Big List, Big Markups, Great Monday Redemption
Santana Row / West San Jose · San Jose · Steakhouse · Visit Website ↗
Updated August 2026
Reviewed June 22, 2026 · How we review
RagingWine reviewed Fleming's Prime Steakhouse & Wine Bar San Jose’s wine list and gave it The Reliable — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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.
· San Jose · Japanese Ramen
Momosan is not a wine destination, and it doesn't pretend to be — but the list it does offer is priced fairly and chosen with more care than most ramen spots bother with. Come for the sake program, but if you want a glass of wine with your bowl, the Brunel Grenache or the Pecorino will do you right. Don't come here expecting depth; do come here expecting a decent pour at a fair price.
Small but Thoughtful
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
Saratoga · San Jose · New American
Sent Sovi isn't a wine destination, but it's a restaurant where the wine list respects the food — and that's rarer than it should be at this price point. If you're driving out to Saratoga for the bacon-wrapped rabbit or the osso buco, you won't feel like an afterthought at the wine stage of the conversation. A solid neighborhood anchor, even if the neighborhood happens to require a reservation.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
· San Jose · New American
The Lexington House is doing more with its wine list than it gets credit for — that Italian section alone beats most comparable spots in the South Bay. The near-total absence of by-the-glass options is a frustrating structural gap, and the familiar crowd-pleasers in the New World section drag the overall ambition down a notch. But if you're ordering a bottle and you know to head straight for the Italian reds or the Director Picks, you'll drink well here.
Solid Range
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
Santana Row · San Jose · Modern Mediterranean
MESO's wine list is small, but it earns its keep by staying on-theme and keeping prices from going completely sideways. The Torres Albariño and Feudo Montoni are genuine finds at the lower end of the price range, and the happy hour window Monday through Friday gives you a legitimate reason to show up early. If you want a deep cellar or an adventurous natural wine program, look elsewhere — but if you want a glass that actually fits what's on your plate at a fair price, this list delivers.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Occasional
Acceptable
· San Jose · Wine Bar
Rootstock is doing something genuinely uncommon for San Jose: building a wine list with a real perspective, fair prices, and enough depth to reward repeat visits. The pét-nat and multi-vintage Reeve presence alone put it ahead of most dedicated wine bars in the Bay. If you care about what's in your glass, this place deserves your attention.
Deep & Eclectic
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
· San Jose · Steakhouse
The Capital Grille San Jose is a reliable but unambitious wine program — it stocks the bottles a Napa-loving business dinner crowd expects and prices them accordingly. If you're looking for discovery or value, you won't find much here; if you need a solid Cab to go with a dry-aged steak and you're on someone else's tab, it does the job.
Plays It Safe
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
· Hoschton · Steakhouse
Jacks is a genuinely fun neighborhood hang with solid food, but the wine program doesn't match the ambition of the kitchen. If wine is your thing, call ahead or bring your own if corkage is an option — otherwise, lean into the cocktails and enjoy the patio. We'd love to revisit this rating if they ever put some real thought into the list.
Crowd Pleasers
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
East Point · Atlanta · Steakhouse
Malone's earns its loyal following on the strength of its pork chops and tenderloin, not its wine list. If wine matters to your meal, you may want to call ahead and ask what's available — or just lean into a cocktail and let the steak do the heavy lifting. This one's a food-first destination.
Crowd Pleasers
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
· Acworth · Steakhouse
AG Steakhouse earns its reputation as a go-to for celebrations and big nights out on Lake Acworth — but the wine program appears to be in service of the experience rather than a destination in itself. If you're splurging on the filet or the Oscar-style halibut, budget accordingly for the bottle too, and don't expect the list to surprise you. A solid place to drink wine; not a reason to come specifically for wine.
Crowd Pleasers
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
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