Matteo’s Osteria

Matteo's Osteria – Imaginative Italian Fare Served in the Heart of Wailea Town Center
Local Expert's Rating:
4 / 5
The Bottom Line:

When you need imaginative Italian fare, upscale drinks, and friendly service, jet on over to Matteo’s Osteria in Wailea. Chef Matteo Mistura goes all out in transforming the freshest local ingredients into truly memorable meals. Vegans rejoice over the separate menu full of veggie-rich fare boasting big flavor in every bite.

- The Local Expert Team

Matteo’s Osteria serves as the place to go for imaginative Italian fare and high-end drinks served with a smile. Located in the heart of Wailea, this upscale restaurant brings in locals and tourists in droves all throughout the year.

Chef Matteo Mistura delights the crowds by transforming fresh, local ingredients into meals of a lifetime. He kicks all the classics up a notch by bringing bright island flavors into the mix. He goes beyond a basic dinner spread with a dedicated vegan menu for whenever you want to skip the meat without compromising on flavor.  

They’re only open for dinner service, so you have to book your spot well ahead of your trip to get through the doors. More often than not, they’re far too busy for walk-ins, although they invite you to give it a try if you can. When you make your reservation, you have to choose between their bar, outside tables, and indoor dining room seating. Expect to stick with your selection, too, since all their other tables will be filled up when you get there.

Even on their busiest days, their service is friendly and warm, ensuring you’ll have the best dining experience around. Upon arriving at the restaurant, your server will lead you to your table of choice, and then give you time to browse through all their menus. You can get started with an appetizer and drinks to buy more time for weighing all the entrée options.

All their pasta is freshly made on the regular, so it’s always a surefire choice. But you really cannot go wrong no matter what you order. Every last one of their menu items come artistically plated and feature bold, bright flavors in every bite. Across their entire menu, expect to see fresh island ingredients taken to the next level with classic Italian flavors and preparations.

If you’d like to elevate your meal even more, they have over 30 wine varieties available by the glass plus 200 more only offered by the bottle. Their specialty cocktails are another great choice, especially if you adore tropical flavors. Want to skip the alcohol? Go with a spritzer or mojito mocktail instead.  

Come on in to try:

G’s Meatballs
If you’re craving meaty goodness, start your meal off right with an order of G’s Meatballs. This starter features meatballs made from all-natural ground turkey, quinoa, chia seeds, flax seeds, and kale. Once they’re done, the meatballs get coated in flavorful pomodoro fresco sauce and parmesan cheese. The dish lands under the broiler until hot and bubbly, and then comes to your table with house flatbread on the side.   

The Bolognese promises rich, bold flavor from the beginning to the end of your meal. To create this dish, the chef browns Maui Cattle Co. beef and Italian sausage. Then, the meat gets added to a housemade tomato sauce before white tagliatelle pasta joins the party. After that, parmigiano reggiano gets sprinkled on top right before serving.

Matteo’s Chicken Parmesan
As the name suggests, Matteo’s Chicken Parmesan is a house specialty. The chef starts this entrée by breading and frying organic chicken breast until golden brown. Then, he puts sauce and melted mozzarella on top of the chicken before putting it under the broiler. Once the cheese looks brown and bubbly, spaghetti pomodoro goes on the side to complete your order.

As you dine on Italian deliciousness, aim to save room in your belly for dessert. They have many exceptional menu items ready to satisfy your sweet tooth in an instant. The Tiramisu is a showstopper, for sure, while the Cannoli never fails to delight. If you simply don’t have enough room for all that, just go with their stunningly good Affogato or any of their other after-dinner drinks, like Choco-Tini, Limoncello, and Kahlua.

Insider Tips:
-They can only accommodate up to 10 people per table at this time.
-Each reservation only lasts for one to two hours depending on the total number of people at the table. Parties of two to three people get one hour and fifteen minutes, while six or more get two full hours.
-Take a moment to hear about the nightly specials before putting in your order.
-Although they do not have a separate gluten-free menu, you have plenty of options to consider, like the Costolette entrée and Torta Del Nonno dessert.