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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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Recommended Reviews - Pailolo Bar & Grill

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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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25 days ago

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4 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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4 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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4 months ago

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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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Maui Brewing - Pineapple Burger

Maui Brewing

3.7(512 reviews)
1.1 mi
•$$

Maui brewing is phenomenal!…read more We came on a couple weekdays and a weekend when we were visiting and loved it each time! It's busy, and weekends there can be a wait for the dining area, but usually there's room to sit at the bar. The ahi salad is phenomenal. It's so balanced and filling, and healthy! Also love the cheese they included on it, it was so smooth. Also for drinks, you can't go wrong with beers or a cocktail. My husband loved the beer, and I loved the guava mule. Great experience overall. I would love to come back here if we're staying in the area again. The rest of the menu looked amazing.

Maui Brewing in Lahaina is most definitely in a most beautiful location on Kaanapali Beach. The…read moreviews are spectacular with perfect sightlines to the cliff jumpers at Black Rock. Inside is massive with plenty of seating in the dining room, a large bar area with a lot of four-tops and a large horseshoe bar. The outdoor patio is sizable also. There was no room at the bar, so the hostess led the four of us us to a four-top in the bar area. TVs were everywhere and we happened to be there for Monday Night Football, so the place was hoppin'! We only ordered beers and seltzers, we did not try any of the food offerings. Prices were a bit on the high side. Service was friendly but inconsistent. It took a bit of time to get additional rounds. We never saw the same server twice at our table. The place was hopping busy though. For sure I'd recommend even just for a drink. Soak up some suds and soak up some awesome scenery.

Photos
Maui Brewing - Bar seating area

Bar seating area

Maui Brewing - Guava BBQ Ribs

Guava BBQ Ribs

Maui Brewing - Mango Sticky Rice

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Mango Sticky Rice

Sergio's Cantina

Sergio's Cantina

4.4(322 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!

First, way, way overpriced for what you get. It feels they are banking on being near resorts with…read morelimited food options that are sit down. But, we stayed. We have been traveling for many hours and wanted to eat before going out our hotel to sleep. We decided on chips and salsa and to share a quesadilla. The salsa came out pink. It looked like pink pasta sauce. Taste wise it was ok and tasted like salsa, but was missing the crisp cilantro I like in a salsa. The quesadilla had mozzarella cheese I think and didn't taste Mexican. Overall still edible, but lacked the flavors I was looking for. Overall ditch it and get pizza across the street. It isn't worth it .

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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

Dollies Pub & Cafe - Remnants of Cheese, Mowie Wowie, and Meat Mongo

Dollies Pub & Cafe

3.4(847 reviews)
2.4 mi
•$$

Dollie's is a great place, best pub to hang out at and watch games. Best pizza ever! Every time we…read morecome to Maui, we always go to Dollies at least one night. And they have great service .

Phenomenal and unique pizza at Dollies! Awesome little local pub…read more While staying in Kahana/Lahaina, Dollies Pub and Cafe was our go-to spot for later in the evening. Convenient too, Dollies was just across the street from our resort. We stayed seven nights in Kahana and Dollies visits were a common theme. Our first visit was the night of our arrival. The four of us sat at a tall four-top where Becky (a different Becky than my wife Becky. LOL!) was our server. I wanted to order the Como-Stase pizza but was out voted. The wives were put-off by the thought of cream cheese on pizza. We instead ordered a Pepperoni, Italian Sausage and jalapeño pie. I remained obsessed with the Como-Stasw and vowed to return for it. The pep/sausage/jala was excellent. Crispy, thin crust. High quality meats and a fantastic cheese pull! At 10:30 PM. Dollies offers pizza by the slice, but only Pepperoni or Cheese. I did not know this when I returned solo for a slice of Como-Stase. Becky (my wife, not the server) stayed back in our condo while our travel companions had alternate plans. I sat at the bar and was warmly greeted by Stephanie who informed me that I'd have to get a whole pie. Well, I made some fast friends at the bar that night when I shared that pizza! Como-Stase marinara sauce, cream cheese, provolone, parmesan, pepperoni, sausage, topped with green onions. Bro! One of the best pizzas that I've ever had! Cream cheese, Provolone and Parm! So good! Gobs of pepperoni and sausage. I, and everybody else at the bar loved it! What a blend of flavors, pure perfection on a great crust. Shout out to Seth as well. He was our barkeep one afternoon when we stopped in for drinks and a t-shirt, of course gotta' rep Dollies back in San Diego! When in Maui, go to Dollies!

