Gulf Views, Safe Pours, Resort Markups Apply
Clearwater Beach · Clearwater · American fine dining with seafood, steak and sushi · Visit Website ↗
Reviewed July 6, 2026
Wingman Metrics
The wine list at Caretta on the Gulf reads exactly how you'd expect from an upscale beachfront resort restaurant — polished, inoffensive, and built to move bottles without scaring anyone. It's the kind of list where you recognize every name but rarely feel excited by any of them. That's not a crime, but it does mean you're paying resort premiums for the comfort of familiarity.
The list clocks in around 80–120 bottles with a clear California-first strategy — Sonoma, North Coast, and Russian River Valley dominate the reds and whites, with supporting roles from Oregon, New Zealand, and a few Italian and French bottles to keep things honest. You'll find La Crema, Sonoma-Cutrer, and The Prisoner doing heavy lifting, which tells you everything about the target audience. There are bright spots — Jermann's Pinot Grigio from Friuli and the Guado al Tasso 'Il Braciato' from Bolgheri add some actual intrigue — but they're surrounded by a lot of Kendall-Jackson and Kim Crawford energy. If you came looking for discovery, you'll need to dig.
The by-the-glass program runs roughly 18–25 options, which is generous for a beach resort and means you're not stuck nursing the house Chardonnay all night. Prices land in the $12–$20 range per glass, reasonable on the surface until you do the math and realize those markups compound fast. The selection rotates with the seasons in theory, but in practice this feels like a Set & Forget situation — the same crowd-pleasers holding down the same slots.
Château Greysac, Médoc, Bordeaux Blend, 2018 — $40–$70 (est.)
A proper Left Bank Bordeaux from a solid vintage tucked into a list that otherwise leans hard California. Greysac consistently punches above its price class, and in a list full of inflated familiar names, this is where the kitchen's gulf seafood and steak dishes actually get an interesting match.
Guado al Tasso 'Il Braciato', Bolgheri, Tuscany, 2022
Nobody at a beachside resort in Clearwater is ordering the Bolgheri blend — and that's exactly why you should. Il Braciato is Antinori's estate working with Cabernet, Merlot, and Syrah on the Tuscan coast, and it's a genuinely interesting bottle hiding between bottles of Ghost Pines and Silver Palm. Order it before someone else figures it out.
Stemmari Moscato, Sicily, 2021
At a 333% markup over retail, this is the single worst value proposition on the list. Stemmari Moscato retails around $12, and even in a resort setting, paying $52 for a casual Sicilian sweet wine is a hard no. If you want something sweet and low-stakes, order a cocktail.
Jermann Pinot Grigio, Friuli, 2023 + Fresh local gulf seafood
Jermann isn't your gas-station Pinot Grigio — it's the real deal from Friuli, with enough texture and mineral lift to actually complement fresh gulf fish without steamrolling it. Most tables at Caretta will default to the Kim Crawford; don't be most tables.
✔️ The Bottom Line
Caretta on the Gulf is a reliable pour in a beautiful setting, but the markups and crowd-pleaser-heavy list make it hard to call it a wine destination — you're really paying for the sunset and the linen napkins. Come for the view, find the Guado al Tasso or the Greysac, and don't look too hard at what anything cost at retail.
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
Clearwater vicinity · Clearwater · Upscale steakhouse with seafood and extensive wine program
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.
Crowd Pleasers
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
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