Best Maui Happy Hour Deals: Sunset Sips & South Maui Specials

The ice clinks against the glass as your bartender slides a lilikoi margarita across the koa-wood bar top. Behind the bottles, the Pacific has turned liquid amber, and Molokini’s crescent silhouette sits on the horizon line like a parenthesis holding the last sentence of the day. This is happy hour on Maui—not a rushed, after-work obligation, but a ritual. And in South Maui, where the sun sets over the ocean nearly every evening, the deals are as generous as the views.

Whether you’re staying in a Kihei condo and want to keep the evening budget-friendly, or you’re based in Wailea and looking for a way to experience resort-quality cocktails without the resort-dinner price tag, South Maui’s happy hour scene has you covered. From beachfront bars with $5 draft beers to upscale restaurants pouring half-price wine, this guide maps out the best deals by neighborhood so you can plan your sunset accordingly.

Wailea’s oceanfront bars turn happy hour into the best show on the island.

Best Happy Hours in Kihei

Kihei is where you’ll find the most variety, the most walkable options from South Maui vacation rentals, and the kind of laid-back atmosphere where flip-flops are the dress code.

Three’s Bar & Grill

Three’s might be the best overall happy hour value in South Maui. Running daily from 2:00–5:00 p.m., their specials include $5 draft beers, $7 well drinks, and a rotating selection of $8 craft cocktails. The food deals are the real draw: $5 pork belly bao buns, $6 ahi poke tacos, and $8 crispy brussels sprouts that have converted more than a few vegetable skeptics. The outdoor patio along Kihei Road catches the afternoon breeze, and the vibe is pure local hangout—you’ll see off-duty surf instructors and construction crews mixing with visitors who’ve figured out the town’s best-kept secret.

Local’s Tip: Arrive by 2:30 on Fridays to snag patio seating. Three’s gets packed by 3:00 on weekends, and the patio doesn’t take reservations during happy hour. If the patio is full, the bar inside has the same deals and solid A/C.

Nalu’s South Shore Grill

Nalu’s runs happy hour from 2:00–5:00 p.m. daily, and it’s one of the few spots in Kihei where you can literally see the ocean from your bar stool. The $6 mai tais are strong and properly made (fresh juice, not from a mix), and the $5 fish tacos use the same fresh catch as their dinner menu. Their ahi nachos for $9 are big enough to split between two people and make a solid pre-dinner appetizer. For a complete rundown of our favorite oceanfront spots, check out our guide to the best outdoor dining in Maui.

For more oceanfront restaurant picks, see our guide to the best outdoor dining in Maui.

Kihei Caffe’s Sunset Sessions

Known primarily as a breakfast powerhouse, Kihei Caffe started offering sunset happy hour sessions from 4:00–6:00 p.m. Thursday through Saturday. The menu features $6 local brews on tap, $8 tropical sangria, and $7 pu pu platters with kalua pork sliders and coconut shrimp. The picnic-table seating and string lights give it a casual backyard-party feel that’s perfect for families who want to enjoy a drink without finding a babysitter.

Kihei’s casual happy hour spots feel like a neighborhood party every evening.

Best Happy Hours in Wailea

Wailea’s happy hours are more polished and pricier than Kihei’s, but the savings over regular menu prices are significant—and the settings are hard to beat.

Monkeypod Kitchen by Merriman

Chef Peter Merriman’s Monkeypod Kitchen runs one of the most popular happy hours on the island, daily from 3:00–5:30 p.m. and again from 9:00–11:00 p.m. The late-night window is a hidden gem for night owls. Highlights include $6 craft beers on their rotating 36-tap system, $9 hand-shaken cocktails (the Bikini Blonde Lager Shandy is dangerously drinkable), and half-price pizzas from their wood-fired oven. The strawberry cream pie—Monkeypod’s famous dessert—drops to $7 during happy hour. The open-air design means every seat has tropical breezes and garden views. For more on Maui’s cocktail culture, see our guide to the best craft cocktails on the island.

