This independant Kīhei hotel boasts 427 guestrooms across two towers. With discount rates of up to 33%, this property on the cusp of ritzy Wailea offers chic, modern interiors rooted in traditional Hawaiian flair. Guests can enjoy a wide range of amenities, including two pools, three hot tubs, pickleball courts, an on-site 24-hour gym and a complimentary electric VW van shuttle available daily from 7 a.m. to 10 p.m. for rides within a 3-mile radius of the hotel, including the Shops at Wailea. It offers all the convenience of a resort without the resort price tag.

From $370/night ($344 kamaʻāina)

After checking in, I like to catch the free shuttle to Monkeypod Kitchen Wailea for happy hour. You can get $4 off handcrafted cocktails, $3 off wine, $2 off beer, $16 pizzas and half off non-seafood pupu. Full disclosure: I work at Monkeypod Kā‘anapali and can vouch for the quality of the food. Daily happy hour runs from 3:30 to 5 p.m. with live music. Stick around a little longer to catch the sunset from Monkeypod’s rooftop lanaʻi.

After a discounted lilikoʻi foam-topped mai tai, or two, head back to Kīhei for a live show at ProArts Playhouse inside the Azeka Center. This theater-slash-cabaret features live music, burlesque performances, comedy shows and full-length musical productions. On our trip, we were lucky enough to see the cheeky burlesque trio Cabaret & Cocktails, with tickets starting at $40, featuring Lily O’Lei, Miss F-Bomb and Sadie Vine. They perform often and also teach one-on-one classes for those interested in learning the coquettish craft, with virtual sessions starting at $35 per hour and in-person lessons at $85 per hour.

Next up, I recommend soaking up some local nightlife at what locals dub “The Triangle” — a collection of bars in Kīhei’s Kalama Village. Haui's Life’s A Beach is my pick for free karaoke and espresso martinis.

I like to start my morning at Kihei Caffe, the hotel’s newly renovated breakfast, lunch and dinner spot. You can order lighter fare like papaya and muesli for $10.95 or go big with the pork fried rice and eggs for $12.95. Breakfast is also offered poolside from 6 a.m. to noon or you can grab something to go inside the lobby. Wherever you decide to eat, the price is the same. It just depends on whether you want something quick or a more leisurely meal.

For two millennials, my sister and I thought this was the perfect spot thanks to its open-air patio and affordable food. It also stays open until midnight if you need a late-night snack.

Once the caffeine hits, I like to put on my hiking gear — sturdy shoes and a hat will suffice — and take a rideshare to Keoneʻōʻio Bay, also known as La Perouse Bay — named after the French explorer who first visited the islands in 1786. A rideshare costs about $30. This is where you’ll find the Hoapili Trail, also known as the King’s Trail. Come prepared. This three- to four-hour hike is best suited for intermediate hikers, with rugged terrain and no shade. Pack sunscreen, water and snacks and be ready to lose cellphone service.

The trail has two options. You can take a 5.5-mile round-trip trek along the King’s Highway to Kanaio Beach or choose a shorter route heading south to Cape Hanamanioa. We did the full hike. My legs still have not forgiven me.

The payoff is worth it. You’ll traverse an ancient royal coastal trail marked by craggy ʻaʻā lava, which is rougher and more jagged than the smooth billows of pāhoehoe lava, formed by Maui’s last lava flow in 1790. Along the way, sweeping ocean and mountain views open up to Molokini, Kahoʻolawe and Haleakalā.

After that, I pop over to Tikehau Lounge, a stellar tiki bar in Wailea voted Best Bar of 2025 by Maui No Ka Oi Magazine. Helmed by co-owner Jessica Sullivan and a top-notch team of mixologists, this thatched hideaway offers happy hour daily from 2 to 5 p.m.

I recommend ordering the Tropical Mai Tai and Rum Cannonball, both $10, along with a mini poke bowl for $12 and a sesame ʻahi tuna slider for $7.

For an upscale dinner, check out Spoon & Key Market, run by chef partners Christopher Kulis and Tarah Principato. The market and cafe prioritizes locally-grown and produced ingredients and serves dinner Wednesday through Sunday. There is a 4-course prix fixe for $125 per person or ala carte menu to choose from. Ala carte entrees run $30-$52. Since you've already pre-gamed with cocktails and pupu at Tikehau around the corner, you could save money by skipping appetizers and going straight for the local catch, S&K steak or Wagyu smash burger.

Spend the morning relaxing poolside at the hotel. After checking out, leave your luggage with the front desk until it’s time to head home. Hop on the free shuttle one last time and ride over to the edge of Wailea at Keawakapu Beach Park.

This beach is ideal for sunbathing and swimming, with stunning views overlooking Molokini and Kahoʻolawe. If, like me, you get restless simply lying in the sun, walk along the boardwalk to ogle million-dollar beachfront homes and nearby resorts. During the winter months, keep your eyes on the water, as this is an ideal spot for whale watching.

After the beach, take a quick walk to The Shops at Wailea, the south side’s luxury mall. You can stay within budget by just window shopping or stick to the more affordable options, such as souvenirs at Coco Nene or local fashion at Mahina.

While there, you can hit up one last happy hour. I love Aurum Maui, run by local husband-and-wife team Natasha and Taylor Ponte. I recommend the P.O.G. Collins ($12), made with Bombay Dry Gin, Angeleno Amaro, Chinola, lilikoʻi, lemon, guava and soda, and the Paniolo Smash Burger ($15), made with local beef, caramelized Maui onions, bacon, American cheese and their proprietary burger sauce.