Big List, Big Markups, Great Monday Redemption
Santana Row / West San Jose · San Jose · Steakhouse · Visit Website ↗
Reviewed June 22, 2026
Wingman Metrics
Fleming's leans hard into its wine identity — the '100 Wines' branding is plastered everywhere before you even sit down. It signals ambition, and honestly the list backs it up more than most corporate steakhouses bother to. That said, you're in a chain, and the pricing will remind you of that fact repeatedly.
The list runs deep on California — Napa Cabernet and Chardonnay are the backbone, with familiar heavy-hitters like Caymus, Silver Oak, Jordan, Cakebread, and Rombauer all present. There's a supporting cast of French, Italian, and Australian bottles that adds some range, but this is fundamentally a California-and-friends program built for business dinners and special occasions. You won't find anything adventurous or off the beaten path — no natural wine, no skin-contact oddities, nothing that'll raise an eyebrow. What you will find is a well-curated roster of crowd favorites executed at a high level of consistency.
The national program promises 25+ wines by the glass, and San Jose follows that playbook. Prices run $14–$28 a pour, which is steep but not shocking for the zip code and concept. The Tomahawk Tuesday promo — two glasses for $22 — is a legitimate reason to show up on a weekday.
Jordan Alexander Valley Cabernet Sauvignon 2018 — $165
Yes, $165 is still a real number. But Jordan at retail is $65, making this a 154% markup — the lowest we clock on the entire bottle list. For a refined, food-friendly Cabernet that doesn't steamroll a steak, it's the most honest buy on the menu. Come on a Monday and it drops to around $82. That's legitimately good.
Silver Oak Alexander Valley Cabernet Sauvignon 2018
Most tables at Fleming's go straight for the Caymus because it's what they know. Silver Oak Alexander Valley is the move most people skip — it's more structured, more age-worthy, and frankly more interesting than the Caymus at a similar price point. It rewards the table that actually wants to think about what they're drinking.
Cakebread Cellars Chardonnay Napa Valley 2021
A 179% markup puts this at $145 for a bottle you can grab for $52 at any decent wine shop. Cakebread is perfectly fine Chardonnay, but there is nothing on this list that justifies paying nearly three times retail for it. Order the Rombauer instead — it's also marked up aggressively, but at least it's a more interesting glass.
Caymus Napa Valley Cabernet Sauvignon 2020 + Prime Bone-in Ribeye
Caymus is a big, plush, fruit-forward Cab and the bone-in ribeye is a big, fatty, richly marbled steak. This is not a subtle pairing — it's two heavy hitters going the same direction together. The fruit in the wine softens the char, the fat in the steak rounds out the tannin. It's the obvious call at a steakhouse for a reason.
Monday — 50% off select bottles of wine on Mondays in the dining room and bar. This is a standing national Fleming's promotion and is active at the San Jose location. Cuts those steep markups down to something approaching reasonable — the Jordan Cab drops to around $82.
✔️ The Bottom Line
Fleming's San Jose is a well-oiled corporate wine program that punishes your wallet but never embarrasses you. Show up on a Monday, grab the Jordan Cab at half price, and it becomes a genuinely solid night out.
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