Looking for the best way to unwind on Maui? Happy hours with live entertainment combine oceanfront views, affordable drinks, and local music for an unforgettable experience. Whether you’re a visitor or a local, Maui’s happy hour culture offers a chance to enjoy discounted food and drinks while soaking in Pacific sunsets and vibrant island vibes.
Key Highlights:
- Affordable Deals: Drinks starting at $2.50, tropical cocktails from $5-$14, and appetizers at half price.
- Live Music: Many venues pair happy hours with performances by local musicians.
- Oceanfront Settings: Enjoy stunning views, sunsets, and even glimpses of sea turtles or whales.
- Top Spots: Favorites include Mala Ocean Tavern, Maui Brewing Co., and Three’s Bar & Grill.
Quick Tips:
- Happy hours typically run mid-to-late afternoon (2–6 PM) but can extend into the evening.
- Reservations are recommended for popular venues, especially during sunset hours.
- Check schedules for live music to plan your visit.
Maui’s happy hours are more than just discounts – they’re a celebration of food, music, and the island’s laid-back lifestyle. From Lahaina to Wailea, every region offers something special. Ready to sip, savor, and relax? Let’s dive into the details.
Maui’s Happy Hour and Live Music Scene
Happy Hours as a Maui Tradition
On Maui, happy hour isn’t just a time slot – it’s a cherished ritual. Typically lasting 2–3 hours in the mid-to-late afternoon (like 2–4 PM or 3–5 PM), some spots stretch the fun into the evening, running as late as 8–10 PM. These hours align perfectly with the island’s laid-back rhythm, giving locals a chance to unwind after work and visitors a moment to relax after a day of exploring.
With over 100 bars and restaurants offering happy hour deals, there’s something for everyone. Whether you’re craving $2.50 tacos at a casual dive or sipping on $12.00 signature cocktails at a luxury resort lounge, Maui delivers. Many places also tempt guests with half-priced appetizers, making it easy to indulge without breaking the bank.
What truly sets Maui’s happy hours apart is the way they blend live music with food and drink specials. Some venues host “Live Music Happy Hours”, where performances coincide with discounted menus, while others use happy hour to lead into evening entertainment starting around 6:00 PM. For instance, Mala Ocean Tavern in Lahaina offers a Live Music Happy Hour from 2–4 PM, featuring a rotating lineup of local talent like Peter D. on Sundays, Karim Benrida on Mondays, and Christina Boyden on Tuesdays. Similarly, Maui Brewing Co. in Kaanapali pairs its happy hour (3:00 PM to 5:00 PM) with live music later in the evening from 6:00 PM to 8:00 PM.
This seamless mix of great timing, delicious offerings, and live performances makes Maui’s happy hour scene truly unforgettable, especially at its oceanfront venues.
Oceanfront Venues and Local Musicians
Oceanfront spots take Maui’s happy hour experience to another level, combining breathtaking views of the Pacific with live music. Many venues design their lanais and outdoor patios to showcase the sunset, creating a magical backdrop for both the food and the tunes. Picture this: as local musicians perform acoustic sets, you might spot honu (sea turtles) gliding through the water just steps away from your table. It’s not just a meal – it’s a feast for the senses.
One of the best parts? Many of these performances come with no cover charge, making incredible live music a regular part of the happy hour experience. Local artists often connect directly with guests, creating a warm, interactive vibe that feels more like a gathering of friends than a formal show. As one visitor, Marco C., shared about his experience:
“Stood on the sidewalk for half an hour to dance. So I’ll give the restaurant a 5 star”
This blend of stunning scenery, talented musicians, and a welcoming atmosphere turns a casual drink into a moment of pure Maui magic. Whether you’re a local or just passing through, it’s an experience that stays with you long after the last note fades.
West Maui Happy Hour Venues with Live Music
West Maui’s happy hour scene is a perfect blend of the island’s Pau Hana tradition, breathtaking ocean views, and lively music performances. These venues create a unique atmosphere where locals and visitors alike can unwind and enjoy the rhythm of Maui.
