Big List, Big Markups, Great Monday Redemption
Santana Row / West San Jose · San Jose · Steakhouse · Visit Website ↗
Updated August 2026
Reviewed by the RagingWine Tasting Desk · June 22, 2026
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.
Downtown · San Jose · Italian-American Steakhouse
Original Joe's isn't a wine destination, but it's not trying to be — it's a reliable room where the wine does its job alongside serious Italian-American comfort food. Send a friend here for the prime rib and a Cab; just don't send them expecting a bargain on the bottle.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Santana Row · San Jose · Rooftop Wine Bar
Cielo is a perfectly fine place to drink wine when the real attraction is the open sky and the Santana Row scene below you. The list won't challenge anyone, the markups are real, but the all-by-the-glass format and a few smart picks like the Twomey keep it from being a total afterthought.
Crowd Pleasers
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
Alameda · San Jose · Wine Bar / Pizza
Hop & Vine is a reliable neighborhood anchor — come for the Monday half-price bottles, stay for the charcuterie and zero-pressure vibe. It won't blow your mind, but it'll absolutely do the job.
Solid Range
Fair
Basic Stemmed
Willing but Green
Active Program
Acceptable
· San Jose · Italian
Palermo isn't a wine destination, but it's a genuinely solid neighborhood Italian with a list that respects the cuisine and won't punish your wallet. Send a friend here if they want a good bottle with dinner — just steer them toward the Italian side of the list.
Solid Range
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
· San Jose · Wine Bar / New American
At $10 a glass, you won't feel robbed — but a wine bar with eight unnamed house pours and zero depth isn't really a wine bar. Grab the Scharffenberger and lower your expectations accordingly.
Grocery Store
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
Santana Row · San Jose · Japanese / Ramen
Momosan's wine list is perfectly adequate for a ramen dinner and perfectly forgettable in every other way. Order the Pinot Noir or the sparkling, enjoy your bowl, and don't overthink it.
Plays It Safe
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
· Atlanta · Steakhouse
Il Premio is a steakhouse that took its wine list seriously enough to skip the obvious plays, and the result is one of the more interesting Italian-focused lists in Atlanta right now. It's compact, priced fairly across the board, and built for exploration — whether you're going glass by glass through the Italian regions or just need a solid bottle of Chianti Classico at $72 to make a steak dinner feel right. We'd send a friend here specifically for the wine.
Small but Thoughtful
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
· Healdsburg · Steakhouse
Stark's is the rare steakhouse that treats wine as something other than an afterthought or a cash grab. The list is compact but genuinely considered, markups are fair across the board, and the full bottle-to-glass availability is a policy every restaurant should copy. If you're eating in Healdsburg and want to drink well without overpaying, this is a legitimate stop.
Small but Thoughtful
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
Downtown Albany · Albany · Steakhouse
Order by the glass and explore: the posted menu gives you Riesling, Chablis, Cahors and Rioja without a bottle commitment. Pentimento at $16 is our price-conscious red starting point. Check the current list before ordering; the complete cellar, service and storage haven't been independently verified.
One wine list review, one adventure pick, one quick tip, and a personal note. Every week. Under 500 words.
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