Cocktail enthusiasts will love our deep dive into the best Maui craft cocktails and mixology bars.

Humble Market Kitchin

Located in the Wailea Gateway shopping area, Humble Market Kitchin by Roy Yamaguchi offers happy hour daily from 2:00–5:00 p.m. The $8 signature cocktails are excellent (try the Hibiscus Lemonade with shochu), and their $6 dim sum baskets are a steal. The misoyaki butterfish sliders at $9 are among the best bites you’ll eat on vacation. The indoor-outdoor bar area looks out over manicured gardens, and the service has the kind of warmth that makes you want to come back every day of your trip.

Ferraro’s Bar e Ristorante

For a true oceanfront splurge that still qualifies as a deal, Ferraro’s at the Four Seasons runs happy hour from 2:00–5:00 p.m. on the lower terrace. The $12 cocktails aren’t cheap by mainland standards, but they’re half the regular price, and you’re drinking them with your toes practically in the sand while watching green sea turtles cruise the reef below. Their $14 Margherita pizza from the wood-fired oven is genuinely great Italian food. This is the spot for a date night warm-up or a special-occasion afternoon. For more romantic evening ideas, explore our Maui date night ideas guide.

Planning a romantic evening? Browse our Maui date night ideas for creative options beyond the typical dinner reservation.

Local’s Tip: Monkeypod’s 9:00–11:00 p.m. happy hour has the same deals as the afternoon session but with zero wait for a table. It’s the best-kept secret in Wailea—most tourists are back at their hotels by then, so you’ll feel like you have the place to yourself.

Happy hour pu pu platters at South Maui restaurants rival full-priced appetizers anywhere else.

Best Beachfront Happy Hours and Sunset Bars

Sometimes the view is worth more than the discount. These spots combine solid deals with the kind of sunset-over-ocean setting that defines a Maui vacation.

Luana Lounge at the Fairmont Kea Lani

The Luana Lounge runs sunset happy hour from 4:00–6:00 p.m., and the setting is unreal—an open-air lounge looking directly at the ocean with Kahoʻolawe Island on the horizon. Drinks range from $8–$12 during happy hour (normally $16–$22), and the pu pu menu includes $10 poke bowls and $12 flatbreads. The white-linen atmosphere is upscale without being stuffy, and they welcome walk-ins at the bar even when the restaurant is fully booked.

Fred’s Mexican Beach House

Fred’s sits right on Keawakapu Beach in South Kihei, and their sunset happy hour (3:00–5:30 p.m.) pairs $7 margaritas with a front-row sunset view that no amount of money could improve upon. The $5 street tacos are excellent, and their $8 guacamole is made tableside. This is one of the few places in South Maui where you can walk directly from the sand to a bar stool without putting on shoes. If you love the beachfront vibe, our guide to Maui’s best beach bars covers more oceanfront drinking spots up and down the coast.

For more barefoot bar experiences, see our roundup of the best Maui beach bars across the island.

5 Palms Restaurant

Perched right on Keawakapu Beach, 5 Palms runs happy hour daily from 2:30–4:30 p.m. with $7 well drinks, $5 Maui Brewing drafts, and $9 pupus. The seared ahi appetizer is the standout. What sets 5 Palms apart is the literal beachfront position—your table might be ten feet from the high-tide line, and the sunset views are among the best in all of South Maui. Our Maui sunset happy hours guide goes deeper into the best spots for golden-hour drinks.

See our complete guide to Maui sunset happy hours and oceanfront bars for more golden-hour picks.

Local’s Tip: Fred’s and 5 Palms share Keawakapu Beach, so you can easily beach-hop between both during overlapping happy hours. Start at 5 Palms at 2:30, then walk south along the sand to Fred’s by 3:30 for round two with a fresh view.

South Maui’s bartenders take pride in craft cocktails made with fresh island ingredients.

