Planning a tropical escape? We asked some of Hawaii’s top hospitality experts to share their favorite recreational activities and cultural destinations with one goal in mind: to help you get the most out of your vacation. Pick and choose from their suggestions to create a personalized itinerary so dreamy, you’ll never want to leave.
The Pro: Alvin Wong, Director of Marketing at Wailea Beach Resort
- Watch the sunrise at Haleakala, a dormant crater that rises 10,023 feet above sea level. Its name translates to “house of the sun” in Hawaiian, and for good reason — sunrise here is so epic, Mark Twain famously described it as “the most sublime spectacle I have ever witnessed.” You’ll need a reservation, which can be made 60 days in advance for $1.50 per car. Visit nps.gov for details.
- Book a five-line Haleakala zip line run with Skyline Eco-Adventures that starts off across an Indiana Jones-style swinging bridge, swoops over 90-foot drops, and continues through a forest of eucalyptus. Plan your visit on a Monday, Tuesday, or Wednesday to experience the Haleakala Bike ’n’ Zip tour, which combines the zip experience with an epic sunrise bike ride to that crater in the sky. You’ll work up quite the appetite, so head to Grandma’s Coffee House in Kula for lunch.
- Visit “Big Beach” on South Maui (it’s also known as Oneloa or Makena) where the locals go for bodysurfing, picnicking, and relaxation. It’s blissfully development-free, so there’s not a resort in sight — just beautiful, picturesque beach stretching two-thirds of a mile. If you’re feeling adventurous, saunter on over the hill to “Little Beach,” where clothing is optional. When in Maui, right?
- If you visit during whale season (November through March), don’t miss the opportunity to head out for an excursion with Hawaiian Outrigger Experience. You’ll learn about Hawaiian history, culture, and language as you cruise along the gorgeous shores of Wailea, peeping whales all the while.
- Ride the waterslide at Wailea Beach Resort (it’s for hotel guests only). Opened recently, this curvy tube of fun has taken the prize for the longest aquatic slide in the state: Part of the resort’s NALU Adventure Pool, it measures 325 feet and drops five-and-a-half stories into a deep pool.
- End your days the Maui way: Settle in somewhere cozy along the southern shoreline with your beverage of choice (we recommend a mai tai, because Hawaii), then turn off your phone, enjoy the view, and breathe in that island air. Paradise. Found.
The Pro: Jonelle Kamai, Cultural Ambassador and Chef Concierge at Fairmont Kea Lani
- Scope out one of the most culturally significant spots in the state: Hale o Pi‘ilani Heiau. Located in the Kahuna Garden, a native forest near the town of Hana, this ancient place of worship dates back to the 13th century. Not only is it one of the largest archaeological sites on Maui, but it’s also the largest heiau in all of Polynesia. Explore the grounds on your own, or sign up for a guided tour.
- Head to Front Street in Lahaina, a bustling beachside destination that’s practically dripping with Hawaiian history (there’s great shopping, too, when you’re ready for a break). Start with the old courthouse, where you’ll learn about Hawaii’s monarchs and missionary influence, then continue on to the Baldwin Home Museum (the oldest home still standing on the island); Hale Pa‘ahao Prison, which was used to detain rowdy sailors in the mid 1800s; and the Hale Pa‘i Printing Museum. Make your way to Mokuhinia Pond, said to be the home of Kihawahine, a powerful lizard goddess (the kids will love this one!), and Moku‘ula Island, where King Kamehameha III resided from 1837 to 1845.
- Soak in the history at Iao Valley State Park, the site of a famous battle between the army of Kamehameha the Great and Maui’s Chief Kalanikūpule in 1790. It’s also the site of a love connection between King Kamehameha and Keōpūolani, the future mother of his children and the most sacred woman in the kingdom. Enough culture for one day? Perfect timing: There are gorgeous nature trails and cool river waters worth exploring here, too.
