Hawaii is an adventurer’s paradise. Whether you like to run, swim, hike, bike, play in the waves or summit towering peaks, these magical islands offer an activity for you. A mecca of triathlons, surfing and a slew of other water sports, you’ll find the perfect training ground on Hawaii’s shores, plus a host of other adventures to spice up your vacation. You can even compete like a pro in a suite of sporting events.
Here is your active guide to Hawaii, island by island.
MAUI
Stay: Ka’anapali Beach Club in West Maui sits minutes from both downtown Lahaina and stunning hikes in Kapalua. Work out with an ocean view in the on-site fitness center, or get your sweat on with any of these island activities.
Train: Link up with Valley Isle Road Runners or Maui Running Company for free Sunday morning group runs in varying locations each week. Just down the road from Ka’anapali Beach Club, the Ka’anapali Beach Walk also offers a 3-mile round trip along boardwalks and beachfront paths. Head out early to avoid the sun and crowds.
Just north of the resort, you can hike or run the 3.5-mile round trip Coastal Trail in Kapalua for a cliffside view of the sea. From the trail’s end at D.T. Fleming Beach Park, continue to the 6-mile Mahana Ridge Trail. You’ll hike up and away from the sea to the Maunalei Arboretum.
About an hour’s drive from Ka’anapali, the 5.5-mile Hoapili Trail is a stunning run or hike across a lava field on Maui’s southernmost coastline. Expect a mix of sand and jagged lava rock underfoot with gorgeous views of mountains above and sea below.
Or, take the road less traveled into the Makawao Forest Reserve for the 5.7-mile Kahakapao Loop Trail, a leaf-covered dirt path shaded by pines. On the slope of the Haleakalā Crater, the Polipoli Spring State Recreation Area offers an extensive trail system.
Lastly, don’t forget to check out Hawaii’s Nā Ala Hele Trail and Access Program, which preserves historic trails and ancient Hawaii’s cross-country running tradition, for even more treks in the area.
Try: Haleakalā National Park is a 33,265-acre wonderland for running, hiking, biking, horseback riding, camping and stargazing. Choose your own adventure in the Kīpahulu District near Hana or Summit District near Makawao to see volcanic landscapes, sub-tropical rainforests and more.
Roll down the 10,023-foot Haleakalā Crater with Bike It Maui after catching sunrise at the peak. Little pedaling but much bravery is required for the journey. For a real challenge, join the brave souls biking up the switchback road.
At sea, amp up your snorkeling with Redline Rafting for an underwater tour of Molokini Crater and the Forbidden Coast. From a high-speed, 35-foot pontoon raft, you’ll snorkel two or three sites in crisp, pristine waters.
Race: The Maui Marathon weekend in October offers a distance for everyone from 5K to marathon runners, including 10K, half-marathon and relay options. The ocean is front and center, with nearly 17 miles of the 26.2-mile race running along the coastline. The finish line is just down the road from Ka’anapali Beach Club, near its namesake beach.
Grab your family and friends to tackle the Hana Relay, a 52-mile race along the famed “Road to Hana,” with 617 curves and 56 bridges underfoot. Teams of a maximum of six runners each complete at least three legs, with two to three miles per leg.
Or, go off-road in October to try the XTERRA Kapalua Trail Runs at the XTERRA World Championship off-road triathlon weekend.
OAHU
Stay: The Modern Honolulu in Oahu, named Hawaii’s best boutique hotel by Thrillist, sits at the gateway to Waikiki Beach. Wake up to morning yoga at the Sunset Pool, or grab a running map with 2- to 7-mile routes along Waikiki Beach. The meandering trails weave through the greens of Ala Moana Park and beyond, and they’re accessible right from the hotel’s doorstep.
Train: Take a 1.6-mile round-trip hike up Honolulu’s Diamond Head crater, a 760-foot volcanic cone, or get out of town on Central Oahu’s 4-mile Kalauao Trail for a steep hike to a waterfall. The connecting Aiea Loop Trail is perfect for a 4.8-mile run with tranquil views of Halawa Valley and the Ko’olau Range. Take your pick of 40 more trails in the Oahu branch of Nā Ala Hele, Hawaii’s trail and access program.
Cyclists can rent a bike on-site and pedal North Shore Bike Park’s 12 miles of mountain bike trails through 850 acres. Trails range from easy to moderate, wide to single track, and sandy oceanside lanes, including a practice pump track.
