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    Pailolo Bar & Grill

    3.4 (277 reviews)
    Open • 11:00 am - 9:00 pm

    Pailolo Bar & Grill Photos

    PAILOLO BAR & GRILL ATMOSPHERE

    What's the vibe?
    Live music
    Moderate noise
    Casual
    Touristy

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    Margarita on the rocks, strawberry pina colada
    Haley S.

    Atmosphere and drinks are awesome! Wish we could stay at the Westin longer! Here on a family trip and the pina colada has been a daily drink

    Sue S.

    IMHO Pailolo is located on our resort property, so very convenient! We enjoyed our first "dinner" of our current visit during their Happy Hour. You can't beat the ambiance at Pailolo. You are right next to the beach amidst swaying palm trees and sometimes enjoying live music. Ahhhhhh. No one was at the host desk, so we planted ourselves at a table. It took a little while to wave a server down to help us, but we were on vacation and chilled. Eventually we chose some delicious cocktails, coconut shrimp, and seasoned fries. My hubby and I had decided that we would try to share most of our Maui meals to save money and not waste food. It worked pretty well for us. I highly recommend it! The service (once we received it) was friendly, and the food was yummy, and just enough! Of course, we'll return!

    Bi Bim Bop Tots
    Ryan L.

    It's been about 10 years coming to Kaanapali. We stopped at Pailolo for lunch. The prices sure have increased over the years. In 2015 the prices of a drink of the day was $6. Now it's $17. But the food is very solid. The drinks are good. They open at 11 and were instantly busy. There were lines of people getting drinks at the bar. It felt a bit understaffed and it took a while for our server to come over, but he was great. No complaints about food or service.

    mai tai and pina colada
    Alana A.

    best drinks for a decent price! staying at the westin and this is the perfect place to walk over to after snorkeling or swimming

    Menu
    Jonna O.

    We love this place. Staff is super friendly and fun. Food is great! We ate here 4 or 5 times in a week!

    Lava flow cocktail
    Shirley N.

    Why so many negative reviews? We're staying next door at the Westin Nanea. We couldn't get a seat at the bar n grill there so we walked over to the sister resort. The landmark is a food truck aptly named Pailolo. Come to realize later that's where the food is made. We spotted several empty tables from the boardwalk so we walked over and sat ourselves. We were soon greeted by a server who brought us water and menus. The three of us all ordered the fish n chips. Battered Ono. Cocktails - hubby had martini, I had a lava flow, and daughter had IPA. Our food came quickly. Small filets but very satisfying. Best battered fish we've had. After asking what's the coating we were told it's pancake batter. So onolicious. The fries were crispy and warm too. Pro tip: live entertainment on T-TH from 5:30p to 8:30pm. Last night (Tuesday) it was a solo guitarist. Both diners and non diners enjoyed the entertainment as the pool loungers are right there. Portion sizes are moderate. Just enough to ease any hunger pains.

    Burger!!  Add bacon and avocado
    Joseph F.

    View is amazing!!! Best sports bar in area! Our group enjoyed the NFL playoff games with many TV's. Our server Zarian was the best server I've had. Food was awesome!!! Will definitely go back. Ask for Zarian's section!!!

    Fresh fish burger

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    3 months ago

    The food was terrific. Atmosphere was fun and relaxing. Live music nearby on one of the evenings that we were there with local songs.

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    3 months ago

    Standard place, exactly what you want and need at a pool bar restaurant. However, at nighttime they have the live music!

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    6 months ago

    Go get Jack N Box. It will be a much cheaper and better tasting meal. This place is horrible and over priced.

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    Sergio's Cantina

    Sergio's Cantina

    4.4(315 reviews)
    0.7 mi
    •$$
    Casual dining
    Locally owned & operated

    We came here after spending the day in Napili beach. Location is great, ambiance is pleasant,…read moreservice is fantastic. As we walked in, we were greeted immediately and asked if we preferred high tables in the bar area or dining and were seated right away. We ended up choosing to sit by the bar and were greeted by our server/bartender timely. We ordered chips and salsa, chips were warm and crisp to perfection salsa was super good! We ended up ordering the burrito, enchiladas and garlic shrimp. Everything was really good BUT the garlic shrimp was to die for! Definitely worth the $40! The sauce, the serving, the size of the shrimp...just amazing. And our server made our visit such a pleasant experience. I'd also like to add, well kept restrooms for customers say so much about an establishment. Highly recommend this place!

