The Ultimate Guidebook to Your Upper Keys Vacation
Food scene
Totally authentic Cuban diner with real Cuban food and espresso. Very inexpensive, and really good rice, beans, plantains, chicken. Plus some interesting grocery items.
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Sunrise Cuban Market & Cafe
91885 Overseas HwyTotally authentic Cuban diner with real Cuban food and espresso. Very inexpensive, and really good rice, beans, plantains, chicken. Plus some interesting grocery items.
New Location! Breezy hangout with homemade French pastries, coffee/espresso. Exellent sandwiches and homie Keys atmosphere.
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Cafe Moka
91731 Overseas HwyNew Location! Breezy hangout with homemade French pastries, coffee/espresso. Exellent sandwiches and homie Keys atmosphere.
Classic old school diner with great, cheap food, Lots of characters eat there, along with the tourists. Breakfast for sure, lunch good, closes at 3pm daily.
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Harriette's Restaurant
95710 Overseas HwyClassic old school diner with great, cheap food, Lots of characters eat there, along with the tourists. Breakfast for sure, lunch good, closes at 3pm daily.
Funky interior, old license plates on the wall, unusual menu items but large portions and good, simple Keys food.
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Mrs. Mac's Kitchen
99336 Overseas HwyFunky interior, old license plates on the wall, unusual menu items but large portions and good, simple Keys food.
One of the few formula retail chains but you can’t go wrong with their simple coffee and donuts.
Dunkin'
91292 Overseas HwyOne of the few formula retail chains but you can’t go wrong with their simple coffee and donuts.
A very good typical Keys restaurant with authentic Florida seafood and other regional items. Dine outside waterfront under tiki thatched roofs. Fun bar with live music at night too. Try the seafood burrito or baked whole hog snapper.
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Snappers Oceanfront Restaurant & Bar
139 Seaside AveA very good typical Keys restaurant with authentic Florida seafood and other regional items. Dine outside waterfront under tiki thatched roofs. Fun bar with live music at night too. Try the seafood burrito or baked whole hog snapper.
Incredible seafood menu, possibly the best in all the upper Keys. Not on the water nor has any great atmosphere but the food makes up for it! Next door is the Fish House Encore, operated by the same people, is slightly more upscale/more expensive, but with even better entrees.
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The Fish House
102401 Overseas HwyIncredible seafood menu, possibly the best in all the upper Keys. Not on the water nor has any great atmosphere but the food makes up for it! Next door is the Fish House Encore, operated by the same people, is slightly more upscale/more expensive, but with even better entrees.
Another highly rated place on TripAdvisor with an awesome menu of interesting Keys and Caribbean-type items. Nice tropical atmosphere, dine on the “porch” amidst the fauna of this old house. Good smoothies, salads, and coffee.
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Key Largo Conch House
100211 Overseas HwyAnother highly rated place on TripAdvisor with an awesome menu of interesting Keys and Caribbean-type items. Nice tropical atmosphere, dine on the “porch” amidst the fauna of this old house. Good smoothies, salads, and coffee.
Sit upstairs or downstairs at tables on the sand at this Keys-casual restaurant. Its elevated dining room allows for great sunsets in Key Largo and views of the Florida Bay. Featuring cocktails, angus steaks, local seafood, and usually has live entertainment in the early evening. Open for lunch and dinner from 11:30am-10pm. Good Sunday brunch
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Bayside Grille & Sunset Bar
99540 Overseas HwySit upstairs or downstairs at tables on the sand at this Keys-casual restaurant. Its elevated dining room allows for great sunsets in Key Largo and views of the Florida Bay. Featuring cocktails, angus steaks, local seafood, and usually has live entertainment in the early evening. Open for lunch and dinner from 11:30am-10pm. Good Sunday brunch
Excellent dining you’d expect from a high class chain hotel. Beautiful ambiance overlooking the water at treetop level.
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas HwyExcellent dining you’d expect from a high class chain hotel. Beautiful ambiance overlooking the water at treetop level.
Finer dining, awesome food. It's a favorite with local people for a reason. Indoor dining only and not real Keys-y atmosphere, but when we host out-of-town guests, this is one place we suggest for a special occasion.
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Old Tavernier Restaurant & Lounge
90311 Old HwyFiner dining, awesome food. It's a favorite with local people for a reason. Indoor dining only and not real Keys-y atmosphere, but when we host out-of-town guests, this is one place we suggest for a special occasion.
We love this place for late breakfast and lunch. Sit outside on the canal and watch boats go by. Awesome crab cake eggs benedict, confetti spinach omelets, and fruit pancakes. No dinner, closes at 3pm.
