Key West is known for its stunning sunsets, laid-back vibe, and, of course, its legendary happy hours. Whether you’re a visitor looking to explore Old Town on a budget or a local wanting to discover a new favorite spot, happy hours offer the perfect way to sip and snack your way around the island without draining your wallet.
Today, we’ll take you on a tour of some of the must-visit happy hours in Key West. From fresh seafood dives to cocktail lounges with killer martinis, this guide will help you find the best drinks, bites, and vibes in town. Plus, we’ll throw in some tips to make the most of your happy hour adventure. But heads up, as prices or deals might slightly change during peak seasons or events, so double-check before you toast!
Grab your flip-flops and appetite because it’s time for a boozy, budget-friendly tour of Key West.
Why Happy Hour Is the Key (West) to Budget-Friendly Fun
Picture this—sunset views, mouthwatering bites, refreshing drinks, and all without breaking the bank. That’s what happy hour in Key West is all about. Most places not only serve discounted cocktails but also offer food specials. It’s the perfect way to eat your way around town without committing to full-sized entrees. You’ll eat, drink (responsibly), and still save enough to enjoy the rest of your Key West escapades.
Now that we’ve set the scene, here are some unforgettable happy hour spots across the island.
Grab our Free Happy Hour List – here.
Top Happy Hour Spots in Key West
1. Alonzo’s Oyster Bar
Harborfront Dining with a Seafood Twist
- When: Daily, 4–6:30 PM
- Deals: Half-off well drinks, beer, and wine by the glass. Discounted seafood bites like peel-and-eat shrimp, crab cake sliders, and conch fritters.
- Why Visit: Located at A&B Marina, Alonzo’s serves up fresh seafood with unbeatable views of the harbor. Watch tarpon swim by, enjoy some people-watching, and savor your discounted oysters with a cold drink in hand.
2. Half Shell Raw Bar
A Local Favorite for Fresh Florida Seafood
- When: Daily, 4:30–6:30 PM
- Deals: Half-off well liquors, house wine, and beers. Fresh oysters often priced around $2–$3 each.
- Why Visit: Their tagline “Eat It Raw” sets the tone for the casual, Old Florida vibe. Get there early to snag a waterfront seat and mingle with the locals.
3. Hurricane Hole
Best Dockside Spot for Chill Vibes
- When: Daily, 3–6 PM
- Deals: Discounted beers, wines, and appetizers like conch fritters, chicken nachos, and pretzels with queso.
- Why Visit: This laid-back gem is dockside and perfect for boat-watching while sipping a cold pint. It’s serene, relaxed, and totally Key West.
4. Martin’s Cocktail Lounge
Upscale Elegance with an Excellent Martini Menu
- When: Daily (excluding holidays), 4–6 PM
- Deals: Half-off signature martinis, well drinks, small plates, and select wines.
- Why Visit: Known as one of Key West’s most posh spots, Martin’s is perfect for martini lovers. Whether you’re into a classic dry martini or something more creative, this is the place. It’s cozy, classy, and their claim of the best martini in Key West is yours to test.
5. Mary Ellen’s Bar
Dive Bar With Big Personality
- When: Mon-Wed and Fri, 3:30–5:30 PM; Thurs, 3:30–5 PM
- Deals: $5 Deep Eddy vodkas, $3 draft PBR, and 25% off food.
- Why Visit: This funky, air-conditioned spot offers plenty of character, sports on TV, and the goodness of Chive TV made for endless giggles.
6. Moondog Cafe and Bakery
Sangria and Eclectic Bites at Hemingway’s Neighbor
- When: Daily, 4–6 PM
- Deals: House-made sangrias (red, white, or rosé), discounted draft beer, wine, and small plates.
- Why Visit: Located near Hemingway House, this spot is perfect for enjoying a sangria and some artistic, funky decor. Pair your drinks with a small plate, and don’t forget to grab a pastry on your way out!
7. The Roost
Hidden Gem for Craft Cocktails
- When: Daily, Noon–6 PM (all-day happy hour!)
- Deals: Discounted cocktails of the day, select wines, and beers.
- Why Visit: This upscale cocktail bar serves expertly crafted cocktails in an intimate setting that’s perfect for pre-dinner drinks or a low-key afternoon date.
8. The Saint Hotel Bar
Chic, Instagram-Worthy Spot With Unique Hours
- When: Daily, 4:17–7:14 PM (yes, those are the actual hours!)
- Deals: 30% off craft cocktails, beer, wine, and small plates.
- Why Visit: This quirky, elegant hotel bar is all about ambiance and aesthetics. Plus, the Hemingway Daiquiri is a must-try.
9. Southernmost Beach Cafe
Breezy Seaside Views and Margaritas
- When: Daily, 4–6 PM
- Deals: Discounted appetizers, draft beer, house wine, and (often) margaritas.
- Why Visit: You just can’t beat the oceanfront setting. Kick back at this casual spot and toast to the day while waves gently roll in. Perfect for a peaceful ending to your Key West adventures.
10. General Horseplay
Roll the Dice and See What You Pay
- When: Daily, 3–6 PM
- Deals: Roll-the-dice drink pricing (as low as $1!) and half-off food.
- Why Visit: This playful bar keeps things fun, from dice-rolling drink prices to expertly executed craft cocktails. They’re renowned for their old-fashioneds, so don’t miss out.
Bonus Picks
- Thirsty Mermaid on Fleming Street for creative seafood bites from 4–6 PM daily.
- Schooner Wharf Bar for morning happy hour from 8 AM–Noon AND an evening one from 5–7 PM, all with great live music.
- First Flight Brewery for history lovers who want to enjoy beer specials at the original Pan Am building.
Tips to Maximize Your Happy Hour Fun
- Start Early: Popular spots fill up fast, so grab a seat as soon as happy hour starts.
- Stay Hydrated: Key West is warm, and the drinks are strong. Balance your cocktails with water to keep the good vibes going.
- Walk or Share Rides: Skip mopeds and e-cars if you’re bar-hopping. Use Uber, Lyft, or your own two feet to get around safely.
- Ask for Recommendations: Bartenders in Key West are like local tour guides. If you’re unsure what to sip or munch on, just ask!
Sip and Snack Like a Local
Happy hour in Key West is not just about saving a few bucks (though that’s a nice bonus). It’s about sipping cocktails, sharing laughs, and soaking up the island vibes. Whether you prefer waterfront views, posh cocktail lounges, or funky dives, Key West’s happy hour scene is second to none.
