The road to Key West is a long one, spanning 130 miles from Miami (according to the sign). If you drive here, take the Florida Turnpike and trust me… it’s a much smoother ride and avoids all the city traffic that I-95 flows through. Think rush hour all the time.
Once you hit that stretch of the Florida Turnpike extension it’s not far before you will begin to feel like things are starting to slow down a bit. Our U.S. Highway 1 is a two lane road, one lane in, one lane out. Drive with caution, always. The 18-mile stretch can be an easy ride as long as no one is in a terrible rush to get anywhere. Accidents happen and now that the highway is divided the entire way by the concrete barriers, it will be a good long while before there is an opportunity to get out of any backed up traffic. There is a second way into the Keys, Card Sound Road. If you just Google Alabama Jack’s you will find your way to Card Sound Road. We used to call it the double-secret-back-way, but it’s a pretty well known route. It is east of the 18-mile stretch and goes over a big bridge where Blackwater Sound is. Get to the end of that road to the stop sign, take a right and continue your way into Key Largo.
There are so many places to stop along the way. I’ll leave that for some other time. The main thing you need to know is you should watch your speed. There are police in random places, some of the cars are actually un-manned. My advice is to download the Waze app and use it to help you navigate the Keys.
The drive will take about 2.5 hours from Key Largo to Key West, providing there is no traffic or accidents. There is also an app from the MCSO (Monroe County Sherriff’s Office) that will also give you an idea of any traffic incidents.
Stops along the way:
- Trading Post – Islamorada – This is a specialty grocery store. It’s a great stop for drinks, snacks, they have grab and go sandwiches, fried chicken, and some amazing looking steaks you can toss on the grill if you are staying in a vacation rental.
- Bad Boy Burrito – Islamorada – There is a little village behind the Trading Post, through the parking lot. The Bad Boy Burrito used to be in Key West and they are now in Islamorada. Great food, wraps, sushi and delicious juices. You can eat there or take it to go.
- Square Grouper Islamorada – One of the best restaurants in the Keys. The original one is closer to Key West in Cudjoe Key. There food fare is a broad variety of fresh fish specials, bacon wrapped shrimp, cracked conch, asian skirt steak and seafood stew … just to name a few favorites. They have a view of the water at this location and the Sunset Lounge is on the top floor with a great view of the water and sunset. The food at the Lounge is a different menu, mostly small plates, and very unique. Two of my favorites are the giant pretzel and the portabello mushroom fries.
- Midway Cafe – Islamorada – just down the street from the Square Grouper on the opposite side of the highway is the Midway Cafe. They serve breakfast and lunch. They have great specialty coffee drinks, muffins, pastries and great food.
- Wordwide Sportsman – part of Bass Pro Shops, this is a fun stop for shopping. The Islamorada Fish Company is right next door if you are hungry. Worldwide Sportsman has a full size replica of Hemingway’s Pilar boat in the center of the shopping. You are welcome to get on it and take a look around. The shop provides a wide variety of fishing tackle, terminal tackle, flies, fly tying materials, clothing for fishing and sun protections, bathing suits, and plenty of gift ideas. A cool place to stop especially if you have kids… (the bathrooms are upstairs – take the glass elevator).
- Keys Fisheries – Marathon – A great place to stop, take the turn at the Stuffed Pig, the restaurant is at the end of the road. They are famous for the Lobster Reuben. My advice, go there during Spiny Lobster Season (August 6 thru March 31) for the authentic sandwich. They offer plenty of fresh seafood specialities and also have burgers, etc. Everything is outdoors and it’s self serve from a pick-up window. Situated on the Gulf side of the Keys with a marina view.
- Burdines – Marathon – Situated on the oceanside of Marathon Key on Boot Key Harbor. This restaurant is elevated with an outdoor tiki hut. Great food, I used to go there for a grilled chicken sandwich and fries, but they also serve fresh seafood. Try the deep fried Key Lime Pie – just so you can say you had it.
- No Name Pub – No Name Key, Big Pine Key – It’s a great place… if you can find it. That’s their motto. The No Name Pub is known for their deep dish pizza, grouper sandwich and they have some pretty darn good chicken wings.
- Boondocks – Ramrod Key – Great place for kids and adults alike. Large tiki hut restaurant with fun food and a great gift shop. One of the other fun things to do at Boondocks is play mini-golf (put put golf). The golf course is open daily into the evening. There is also a farmer’s market in the parking lot at Boondocks on Saturdays from 9-2PM.
- Morning Joint – Coffee and yummy food open early until 4:20PM (imagine that)… Mary Jane’s Closet is just next door and has amazing gifts from many local artists in the Keys along with some food items for sale.
- Square Grouper Bar & Grill / My New Joint – Awesome place with a great menu just like the place in Islamorada. The upstairs My New Joint opens at 4:20PM, closed on Sunday & Monday.
- South of the Seven – Sugarloaf Key – One of my favorite restaurants since it’s right in my neighborhood. They are known for their tomahawk steaks, fresh seafood, whole fried fish Thai style, deep fried fish collars and amazing craft cocktails. The restaurant is bright and airy and offers a view of the water and the Sugarloaf Lodge Tiki hut. The interior is filled with memorabilia from local fishing legends along with beautiful artwork from local artists. Each table has been painted by local artists and provide for a very colorful experience. They are closed Sunday & Monday.
- Geiger Key Marina & Restaurant – Geiger Key (Big Coppitt Key) – Truly the backside of paradise, right on the water and accessible by boat or car. My favorite dish – tuna nachos – but it’s the perfect place to cook your catch or for a burger if you are in the mood for your Cheeseburger in Paradise.
- The Docks – Stock Island – A newer restaurant on the scene on Front Street on Stock Island. Great food, the freshest of the fresh fish – they even have a fish market on site now. Full bar, craft cocktails and great specials. My recommend is to go during the day or near sunset as the restaurant faces the sunset and get get a little hot. There is A/C in the rear of the building so you can request to sit back there too. The daily ceviche is amazing.
- Hurricane Hole Restaurant – Stock Island – Fun place on a working marina. Great bar and fun for happy hour. Their food is always great, vast selection from fresh fish, burgers, and the most amazing chicken tenders (in my opinion).
So there’s my eating tour of the Keys. Key West is a whole other animal. So many great places it’s hard to name them all in one post.