Matteo's Osteria - Hawaii Restaurant
#9 of 46 Restaurants in Wailea Italian

Matteo's Osteria

4.4(1,255 community reviews)
Upscale ($$$)

About

Discover Matteo's Osteria, offering the best Bar experience in Kīhei. Enjoy Upscale ($$$) meals, explore their menu, and read reviews from the community on TasteHi.

A Slice of Italy in the Heart of Wailea

Stepping into Matteo's Osteria feels less like entering a Wailea dining room and more like stumbling upon a bustling trattoria tucked away in a quiet corner of Tuscany. Chef Matteo Mistura brings a refreshing, unpretentious approach to Italian dining, focusing on locally sourced Maui ingredients that bridge the gap between Mediterranean tradition and island freshness.

Hand-Crafted Flavors

The menu centers on house-made pastas and wood-fired pizzas that fill the air with the scent of charred dough and fresh basil. If you are debating what to order, the Pappardelle al Cinghiale remains a local favorite—rich, savory, and perfectly balanced. The wine list is equally impressive, favoring small-production Italian labels that pair beautifully with the fresh catch specials brought in from Maui waters earlier that morning.

The Atmosphere

The space is lively, often punctuated by the clinking of glasses and the low hum of conversation bouncing off the rustic decor. It is an ideal spot for couples looking for a relaxed date night or small groups eager to share a few bottles of Chianti. Be aware that during the height of the dinner rush, the acoustics can lean toward the energetic side; if you prefer an intimate conversation, aiming for an earlier seating or a table on the periphery helps significantly.

Matteo's manages to hit that sweet spot of sophistication without the stiff formality often found in upscale resort dining. You might find the bar area a bit cozy when things are in full swing, but that proximity to the action is exactly what gives this place its soul. Whether you are craving a rustic lasagna or just want to experience the best Italian food in South Maui, this neighborhood staple is a must-visit for anyone who values honest cooking over culinary theater.

Location

161 Wailea Ike Pl Suite A107, Wailea, Hawaii, 96753-6521

Directions

Reviews

Showing 10 of 1255 community reviews
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Yung PGoogle Maps

Recently

Came to make a visit to Matteo Osterio after seeing a clip of Guy Fieri eating here. Ordered Fettuccine frutti di mare squid ink pasta with crab, clams, shrimp, with tomato, garlic, white wine, lobster veloute sauce. Ordered Bolognese which is made with tagliatelle pasta with maui co beef and Italian sausage with tomato and Parmigiano-Reggiano. The fettucine frutti di mare and the bolognese were probably some of the best I have ever had. I know they are known for the Bolognese and lasagna but I highly recommend trying the fettucine frutti di mare if you make a visit here. Also ordered the tiramisu for dessert. The mascarpone cream was a little too sweet for my liking but overall it was a great and to a phenomenal dinner. Reservations are highly recommended. Parking is free and adequate spots located in plaza parking lot.

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Monica HGoogle Maps

Recently

Matteo’s has excellent customer service and (mostly) good food/drink - I’d be happy to come back! Good: the hostess and wait staff were a highlight. Food runners included, all were so kind and courteous, and made personal connections with us and other tables. Definitely worth the gratuity tip. Our table of three and a half (three adults, one baby) was ready when we arrived at our reservation time with the high chair already set up! The meatball appetizer, focaccia, carbonara, and isola special were all great (the isola in particular was the favorite), then ended with an affogato. Not so good: the sauce on the arrabbiata was perfect, but the pasta itself was overcooked. Very disappointing to be served overdone pasta at an Italian place but then it was topped with sausage that was burnt - this was the only dish not finished at our table We enjoyed our meal overall and how family friendly the restaurant was. Would definitely dine here again! Mahalo

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Dennis KulpGoogle Maps

Recently

Fantastic food! We had a great experience and everyone would come back. The only hiccup (that doesn't lower the score) was our party of 7 not being checked in when we got there so we waited for a good 15 minutes however another hostess fixed this. Service was impeccable and fast with constant attention that wasn't imposing. Our server, Michael, was enthusiastic, energetic, and had a wet sense of humor. He was very patient while we asked for a dish of olives.

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Beau HeskethGoogle Maps

Recently

This place is absolutely delicious. They might have the best lasagna that I have ever had. It seems to have less tomato sauce, or the sauce was not as clumpy as it is can be in certain recipes. I would definitely eat here again and recommend this anyone looking for Italian. My one complaint is the restroom. It is located outside of the Restaraunt and it was being completely assaulted by bugs. They made it through 3 separate doors.

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Jason SplotchGoogle Maps

Recently

We had an excellent experience at Matteo’s while on vacation in Maui. Our server Keira was great, very friendly and quick with recommendations and some humor. The food was amazing, and we will be going back when we return to Maui.