- Even the beaches in Maui are rich with history. Check out Ka‘anapali Beach, where the famous Black Rock, or Pu‘u Keka‘a (which means “rumbling hill” ), rises majestically out of the water. Here, hundreds of years ago, Chief Kahekili II made lele kawa (the act of leaping feet-first from a cliff into water without splashing) an exercise for his warriors as he assessed their courage and loyalty. These days, pencil diving off Black Rock is a fun pastime for locals and visitors alike.
The Big Island
The Pro: Craig Anderson, VP of Operations at the Mauna Kea Beach Hotel
- Stroll the beach along Kauna‘oa Bay at the Mauna Kea Beach Hotel; each lap is about a quarter-mile. Then take a 200-yard swim out to the hotel’s iconic float. While it’s easier for hotel guests to do this, there are about two dozen or so public parking spots. (Hint: Morning is the best time to get one.)
- Get the adrenaline flowing at Kohala Zipline, the only all-canopy zip line in the state. (Translation: You’ll be high in the treetops the entire time). Can’t decide which tour to choose? Opt for the Zip and Dip, which ends with a refreshing swim under a waterfall.
- Drive to Volcanoes National Park, where you can explore the summit of Kīlauea volcano via Crater Rim Drive. The 11-mile road encircles the summit and passes through both desert and lush tropical rain forest.
- Hike down to the beach at Waipio Valley, if only so you can tell your friends you conquered one of the steepest roads in the world. It’s a mile to the beach at a 25 percent grade, so give yourself 30 minutes to get down and 45 to hike back up. Stop for a malasada (sweet fried dough) at Tex Drive In Honoka’a on your way home — you deserve it.
- Summit Mauna Kea, which entails an hour-plus drive to a parking lot and a 7-mile hike to the top. If it’s offered, take the stargazing tour.
- Discover why the Big Island is famous for night diving. Big Island Divers has options for scuba divers and snorkelers alike; be on the lookout for Hawaii’s graceful manta rays.
The Pro: Donna Kimura, Director of Marketing, Island of Hawaii Visitors Bureau
- Explore historic Kailua-Kona with a walk down Ali‘i Drive, home to Hulihe‘e Palace, a former vacation home of Hawaiian royalty, and Moku‘aikaua Church, the oldest Christian church in Hawaii.
- Head north along the Kohala Coast for a stop in Waimea, a town rich in paniolo (Hawaiian cowboy) history and culture. The rolling pastures here offer an unexpected respite from the surf, sand, and palm trees.
- Take a quick trip up Kohala Mountain Road to Kapa‘au for a picnic lunch — and don’t leave without snapping a selfie with the statue of King Kamehameha, the man credited with uniting the islands into one royal kingdom.
- Follow the Hamakua Heritage Corridor, a scenic drive filled with gardens and waterfalls, to Hilo. There, duck into the ‘Imiloa Astronomy Center and Planetarium for a dose of astronomy, or check out the waterfront Japanese gardens at Lili‘uokalani Gardens, which just celebrated its 100th anniversary.
- To complete the circle-island adventure, head back to Hawaii Volcanoes National Park to see what Halema‘uma‘u Crater’s glowing red lava looks like after dark.
The Pro: Rebecca Pang, Public Relations, Rebecca Pang & Co.
- Take a morning hike to the top of Diamond Head (or Le‘ahi, as the Hawaiians say), a 1.6-mile round-trip. The trail, built in 1908 as part of Oahu’s coastal defense system, originally led to a center that directed artillery fire, and walking it is like taking a trip back in time. The reward after an ascent up steep stairs and through a lighted 225-foot tunnel is a prime view of Waikiki and beyond, from a vantage point only reachable on foot.
- Take a surf lesson on world-famous Waikiki Beach. For decades, locals and travelers have gotten their cowabunga stoke on these perfect small rolling waves, and you can too. The beach is filled with opportunities to rent a board, including Faith Surf School in front of the Outrigger Waikiki. If surfing isn’t your thing, try stand-up paddleboarding.
- Explore the North Shore with Climb Works Keana Farms, a three-hour guided zip line tour. It includes lines ranging from 500 feet to almost half a mile and features eight dual lines, two rappels, and three skybridges that stretch over beautifully expansive farmland.