Try: An ancient Polynesian sport, surfing thrives in Hawaii. Oahu in particular is the surf capital of the world. No trip to Honolulu is complete without a lesson at the modern sport’s home — Waikiki Beach. Learn the art of catching waves on a surfboard, outrigger canoe or stand-up paddleboard with Faith Surf School. Or, book a personalized surf tour with Big Wave Dave Surf. With 112 miles of coastline, more than 125 beaches and some of the sport’s most famous swells, Oahu offers a barrel for every level of wave-rider.
In the summer months (winter brings large swells), snorkel or dive Shark’s Cove on the island’s north shore — often named one of the top shore-diving spots in the world, thanks to its clear, shallow water filled with rock formations and coral reefs.
For a uniquely Hawaiian experience, paddle in an outrigger canoe. Outfitters like Faith Surf School and Big Wave Dave Surf offer lessons. Come out to the beach during the March to October regatta season to watch Oahu Hawaiian Canoe Racing Association crews paddle in head-to-head competition. The group’s 38-mile, open ocean Molokai-to-Oahu race draws more than 1,000 paddlers from around the world.
Race: The beginner-friendly Honolulu Marathon in December has no cut-off time and a course that winds through downtown Honolulu and around Diamond Head crater, with ocean views, too. With 20,000 finishers, it’s one of the five largest marathons in the U.S. Bonus: The Modern Honolulu is a short walk to both the starting line and race expo.
The Hapalua in April is Hawaii’s largest half-marathon. The course — through Waikiki, downtown and Diamond Head — runs right past The Modern Honolulu, making it easy for your spectators to cheer you on.
Off-road, the XTERRA Trail Run World Championship in December includes races for everyone from 5K to half-marathon participants, plus kids’ sprints and an adventure walk. The courses treat participants to mountain, beach, rainforest and valley views in the 4,000-acre Kualoa Ranch, the setting for “Jurassic Park,” “Pearl Harbor,” “50 First Dates,” “LOST” and many other Hollywood productions. The November weekend is one of the rare times the cattle ranch’s trails are open to the public.
KAUAI
Stay: The Point at Poipu overlooks the sands of Keoneloa Bay (“Shipwreck Beach”) on Kauai’s sunny southern shore. From your doorstep, run or hike the 4-mile round-trip Maha’ulepu Heritage Trail, a rugged coastal path along sand dunes, cliffs, limestone formations and rocky inlets.
Train: The Garden Isle is an adventurer’s paradise; 90% of the island is inaccessible by car. You’ll want to lace up your shoes, hop on a horse or hit the seas and skies to see the island’s mountain trails, volcanic peaks and 50 miles of sandy beaches up close.
Though it remains closed as of May 2019 for restoration work, Kalalau Trail on the island’s north side presents 11 miles of technical terrain, taking trekkers deep into Kauai’s famed Nāpali Coast. The 3,000-foot cliffs, carved into one of the wettest places on Earth, are lined with waterfalls, lush foliage, steep drops and awe-inspiring scenery. The trail provides Nāpali’s only land access, crossing five valleys before reaching Kalalau Beach, where the cliffs meet the sea. Reaching the beach means an arduous but unforgettable 22-mile round trip.
For a gentler trek, bike or run Ke Ala Hele Makalae — “the path that goes by the coast” — a rec trail lining Kauai’s eastern shore. Nearly eight miles of flat, paved pathways link secluded beaches between Lydgate Park and Kuna Bay along Kauai’s Coconut Coast. The views are ‘Gram-bait — think crashing waves, sandy beaches, sunbathing seals and seasonal humpback whales.
The 14-mile long and 3,600-foot deep Waimea Canyon is known as “The Grand Canyon of the Pacific.” With 45 miles of trails on a plateau at 4,200 feet, neighboring Kōke’e State Park offers vistas of the canyon you won’t find elsewhere. Be prepared: Temps range from 45 to 65 degrees Fahrenheit with a good chance of rain.
Try: Grab a paddle to explore the island’s inaccessible shoreline, waterfalls and beaches with Kayak Kauai. The island is also home to Hawaii’s only navigable river. Pair a paddle up the Wailua River with a hike to a secluded waterfall by venturing with Kayak Kauai, too.
To explore on horseback, saddle up with Silver Falls Ranch to wander into the interior of Kalihiwai and Kamookoa Ridge for mountain views and dips in pristine natural pools.
To truly appreciate the Nāpali Coast’s splendor, see it by sea or air. Choose one of the many companies like Holo Holo Charters that offer snorkel trips, sunset sails or kayak adventures along the legendary shoreline that served as the backdrop for “Jurassic Park.” Or, hop aboard Blue Hawaiian Helicopters for an aerial tour of the entire island, including Nāpali Coast, Waimea Canyon and waterfalls visible only by air.
