks, and the shop’s signature longboard letters, which function as one-of-a-kind signs with customizable letters, icons, and characters attached to a wooden surfboard base. If you’re looking for some wall art, pay special attention to the palm-and-wave paintings on birchwood by Danielle Groff and the larger, laser-engraved maps of the Hawaiian Isles.
  • 627 N La Peer Dr, West Hollywood, CA 90069, USA
    Decidedly more upscale and art-focused than other Kimpton properties, the La Peer takes fitting into its surrounding neighborhood very seriously. Located off Sunset Boulevard on the quiet and walkable La Peer Drive, the hotel is in the heart of West Hollywood’s design district, surrounded by galleries, boutiques, restaurants, and more. While there’s a separate entrance for celebrities, the property is actually quite welcoming to all. The lobby feels like your artist friend’s cozy but consciously designed living room, with little nooks for reading and working, as well as large-scale art pieces sprinkled throughout. Step out back to the indoor-outdoor bar, patio, and small but serviceable pool area to peep a piece by Retna and grab a drink and snack. For something more substantial, there’s also lobby restaurant Viale Dei Romani, an Italian trattoria that’s garnered critical approval for chef Casey Lane’s fine cooking.
  • 700 Wilshire Blvd, Santa Monica, CA 90401, USA
    Santa Monica is officially on the map with this spectacular property, the second hotel for the Proper brand after its debut in San Francisco in 2017. Like at the first location, celebrity interior designer Kelly Wearstler heads up interiors and has produced an absolute stunner, drawing inspiration from her own Malibu home as well as the hotel’s circa-1928 Spanish Colonial Revival building. (The property actually straddles two buildings; the other half is a sleek new construction, connected by a courtyard and sky bridge to the historic part.) The 271 pet-friendly rooms feature original Kelly Wearstler wallpaper, vintage lamps and tables, and custom-made sunburst headboards that remind you you’re near the beach. Guests can also look forward to roomy bathrooms, complete with travertine marble, full-size Aesop bath products, and super-soft Parachute for Kelly Wearstler robes.
  • Av Balboa s/n, Panamá, Panama
    Panama’s extensive, sinuous coastline provides some of the world’s most delicious seafood. Options are infinite, especially at the capital city’s Mercado de Mariscos. The offering is downhome, traditional and absolutely scrumptious. Pick up something to cook later or just plop down at one of several in-market restaurants for instant gratification. Savoring your ceviche and an ice-cold brew as the market roils around you is pure Panama.