- Walk Kailua Beach at sunrise. This 2.5- mile stretch of white flour-like sand is famous for its beauty. Bring a boogie board; you’ll find a couple of spots that are great for beginners.
- Show off your sick boogie boarding and bodysurfing skills at Makapuu Beach Park on Oahu’s east side. This wild beach is best suited to those with complete confidence in their abilities; novices should stick to calmer waters.
- Indulge in the island’s delicious seafood at a restaurant known for its sustainable options, like Mud Hen Water or The Pig & the Lady.
The Pro: Gerald Glennon, General Manager of the Kahala Hotel & Resort
- Take a sunrise walk along Waikiki, stopping to read the plaques created by cultural historian George Kanahele and his crew along the way, and imagine what this metropolis was like hundreds of years ago. Start at the east end at the beach, at what is now the Kaimana Beach Hotel (formerly Sans Souci, Waikiki’s first hotel), and continue to Kapahulu Groin. Today, the popular surf spot is crowded with surfers from around the world — but when the chiefs ruled the land, a commoner might have lost his life by daring to ride those royal waves.
- Check out the banyan tree in the center of the courtyard at the Moana Surfrider Hotel, where Robert Louis Stevenson is said to have written poems with the lovely Princess Kaiulani. The princess grew up on an estate just across the street (where the Sheraton Kaiulani stands today). A little farther down the road, between the Halekulani and Outrigger Reef, you’ll find Gray’s Beach. Dip into its waters to heal whatever might be ailing you, as it was once famous for its restorative powers. Hey, it can’t hurt!
- Sign up for a guided tour at Iolani Palace, the only true-blue palace on U.S. soil. Fun fact: If you happen to have seen the movie “Princess Kaiulani” (it’s usually offered on Hawaiian Airlines) you’ll recognize this spot. Be sure to visit the corner bedroom where Queen Lili‘uokalani was imprisoned for eight months, during which time she wrote the famous song “Aloha ‘Oe.”
- When you’ve had enough of the beach, visit the Bernice Pauahi Bishop Museum, home to more than 24 million (!) historical, cultural, and natural Hawaiian treasures. Consider the Monarchs and Behind the Scenes tours, and plan to stay for a while — it’s a good one.
- Sign up for a guided tour through Waimea Falls, and prepare to have your mind blown by the flora and fauna — including rare species of birds and plants along the path that winds past an ancient Hawaiian village. When you’re done, make time for a swim in the cool, refreshing waters off Waimea Beach.
- Stop at the Pali Lookout, which has deep historical significance. Pali means cliff in Hawaiian, and this one is the site of the Battle of Nuuanu, where in 1795 Kamehameha the Great won the struggle that finally united Oahu under his rule. Whether you hike or drive, you’ll be rewarded by an expansive view of Kane’ohe and Kailua bays.
- Spend cocktail hour at the Kahala Hotel, which when built in 1964 for $11 million was the most expensive hotel in the world. In fact, the spot was affectionately known as “Kahollywood” for the movie stars who flocked here. As you sip that cool, refreshing Maui Mule, contemplate the fact that in 1795, on this very spot, Kamehameha the Great landed many of his canoes (which came from Maui) en route to the Battle of Nuuanu, which led to the unification of the Hawaiian Islands. Eventually, the kanaka or native islanders began to settle in Kahala.
The Pro: Denise Wardlow, General Manager at Westin Princeville Ocean Resort Villas
- Take a morning run around the picturesque Princeville area, keeping your eyes peeled for nene geese, the Hawaii state bird, along with albatross, rainbow eucalyptus, and more. If you happen to be staying at the Westin, ask for a RunWestin running route (either a 2.5- or 5-mile map) to help lead the way.
- Drive to Waioli Hui‘ia Church, an iconic and frequently photographed Hanalei destination established by American Christian missionaries in 1834. In Kilauea, the Kilauea Lighthouse and Wildlife Refuge offers a unique opportunity to observe seabirds in their habitat and visit a lighthouse built in 1913. If the timing works out, catch a yoga class in Kilauea town.
