Hawaii

Looking for the best chillin in Hawaii? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Hawaii. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Hawaii

  • Kilauea, Hawaii

    Secret Beach

    4.8
    0.47 mi / 200 ft gain
    Is a so-called ‘secret beach’ that sits on Secret Beach Road considered secret anymore? Perhaps not, but don’t let that deter you from exploring the depths of Kauai’s renown Kauapea Beach, more widely known as Secret Beach. The 3,000-foot long north shore beach is known for it’s size, privacy, a...
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  • Kahuku, Hawaii

    Hike from Turtle Bay to Kawela Bay

    5.0
    3 mi / 0 ft gain
    Once you get to the Turtle Bay resort, you just follow the signs to Kawela Bay/ the Stables. From there the signs are super easy to follow, with options ranging from 0.5mi to 3.0mi. and you can do this as a simple out-and-back or as a longer loop that takes you through Banyan forests, beaches and...
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  • Princeville, Hawaii

    Hike to Turtle Cave

    3.8
    0.75 mi / 62 ft gain
    Turtle Cave is located within a small bay on the Princeville side of Kauai. This hike requires swimming, repelling down a steep cliff and potentially high tides.  This particular access point is located on private property, so you should be staying in one of the rentals or traveling with a guest....
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  • Kula, Hawaii

    Pa Ka'oao (White Hill) on Haleakala

    4.5
    0.42 mi / 164 ft gain
    Haleakala means "House of the rising sun" and is a wonderful description of the mountain. Haleakala is a large dormant volcano that makes up ~75% of the island of Maui. On the slopes of Halekala are rain forests, pastures, endemic birds, the endangered but beautiful silversword, and a summit that...
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  • Honolulu, Hawaii

    Makapu'u Point Lighthouse Trail

    4.4
    3.62 mi / 1263.45 ft gain
    If you're looking to get moving and get your heart rate up or want a place to snap great photos, start with hiking to Makapu’u Lighthouse. The lighthouse was built in 1909 on a 600-ft cliff, which overlooks Makapu’u beach. The hike is more of an uphill walk and can be done in sandals unless you’...
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  • Hanapepe, Hawaii

    Hike the Pihea & Alaka'i Swamp Trail

    5.0
    7 mi / 1500 ft gain
    A strenuous 7 mile hike, depending on which way you start, that takes you from the world renowned Kalalau Valley from Pu'u O Kila lookout, through dense mossy forests, across a stream, up to the highest swamp in the world and ends in views of Kaua'i's north shore of Wainiha valley and Hanalei Bay.
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  • Kilauea, Hawaii

    Anini Beach Park

    5.0
    The shallow nearshore ocean bottom makes Anini a great beach to visit if you have kids. Anini Beach Park is also a snorkeler's delight - here you may spot Hawaii's state fish, the humuhumunukunukuapua'a (triggerfish) and uhu (parrotfish), kala (unicornfish) and other tropical fish. On the downsid...
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  • Kapaa, Hawaii

    Hike the Kuilau Ridge Trail

    4.0
    5 mi / 488 ft gain
    Parking at the trailhead is limited to approximately four vehicles, so arrive early. If you are unable to park, continue down Highway 580 and you will find parking next to Kawi Stream. The beginning of the trail, an old fire road, starts with a gradual incline where you are exposed to a variety o...
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  • Naalehu, Hawaii

    Papakōlea Green Sand Beach

    4.9
    5.62 mi / 325.46 ft gain
    Papakolea Beach aka Green Sand Beach is situated in a bay cut into a side of a cinder cone that erupted thousands of years ago. The green sand is created by a silicate deposit (mineral deposit) of lava called, which stays on this beach because it is heavier than the other, lighter components of t...
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  • Kula, Hawaii

    Backpack the Haleakala Wilderness: Halemau'u to Sliding Sands Trail

    5.0
    19 mi / 3643 ft gain
    Day 1, the trailhead begins just off the highway at 7,990 feet elevation and takes you to the north and east to an opening in the ridgeline. After 1.1 miles, you will begin your 2.6 mile descent from the crater ridge south, into the heart of the wilderness area and where you will arrive at Holua ...
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  • Eleele, Hawaii

    Glass Beach

    3.7
    The shoreline of Glass Beach is covered with millions of brown, aqua, clear and blue sea glass pebbles, but also consists of other remnants from what looks to be a former salvage yard (do not walk barefoot in this area). Although that may be the case, there is a lot of beauty to be captured here...
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  • Kailua, Hawaii

    Paddle to Moku Nui

    5.0
    There are two islands off the coast of Kailua known as the Mokulua or 'Mokes'. The island on the right, Moku Iki, is off-limits. However, the larger of the two islands, Moku Nui, is accessible via a 30 minute kayak, SUP or outrigger.You can push off from Kailua Beach Park for a longer paddle or h...
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  • Kahului, Hawaii

    Road to Hana

    4.4
    48.99 mi / 9608.92 ft gain
    Start near Paia on Highway 36 and head east. The road is famous for its many twists and turns, so consider taking lots of breaks to get some fresh air and avoid getting car sick. There are many stops along the way, from ice cream to medium length hikes. Some of the Best Stops: Coconut Glen's:...
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  • Lahaina, Hawaii

    Kaanapali Beach

    4.6
    Kaanapali Beach is about a 45-minute drive from Kahului Airport, and only two miles from Lahaina.  Nearly all of the seaside resorts here back right up to the beach, making it an ideal place to stay if beach time is your top priority.  If you are not staying on Kannapali, there are several pay-to...
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  • Kalaheo, Hawaii

    Swim in the Waikoko Stream & Waterfall

    1 mi / 166 ft gain
    You will need a 4WD high clearance vehicle to reach this trail. To reach the trailhead, take Highway 580 which will eventually turn to dirt. You'll cross over a couple of streams and when you reach a Y, take a left. In one more mile, you will reach a second Y which you will turn left. If the gate...
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  • Kapaa, Hawaii

    Hike to Ho'opi'i Falls

    4.0
    2.2 mi
    Easiest/Direct route: When in the Kapa'a area from the main highway turn left onto Kawaihau road. Follow Kawaihau all the way up until you see a sign for Kapahi road, turn left onto that road. Driving in, you'll see a red gate on your left-hand side. The parking area is just after the gate, along...
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