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Jennifer RGoogle Maps

Recently

Italian on the island! It was a great night of pasta and wine. My hubby had the sausage gnocchi and the chicken Parmesan. We shared a salad and I had the sausage bolognese. We topped it with the chocolate cake. Fantastic server, friendly staff made the night worth it.

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Nick WeissGoogle Maps

Recently

Brought the whole family out for disappointing, bland pasta. We tried the squid ink pasta, bolognese, and the chicken parm, but the best tasting entree was butter noodles… This was overpriced and a major misstep during our Maui vacation. The chicken was overcooked. The seafood was under-seasoned. The appetizers were fine, but not exceptional. The wait staff and venue are lovely. We just didn’t enjoy any of the food.

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Kakaʻako LifestyleGoogle Maps

Recently

Last night we enjoyed another outstanding dinner at Matteo’s in Wailea! This place never disappoints. The service from Suki was excellent. He was warm and attentive. I began with my favorite blood orange Italian soda and Suki recommended to add fresh mint, which was a delightful touch. We always start with our favorite meatball appetizer, it’s the perfect way to begin the meal. The Cesar salad was fresh and full of flavor. Chicken parm is our go-to entrée, and we love that you can swap out the pasta to suit your taste (a small detail that makes a big difference!). We also ordered our other favorite dish, the baked lasagna. Warning, this dish comes out piping hot and packed with rich, comforting flavors, it’s definitely a dish to enjoy at a mindful pace. Consistently delicious food, great service, and a welcoming atmosphere make Matteo’s a favorite we return to again and again!

M

Maui World TravelersGoogle Maps

Recently

Oh, how the years keep piling on. My gang took me out for my birthday dinner here. It was the first time for all of us and definitely won't be our last. LOCATION: They're within the Wailea Town Center, a small strip mall located behind the new Residence Inn Marriott. Parking at night was plentiful due to the other businesses being closed. ATMOSPHERE: They've done a great job with transforming the space into a very warm, inviting and chic eatery. Seating is a mix of in and out, with a small bar, all-glass wine "cellar" and open-view kitchen. MENU: Italian fare including apps, salads, pastas, pizzas, fish, steak, kids menu, happy hour. BEVERAGE: Sicilian Rose This Ketel One martini included prosecco which gave it a nice fizz and sweetened with a white peach nectar. Absolutely delish. So much so, I had four of them!? Or was it five? I wasn't driving so I didn't care, lol! FOOD: House Bread My dislike for focaccia is slowly fading as I loved this. Instead of butter, it came with a healthier hummus spread. Caesar Salad The chunky-cut Romaine leaves were fresh and well-coated in a creamy-tangy caesar dressing and sprinkled with shaved parmesan. Very good version. Bruschetta Al Tonno Because we were a party of four, we added an additional bruschetta so we could each have one. The raw ahi was utmost fresh and teamed with a mix of fresh tomatoes, salty capers, garlic and basil. Crunchy, savory, sweet; the best of three worlds. Bruschetta slices were a bit small but the wonderful flavors made up for their petiteness. Filetto I was torn between the bolognese pasta and this dish but after seeing pics of this, I was sold due to its mouth-watering dark brown sauce. The tenderloin was amazingly tender. I asked for medium rare but it came out more medium; no biggie. Flavor and moisture were strengths of this dish as it was doused in a savory, dark brown demi mushroom sauce. Total heaven. Stewed cherry tomatoes added a nice acidic balance. I failed to comprehend that the lumpy (a positive to me) mashed potatoes were infused with chunks of gorgonzola cheese, a variety I'm not fond of due to its boldness, and was the only downfall. DESSERT: I was treated to a decadent tiramisu in a cup, topped with a sole birthday candle. So sweet of them! One of my friends opted for the affogato which looked divine and must've been as it was devoured in a snap! SERVICE: Absolutely professional, friendly and took great care of us the entire night. Thank you! OVERALL: I'm being more austere with my five star ratings but Matteo's truly deserves it.

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Jason MazeGoogle Maps

Recently

A Hidden Gem in Maui! The atmosphere is warm and welcoming, with a cozy, upscale vibe that still feels relaxed. I ordered the lasagna and was completely blown away, easily one of the best I’ve ever had. It was rich, flavorful, and perfectly layered with just the right balance of cheese, sauce, and pasta. You can really tell it’s made from scratch with high-quality ingredients and a lot of care. The service was also top-notch, friendly, attentive, and knowledgeable about the menu. Whether you’re a local or just visiting, I highly recommend stopping by Matteo’s. I’ll definitely be coming back next time I’m in town!

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Frequently Asked Questions about Matteo's Osteria

Common questions from diners about Matteo's Osteria in Wailea.

They serve Italian Soulfood, including homemade pastas, pizzette, and entrées.

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