A Hundred Glasses Deep, Zero Surprises
Clearwater vicinity · Clearwater · Upscale steakhouse with seafood and extensive wine program · Visit Website ↗
Reviewed July 6, 2026
Wingman Metrics
The wine list at Fleming's arrives looking like a statement — 100 wines by the glass is a real number, not marketing fluff, and it commands attention. The room feels built for big bottles and bigger occasions, all dark wood and soft lighting. You're in good hands here, but you're also paying for the zip code and the brand name on the door.
The list leans hard into California, with Napa Valley Cabernets and Chardonnays doing most of the heavy lifting — Caymus, Silver Oak, Stag's Leap, Far Niente, Jordan. These are crowd-pleasing, recognizable bottles that will keep the table happy but won't challenge anyone's palate. There's representation from Sonoma and the Pacific Northwest, and France shows up in a supporting role, but don't expect a deep dive into Burgundy villages or Rhône crus. The list is broad in volume but narrow in spirit — it's a greatest-hits album, competently curated and strategically safe.
One hundred by-the-glass options is genuinely impressive on paper, and Fleming's delivers on the promise — you can drink well without committing to a bottle all night. The range spans entry-level pours through serious Napa names at the top end, with glass prices running from around $12 up to $40 and beyond. The tradeoff is that the program tilts toward safe, familiar California labels rather than anything adventurous or rotating.
Jordan Cabernet Sauvignon, Alexander Valley — $18–$22/glass
Jordan consistently overdelivers for its price point — it's polished, food-friendly, and doesn't carry the inflated prestige markup of a Caymus or Silver Oak. At a steakhouse with 4x bottle markups standard across the industry, getting Jordan by the glass is the smart play.
Duckhorn Merlot, Napa Valley
Everyone at a steakhouse reaches for Cab, which means the Duckhorn Merlot often gets ignored. That's a mistake. It's a richer, softer alternative that holds its own against red meat and skips the tannin sledgehammer — worth the ask.
Caymus Cabernet Sauvignon, Napa Valley
Caymus is everywhere, which is part of the problem — it's a reliable bottle that's also one of the most marked-up wines in the American steakhouse ecosystem. You're paying a premium for a label that's on every wine list from Tampa to Tacoma. There's better value in this same list.
Far Niente Chardonnay, Napa Valley + Lobster or crab-stuffed seafood special
Far Niente Chardonnay is full-bodied and rich with restrained oak — it matches the buttery weight of a stuffed lobster without steamrolling the shellfish. It's the rare Napa Chard that actually works with seafood instead of fighting it.
✔️ The Bottom Line
Fleming's is a reliable machine — excellent execution, real wine depth by-the-glass, staff that knows the list, and no surprises in a bad way. Just don't expect discovery; expect comfort, and budget accordingly for markup.
Westshore · Clearwater · Fine-dining steakhouse
The Capital Grille is a reliable machine — the wine program is competent, well-staffed, and properly executed, but the markups are steep and the list plays it extremely safe. Send a friend here for a business dinner, but tell them to order Jordan before anyone at the table reaches for the Opus One.
Solid Range
Steep
Varietal Specific
Knowledgeable & Friendly
Set & Forget
Proper
Indian Rocks Beach · Clearwater · Seafood / American
Guppy's won't win any awards for adventurous curation, but the list is fairly priced, thoughtfully stocked for a seafood crowd, and broad enough that everyone at the table finds something. Send a friend here for the grouper and tell them to drink the Cloudy Bay.
Solid Range
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Belleair Bluffs · Clearwater · American Steakhouse
E&E Stakeout Grill is a perfectly decent neighborhood steakhouse wine list that asks too much on most nights — but Wine Wednesday flips the math entirely and makes this one of the better value plays in the Clearwater area. Come on a Wednesday, order the Chianti Classico, and you'll have zero complaints.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Active Program
Acceptable
Clearwater Beach · Clearwater · Mediterranean and Mexican-inspired wine bar and bistro
This is the best wine program you're likely to find within walking distance of Clearwater Beach, and that's not faint praise — it's a genuine destination for the wine-curious crowd that usually has to settle for whatever's on draft. Wednesday's half-price U.S. bottle deal seals it: show up, order spaghetti, drink better than you planned.
Solid Range
Fair
Basic Stemmed
Willing but Green
Active Program
Acceptable
US-19 / East Clearwater · Clearwater · Italian
Carrabba's Clearwater is a solid, honest chain wine program — fair prices, recognizable producers, nothing offensive. Send a friend here if they want Italian comfort food and an easy bottle of Chianti; don't send them if they're hoping to find something worth talking about.
Crowd Pleasers
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
US-19 / East Clearwater · Clearwater · Seafood Grill
Bonefish Grill Clearwater is a perfectly fine place to eat seafood and a genuinely bad place to spend money on a bottle of wine. Order by the glass, stick to the $9 pours, and save your wine budget for somewhere that earned it.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
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