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.
Campbell · San Jose · Steakhouse with Italian influences
Be.Steak.A is doing more with its wine list than most South Bay steakhouses bother to attempt — the sommelier is real, the selections have personality, and the Massican pick alone earns genuine respect. The markups are on the steeper side, which is expected at this level, but the list has enough character that you're paying for something worth the splurge.
Solid Range
Steep
Varietal Specific
Knowledgeable & Friendly
Occasional
Proper
Downtown San Jose · San Jose · Steakhouse and Classic American
GrandView is doing exactly what a mountaintop steakhouse with jaw-dropping views over Santa Clara Valley is supposed to do — it's feeding the occasion, not the curiosity. Bring someone you want to impress, order the Mt. Brave, and enjoy the sunset.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Saratoga · San Jose · Modern Californian/New American
Plumed Horse is one of the most serious wine destinations in the South Bay, full stop. The markup will make your eyes water in places, but if you're willing to explore the list with help from the sommelier team, there's genuinely exceptional drinking to be done here.
Deep & Eclectic
Steep
Varietal Specific
Knowledgeable & Friendly
Set & Forget
Proper
Los Gatos · San Jose · Contemporary Californian tasting menu
Manresa is as serious a wine destination as you'll find in the South Bay, and the list earns every bit of that reputation. Just go in knowing the bottle prices climb fast, and strongly consider letting the sommelier drive with the pairing menu.
Deep & Eclectic
Steep
Varietal Specific
Knowledgeable & Friendly
Set & Forget
Proper
Santana Row / West San Jose · San Jose · Italian-American
Maggiano's San Jose is a perfectly competent chain Italian dinner, but the wine list is working against you — steep markups on recognizable labels with no depth, no discovery, and no reason to linger over a second bottle. Order the Antinori, enjoy your rigatoni, and save the serious wine drinking for somewhere that's actually trying.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Santana Row · San Jose · French Brasserie
Left Bank Santana Row is a reliable French brasserie wine list with real highlights if you know where to look — just avoid the Instagram rosé and come during happy hour whenever possible. We'd send a friend here without hesitation, as long as they knew to ask about the Chave.
Solid Range
Steep
Basic Stemmed
Willing but Green
Occasional
Acceptable
I-35 / North Creek · Laredo · Steakhouse
Outback Laredo's wine program is a national chain doing national chain things — predictable, overpriced relative to quality, and staffed by people who aren't expected to know anything about what they're pouring. Come for the Bloomin' Onion, stick to a cocktail, and save the wine order for somewhere that cares.
Grocery Store
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
North Creek / I-35 · Laredo · Steakhouse
Logan's Roadhouse is not a wine destination — it's a steakhouse chain where wine clearly wasn't part of the concept. Order a beer, order a cocktail, and save the bottle for a restaurant that's actually trying.
Grocery Store
Steep
Basic Stemmed
MIA
Set & Forget
Acceptable
Mall del Norte Area · Laredo · Steakhouse
Texas Roadhouse Laredo is a great spot for a $17 steak and a bucket of rolls — the wine list is an afterthought and everyone involved knows it. Order a margarita, or grab the Ste. Michelle Riesling and call it a night.
Grocery Store
Fair
Basic Stemmed
MIA
Set & Forget
Acceptable
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