Ultimate Guide to the Florida Keys

Updated March 2023.

The DL: I have been to the keys a few times, and it never disappoints. The waters of the keys are the most beautiful blue and super clear. The overall vibe feels like you are in the Caribbean and you don’t have to ever leave the United States. Lots of the Keys go by mile markers so keep that in mind when planning. Also make sure to get fresh key lime pie and try the famous hog fish when you are exploring!

There are tons of little islands in the keys but the most visitor friendly tend to be:

• Key Largo
• Islamorada
• Big Pine
• Marathon
• Key West – lost of bars, restaurants, water activities

How to get the Keys:

I have always either flow into Ft Lauderdale or Miami, and rented a convertible and then hit the road right away (convertible is a must). If doing the full Keys experience head to the first key, Key largo and work your way down throughout the other Keys. On the way down we split up the drive and stayed in one of the Keys on the way down and then on the way back just drove straight through, its around a 3.5-4 hour drive. You can also fly straight into Key west, the prices tend to be higher. I think either way, having a car is ideal unless you are planning to just stay in Key West and ride share or bike.

What to do in the Keys:

Key Largo

*We personally didn’t spend a lot of time here but there are great options for nature lovers

• John Pennekamp Coral Reef State Park
• Everglades National Park
• Scuba dive and see the Spiegel Grove wreck
• Florida National Marine Park
• Harry Harris park and beach 
• Kayak through the mangroves of the everglades
• Mrs Macs kitchen – dive bar home to the key lime freeze

Islamorada

• Explore the sea life by boat or in the water
• Feed tarpons at Robbys Marina
• Islamorada is known for its smaller surrounding islands, which make perfect day trips
• Diving Museum
• Theater of the Sea
• Lots of local breweries to visit here
• Wahoos for lunch on the marina
• Alligator Reef Lighthouse
• Annes Beach
• Blonde Giraffe Key Lime Factory
• Stay – Amara Cay Resort and access their 3 other sister resorts.

Big Pine Key

• Bahi Honda State Park – must go to, one of the most beautiful beaches in America
• Calusa Beach – go at sunset
• Deer Refuge – this island is known for the tons and I mean tons of deer that live here – you can stroll through the preserve and explore the blue hole – one of the only fresh water lake
• Fishing for tarpoon is big here
• Snorkeling

Marathon

• 7 Mile Bridge
• Turtle Hospital
• Sombrero beach and reef – the third largest barrier reef in the world
• Dolphin Research Center
• Popular for boating activities
• Deep sea fishing
• Paddle boarding and Kayaking
• Pigeon Key Island – railroad history
• Aquarium encounters where you can feed sting rays
• Isla Bella and Hawks Cay are popular places to stay on this island

Key West

• Ernest Hemmingway House
• Mallory Square – very touristy, tons of vendors, usually some homeless people but the best sunset viewing spot on the island
• Southernmost point – this is statue you can get a picture with and see the mile zero sign 
• Must do lattitudes on sunset key, this is a restaurant but had to put it as a must do – you can get there by a boat on key west – Your reservation time is actually your boat departure time. Please arrive 5-10 minutes prior to check in with our
• Botanic garden next to higgs beach dog park 
• Duval Street – like a mini bourbon street of New Orleans, not as dirty but a strip of bars and restaurants.
• Martello tower gardens
• Harbor walk
• Kinos Shop – handmade leather sandal factory only made in the keys

Water Activities 

Most of the beaches in Key west have very little sand and more rocky terrain, so most of your time if not at the hotel pool or little sandy area you can find. will be on the water!

• Parasailing we used Fury Cat and had a super fun time!
• Jet Ski use Barefoot billys, they have a tour around the island which is really fun!
• Sunset cruise
• We took a fishing charter that allowed you to catch fish and then grill it for lunch on the boat
• Glass bottom boat
• Dolphin Tour

Tip – lots of these water activities can be found on all the islands above, key west has the most options being at the tip and home to a cruise port

