A Memorable Dinner Experience in Wailea
- Jason raffin
- Oct 20
- 6 min read
Updated: 2 days ago
Everything started that morning with a drive from Lahaina down the coast toward Wailea. The sky was clear, the light hit the water just right, and I could already tell it would be one of those days where the island energy aligns perfectly with the food.
When I cook as a private chef, the menu always begins with what’s fresh that day. Maui tells you what to make if you pay attention. My plan was to build a five-course tasting menu that blended comfort and elegance. I wanted something that felt soulful and local but still refined enough to surprise people.
The menu ended up becoming one of my favorites of the year.
The Dishes
Braised Short Rib with Blueberry Jus and Polenta
Housemade Rigatoni with Pork Ragu
Cucumber Salad with Furikake and Shaved Ice
Seared Ahi Sashimi Ahi Crudo with Ginger Ponzu and Sweet Pepper Relish
Each dish represented a stop on the island that day. Each one connected me to a person, a farm, or a flavor that belongs to Maui.
Morning in Upcountry Maui
The first stop was Kula Country Farms. I love going there early when the air is still cool and the view stretches all the way down to the ocean. Their herbs and greens always taste alive. That morning they had fresh blueberries, tiny young carrots, and sweet Maui onions. I grabbed a few baskets of blueberries right away because I already knew I wanted to reduce them into a sauce for the short ribs.
From there, I stopped in Kahului at a small butcher shop that carries local beef. The short ribs looked perfect, thick-cut with just the right marbling. I always prefer local beef for braising because the flavor feels truer to the island. It cooks beautifully when you give it time.
By midmorning, the back of the car smelled like herbs, citrus, and freshly cut greens. The energy of gathering ingredients this way always sets the tone for the night. You already know the food will taste better when you’ve met the people who grew or caught it.
The Ocean Connection
Before heading to Wailea, I stopped by a small fish market near Kihei. It’s the kind of place that doesn’t look fancy but always has the best catch. The ahi that morning was deep red and glistening just hours out of the water. When I picked it up, I could feel how cool and clean it was. That’s when the menu locked in. I knew I’d serve it two ways: once seared simply, and once raw as a crudo with a ginger ponzu and a sweet pepper relish.
Working with fish that fresh changes everything. You barely have to do anything. The goal becomes to step out of the way and let the flavor speak for itself.
Setting Up in the Villa
The villa in Wailea sat right on the hillside, overlooking the ocean. The kind of place where the air moves differently. My team and I unpacked the ingredients, the plateware, the silverware, and all the setup pieces that make a private dinner feel complete. I always bring everything needed so guests can just relax.
There’s a moment before every event where I stop and take in the space. The kitchen, the light, the energy. I start to imagine where each plate will land on the table and how it will feel when the guests take their first bite. That imagination is part of the cooking.
The braised short ribs went in first. I seared them until they were almost black on the edges, then lowered them into a pot with red wine, onions, garlic, and herbs. They cooked low and slow while we set up.
Next came the pasta. I mixed the dough by hand, rolled it, and cut thick rigatoni pieces one by one. It’s impossible not to smile while making fresh pasta in a Maui kitchen with the ocean breeze rolling in. It feels like the most natural thing in the world.
The cucumber salad came together last. Thinly sliced cucumbers, fresh herbs from Kula, furikake, and a touch of shaved ice for contrast. It’s a simple idea, but on a warm night in Wailea, that brightness cuts through the richness of the other courses and refreshes the palate perfectly.
The Dinner Flow
As the sun set over the water, guests arrived and we began the evening with the ahi crudo. I plated it with a ginger ponzu that had a light citrus note and a sweet pepper relish for texture. The color of the fish against the wooden plates looked beautiful in the candlelight.
Next came the cucumber salad. Cold, crisp, and aromatic. It was the dish everyone talked about more than I expected. Sometimes the simplest course leaves the biggest impression.
Then came the housemade rigatoni with pork ragu. It had been simmering for hours while we worked, and by the time it hit the plate, it had that perfect richness where every noodle carries the sauce evenly. I grated Parmigiano right at the table so guests could smell the warmth of it as it melted.
The short rib was the centerpiece. Braised until it barely held together, laid over creamy polenta, and topped with a blueberry jus that tied the entire meal back to that morning in Kula. Watching people take that first bite and lean back with a smile — that’s the best moment of the night.
We finished with the seared ahi sashimi, light and clean, dressed with Hawaiian sea salt and microgreens. It served as a kind of reset at the end of the menu. The ocean on a plate.
The Story Behind Each Dish
The dinner wasn’t just a menu. It was a loop around the island. The short rib carried the sweetness of Kula’s blueberries. The pasta reflected the comfort of Italian cooking translated through Maui ingredients. The cucumber salad echoed the freshness of the trade winds. The ahi sashimi honored the fishermen who bring in the catch every morning. The ahi crudo showed how a touch of acidity and balance can turn something simple into something unforgettable.
When guests taste that story, it becomes more than food. It becomes memory. That’s what I try to create every time — not just plates, but moments that stay with people.
Cooking as Connection
Being a private chef in Maui means constantly balancing art and hospitality. You’re creating fine dining meals in someone’s home, but you’re also part of their experience on the island. You’re there to make them feel cared for, not just fed.
In Wailea, the villas have these beautiful open kitchens that make it easy to interact with guests. I love when people wander over between courses to ask questions about ingredients or technique. Those little conversations are what make it personal.
We talked about the blueberries from Kula, about how the sea salt in the sashimi comes from a local Hawaiian producer, about how the pasta dough changes texture depending on the humidity. It turns into a kind of shared workshop, but one where everyone is relaxed, barefoot, and surrounded by ocean air.
That connection is what makes this work feel meaningful. The island becomes part of the story.
Ending the Night
When the plates were cleared and the lights dimmed, the sound of the ocean took over again. Guests lingered around the table talking, still tasting the food, still smiling. That’s the energy I always chase.
Before packing up, I took a moment to look around the villa. The kitchen that had been quiet in the afternoon was now warm, full of laughter, and the scent of slow-cooked beef and seared fish. I thought back to that drive from Lahaina that morning and how every stop, every ingredient led to this exact feeling.
Cooking this way is never routine. Every night is a new mix of people, ingredients, and inspiration. The goal is always the same, though: to make something that feels true to Maui and personal to whoever is sitting at the table.
Serving the Island
That Wailea dinner was just one example of what we create all over the island. Some nights are in Lahaina villas with oceanfront setups. Others are in the quiet hills of Kula or the resorts of Kapalua and Kihei. Every location brings a slightly different rhythm, a different light, and a new reason to be grateful for this work.
If you’re planning a dinner on Maui and want a private chef experience that brings the restaurant to you, I’d love to cook for you. Whether it’s a tasting menu for two, a family gathering, or a celebration dinner, every event is customized from start to finish.
Visit www.JasonRaffin.com to see sample menus, photos, and reviews.
You can also find more of my work on Instagram at @jraffattacker.
Mahalo for reading and for supporting local chefs and farms that make Maui’s food scene what it is today.
Every dinner begins with the same intention: to make something beautiful, honest, and full of aloha.
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