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SLUG-AA/TASTE19—DATE-4/10/2001—LOCATION-Pussers’s Landing Photo by Marvin Joseph/The The Washington Post via Getty Images

Where to Eat in the Florida Keys

Soak up those scenic views at these top spots

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Road trips have become the preferred mode of travel for many and South Floridians are fortunate to have one of the most scenic drives in the country when heading to the beloved and quirky Southernmost city of Key West. The 113 mile trip on the famed Overseas Highway offers a restorative balance of scenery along with great food along the way, and here are 14 restaurants that can’t be missed.

The latest CDC guidance for vaccinated diners during the COVID-19 outbreak is here; dining out still carries risks for unvaccinated diners and workers. Please be aware of changing local rules, and check individual restaurant websites for any additional restrictions such as mask requirements. Find a local vaccination site here.

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Note: Restaurants on this map are listed geographically.

1. The Fish House

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102401 Overseas Hwy
Key Largo, FL 33037
(305) 451-4665
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This Upper Key favorite has been around since 1982 serving fish like mahi mahi, yellowtail snapper, and grouper in a myriad of creative ways that includes Black and Bleu (topped with blue cheese crumbles and baked, then topped with a cream sauce of bleu cheese, garlic, blackening seasoning, and white wine) and Hemingway (lightly breaded with Italian breadcrumbs and baked, topped with a white wine, garlic, basil cream sauce). Other popular items include fried cracked conch and coconut shrimp served with poppyseed mango dressing.

2. Key Largo Fisheries Backyard Cafe

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1313 Ocean Bay Dr Suite A
Key Largo, FL 33037
(305) 451-3784
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If the name rings a bell it’s because this spot serves as one of the coast’s biggest fish exporters, making most of the meals literally “fresh off the boat.” With so much to choose from the menu can be overwhelming but classics like conch fritters with remoulade, peel and eat Key West shrimp, and stone crab chowder (when in season) are good starts. Don’t miss the lobster reuben, which like the original reuben comes served on toasted rye bread with sauerkraut, Swiss cheese, and Thousand Island dressing swapping corned beef with a generous serving of lobster.

3. Lorelei Restaurant & Cabana Bar

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96 Madeira Rd
Islamorada, FL 33036
(305) 664-2692
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Come for the nightly sunset celebrations overlooking idyllic Florida Bay and listen to local bands while sampling favorites like Lorelei’s smoked fish dip, Key lime peppercorn snapper, and twin lobster tails. Don’t pass on Lorelei’s World Famous “Frozen” Key Lime Pie for dessert, which is less tart than standard key lime pie and comes topped with mango sauce and whipped cream.

4. Robbie's

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77522 Overseas Hwy
Islamorada, FL 33036
(305) 664-8070
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Serving freshly caught fish sandwiches and drinks like the Islamorada Ice Pick (ice tea vodka, lemonade, and a splash of champagne) overlooking turquoise waters, this spot knows how to get the vacation vibe going right away. Afterwards, head over to feed the tarpon where more than 100 of the large fish will grab bait almost out of one’s hand.

5. Castaway Waterfront Restaurant & Sushi Bar

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1406 Ocean View Ave
Marathon, FL 33050
(305) 743-6247
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Beer lovers take note: there are 52 beers on tap to go along with this restaurant’s expansive menu. Founded in 1951, it was originally the place to stop for a beer and shrimp steamed in beer, that is, until John Mirabella and his wife Arlene sailed from Los Angeles to the Keys purchasing the restaurant in 1999 and expanding the menu to include offerings like oysters Moscow (raw oysters on the half shell served with sour cream, horseradish, and red and black roe) and snapper BLT (fried yellowtail snapper, bacon, chipotle aoili sauce) and, of course, shrimp steamed in beer.

6. South of the Seven

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17075 Overseas Hwy
Upper Sugarloaf Key, FL 33042
(305) 741-7115
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Tucked inside the Sugarloaf Lodge, owners chef Paul Kapsalis and Kris Kubik serve modern American fare like Apalachicola oysters roasted in their shell with chorizo, manchego, garlic butter, cilantro, and lime and locally-caught whole fish fried Thai style. Carnivores are not forgotten either with the menu having a generous selection of meat dishes like the 40-ounce Tomahawk steak, ribeye steak, and Sugarloaf burger.

7. Matt’s Stock Island Kitchen & Bar

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7001 Shrimp Rd Suite 200
Key West, FL 33040
(305) 294-3939
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A little removed from the party scene on Duval Street, this peaceful American restaurant inside the Perry Hotel Key West is offering some of the best meals on the island. Self-described as American coastal comfort food, appetizers like the crab beignets with lemon powder and stone grain mustard aoili and the oyster Rockefeller with parmesan, kale, bacon, and anise are not to be missed. Grouper gnudi (gnocchi-like dumplings made with ricotta) or shrimp and grits with tomato bacon gravy and manchego cheese are both must-try dishes.

