An uncountable number of beaches lining South Maui's 15-mile shoreline create a laid-back vibe among visitors and residents that resonates from the quirky beach community of Kihei to the upscale resort area of Wailea, and on to the secluded sandy shores of Makena. On the South side, sandals, or "slippahs" are always welcome, suits and ties are unheard of, and spectacular sunsets paint a magical backdrop to happy hour.
At first glance, Kihei appears to be no more than a lengthy stretch of condominium complexes, strip malls, and souvenir shops. Dig further to uncover a happening beach scene and a variety of bars to keep you busy during moonlight hours. Enjoy a day at one of the Kama'ole beaches or Charley Young Beach to catch some rays alongside friendly residents. You'll usually find the water pleasantly calm and the weather thankfully dry in this area. Learn to surf at Cove Park or test your volleyball skills at Kalama Park, both located across the street from a medley of souvenir shops, restaurants, bars, and boutiques.
Speaking of happy hour, be sure to visit the area known as "The Triangle" located across from Kalama Park and next to Kihei Town Center. You'll find a handful of unique, island-inspired bars – all within crawling distance of each other – that provide live local music, deejays, and food and drink specials throughout the week. Sansei Seafood Restaurant and Sushi Bar, located across the Kihei Town Center parking lot, offers karaoke and half-off sushi and drink specials after 10 pm on weekends. Venture a mile south for rip-roaring Taco Tuesdays at Fred's Mexican Cafe complete with cheap tacos and giant margaritas.
You'll know you've reached Wailea when you begin seeing luxury homes, gated communities, manicured landscapes, golf courses, and fancy seaside resorts along the roadside. Mainstays, including the Four Seasons Resort, the Grand Wailea Resort and Spa, and the Fairmont Kea Lani, set the bar for Wailea's sense of luxury and exclusivity. To satisfy your spending urges, browse The Shops at Wailea, an open-air shopping center filled with high-end boutiques and restaurants. Golfers can tackle challenging courses in a pristine tropical setting at the Wailea Golf Club or the Makena Golf Course. Thankfully, development remains fairly spread out in this area, keeping Wailea beautiful and serene.
And of course, there's plenty of beach to explore. Keawakapu Beach, Mokapu Beach, Ulua Beach, Wailea Beach, and Polo Beach spread out before Wailea's resorts, and there's even a walking path that runs between them all. Remember, all beaches in the state of Hawai'i are open to the public, so as long as you follow the blue "Beach Access" signs to the sand, you're welcome to set up your chair and umbrella anywhere you choose. In addition to providing hobnobbing and people-watching opportunities, Wailea's beaches also offer delectably clean blue water as well as decent boogie boarding, snorkeling, diving, kayaking, and sailing. Check out Mulligan's on the Blue, an upscale, open-air Irish pub and restaurant located on the Wailea Golf Club's Blue Course, for a hopping weekend bar scene featuring the island's best local entertainment.
Continue driving south for beach and ocean experiences unfettered by major development and commercial activity. At Big Beach and Chang's Beach, it's just you, the sand and sea, and others looking to immerse themselves in the island's raw beauty, without a resort or strip mall in sight. Catch a snorkel at Makena Landing, Oneuli Black Sand Beach, or in the Ahihi Kina'u Nature Preserve area to encounter a bounty of tropical fish, sea turtles, and other aquatic life. You may also continue to the end of Makena Alanui Road until you reach the lava fields of La Perouse Bay, where hiking trails lead you through ancient Hawaiian ruins to secret beaches and alcoves hidden among the vast expanse of lava rocks.