Where to eat North to South Keys

Upper Keys: mile markers 108-65                                                  

• 106 – Key Largo chamber of commerce                                                         
• 103.5 – 1920s Key Largo Rock Castle                                        
• 102.4 – Fish house – key largo                       
• 101.5 – Hobo’s – burgers                                               
• 100.5 – Key Largo Chocolates – key lime pie on a stick                                                                                                
• 100- Pilot House Marina – glass bottom boat bar                                                                                      
• 99.7 – African Queen Steamboat                                                        
• 99.4 – Mrs. Macs Kitchen –                              
• 95.7 – Harriettes – southern breakfast offerings  – $10-15 for sandwiches, frozen key lime pie               
• 88- Marker 88 – famous on bloodlines *** lots of good food reviews 
• 88 – MEAT – on dives and drives show                                                                            
• 86.7 – Rain Barrel Artisian Village                               
• 83.5 – Wahoos bar and grill                           
• 82- Lorelei – fish dip, strong drinks, conch fritters (on bloodlines) * good food, view isn’t incredible                                                    
• 82- Ma’s Fish Camp – only dinner                               
• 81.5- Islamorada fish Company – fish is right from boat                                                        
• 80.4 Midway Café          
• 79.8 – Lazy Days South*** – rates on yelp as #1 for awhile                                                             
• 77.5- Robbies Marina ***                                                         
• 77.5 – The Hungry Tarpon***                                                   
• 73.5- Habanos – Cuban                                                           
• 73- Channel 2 bridge – built by WW2 vets                                                      

Middle Keys: 64-40                                            

• 65.8 – Long Key Fishing camp – where Teddy Roosevelt, Herbert Hoover etc. spent time fishing and writing                                                         
• 59 – Dolphin Research center                                     
• 58- Grassy Key Outpost – shrimp and grits                                         
• 54 – Key Colony Inn Restaurant   
• 54 – Island Fish Co                             
• 51- Brutus Seafood Market and Eatery – fresher than fresh – shrimp is good ***                                           
• 49 – The Stuffed Pig
• 49 – Keys Fisheries***                                           
• 48.5 – Turtle hospital                                                
• 48.5 Butterfly Café***   
• 48 – Burdines***           
• 48 – Castaway sushi bar = waterfront*      
• 48- Chiki Tiki Br and Grille and Burdines Waterfront                                                 
• 47.3- Sunset Grille and Raw Bar                               
• 47- Pigeon key bridge/ 7 mile bridge                                                 
• *Wooden Spoon- breakfast opens at 5:30     
• 47 – 7 mile grille                                                         

Lower Keys: 40-0                                                                    

• 38.7 or 37 or 36- Bahia Honda                                               
• 30.2 – Big pine key – Key Deer boulevard to see the deer                                                      
• 31- National Deer Refuge                                                       
• 30 – no name pub – known for pizza                                                  
• 28.1- Kikis Sandbar and grille  – food is average but go for downstairs outdoor bar                                                            
• 27.5 – Boondocks grille and drafthouse – tiki bar and entertainment                                                            
• 20 – Mangrove Mamas – key lime pie                                                             
• 15- Babys Coffee***                                                              
• 5.1 – Hogfish bar and grill – killer hogfish sandwich                           

Where to Eat in Key West: (favorites are starred)

• Lobster Shack 
• Santiagos Bodego – Tapas, not seafood but very popular
• Blue heaven – brunch in a tropical jungle like oasis***
• Sarabeths – brunch
• Little Pearl
• Thirsty Mermaid – oysters and ceviche
• Key plaza creperies
• Bien – one of the number one spots – cuban food
• Lattitudes on sunset key – go at sunset ***
• Better than Sex Dessert Shop ***
• Kermits – key lime pie on a stick ***
• Pepes cafe – lots of people like this spot
• Off the hook
• Garbos grill – food truck , tacos and korean burgers 10-14 a plate ***
• Conch republic seafood company
• Cuban Coffee – favorite for people
• El Siboney – cuban spot
• Salty angler
• Hard rock 
• Margaritaville
• Grand café
• Bagatelle
• Red fish blue fish
• ON THE WATER: 
• Commodore Steak and Lobster
• Salute on the beach
• Hot tin roof
• Meson de pepe 
• Dantes Prime Steak
• Henry Waterfront brewery – bar  
• Deuces off the grill 
• Hogfish bar and grill ***
• Southernmost beach café 
• Louis backyard at sunset

Bars

• Sloppy Joes
• Green Parrot Bar
• Rum Bar
• The Green Room
• The Tree house
• Smokin Tuna Saloon
• Ricks bar
• Little Jazz room
• The Tiki bar Vinos on Duval
• Hogs Breath
• Sunset Pier

Where to stay in Key West

We stayed at the Waldorf Astoria – Casa Marina and it was fabulous!

I would pick where you want to spend most of your time, since we had a car we weren’t as concerned about walkability. Hotels on the east side have a beach, hotel on the west are more convenient to everything but will have no sandy beach areas. Parking can be limited in most areas, so if you can walk or bike that’s a nice option. The whole island across at its widest is no longer than 2 miles so all really is walkable.

Looking for an international beach trip – check out my St. Croix guide.