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Made 2 Order
90691 Old HwyWe love this place for late breakfast and lunch. Sit outside on the canal and watch boats go by. Awesome crab cake eggs benedict, confetti spinach omelets, and fruit pancakes. No dinner, closes at 3pm.
Possibly our favorite place to eat, mainly for its awesome location right on the beach with open water view of the sunset. Sit in covered 6-top glider swings and enjoy a huge menu with lots of seafood items. Can be busy at sunset on weekends so make a reservation. Try the coconut crusted snapper or tuna tataki.
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Marker 88
88000 Overseas HwyPossibly our favorite place to eat, mainly for its awesome location right on the beach with open water view of the sunset. Sit in covered 6-top glider swings and enjoy a huge menu with lots of seafood items. Can be busy at sunset on weekends so make a reservation. Try the coconut crusted snapper or tuna tataki.
Another of our favorites, just across the Snake Creek drawbridge on the left going south, also accessible via boat. Nice deck dining and outdoor sand dining on the water. Live entertainment on the weekends. Love the spicy tuna roll and the fish tacos, fish chowder, and the daily specials are also very good.
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Island Grill
85501 Overseas HwyAnother of our favorites, just across the Snake Creek drawbridge on the left going south, also accessible via boat. Nice deck dining and outdoor sand dining on the water. Live entertainment on the weekends. Love the spicy tuna roll and the fish tacos, fish chowder, and the daily specials are also very good.
Extremely good food, lots of custom special dishes, plenty of seafood. Almost any day, you will need a reservation.
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Chef Michael's
81671 Overseas HwyExtremely good food, lots of custom special dishes, plenty of seafood. Almost any day, you will need a reservation.
Wow, everything you could want in a Keys classic restaurant. Décor, atmosphere, setting—it has it all. Sit at tables on the sand beach and watch the sunset. Caribbean entrees you’ve probably never had before or even heard of. A little pricey but don’t worry about that, you’re on vacation making memories, and this is one of those memorable places. Busy on weekends at dinner time. Next door is Pierre’s, an ultra exclusive (expensive) place we’ve never been to but know it’s off the charts - perfect if money is no object.
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Morada Bay
81600 Overseas HighwayWow, everything you could want in a Keys classic restaurant. Décor, atmosphere, setting—it has it all. Sit at tables on the sand beach and watch the sunset. Caribbean entrees you’ve probably never had before or even heard of. A little pricey but don’t worry about that, you’re on vacation making memories, and this is one of those memorable places. Busy on weekends at dinner time. Next door is Pierre’s, an ultra exclusive (expensive) place we’ve never been to but know it’s off the charts - perfect if money is no object.
Famous place, been here forever, great reputation. Popular with locals, great social bar, slightly upscale dining with lots of steaks but mostly seafood.
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Green Turtle Inn
81219 Overseas HwyFamous place, been here forever, great reputation. Popular with locals, great social bar, slightly upscale dining with lots of steaks but mostly seafood.
Next to giant World Wide Sportsman store. Great location on the water; see live tarpon swim in the lagoon while you eat. Food is classic Keys seafood and not real expensive. Would eat here more for atmosphere than for extraordinary food. Don’t forget to shop at World Wide Sportsman!
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Islamorada Fish Company
81532 Overseas HwyNext to giant World Wide Sportsman store. Great location on the water; see live tarpon swim in the lagoon while you eat. Food is classic Keys seafood and not real expensive. Would eat here more for atmosphere than for extraordinary food. Don’t forget to shop at World Wide Sportsman!
One of the newer restaurants in Islamorada, with a big sister in Cudjoe Key. You won’t be disappointed by the food; the ambiance is first-class and the bay side view is stunning.
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Square Grouper Islamorada
80460 Overseas HighwayOne of the newer restaurants in Islamorada, with a big sister in Cudjoe Key. You won’t be disappointed by the food; the ambiance is first-class and the bay side view is stunning.
Activities
There are tons of things to do in the upper Keys. If you’re only here for 3-4 days, our recommendation is to stay up here so that you don’t spend so much of your valuable time sitting in the car. But if you’re here for 4+ days, Key West is worth a day trip. It’s a beautiful scenic drive but traffic can be bad and parking in Key West is challenging.
Find a spot on a side street or get lucky with a space at the parking garage at the north end of Duvall Street. Worth the $20 to park there.
Then, spend the day walking around or rent bikes/mopeds. Explore great restaurants and numerous attractions; Conch Tour Train is fun, Sea Aquarium, couple historical museum houses, charming architecture, and more.
You must stay for the Sunset Celebration at Mallory Square. No admission, and starts a couple of hours before sunset with incredible street performers doing outlandish acts of impressive stunts. Trained cats, chainsaw juggling, sword swallowing, that sort of thing.