8. Cuban Coffee Queen

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284 Margaret St
Key West, FL 33040
(305) 292-4747
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Several outlets throughout town make it easy to get a regular caffeine fix along with breakfast sandwiches and plenty of merch like t-shirts with cheeky messages like “Drink More Cuban Coffee and Do Stupid Things Faster.” Coffee is available for purchase by the pound, which means the caffeine party can continue at home.

9. B.O.'s Fish Wagon

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801 Caroline St
Key West, FL 33040
(305) 294-9272
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Epitomizing the relaxed vibe of Key West this colorful venue made from driftwood welcomes diners with a junk car swathed in bumper stickers. The menu is a simple and straightforward array of fresh seafood caught from the docks a few blocks away along with the prerequisite burger. The fried conch sandwich is a must as is an order of gigantic onion rings.

10. Azur Restaurant

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425 Grinnell St
Key West, FL 33040
(305) 292-2987
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Within walking distance from all the action on Duval, this local favorite is the ideal brunch spot. Grab a table in the lush, outdoor patio and indulge in Key lime French toast (yes, there’s pie in there!) as well as the crab cake benedict served on flatbread or Roesti potato pancake with brie, prosciutto, arugula, and hollandaise.

11. Eaton Street Seafood Market & Restaurant

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801 Eaton St
Key West, FL 33040
(305) 295-3474
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Primarily a seafood market for the locals, this spot also serves one of the best lobster rolls south of Maine. The secret is the lobster-to-bun ratio. While many lobster rolls are guilty of overdoing it with carbs, here, diners are treated to a tidy, buttery, toasted bun generously packed with chilled lobster salad heavy on the lobster meat. There’s no real seating inside, so grab it to go or snag one of the spots outside.

12. 5 Brothers Grocery and Sandwich Shop

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930 Southard St
Key West, FL 33040
(305) 296-5205
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This tiny corner grocery has been doling out some of the best Cuban sandwiches and Cuban coffee for several generations. There’s the traditional Cuban sandwich, or better yet, the Cuban mix (ham, pork, salami, swiss cheese, lettuce, tomato, and pickles.) Feel like ending the meal with a cigar? No worries, 5 Brothers sells those too.

13. Little Pearl

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632 Olivia St
Key West, FL 33040
(305) 204-4762
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A meal here will leave diners feeling as if they’ve stumbled upon a gem, or little pearl. Dishes are thoughtful and well executed, with a tasting menu currently in place featuring items like crab and mushroom bisque, garlic black pepper prawn, and swordfish with sesame soy broccolini, fingerling potatoes, and miso brown butter. End with a cheese plate or moscato ginger and poached pear. Wine pairing is also available. Reservations required.

14. Blue Heaven

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729 Thomas St
Key West, FL 33040
(305) 296-8666
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Known as one of the top brunch spots in town, this Key West staple offers bites like Florida shrimp omelet or Blue Heaven BLT benedict (bacon, lobster and tomato). Sit in the courtyard where chickens and cats roam free.

1. The Fish House

102401 Overseas Hwy, Key Largo, FL 33037

This Upper Key favorite has been around since 1982 serving fish like mahi mahi, yellowtail snapper, and grouper in a myriad of creative ways that includes Black and Bleu (topped with blue cheese crumbles and baked, then topped with a cream sauce of bleu cheese, garlic, blackening seasoning, and white wine) and Hemingway (lightly breaded with Italian breadcrumbs and baked, topped with a white wine, garlic, basil cream sauce). Other popular items include fried cracked conch and coconut shrimp served with poppyseed mango dressing.

102401 Overseas Hwy
Key Largo, FL 33037

2. Key Largo Fisheries Backyard Cafe

1313 Ocean Bay Dr Suite A, Key Largo, FL 33037

If the name rings a bell it’s because this spot serves as one of the coast’s biggest fish exporters, making most of the meals literally “fresh off the boat.” With so much to choose from the menu can be overwhelming but classics like conch fritters with remoulade, peel and eat Key West shrimp, and stone crab chowder (when in season) are good starts. Don’t miss the lobster reuben, which like the original reuben comes served on toasted rye bread with sauerkraut, Swiss cheese, and Thousand Island dressing swapping corned beef with a generous serving of lobster.

1313 Ocean Bay Dr Suite A
Key Largo, FL 33037

3. Lorelei Restaurant & Cabana Bar

96 Madeira Rd, Islamorada, FL 33036

Come for the nightly sunset celebrations overlooking idyllic Florida Bay and listen to local bands while sampling favorites like Lorelei’s smoked fish dip, Key lime peppercorn snapper, and twin lobster tails. Don’t pass on Lorelei’s World Famous “Frozen” Key Lime Pie for dessert, which is less tart than standard key lime pie and comes topped with mango sauce and whipped cream.

96 Madeira Rd
Islamorada, FL 33036

4. Robbie's

77522 Overseas Hwy, Islamorada, FL 33036

Serving freshly caught fish sandwiches and drinks like the Islamorada Ice Pick (ice tea vodka, lemonade, and a splash of champagne) overlooking turquoise waters, this spot knows how to get the vacation vibe going right away. Afterwards, head over to feed the tarpon where more than 100 of the large fish will grab bait almost out of one’s hand.