Mala Ocean Tavern
Located on Front Street in Lahaina, Mala Ocean Tavern is a top choice for oceanfront happy hour enthusiasts. Their daily Live Music Happy Hour runs from 2:00 PM to 4:00 PM, featuring a rotating lineup of talented local musicians. As Russell Snyder from Maui Happy Hours puts it:
“As far as ocean front or ocean view dining, Mala gets you as close to the actual water as any restaurant on Maui”.
The happy hour menu offers a great mix of drinks and bites, including $8 beers, $9 wines, $12 well drinks, and $14 signature cocktails. Food options range from $5 oyster shooters and $14 flatbreads to $17 Coconut Shrimp and Seared Ahi Bruschetta priced at $19 (half) or $38 (full). Mala’s reputation extends far beyond happy hour, with accolades like being ranked #4 in Toast’s “Top 20 Best Outdoor Dining in the States” and earning a spot on OpenTable’s Top 100 Brunch Restaurants in America for 2025. Reservations are highly recommended, and parking is available on-site or at the nearby Lahaina Cannery Mall.
Other West Maui Options
West Maui offers plenty of other spots for live music and happy hour vibes. While some Lahaina venues were affected by the 2023 fires, the Kaanapali area continues to thrive with places like Monkeypod Kitchen at Whalers Village, Leilani’s on the Beach, Cliff Dive Grill at The Sheraton Maui (happy hour from 3:00–4:00 PM daily), and Hale Mo’olelo at the Westin Maui.
Further north, Merriman’s Kapalua provides a more refined setting with live music during happy hour from 4:00 PM to 5:00 PM. Guests can enjoy the tunes at both the Point Lounge and the main bar, making it a perfect spot to relax as the sun sets.
South Maui Happy Hour Spots with Live Music
South Maui’s happy hour scene has something for everyone, from the relaxed beach bars of Kihei to the polished venues of Wailea. Whether you’re in the mood for casual vibes with local musicians or ticketed events with a lively crowd, this area offers plenty of options for a fun-filled evening. Here are three standout venues that bring together great drinks, delicious food, and live music.
Three’s Bar & Grill
Located in Kihei, Three’s Bar & Grill is a favorite for its daily happy hour from 3:00 PM to 6:00 PM, featuring live performances by rotating local artists. This spot even caught the attention of the Food Network’s Diners, Drive-ins, and Dives. One reviewer, Hope B., called it the “best happy hour in town”.
The menu is packed with deals: $6.50 Southside Mai Tais and Margaritas, $6.25 well drinks, $7 draft beers (14 oz), and $8 wine. On the food side, you’ll find $3.75 oysters, sushi rolls ranging from $5.25–$9, $11.50 Kalua Pork Quesadillas, and $6.75 Coconut Crusted Fish Tacos. Plus, Hawaii residents with valid ID can snag these deals all day long. Ready for a change of pace? Let’s head to an Irish pub with a twist.
Mulligans on the Blue
For a mix of Irish charm and island vibes, Mulligans on the Blue in Wailea delivers. Known as South Maui’s go-to music venue, it hosts live entertainment Thursday through Sunday. There’s a $10 cover charge on Thursdays and $5 on Sundays, adding to the lively atmosphere. Sports fans will also appreciate the “Mulligans Music Box”, which features 14 HD TVs for catching the game while enjoying the show.
The menu combines traditional pub favorites with island-inspired dishes, all served with breathtaking ocean views. Reservations via OpenTable are recommended for show nights, as some events require separate tickets. If you’re looking for something more relaxed with ocean views, check out the next spot.
Gather on Maui
Nestled in Wailea, Gather on Maui offers a daily happy hour from 3:00 PM to 5:00 PM. This walk-in-only venue boasts stunning views of the Pacific Ocean and Molokini Island, making it a perfect spot to unwind.