- Stop for local goodies at one of the Garden Isle’s many farmers markets. In addition to fresh produce produced by Kauai’s robust agricultural community, they offer ready-to-devour food like traditional lunch plates and Kauai-made items like jewelry and honey.
- Visit Waimea Canyon and Koke‘e State Park, nicknamed “the Grand Canyon of the Pacific.” The canyon, on Kauai’s west side, is 14 miles long, one mile wide, and more than 3,600 feet deep. Although not as big or as old as its Arizona counterpart, this geological wonder is unique in the islands and provides panoramic views of crested buttes, rugged crags, and deep valley gorges. Numerous trails are available for beginner and seasoned hikers.
- Walk along the picturesque Poipu Beach to RumFire at the Sheraton Kauai Resort for arguably the best sunset views in Poipu. If you’re feeling charitable, participate in the restaurant’s Table 53 program, which to date has raised more than $185,000 for Kauai-based nonprofits by donating proceeds from the diner’s bill.
The Pro: Sue Kanoho, Executive Director of the Kauai Visitors Bureau
- Feast on delicious Kauai shrimp via a Tasting Kauai tour, then take a trip down crustacean lane at Opaekaa Falls on the south shore. (Opaekaa means “rolling shrimp,” alluding to the freshwater shrimp’s one-time abundance in the tumbling cascade of the waterfall.)
- Reflect on the past at Poli‘ahu Heiau, one of seven ancient Hawaiian temples on the Wailua River. This one, situated on a bluff above water, offers impressive views of Wailua Bay and the verdant mountains Nounou and Kalepa. Though it’s unclear when this particular heiau was built, there is evidence it was used as early as the 1600s.
- Set off on a 10-mile walk, bike ride, or drive along Ka Ala Hele Waiwai Ho‘olina o Koloa, or the Koloa Heritage Trail. There are 14 stops and monuments, and marked signs highlight the natural history, archaeology, and culture of the Koloa District of Kauai and its people. Look for the birthplace of Prince Jonah Kuhio Kalanianaole, born in Koloa in a grass hut to Princess Kinoike Kekaulike and High Chief David Kahalepouli Pi‘ikoi. Jonah became a delegate to the U.S. Congress after Hawaii became a territory in 1900, serving for 19 years. His name can be found throughout the state, including Kuhio Avenue, one of the main roads in Waikiki.
- Spend a rainy afternoon exploring the Kauai Museum in Lihue, where you’ll be able to see the Ha‘aheo artifacts from King Kamehameha II’s sunken yacht in addition to various exhibits about Kauai life long ago.
- Learn how to make a haku (braided) flower lei, using a variety of colorful blossoms found throughout the island, with award-winning lei maker Elvrine Chow of Heavenly Hakus.
- Roam through the McBryde Garden, nestled in the picturesque and historic Lawa‘i Valley on the south shore of the island. Home to the largest collection of native Hawaiian flora in existence, it’s arguably one of the most beautiful places in the world.
- Treat yourself to an island-inspired dinner at the Westin Princeville. Twice monthly, the resort partners with the Waipa Foundation for He ‘Aina Ola (a nourishing feast), a farm tour and dinner event. The event begins with a walking tour of Waipa’s orchard and gardens as the foundation’s staff relays details on the history of the area and the organization’s efforts to practice cultural stewardship in the ancient ahupua‘a (land division). Following the tour, a three-course dinner with wine pairings is offered in Waipa’s Laukupu Hale Imu. Prepared by a resort culinary team, the meal features locally sourced ingredients, including produce grown at Waipa, and live entertainment is provided by the Waipa ‘ohana, or family.
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Mimi Towle is a Marin-based writer and editor. Currently the editor of Marin Magazine, she enjoys the various perks of her job, which include meeting chefs, winemakers, and inspiring characters. As a volunteer philanthropic advisor for the EACH Foundation, she focuses on needs in her home state of Hawaii. Some of her favorite nonprofits include City Beat, Hawaii Land Trust, and University of Hawaii Cancer Center.