Race: The Kauai Marathon & Half Marathon during Labor Day Weekend is epic, both in terms of jaw-dropping scenery and heartbeat-accelerating terrain. Only three of 484 American marathons present a tougher challenge, according FindMyMarathon.com. The 26.2-mile course climbs 2,171 feet through Kauai’s famous 100-year-old Tree Tunnel, tropical rainforests and backcountry roads, with panoramic ocean views from the course at Kalaheo. The half-marathon presents a gentler course, but shares the same waterfront finish and “aloha spirit” with hula dancers and Hawaiian musicians lining the way. A 3-mile fun run and kids’ races round out the weekend.
HAWAII
Stay: Live out your IRONMAN dreams at the Royal Kona Resort, which sits less than one mile to the start and finish line of the most legendary triathlon on earth. With an address on Ali’i drive, you’ll be mere steps to the most famous run on the island and minutes to a swim in Kailua Bay.
Train: The island of Hawaii is the triathlon capital of the world. Home to the IRONMAN World Championship in Kailua-Kona, it’s the perfect place to get your training on. Hawaii island might have the most picturesque natural swimming pool in the entire state: Kauna’oa Bay is a crescent-shaped, sandy-bottom lagoon with calm, crystal clear water perfect for swimming laps.
Pedal along the Queen Ka’ahumanu Highway, home to the IRONMAN’s bike course. The round trip from the center of Kailua-Kona to the northern tip of the island is 100 miles. You’ll see plenty of cyclists in the bike lane, spinning beside iconic black lava rock.
If running is your sport, the IRONMAN’s iconic Ali’i Drive in Kailua-Kona is 7-miles long from start to finish with markers every half mile. Start early to beat the heat and traffic, and expect a few big hills and lots of Insta-worthy scenery. Or, head to Mana Road in Waimea to pound more than 40 miles of rolling hills on the edge of the snowcapped Mauna Kea. Be prepared for mercurial weather including strong winds, rain and sunshine. Don’t worry — the scenery is worth it.
If you only have time for one outdoor adventure, slather on sunscreen and head to Hawai’i Volcanoes National Park. With 150 miles of hiking trails around two active volcanoes, Kīlauea and Mauna Loa, the park offers a once-in-a-lifetime journey through lava fields, craters and more. You don’t have to go it alone. Hawaii Outdoor Guides and Native Guide Hawaii both offer excellent hiking tours around the park’s 333,000 acres.
Try: Rappel more than 250 feet down two waterfalls and a cave to splash down in a river with Umauma Falls Zipline in the tropical rainforests of the Hamakua Coast. On the water, board Kohala Sail & Sea‘s luxurious sailing yacht for intimate dolphin-watching year round or whale-watching in the winter months. Or, grab a boogie board — invented in Kailua-Kona — and get in the water at Laalao Beach near Kona town, famous for its “magic” disappearing sands during tidal shifts. It’s considered one of the best boogie-boarding beaches on the island.
Take in the scenery at Hawaii’s tallest peak, the 13,796-foot summit of Mauna Kea. When measured from its base at the ocean floor, it’s the tallest mountain in the world. The 6-mile summit trail climbs 9,200 feet and takes experienced hikers an average of eight hours round trip, according to the Mauna Kea Visitor Information Station. Weather on the mountain ranges from below freezing to 50 degrees Fahrenheit. The area is also home to the world’s largest observatory for optical, infrared, and submillimeter astronomy. Or, skip the hike and let Hawaii Forest & Trail drive you to the summit for sunset followed by high-powered stargazing.
Race: While competitors must qualify for the grueling 140.6-mile IRONMAN World Championship, anyone can compete in the event’s half-sized sibling, the IRONMAN 70.3 Hawai’i in June. The course takes racers through the waters of Hāpuna Beach State Park on the swim, along the northern half of the IRONMAN bike course and past ancient petroglyph fields to the shoreline of The Fairmont Orchid for the run.
For runners looking to score a personal best, it doesn’t get any swifter than REVEL Kulia Marathon & Half Marathon in January, which takes racers 5,548- and 2,505-feet downhill from the high meadows of Mauna Kea to the lava fields of Waikoloa. It’s the fastest marathon course in the U.S., according to FindMyMarathon.com.
Or, cap off your year at the Jingle Bell Beach Run, a holiday 5K, kids’ race and costume contest set along Ali’i Drive.
For the adventurous at heart, Hawaii is a must-visit destination. Begin planning your trip to this magical part of the world by visiting Diamond Resorts today.