Drink specials include $10 specialty cocktails, $8 classic cocktails, and $6 draft beers. Pair your drinks with menu favorites like $13 Hurricane Fries, $20 Poke Nachos, or a $19 Smash Burger. Arriving early is key to snagging the best ocean-view seating.
Central and North Maui Happy Hour and Live Music
Central and North Maui bring a relaxed atmosphere with sports bars, historic spots, and happy hour deals that often feature live music. Here are three standout venues that showcase the area’s charm:
Kahului Ale House
Kahului Ale House is a lively sports bar that hosts a daily happy hour from 3:00 PM to 6:00 PM, complete with local musicians. Drink deals include $1 off draft beers and $6 house wines by the glass. For food, you can grab $12.25 pizzas, $8.75 mini nachos or sliders, and $5.99 sides.
Milagros Food Company
Located in Paia, Milagros Food Company offers live entertainment in a casual, beachside setting. Be sure to check their schedule to catch the latest performances.
Colleen’s at the Cannery
Set in Haiku’s historic Cannery Marketplace, Colleen’s combines a family-owned feel with a daily happy hour from 3:30 PM to 5:30 PM. Drink specials include $5 draft beers (bottles and cans), $10 wine by the glass, and $7 zero-proof cocktails. Food options feature $4.75 pizza slices (Cheese, Pepperoni, or Veggie). Occasionally, live music adds to the experience, and standout menu items like the venison burger and fish and chips make it a favorite. As Doug S. put it:
“I think they serve the best burgers on the island. There, I’ve said it. Friendly service, always a pleasure to visit when we are on Maui.”
| Venue | Happy Hour Times | Drink Specials | Entertainment Type |
|---|---|---|---|
| Kahului Ale House | 3:00 PM – 6:00 PM Daily | $1 off drafts, $6 house wine | Local Musicians |
| Milagros Food Company | Varies | – | Live Entertainment |
| Colleen’s at the Cannery | 3:30 PM – 5:30 PM Daily | $5 beers, $10 wine, $7 zero-proof cocktails | Occasional Live Music |
Planning Your Maui Happy Hour Visit
To make the most of Maui’s happy hour charm, a little planning goes a long way.
How Schedules Can Change
Happy hour and live music schedules in Maui aren’t set in stone – they often shift due to weather, artist availability, or holidays. Weather, in particular, plays a big role, especially at oceanfront venues where rain, wind, or storms can lead to cancellations.
Take January 2026, for example: heavy rains, with 2–3 inches falling per hour, caused flood warnings in areas like Kapalua, Nāpili-Honokōwai, and Pāʻia. Many venues, such as Down The Hatch and Mala Ocean Tavern, help guests stay in the loop by updating their weekly calendars online with the latest performer schedules.
Booking Reservations at Popular Venues
If you’re eyeing a spot at a favorite oceanfront venue like Mala Ocean Tavern, it’s smart to book ahead, especially during peak hours (typically 2:00–4:00 PM). Reservations can often be made by phone – Monkeypod Wailea, for instance, can be reached at 808-891-2322 – or online. While many places welcome walk-ins, seating can fill up fast during the popular sunset window.
Russell Snyder from the Maui Happy Hours team shares this about Mala Ocean Tavern:
“Although this restaurant is super popular and reservations are highly recommended, you can still pop in for happy hour and get a seat at the bar most days.”
Some venues stick to a first-come, first-served policy. For example, “The Point” at Merriman’s Kapalua doesn’t accept happy hour reservations. If you’re heading to one of these spots, arriving 15–30 minutes early can help you snag a prime oceanfront seat.
Once you’ve secured your spot, plan your arrival to soak in the atmosphere and enjoy the oceanfront setting.
Getting the Most from Oceanfront Entertainment
Timing is everything when it comes to enjoying Maui’s happy hour entertainment. Arriving at the start of happy hour – usually between 2:00–3:00 PM – gives you the best chance to claim a great ocean-view seat and enjoy live music before the venue winds down for sunset.