    Got there right at 12 when they open. I ordered to go -…read moreSergio's grade burrito with shredded beef , it was loaded with beef nothing else , very little bit rice or beans or cheese , average taste Kids tacos - forgot to give the tortillas with the order , had to go back and then they only gave two when the lady specifically mentioned it comes with 3 tortillas Maiz con queso - this was pretty good it come with chips but the lady said for to go orders we give complementary chips and salsa . There was no extra chips only whatever came with the dip. And the salsa wasn't very good either . Overall below average , may be other dishes are better but based on what we ordered it was average.

    Photos
    Sergio's Cantina - Ladies restroom-well kept

    Ladies restroom-well kept

    Sergio's Cantina - Taco salad with steak

    Taco salad with steak

    Sergio's Cantina - The refresher, super refreshing

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    The refresher, super refreshing

    Captain Jack's Island Grill - New breakfast menu, Country Fried Steak, Huevos Rancheros and Banana Mac Nut French Toast

    Captain Jack's Island Grill

    4.1(1.3k reviews)
    2.3 mi
    •$$
    Free parking
    Family-owned & operated

    First off the food is amazing!! It comes out fast and the service is friendly! You get a beautiful…read moreview of the ocean . This was one of my favorite places to eat while in Maui We had a party of 13 of us and at captain jack's they made us feel welcome with no problem. Unlike a lot Of other places here that made us feel like an issue or flat out refused to help us . Even when we tried to make reservations!

    My husband and our friends came here one evening for dinner and it did not disappoint!!! Upon…read morewalking in, we were greeted immediately and were seated outdoors in about 5 minutes! IT WAS BEAUTIFUL outside with plentiful seating and a perfect view of the sunset on the beach. I ordered the fish and chips, my husband ordered the hot booty ruben, our friends ordered the ribs and chicken wings. For an appetizer, we got the nachos and man, did it hit the spot! You know how sometimes when you order nachos and they come out soggy? This didn't, it was nice and crunchy and after a beach day, it was just right with the beans, pico, jalapenos, and sour cream. The fish and chips were delicious- the fish was nicely battered with a THICK chunk of fish, not skimpy at all and the ribs were nice and juicy and fell off the bones!! Our favorite was the hot booty ruben sandwich- full of flavor, juicy meat along with the tartness of the sauerkraut! Our least favorite were the chicken wings, it wasn't as juicy as we hoped it was going to be but it was a chunky and at least got us the protein we needed. All in all, we are going to come back again. We all agreed that this was a winner. PS, try their house made Maui mules!! All of us tried it and it was so refreshing, especially with the candied ginger on top! Not only did we come here once, we came back again another night to try other foods!

    Photos
    Captain Jack's Island Grill - Located by the pool at The Sands of Kahana Resort!

    Located by the pool at The Sands of Kahana Resort!

    Captain Jack's Island Grill - Sunsets cant be beat

    Sunsets cant be beat

    Captain Jack's Island Grill - Storefront

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    Storefront

    Leilani's On The Beach

    Leilani's On The Beach

    4.0(3.8k reviews)
    1.3 mi
    •$$$

    Ambiance - outdoor restaurant with overhead coverage, live music, great for small to large parties,…read morerecommend making a reservation Service - exceptional, our server was super nice & food came out quickly Food - filet mignon was slightly more cooked than our request, taro chips was extra crispy with the poke, don't skip on the hula pie (definitely meant to be shared)

    My wife made a reservation at this restaurant ahead of the busy Labor Day weekend Monday. When we…read morearrived at the busy location we waited patiently for or table for two. We were shown to a 6 top table (for a reservation for two people) during an obviously busy night. There was a reason that the table had been empty: on a breezy evening this table had zero air movement. We were stuck in a corner, even though the window was wide open. The entire restaurant has ceiling fans whirring. Table #120 is a dead zone, no breeze. No ceiling fan. When we mentioned this fact to our server she had a "standard" answer about how the heat is building because of the hurricane. BS! We had just walked to the restaurant along the beach to the with a strong breeze blowing at our backs. Table 120 is in a back section of the restaurant without a ceiling fan. When I complained to the hostess who seated us she began to tell me that the open air restaurant was entirely composed of hot tables. This place is busy because of where it is located. We had decided to have a selection of starters for our dinner. Dry ribs. Poor humus. Without its location on the beach it would fall flat on its face. Give this place a pass.

    Photos
    Leilani's On The Beach
    Leilani's On The Beach
    Leilani's On The Beach

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    Pailolo Bar & Grill - sportsbars - Updated October 2026

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