If it’s your first time in Hawaii, or you only have time for a short getaway, Oahu and Maui make a good pair for taking a quick plunge. Both share in Hawaii’s wealth of inviting sandy beaches and verdant mountains, along with a multicultural society united by the aloha spirit — treating others with kindness and respect. Each island has unique experiences visitors should not miss.
This three-day island-hopping itinerary will allow you to sample some of the islands’ highlights. What amazement lies ahead? Your trip is dotted with Oahu’s impressive collection of World War II memorials and museums at Pearl Harbor, water sports at Waikiki Beach, Maui’s breathtaking tropical foliage and much more.
You’ll only need to take a short flight to move between the two islands. On Oahu, it’s easy to get around by walking, cabs, ride-shares and airport shuttles, but you’ll want to rent a car on Maui. And as always, check for travel guidelines and closures before planning your trip.
Friday: Dive In to History and Sandy Beaches
Wake up early in Waikiki for a cup of Kona coffee to pair with a fruit-laden açaí bowl or taro bagel from Island Vintage Coffee. Afterward, travel to the Pearl Harbor National Memorial. It’s free to visit the galleries about the December 7, 1941, attack on this active military base and the haunting USS Arizona Memorial, built above one of the battleships sunk that day. You’ll need a reservation, however, for the Navy shuttle boat to the USS Arizona Memorial.
Other attractions include the Battleship Missouri Memorial, the Pearl Harbor Aviation Museum and the USS Bowfin Submarine Museum & Park; they each charge entry fees, but there’s a free shuttle between them. For lunch, tuck into a kalua pig wrap or all-American burger at the aviation museum’s Hangar Cafe. And make sure to cool down with a shave ice by the Missouri before returning to Waikiki by cab or ride-share.
Rejuvenate with a dip in the warm, rolling waters of Waikiki Beach, overseen by the lei-draped statue of surfing icon Duke Kahanamoku. Follow in his footsteps by booking a late-afternoon surf lesson with Stoke Drift.
Everything in Waikiki is within walking distance, including the Mai Tai Bar at the Royal Hawaiian, a Luxury Collection Resort, opened in 1927. Enjoy a sunset cocktail while admiring the pink-tinted hotel’s vintage Spanish-Moorish flourishes.
Then tread a few steps to its beachfront Azure restaurant for an elegant, island-sourced tasting menu. For more casual fare, nab a seat under the banyan tree at the Beach Bar at nearby Moana Surfrider, A Westin Resort & Spa, Waikiki Beach, and dine on a poke bowl or huli huli chicken (rotisserie chicken in a teriyaki-style marinade) while listening to live Hawaiian music.
The evening ends with a walk on moonlit Waikiki Beach, framed by glittering city lights and the dark form of Diamond Head crater.
Saturday: Snorkeling, Sailing and Sightseeing
Pick up a flaky, fruit-topped kouign amann pastry at Kona Coffee Purveyors before jumping on Waikiki Sailing Company’s morning snorkeling cruise right off of Waikiki Beach, which leaves early enough to enjoy calmer waters and a full day afterward. Alternatively, combine breakfast with the scenic “coffee cruise” on the Vida Mia — a luxurious motor yacht departing from Waikiki’s Ala Wai Harbor. Its delectable spread includes pastries, bagels and lox, egg bites, fruit and Honolulu Coffee brews.
After checking out of your hotel, drive to Honolulu’s Chinatown Historic District, passing the Hawaii State Capitol and the Cathedral of St. Andrew en route. Browse the Hawaiian, Filipino, Thai and Chinese food stalls at bustling Maunakea Marketplace or order char siu manapua (steamed buns filled with roast pork) to go from Sing Cheong Yuan Bakery for a quick lunch before your 40-minute flight to Maui.
After landing on Maui, from the airport in Kahului, it’s a 20-minute drive to Iao Valley State Monument, where admission and parking are by reservation only. A half-mile paved trail below forested ridges and above a surprisingly cool burbling stream leads uphill to a spectacular view of the 1,200-foot-tall emerald pillar nicknamed the “Iao Needle.”
Afterward, cross the former sugar-cane fields of Central Maui and drive past Kealia Pond National Wildlife Refuge en route to Wailea, which is famed for golf courses, luxury resorts and a string of sandy beaches. Check in to your hotel, and then dine on island-inspired cuisine such as saimin (noodle soup with roast pork) or poke tacos at Monkeypod Kitchen.
If you desire a nightcap, the Pint & Cork stays open until midnight and has 16 beers on tap.
Sunday: A Stunning Summit and Island Cuisine
Because you’ll be hiking today, kick off the day with a hearty breakfast, such as organic chicken and waffles or an ahi tuna eggs Benedict at Nalu’s South Shore Grill in Kihei, just north of Wailea. You’ll also want to bring jackets, sunscreen, sturdy shoes and lots of water for traversing the sunny but much cooler trails in the forests and cinder-covered crater of 10,026-foot-high Haleakala (Hawaiian for “House of the Sun”), one of two massive volcanoes that formed Maui.
Along the 37-mile Haleakala Highway from Kahului to the summit, stop en route at local institution Pukalani Superette for a bento box or other picnic lunch (there’s no food or drink sold inside Haleakala National Park). After a 35-minute winding drive to the southeast, alight at Hosmer Grove, where you can hear native birdsong along a half-mile forest trail at almost 7,000 feet of elevation.
Duck inside the park’s nearby Headquarters Visitor Center to learn about the dormant volcano’s environment and cultural significance before continuing uphill for another half-hour to Haleakala Visitor Center at 9,740 feet. Soak in the panoramic ocean and island views before tackling some of the Keoneheehee (Sliding Sands) Trail, heading downhill on rock-strewn ocher and black sand toward craggy cinder cones and past rare, spiky native silversword plants in a seemingly endless expanse. There won’t be time to walk the full 11 miles, so turn back when you’re ready to devour your lunch.
Return to Wailea to peruse Tribe Maui and other eclectic boutiques along rustic Makawao’s Baldwin Avenue, or keep going to allow time for a swim at Wailea Beach. Dinner is at Lineage, one of Maui’s most innovative restaurants, introducing gourmet flair and island ingredients to diverse Asian dishes (including Japanese, Chinese, Filipino and Korean fare). Dig in to some wagyu kalbi short ribs and Korean fried chicken, both served with spicy-savory Guamanian sauces.
And then indulge in the best way to cap off the end of your three-day trip — an after-dinner soak in your hotel’s hot tub.
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