Clear skies can make the experience even more magical, offering glimpses of green sea turtles in the waves or breaching whales during the winter months. Before heading out, it’s worth checking updates from the National Weather Service, as weekend frontal systems can bring unsettled weather. When storms stir up the ocean or heavy clouds roll in, wildlife sightings and sunset views might not be as vibrant.
Conclusion
Maui’s happy hour scene is a true delight – a chance to enjoy affordable drinks, live island music, and breathtaking oceanfront views. With over 100 venues offering mid-afternoon specials, ranging from lively local hangouts to elegant oceanfront restaurants, it’s an opportunity to savor award-winning cuisine and handcrafted cocktails without the dinner-time price tag. Whether you’re taking in the scenic beauty of West Maui or soaking up the vibrant energy of Kihei in South Maui, every region offers its own charm, blending local flavors, live entertainment, and unforgettable Pacific sunsets that embody the spirit of Maui’s cherished “Pau Hana” tradition.
“Happy Hour on Maui is more than just great deals – it’s the perfect way to relax, soak in ocean views, and enjoy fresh poke, local favorites, tropical cocktails, and craft beers.” – Ali’i Resorts Team
By supporting these locally owned businesses, you’re not only enjoying a memorable experience but also contributing to the preservation of what makes Maui so special. These venues, with their mix of local charm, live music, and oceanfront dining, perfectly capture the essence of the island’s iconic happy hour culture.
Don’t forget to bring your Hawaii ID for local discounts, check daily schedules, and immerse yourself in live music, fresh seafood, and those stunning Pacific sunsets. For more details on oceanfront dining and happy hour specials, visit the Maui Oceanfront Dining Directory 2026. Your ideal oceanfront spot is just waiting to be discovered.
FAQs
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Where can I find the best oceanfront happy hour spots in Maui with live entertainment?
Maui offers some amazing oceanfront spots where you can soak in stunning views, sip on refreshing drinks, and enjoy live entertainment. Mala Ocean Tavern in Lahaina is a top pick, hosting happy hour daily from 2:00 PM to 4:00 PM. Here, you can indulge in handcrafted cocktails, mouthwatering flatbreads, and tasty appetizers, all while enjoying live music in a gorgeous seaside setting. The laid-back vibe and picture-perfect location make it a go-to spot for both locals and travelers.
For a more casual scene, head to Haui’s Life’s A Beach in Kihei. This easygoing beachside hangout offers an all-day happy hour featuring tropical favorites like Mai Tais and margaritas. With ocean views, lively karaoke sessions, and an upbeat atmosphere, it’s the ideal place for a fun and relaxed outing. These venues capture the essence of Maui’s happy hour culture, blending incredible scenery with great drinks, food, and entertainment.×
Where can I find happy hour spots in Maui with live music?
If you’re looking to enjoy happy hour in Maui with some live music, your best bet is to check local event calendars or visit the websites of popular venues. Many oceanfront restaurants and breweries on the island often host live performances during their happy hour specials. Some spots might have daily happy hours with live music, while others spice things up with themed events like DJ nights or karaoke.
Taking a few minutes to browse these schedules ahead of time can make all the difference in finding the ideal place to sip on great drinks, soak in live entertainment, and experience the lively Maui vibe.×
What are some tips for enjoying Maui’s happy hours with live entertainment?
Planning ahead is key to making the most of Maui’s lively happy hours with live entertainment. Since hours and specials can change, especially during busy times, it’s worth checking the venue’s schedule in advance. Arriving early is also a smart move, especially at popular spots with oceanfront views or live music, to snag a great seat.
Pay attention to the drink and food specials – many places feature discounted cocktails, beers, and appetizers, perfect for enjoying without breaking the bank. If you’re up for some extra fun, look out for themed nights or special events like live music or karaoke. With a little preparation, you can dive into Maui’s vibrant happy hour scene and soak up the island’s laid-back charm.
