Driving the Overseas Highway from Key Largo to Key West takes about two hours if you do not stop, but there is no fun in that! Here are the two places you absolutely must visit in the Keys.

Gilbert’s Resort
The FIRST stop you have to make is at Gilbert’s Resort in Key Largo!

Gilbert’s is a tiki bar, restaurant, beach, and resort with a pool. You do not have to be a guest at the resort to eat at the restaurant, drink at the tiki bar, or take a dip in the water. 

Their house special drink is a “booby” and it is basically a spiked smoothie that comes in any flavour you could think of. 

We ordered snow crab, fried coconut shrimp with orange marmalade, a Bleu cheeseburger, and ahi tuna nachos with seaweed and wasabi aioli. 

Everything was fresh and delicious. 

The huge tiki bar and restaurant is covered so you do not have to worry about getting scorched by the sun. One side runs along a dock where boaters can tie up and visit the resort instead of driving.

Gilbert’s has its own marina if you wish to stay for a few days or long term. 

Guests at the resort can also rent jet skis, kayaks, boats, paddle boards, and go fishing at the marina. 

I loved being out by the water while out of direct sun, and it was a great place for people watching. Gilbert’s has live bands in the tiki bar on a regular basis too. 

The small roped off beach area nearest the bar is kind of a kids zone, but there is a lot more beachfront beyond it that was sparsely populated and quieter.

 

Robbie’s of Islamorada
The SECOND stop you have to make is at Robbie’s of Islamorada!

Robbie’s is just 40 minutes away from Gilbert’s, but you could spend hours exploring the area in between locations. We actually visited Robbie’s on our way back up through the keys. 

Robbie’s is also a large, outdoor restaurant by the water, but visitors flock here for the tarpon feeding.

The Hungry Tarpon Restaurant & Thirsty Tarpon Bar have a lot of fresh seafood and flavours. 

Below is the signature frozen Key Lime Martini.

Robbie’s offers guided ecotours, party cruises, sunset cruises,  parasailing, jet skiing, snorkeling, and multiple types of fishing cruises based on where you want to go, what you want to catch, and how you want to do it.

You can also rent a boat, kayak, paddleboard, or jet ski and go do your own thing.

Tarpon are giant fish that have the ability to thrive in brackish water, and are often seen around docks and polluted areas. They can grow up to eight feet long and weigh nearly 300 pounds.

Look closely in the photo below and you can see how large they are compared to pelicans.

Tarpon need to take in oxygen above the surface and have a special “swim bladder” that helps them store emergency oxygen.

They do a particular rolling movement when they come up for air, and are sometimes mistaken for dolphins. When the light hits their sparkling silver, green, and blue scales, it is actually lovely. 

Pelicans are notorious pests here, charging you and snapping at visitors when they go near the tarpon. Pelicans often try to eat the baby tarpon, so you are viewed as competition.

Staff has mesh shields around the tarpon feeding area to regulate some of this, but be careful.

The dock path is narrow with no guard rails. Pelicans will trip you when you are walking, and they will stare you down while refusing to move out of the way. We had to grab a broom a few different times and gently shoo them into the water so we could leave.

I have never been more convinced of birds’ direct relation to dinosaurs than I have since this encounter. 

Visit the Robbie’s open air market with local vendors, antiques, souvenirs, beach gear, and sports apparel  while you wait for a table, or after you eat.

You can sit out of the sun or right along the water. 

Cruising the Keys
As for the rest of the journey along Overseas Highway, check out the John Pennekamp Coral Reef State Park in Key Largo, then the Garden Club of the Upper Keys and the Laura Quinn Wild Bird Sanctuary in Tavernier.

We learned about a very significant figure in the Keys, Henry Flagler, after seeing his name on a few memorial signs.

My Florida friend told us about the Flagler Hotel which was the first to have power, and is now Flagler College. Flagler founded Standard Oil and the Florida East Coast Railway, and he is credited for developing most of Florida’s east coast and founding multiple cities.

This bridge is part of his old railway circuit. 

The Islamorada Village of Islands has several interesting spots like Founders Park, Rain Barrel Village, History of Diving Museum, Islamorada Brewery & Distillery, and the nearby Windley Key Fossil Reef Geological State Park.

Lorelei Restaurant & Cabana Bar is similar to Gilbert’s as far as having waterfront dining, a dock/marina space, and a Cabana theme, but they were closed. This huge mermaid painting in front of it can be seen from half a mile away and is sometimes called the Islamorada Mermaid. 

In the area for a while? Follow us to Key West, the Everglades National Park, and Naples!

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