Don’t fall asleep on the long drive back from Key West, and be aware that our Monroe County Sheriffs’ patrol the highway for speeders all the time. Don’t ruin your vacation with a ticket, and don’t drink and drive!
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Key West
There are tons of things to do in the upper Keys. If you’re only here for 3-4 days, our recommendation is to stay up here so that you don’t spend so much of your valuable time sitting in the car. But if you’re here for 4+ days, Key West is worth a day trip. It’s a beautiful scenic drive but traffic can be bad and parking in Key West is challenging.
Find a spot on a side street or get lucky with a space at the parking garage at the north end of Duvall Street. Worth the $20 to park there.
Then, spend the day walking around or rent bikes/mopeds. Explore great restaurants and numerous attractions; Conch Tour Train is fun, Sea Aquarium, couple historical museum houses, charming architecture, and more.
You must stay for the Sunset Celebration at Mallory Square. No admission, and starts a couple of hours before sunset with incredible street performers doing outlandish acts of impressive stunts. Trained cats, chainsaw juggling, sword swallowing, that sort of thing.
Don’t fall asleep on the long drive back from Key West, and be aware that our Monroe County Sheriffs’ patrol the highway for speeders all the time. Don’t ruin your vacation with a ticket, and don’t drink and drive!
Probably the biggest attraction in Key Largo. Pay the entry fee as you drive in, then decide what to do. There are displays and exhibits on land but the real attraction is under the water. You can go out on a snorkel boat and see the fish and coral reef—its awesome.
Or, if you are not into getting wet, go on the glass bottom boat and see the same awesome reefs as the divers do.
Rent paddle boards or kayaks and explore the beautiful mangrove shoreline.
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John Pennekamp Coral Reef State Park
102601 Overseas HwyProbably the biggest attraction in Key Largo. Pay the entry fee as you drive in, then decide what to do. There are displays and exhibits on land but the real attraction is under the water. You can go out on a snorkel boat and see the fish and coral reef—its awesome.
Or, if you are not into getting wet, go on the glass bottom boat and see the same awesome reefs as the divers do.
Rent paddle boards or kayaks and explore the beautiful mangrove shoreline.
Free admission, and workers there are all volunteers. Even if you know nothing about our winged friends, it's a great display of local Keys birds anyone would find interesting, most who are there as a result of an injury. There is a donation box to keep this worthwhile program running.
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Laura Quinn Wild Bird Sanctuary
93600 Overseas HwyFree admission, and workers there are all volunteers. Even if you know nothing about our winged friends, it's a great display of local Keys birds anyone would find interesting, most who are there as a result of an injury. There is a donation box to keep this worthwhile program running.
Swim with the dolphins! A great water park with lots of options to get up close and personal with these amazing animals. We see them in the wild around the Keys but can never get close, so this is a chance to make an incredible memory with a dolphin encounter. A 45-minute dolphin swim makes a great gift for someone or a lasting impression on the kids.
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Dolphins Plus Bayside
101900 Overseas HwySwim with the dolphins! A great water park with lots of options to get up close and personal with these amazing animals. We see them in the wild around the Keys but can never get close, so this is a chance to make an incredible memory with a dolphin encounter. A 45-minute dolphin swim makes a great gift for someone or a lasting impression on the kids.
Our recommendation for your scuba and snorkeling trip. Two really fast, stable dive boats get you to the best parts of the reef for a snorkel and dive.
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Florida Keys Dive Center
84001 Old HwyOur recommendation for your scuba and snorkeling trip. Two really fast, stable dive boats get you to the best parts of the reef for a snorkel and dive.
Highly recommended on Trip Advisor and a great family water park with shows and exhibits. You can also pay to swim with dolphins here but there's a lot more going on; seal shows, birds, shark touch tanks, displays, and there are shows with dolphins and seals doing tricks.
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Theater of the Sea
84721 Overseas HwyHighly recommended on Trip Advisor and a great family water park with shows and exhibits. You can also pay to swim with dolphins here but there's a lot more going on; seal shows, birds, shark touch tanks, displays, and there are shows with dolphins and seals doing tricks.
History of Diving Museum is another cool place to go on a rainy or windy day when you can’t go out on the water. Fascinating history of man’s quest to breath underwater. Not just of interest for divers.
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History of Diving Museum
82990 Overseas HwyHistory of Diving Museum is another cool place to go on a rainy or windy day when you can’t go out on the water. Fascinating history of man’s quest to breath underwater. Not just of interest for divers.
The quarry is a cool place to hike and explore, worth a trip and free. Difficult to find the entrance but there's just a tiny, little sign roughly across from Theater of the Sea. Wear good shoes and hike the tropical pathways of this old, retired coral quarry. They used to cut beautiful solid coral out here for furniture and walkways. An interesting landmark to explore.