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Dollies Pub & Cafe - Bar

Bar

Dollies Pub & Cafe - The half of the roach that stuck to the wall after it ran off my table and I smashed it.  The other two are still out there.

The half of the roach that stuck to the wall after it ran off my table and I smashed it. The other two are still out there.

Dollies Pub & Cafe

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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

In 2019 we visited Captain Jack's for lunch while visiting Lahaina. It was on Front Street and…read moreunfortunately did not survive the fire of 2023. Captain Jack's has been resurrected on the Sands of Kahana resort property and it is absolutely fantastic! Sweeping views of the ocean, bright and airy with a festive Island vibe. The entire place opens up and there is plenty of seating. The bar is a big horseshoe, the surrounding bar area is plenty large as is the dining room. Just a short walk from our resort. We were in Kahana for a week and we hit Captain Jack's at least once every day. Breakfast, lunch, dinner, drinks. All exceptional. The first night we rolled in met our bartender, Travis. What a cool cat this guy is! He plays bass in a Surf Rock band Sting Kong. (on Spotify and IG @stingkong808) check 'em out! Awesome barkeep. We also ran into Travis off-duty grabbing a drink at Dollies one night. We were even able to watch the Padres game one morning when they had a 10:00 AM local time start. I won't bore you further with in depth descriptions of the food we tried between the four of us. Just know that it was all outstanding. Notable standouts were the grilled fish tacos, calamari. The Loco Moco with Portuguese sausage was off the hook! *Fresh Fish Taco grilled fresh fish, corn tortillas, cheese, bacon aioli, cabbage, pico de gallo. *Nachos tortilla chips, black beans, cheddar & jack cheese, jalapenos, cheese sauce, pico de gallo, avocado crema, salsa, sour cream and cilantro. Add pulled pork or chicken for 7 (We chose chicken) *Kracken Calamari six panko crusted fried calamari strips, spicy house tartar, cocktail sauce *Loco Moco with Portuguese Sausage *Eggs Benedict = Traditional poached eggs on a split English muffin and topped with hollandaise sauce w/breakfast potatoes *Biscuits and Gravy biscuits and sausage gravy. Add Eggs for 5 *Country Fried Steak and ggs country fried steak, sausage gravy, 2 eggs any style and home fries All hit! Check out Sting Kong!

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!

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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

Monkeypod Kitchen - Fresh Caught Fish Tacos

Monkeypod Kitchen

4.1(3.8k reviews)
1.2 mi
•$$

We decided to check Monkeypod Kitchen out as we heard about their Mai Tais being the "best" from…read morefellow hotel guests. We went during happy hour (2:30 - 5pm) where their hand crafted cocktails were $4 off. Prior to this, I haven't had a Mai Tai before so was unsure how they should taste but the Monkeypod version contained honey-lilikoi foam which made them bright, inviting, and iconic. Well everyone in the family loved these. They were simply delicious. From their happy hour food menu (appetizers were half off except anything containing seafood), the Roasted Chicken Wings were a hit with my sons. The Poke Tacos which were beautifully presented were fresh and tasty. One order comes with 3 so we ordered an extra taco which turned out to be the right move as they are on the small side. And I wanted to point out since the Tacos contained seafood, it was not eligible for the discount. Pizzas were priced at $16 (except for the Bourgeois) so we opted for the Margherita and Kahlua Pork and Pineapple. The latter was our family favorite. The pork was tender and flavorful which contrasted nicely with the sweet pineapple. We did order the Fish and chips from their regular menu. Mahi mahi was the fish of the day and it was good, but nothing exceptional. The fish came out nice and hot but the temperature of the fries were not so was a little disappointed. We ended our meal with the Banana Cream Pie. We all agreed that it was hands down the best Banana cream pie that we have had. The bananas were so fresh and flavorful, so much umami. The restaurant was open/airy and the view was amazing. Our server was friendly and the service went without a hitch. We will definitely be back.

Came here for an early lunch and were able to grab a spot with a beach view…read more Food is solid Fish n chips 3.5/5 good flakey fish with decent fries Mushroom truffle pizza 4/5, had decent truffle flavor and huge cheese pull, i with the crust was more charred or had a little char I think food is decent but you're more here for the view. I would say if you're able to come for happy hour then it would be a better value especially for the pizzas. It's about $5 cheaper for most of the pizzas. They also validate parking for 2hrs

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Monkeypod Kitchen - The atmosphere here!

The atmosphere here!

Monkeypod Kitchen - Seared Ahi Steak

Seared Ahi Steak

Monkeypod Kitchen - Ube Rey

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Ube Rey

Pailolo Bar & Grill - sportsbars - Updated November 2026

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