Osteria Umbra
Long Island's Italian wine secret hiding in plain sight
Smithtown · Smithtown · Italian, Steakhouse · Visit Website ↗
Reviewed April 20, 2026
Wingman Metrics
First Impression
The wine list at Osteria Umbra lands with a confidence you don't expect from a strip-mall-adjacent suburban Italian spot. It's focused, it's Italian-forward, and it clearly has a point of view — this isn't the generic Pinot Grigio-and-Chianti checklist your uncle's favorite red-sauce joint hands you. The Wine Spectator Award of Excellence since 2020 isn't just a wall decoration here.
Selection Deep Dive
The 100-150 bottle list leans hard into Italy, and that's exactly right for what Osteria Umbra is trying to do. Piedmont shows up strong with Barolo in the mix, Brunello di Montalcino anchors the Tuscan section, and the Super Tuscans — Sassicaia and Tignanello — signal that someone here takes this seriously. Chianti Classico Riserva fills the middle ground nicely for those who want Tuscany without the splurge. The real surprise is the New York section: Finger Lakes Riesling and Long Island Merlot from Wolffer Estate and Bedell Cellars give the list a local identity that most Italian restaurants in the suburbs never bother to develop.
By the Glass
With 12-20 pours available in the $10-$18 range, the by-the-glass program is more than serviceable — it's actually a reason to come here. That price ceiling of $18 is refreshingly honest for a restaurant with this level of ambition. We'd like to see more rotation and a few surprises, but the range covers enough ground that you're not stuck choosing between Pinot Grigio and house red.
Chianti Classico Riserva — $40–$60
Chianti Classico Riserva at the lower end of this list's pricing is where the sweet spot lives — structured enough to stand up to the Veal Ossobuco, honest Italian character, and none of the premium-label markup that the Super Tuscans command.
Bedell Cellars Merlot (Long Island)
Most people come here for the Italian names and completely sleep on the Long Island section. Bedell Cellars has been making serious Merlot on the North Fork for decades — it's the kind of wine that surprises people who think Long Island is a punchline, and at this price point it's hard to argue with.
Sassicaia
Sassicaia is a great wine. It's also a wine you can find on a hundred lists at roughly the same markup. Unless you're celebrating something, there's no reason to spend at the top of this list when the mid-tier Italian bottles are doing the real heavy lifting.
Brunello di Montalcino + Veal Ossobuco
Brunello's firm tannins and earthy depth are exactly what braised veal needs — the wine's acidity cuts through the richness of the marrow while the Sangiovese fruit echoes the tomato in the gremolata. This is the order you make when you want to feel like you're eating in Siena.
🎲 The Bottom Line
Osteria Umbra is doing something genuinely worthwhile for the Long Island suburbs — a focused Italian list with real depth, fair prices, and the rare courtesy of including local New York producers. Send a friend here who thinks good wine only happens in the city.
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