clock menu more-arrow no yes
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

View as Map

COVID-19 has redefined much of how we do things and travel is no exception. Road trips have become the preferred mode of travel 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 and a sense of freedom after months of feeling cooped up. Along the way there are plenty of tasty pitstops to consider. Here are some not to be missed.

Editor’s Note: Most Florida restaurants have resumed indoor and outdoor dining services. However, this should not be taken as endorsement for onsite dining, as there are still safety concerns: for updated information on coronavirus cases in your area, please visit the Florida Health Department’s website. Studies indicate that there is a lower exposure risk when outdoors, but the level of risk involved with patio dining is contingent on restaurants following strict social distancing and other safety guidelines.

Read More
Note: Restaurants on this map are listed geographically.

1. The Fish House

Copy Link
102401 Overseas Hwy
Key Largo, FL 33037
(305) 451-4665
Visit Website

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 Conch House

Copy Link
100211 Overseas Hwy
Key Largo, FL 33037
(305) 453-4844
Visit Website

This family-owned restaurant has caught the eye of culinary powerhouses like Emeril Lagasse and The Food Network with local favorites like conch fritters, blackened hogfish, and crab stuffed mahi-mahi (broiled with a blue crab and mango stuffing topped with lobster bisque.)

3. Key Largo Fisheries Backyard Cafe

Copy Link
1313 Ocean Bay Dr Suite A
Key Largo, FL 33037
(305) 451-3784
Visit Website

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.

4. Lorelei Restaurant & Cabana Bar

Copy Link
96 Madeira Rd
Islamorada, FL 33036
(305) 664-2692
Visit Website

Come for the nightly sunset celebrations overlooking idyllic Florida Bay and listen to local bands while sampling favorite dishes 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.

5. Robbie's

Copy Link
77522 Overseas Hwy
Islamorada, FL 33036
(305) 664-8070
Visit Website

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.

6. Castaway Waterfront Restaurant & Sushi Bar

Copy Link
1406 Ocean View Ave
Marathon, FL 33050
(305) 743-6247
Visit Website

Beer lovers take note: there are 52 beers on tap to go along with this eatery’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.

7. Square Grouper Bar and Grill

Copy Link
22658 Overseas Hwy
Cudjoe Key, FL 33042
(305) 745-8880
Visit Website

For the past 15 years this eatery has been a favored stop offering cocktails, inventive seafood dishes, and decadent desserts. Flash fried conch with wasabi drizzle and house smoked fish dip are worthy starters followed by grouper piccata or seafood stew for main course. There are also jasmine rice bowls that come with Thai sweet chili butter sauce, spinach, and chopped cashews then topped with a choice of protein (or roasted cauliflower) and pasta bowls with Key lime butter sauce and roasted tomatoes doing the same.

8. South of the Seven

Copy Link
17075 Overseas Hwy
Upper Sugarloaf Key, FL 33042
(305) 741-7115
Visit Website

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, having a generous selection of meat dishes like the 40-oz. Tomahawk steak, ribeye steak, and Sugarloaf burger.

9. Matt’s Stock Island Kitchen & Bar

Copy Link
7001 Shrimp Rd Suite 200
Key West, FL 33040
(305) 294-3939
Visit Website

A little removed from the party scene on Duval Street, this peaceful newcomer tucked 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 dreams.

10. Cuban Coffee Queen

Copy Link
284 Margaret St
Key West, FL 33040
(305) 292-4747
Visit Website

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.

11. 5 Brothers Grocery and Sandwich Shop

Copy Link
930 Southard St
Key West, FL 33040
(305) 296-5205
Visit Website

It’s a good sign when there’s a line of local cops, plumbers, and handymen waiting for lunch. The 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, they sell those too.

12. Little Pearl

Copy Link
632 Olivia St
Key West, FL 33040
(305) 204-4762
Visit Website

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.

13. Blue Heaven

Copy Link
729 Thomas St
Key West, FL 33040
(305) 296-8666
Visit Website

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 Conch House

100211 Overseas Hwy, Key Largo, FL 33037

This family-owned restaurant has caught the eye of culinary powerhouses like Emeril Lagasse and The Food Network with local favorites like conch fritters, blackened hogfish, and crab stuffed mahi-mahi (broiled with a blue crab and mango stuffing topped with lobster bisque.)

100211 Overseas Hwy
Key Largo, FL 33037

3. 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

4. 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 favorite dishes 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

5. 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

6. 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 eatery’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

7. Square Grouper Bar and Grill

22658 Overseas Hwy, Cudjoe Key, FL 33042

For the past 15 years this eatery has been a favored stop offering cocktails, inventive seafood dishes, and decadent desserts. Flash fried conch with wasabi drizzle and house smoked fish dip are worthy starters followed by grouper piccata or seafood stew for main course. There are also jasmine rice bowls that come with Thai sweet chili butter sauce, spinach, and chopped cashews then topped with a choice of protein (or roasted cauliflower) and pasta bowls with Key lime butter sauce and roasted tomatoes doing the same.

22658 Overseas Hwy
Cudjoe Key, FL 33042

8. 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, having a generous selection of meat dishes like the 40-oz. Tomahawk steak, ribeye steak, and Sugarloaf burger.

17075 Overseas Hwy
Upper Sugarloaf Key, FL 33042

9. 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 newcomer tucked 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 dreams.

7001 Shrimp Rd Suite 200
Key West, FL 33040

10. 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

11. 5 Brothers Grocery and Sandwich Shop

930 Southard St, Key West, FL 33040

It’s a good sign when there’s a line of local cops, plumbers, and handymen waiting for lunch. The 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, they sell those too.

930 Southard St
Key West, FL 33040

12. 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

13. 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

Related Maps