77522 Overseas Hwy
Islamorada, FL 33036

5. Castaway Waterfront Restaurant & Sushi Bar

1406 Ocean View Ave, Marathon, FL 33050

Beer lovers take note: there are 52 beers on tap to go along with this restaurant’s expansive menu. Founded in 1951, it was originally the place to stop for a beer and shrimp steamed in beer, that is, until John Mirabella and his wife Arlene sailed from Los Angeles to the Keys purchasing the restaurant in 1999 and expanding the menu to include offerings like oysters Moscow (raw oysters on the half shell served with sour cream, horseradish, and red and black roe) and snapper BLT (fried yellowtail snapper, bacon, chipotle aoili sauce) and, of course, shrimp steamed in beer.

1406 Ocean View Ave
Marathon, FL 33050

6. South of the Seven

17075 Overseas Hwy, Upper Sugarloaf Key, FL 33042

Tucked inside the Sugarloaf Lodge, owners chef Paul Kapsalis and Kris Kubik serve modern American fare like Apalachicola oysters roasted in their shell with chorizo, manchego, garlic butter, cilantro, and lime and locally-caught whole fish fried Thai style. Carnivores are not forgotten either with the menu having a generous selection of meat dishes like the 40-ounce Tomahawk steak, ribeye steak, and Sugarloaf burger.

17075 Overseas Hwy
Upper Sugarloaf Key, FL 33042

7. Matt’s Stock Island Kitchen & Bar

7001 Shrimp Rd Suite 200, Key West, FL 33040

A little removed from the party scene on Duval Street, this peaceful American restaurant inside the Perry Hotel Key West is offering some of the best meals on the island. Self-described as American coastal comfort food, appetizers like the crab beignets with lemon powder and stone grain mustard aoili and the oyster Rockefeller with parmesan, kale, bacon, and anise are not to be missed. Grouper gnudi (gnocchi-like dumplings made with ricotta) or shrimp and grits with tomato bacon gravy and manchego cheese are both must-try dishes.

7001 Shrimp Rd Suite 200
Key West, FL 33040

8. Cuban Coffee Queen

284 Margaret St, Key West, FL 33040

Several outlets throughout town make it easy to get a regular caffeine fix along with breakfast sandwiches and plenty of merch like t-shirts with cheeky messages like “Drink More Cuban Coffee and Do Stupid Things Faster.” Coffee is available for purchase by the pound, which means the caffeine party can continue at home.

284 Margaret St
Key West, FL 33040

9. B.O.'s Fish Wagon

801 Caroline St, Key West, FL 33040

Epitomizing the relaxed vibe of Key West this colorful venue made from driftwood welcomes diners with a junk car swathed in bumper stickers. The menu is a simple and straightforward array of fresh seafood caught from the docks a few blocks away along with the prerequisite burger. The fried conch sandwich is a must as is an order of gigantic onion rings.

801 Caroline St
Key West, FL 33040

10. Azur Restaurant

425 Grinnell St, Key West, FL 33040

Within walking distance from all the action on Duval, this local favorite is the ideal brunch spot. Grab a table in the lush, outdoor patio and indulge in Key lime French toast (yes, there’s pie in there!) as well as the crab cake benedict served on flatbread or Roesti potato pancake with brie, prosciutto, arugula, and hollandaise.

425 Grinnell St
Key West, FL 33040

11. Eaton Street Seafood Market & Restaurant

801 Eaton St, Key West, FL 33040

Primarily a seafood market for the locals, this spot also serves one of the best lobster rolls south of Maine. The secret is the lobster-to-bun ratio. While many lobster rolls are guilty of overdoing it with carbs, here, diners are treated to a tidy, buttery, toasted bun generously packed with chilled lobster salad heavy on the lobster meat. There’s no real seating inside, so grab it to go or snag one of the spots outside.

801 Eaton St
Key West, FL 33040

12. 5 Brothers Grocery and Sandwich Shop

930 Southard St, Key West, FL 33040

This tiny corner grocery has been doling out some of the best Cuban sandwiches and Cuban coffee for several generations. There’s the traditional Cuban sandwich, or better yet, the Cuban mix (ham, pork, salami, swiss cheese, lettuce, tomato, and pickles.) Feel like ending the meal with a cigar? No worries, 5 Brothers sells those too.

930 Southard St
Key West, FL 33040

13. Little Pearl

632 Olivia St, Key West, FL 33040

A meal here will leave diners feeling as if they’ve stumbled upon a gem, or little pearl. Dishes are thoughtful and well executed, with a tasting menu currently in place featuring items like crab and mushroom bisque, garlic black pepper prawn, and swordfish with sesame soy broccolini, fingerling potatoes, and miso brown butter. End with a cheese plate or moscato ginger and poached pear. Wine pairing is also available. Reservations required.

632 Olivia St
Key West, FL 33040

14. Blue Heaven

729 Thomas St, Key West, FL 33040

Known as one of the top brunch spots in town, this Key West staple offers bites like Florida shrimp omelet or Blue Heaven BLT benedict (bacon, lobster and tomato). Sit in the courtyard where chickens and cats roam free.

729 Thomas St
Key West, FL 33040

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