🦜 Tipsy’s Guide to Eating Your Way Through Key West
20 places worth leaving the hammock for.
From Cuban food and dockside seafood to date-night dinners and legendary Key lime pie, these are some of our favorite places to eat around the island.
🦜 The Tipsy Parrot’s Favorite Key West Restaurants
Key West has a surprisingly serious food scene for such a small island. You’ll find everything from backyard Caribbean joints and Cuban institutions to tiny chef-driven restaurants and waterfront dinners worth dressing up for.
Here are some of Tipsy’s favorites.
1. Blue Heaven 🌴
Bahama Village • Caribbean/American • $$
Funky outdoor courtyard, roaming chickens, live music, legendary breakfast and Key lime pie. Even better, it’s right in The Tipsy Parrot neighborhood.
🦜 Tipsy Says: Go for breakfast or brunch. Stay for the Key lime pie.
2. Santiago’s Bodega 🍷
Bahama Village • Tapas • $$
One of the best places on the island for sharing plates, wine and a long dinner. It’s also only a short stroll from Mickens Lane.
🦜 Tipsy Says: Order several plates for the table and pretend you’re going to share everything.
Visit Santiago’s Bodega
3. Little Pearl 🐚
Old Town • Seafood Tasting Menu • $$$$
Tiny, intimate and very food-focused. Little Pearl is an excellent choice when you want dinner to be the evening rather than simply the thing you do before going out.
🦜 Tipsy Says: Save this one for date night or when dinner deserves to be the main event.
Visit Little Pearl
4. Red Shoe Island Bistro 👠
Bahama Village • Seafood/New American • $$$
Another excellent neighborhood choice. Small, chef-driven and known for fresh seafood and a particularly well-regarded Key lime pie.
🦜 Tipsy Says: Another great dinner practically in the Parrot’s backyard.
Visit Red Shoe Island Bistro
5. Cafe Marquesa 🍽️
Old Town • Contemporary American • $$$$
Elegant without feeling stuffy. This is where we’d send guests celebrating an anniversary, birthday or looking for one truly polished dinner in Key West.
🦜 Tipsy Says: Put on something nicer than your beach shorts. Probably.
6. Louie’s Backyard 🌊
Atlantic Ocean • Floribbean • $$$$
One of the quintessential Key West experiences. Historic house, oceanfront decks, cocktails and excellent seafood.
🦜 Tipsy Says: Sunset cocktails followed by dinner. This is Key West doing its thing.
7. Latitudes 🌅
Sunset Key • American/Seafood • $$$$
The boat ride is part of dinner. You cross over to Sunset Key and dine overlooking the water, making this one of the island’s classic romantic splurges.
🦜 Tipsy Says: When dinner starts with a boat ride, you’re already doing pretty well.
Visit Latitudes
8. El Siboney 🇨🇺
Old Town • Cuban • $$
Cuban food is part of Key West’s history, not merely another cuisine option. El Siboney is a longtime local favorite for roast pork, ropa vieja, picadillo, rice, black beans and plantains.
🦜 Tipsy Says: Come hungry. Cuban comfort food does not believe in tiny portions.
9. Azur Restaurant 🍷
Old Town • Mediterranean • $$$
A quieter neighborhood restaurant away from the Duval frenzy. Excellent brunch, Mediterranean-inspired seafood and a more intimate dinner atmosphere.
🦜 Tipsy Says: A good choice when you want excellent food and Duval Street can wait.
10. Bagatelle 🏡
Duval Street • American/Caribbean • $$$
A beautiful historic house with porch and balcony dining. Local seafood, steaks and a prime location for watching the wonderfully strange parade of humanity that is Duval Street.
🦜 Tipsy Says: Try for a porch or balcony table and let Duval provide the entertainment.
11. Pepe’s Cafe ⚓
Historic Seaport • Old Key West • $$
Serving Key West since 1909, Pepe’s is packed with old-island character. Think fresh-shucked oysters, breakfast, steaks, seafood and the sort of atmosphere you can’t manufacture.
🦜 Tipsy Says: Old Key West, cold drinks and oysters. Don’t overthink it.
12. Half Shell Raw Bar 🦪
Historic Seaport • Seafood/Raw Bar • $$
This is the flip-flops-and-cold-beer seafood experience. Oysters, Key West pink shrimp, conch ceviche and fishing boats coming and going outside.
🦜 Tipsy Says: Order something raw, something cold and something that came out of the water.
13. Conch Republic Seafood Company 🐟
Historic Seaport • Seafood • $$–$$$
Big waterfront atmosphere, fresh seafood and live music. The building was formerly the Singleton Fish House and Ice Plant, where Key West shrimpers once unloaded their catch.
🦜 Tipsy Says: Come for the seafood. Stay because leaving the waterfront seems unnecessary.
Visit Conch Republic Seafood Company
14. Eaton Street Seafood Market & Restaurant 🐠
Old Town • Seafood Market • $$
Less polished and more local. Choose from fresh local seafood and have it prepared right there.
🦜 Tipsy Says: One of our picks for a casual seafood lunch without the waterfront price tag.
15. Atlas Izakaya 🍣
Old Town • Japanese • $$$
A welcome curveball among all that grouper and conch. This chef-owned Japanese izakaya specializes in creative small plates and offers something very different from the typical Key West seafood restaurant.
🦜 Tipsy Says: When you’ve reached your temporary lifetime limit on conch fritters, go here.
16. Hot Tin Roof 🌅
Mallory Square • Seafood/Latin-Caribbean • $$$$
Beautiful harbor views at the end of Duval with a more refined atmosphere. An excellent choice for guests wanting to build dinner around the sunset.
🦜 Tipsy Says: Time the reservation with sunset and let Mother Nature handle the appetizers.
17. The Flaming Buoy Filet Co. 🔥
Old Town • Seafood/New American • $$$
Small, quirky and very Key West. Seafood, steak and plenty of personality without the big-resort feeling.
🦜 Tipsy Says: Small restaurant, big personality. We approve.
18. Frita’s Cuban Burgers 🍔
Old Town • Cuban Street Food • $–$$
Cuban frita burgers, sandwiches and casual outdoor dining. It’s the sort of place guests remember because it feels like Key West rather than a vacation-resort restaurant.
🦜 Tipsy Says: Fancy clothes absolutely not required.
19. DJ’s Clam Shack 🦞
Duval Street • Casual Seafood • $$
Lobster rolls, fried clams, conch fritters and chowder. Perfect when somebody wants great seafood without turning dinner into a three-hour production.
🦜 Tipsy Says: Lobster roll. Cold drink. Keep moving. Duval awaits.
20. Moondog Cafe & Bakery 🥐
Old Town • Café/Bakery • $$
A great breakfast and lunch stop with an excellent bakery. It’s an easy place to wander into for coffee and somehow emerge carrying significantly more pastry than originally planned.
🦜 Tipsy Says: The bakery case has absolutely no respect for your self-control.
🦜 Tipsy’s Restaurant Advice
Key West dining runs from flip-flops and fish sandwiches to tasting menus and sunset dinners, so don’t spend the whole trip eating one way.
Have a Cuban lunch. Order seafood somewhere overlooking the harbor. Splurge on one great dinner. Find a bakery in the morning. Eat somewhere because a local told you to.
And remember, reservations are your friend during high season, particularly for the smaller restaurants and sunset dining spots.
Then wander back to The Tipsy Parrot, loosen the belt one notch and start arguing about where you’re eating tomorrow. 🌴