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Windley Key Fossil Reef Geological State Park
84900 Overseas HwyThe quarry is a cool place to hike and explore, worth a trip and free. Difficult to find the entrance but there's just a tiny, little sign roughly across from Theater of the Sea. Wear good shoes and hike the tropical pathways of this old, retired coral quarry. They used to cut beautiful solid coral out here for furniture and walkways. An interesting landmark to explore.
Indian Key State Historic Site is a small Island located 1/2 mile from shore oceanside across from Robby's. You can be adventurous and rent kayaks to paddle over and visit. Pack a lunch and drinks. Upon arrival, beach your kayaks and take the self-guided tour around the grounds; it's all free and sometimes you have the cool place all to yourselves. It was the county seat of the Keys over 100 years ago, until Native Americans reclaimed what was once theirs.
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Indian Key Historic State Park
Offshore IslandIndian Key State Historic Site is a small Island located 1/2 mile from shore oceanside across from Robby's. You can be adventurous and rent kayaks to paddle over and visit. Pack a lunch and drinks. Upon arrival, beach your kayaks and take the self-guided tour around the grounds; it's all free and sometimes you have the cool place all to yourselves. It was the county seat of the Keys over 100 years ago, until Native Americans reclaimed what was once theirs.
Lignumvitae Key Botanical State Park is another very cool destination you can only reach by boat. Like going to Indian Key, you can take a tour boat or rent kayaks at Robby's and paddle north bayside up to this historical spot where a park ranger will be happy to great you and tell you all about this cool spot. A house built 100+ years ago still stands, surviving 100s of hurricanes. Beautiful tropical grounds full of very rare and unusual trees and plants. Also free of charge.
Lignumvitae Key Botanical State Park
77200 Overseas HighwayLignumvitae Key Botanical State Park is another very cool destination you can only reach by boat. Like going to Indian Key, you can take a tour boat or rent kayaks at Robby's and paddle north bayside up to this historical spot where a park ranger will be happy to great you and tell you all about this cool spot. A house built 100+ years ago still stands, surviving 100s of hurricanes. Beautiful tropical grounds full of very rare and unusual trees and plants. Also free of charge.
Jet ski tours and boat rentals! Follow a jet ski guided tour around the islands of the Upper Keys. Ts is the best way to rent jet skis: with a guide and covering some ground. Hotels rent them but you have to stay in a small 1/4 miles square area in front of the hotel and race back and forth. Its ok, but touring is much more fun on jet skis. You have to be 18 to drive, but you can double up and ride with your young kids.
They also provide 18 - 22’ power boats for rent by the hour or day. Head out to the famous sandbar and relax or if it’s calm and if adventurous, head out to the reef to snorkel and fish.
There are numerous marked spots with large white buoys you can tie to snorkel or hang out. "Hens and Chickens" or "Cheeca Rocks" are easy to find, and awesome snorkel spots.
Company is very reputable and their equipment is excellent.
Florida Keys WaterSports Co.
Jet ski tours and boat rentals! Follow a jet ski guided tour around the islands of the Upper Keys. Ts is the best way to rent jet skis: with a guide and covering some ground. Hotels rent them but you have to stay in a small 1/4 miles square area in front of the hotel and race back and forth. Its ok, but touring is much more fun on jet skis. You have to be 18 to drive, but you can double up and ride with your young kids.
They also provide 18 - 22’ power boats for rent by the hour or day. Head out to the famous sandbar and relax or if it’s calm and if adventurous, head out to the reef to snorkel and fish.
There are numerous marked spots with large white buoys you can tie to snorkel or hang out. "Hens and Chickens" or "Cheeca Rocks" are easy to find, and awesome snorkel spots.
Company is very reputable and their equipment is excellent.
Shopping
One of our favorite places to stop to browse the amazing pottery and sculpture, plus a short little trail through some native foliage. Cindy and Dwayne are very friendly and love to show off their gem of a find. Make sure you take the time to check out the orchids that are in bloom at different times of the year.
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Old Road Gallery
88888 Old HwyOne of our favorite places to stop to browse the amazing pottery and sculpture, plus a short little trail through some native foliage. Cindy and Dwayne are very friendly and love to show off their gem of a find. Make sure you take the time to check out the orchids that are in bloom at different times of the year.
Located very close to the Old Road Gallery. Paradise is full of local artists as well as regional; a very beautiful gallery with a lovely casual atmosphere. Classes also offered in beginning and intermediate levels.
Our Place in Paradise
88711 Overseas HighwayLocated very close to the Old Road Gallery. Paradise is full of local artists as well as regional; a very beautiful gallery with a lovely casual atmosphere. Classes also offered in beginning and intermediate levels.