Happy Hour Tips: How to Maximize Your Savings

A few insider strategies can stretch your happy hour budget further and help you avoid the most common mistakes visitors make.

Timing is everything. Most South Maui happy hours end between 5:00 and 6:00 p.m., but a few places—Monkeypod being the notable exception—don’t offer a second evening window. If you’re eating dinner out, using happy hour as your appetizer course at one restaurant and then walking to a different spot for dinner is a classic local move that saves $30–50 per couple.

Many restaurants honor happy hour pricing at the bar only, not at tables. If you want the deals, grab a bar seat or a spot in the bar-adjacent lounge area. Some places, like Monkeypod and Three’s, extend the pricing to the entire restaurant, but it’s always worth asking when you sit down.

Don’t overlook the food deals. At many South Maui happy hours, the discounted appetizers are the real value play. A couple sharing three $6–$9 happy hour appetizers and two $6 drinks can eat and drink oceanfront for under $45 before tip—that’s less than a single entrée at some Wailea restaurants.

If you’re staying in a vacation rental with a full kitchen, the best strategy is to cook breakfast and lunch at home, then use happy hour as your main evening meal. Stock up at local grocery stores—our guide to South Maui grocery stores has recommendations for the best spots to fill your rental kitchen.

Local’s Tip: Download the Yelp app and search “happy hour” near your location—many South Maui restaurants update their happy hour menus on Yelp more consistently than on their own websites. You’ll also catch seasonal specials and limited-time promotions that don’t make it to Google listings.

Where to Stay for the Best Happy Hour Access

The best happy hour circuit requires zero driving. Here’s how your vacation rental location unlocks South Maui’s best sunset drinking and dining.

Staying in central Kihei puts you within walking distance of Three’s, Nalu’s, and a dozen other happy hour spots along South Kihei Road. A vacation rental in this area means you can walk to happy hour, enjoy two or three drinks without worrying about driving, and stroll home along the beach as the last light fades over the water.

Wailea vacation rentals put Monkeypod Kitchen, Humble Market Kitchin, and the resort bars within easy reach. The Wailea Beach Walk connects several hotels and restaurants along a paved oceanfront path—perfect for a sunset stroll that ends at your favorite bar.

Luxe Maui Properties manages vacation rentals throughout Kihei and Wailea that are specifically selected for walkability to dining, shopping, and nightlife. Having a full kitchen in your rental means you’re not eating out for every meal—you can save your dining budget for the experiences that matter most, like that sunset cocktail at Ferraro’s or the ahi nachos at Nalu’s.

A Kihei vacation rental puts you walking distance from South Maui’s best sunset sips.

Browse South Maui vacation rentals →

Quick-Reference: Best Maui Happy Hour Deals

• Three’s Bar & Grill (Kihei): Daily 2:00–5:00 p.m. — $5 drafts, $7 wells, $5–$8 pu pus

• Nalu’s South Shore Grill (Kihei): Daily 2:00–5:00 p.m. — $6 mai tais, $5 fish tacos

• Kihei Caffe (Kihei): Thu–Sat 4:00–6:00 p.m. — $6 local brews, $7 pu pu platters

• Monkeypod Kitchen (Wailea): Daily 3:00–5:30 p.m. & 9:00–11:00 p.m. — $6 beers, $9 cocktails, half-price pizzas

• Humble Market Kitchin (Wailea): Daily 2:00–5:00 p.m. — $8 cocktails, $6 dim sum

• Ferraro’s at Four Seasons (Wailea): Daily 2:00–5:00 p.m. — $12 cocktails, $14 pizza

• 5 Palms (Kihei): Daily 2:30–4:30 p.m. — $7 wells, $5 drafts, $9 pu pus

• Fred’s Mexican Beach House (Kihei): Daily 3:00–5:30 p.m. — $7 margaritas, $5 tacos

• Luana Lounge at Fairmont (Wailea): Daily 4:00–6:00 p.m. — $8–$12 drinks, $10 poke bowls

Talk to our local Maui team for personalized recommendations →