Florida Keys Vacation Guide

This year marked our 4th annual trip to the Florida Keys.

I decided to compile a list of our favorite restaurants and activities, so that you can have your very own travel guide should you ever be visiting.

We've been to Islamorada, Duck Key, Marathon, Big Pine Key, No Name Key, and Key West. I have organized the list as if you are driving from Miami down to Key West. Even though I enjoy being spontaneous, it's usually helpful to have some ideas of things to do while on vacation.

One perk of the Florida Keys is that there is one main road the entire time - known as the Overseas Highway or US 1. Almost all of the places below are located on the main road and easy to find (with the exception of No Name Pub). All of the activities below are also family-friendly (with the exception of The Brass Monkey).

If you would like to read about some of our previous trips, just click on the posts below:

Flight/Rental Car
We have always chosen to fly into the Miami airport, since the flights tend to be cheaper than flying into Key West. Expect about a 2 hour drive (without heavy traffic) to get from Miami to Marathon, FL.

Our best rental car experience has been with E-Z Rent-A-Car.

Theater of the Sea
Fun and interactive. No reservations needed. You get to see dolphins doing tricks, sea lions giving kisses, and much more. Expect to spend 3-4 hours here.
Postcard Inn at Holiday Isle
You do not have to stay at this Inn in order to visit for the day. The have a beach where you can pay for jet ski rides, snorkeling, etc. They have a Tiki Bar that overlooks the ocean. We have only briefly stopped here, but the staff and concierge were extremely friendly and recommended many things for us to do.
The Rain Barrel 
Shopping and artwork. You will notice their landmark is a huge lobster! You can't miss it!
Tarpon feeding is perhaps their biggest attraction, but they also have a restuarant, shopping, and other entertainment.
One of the few - if not only - pizza restaurants that we saw while we were in Islamorada. Tasty pizza, decent service from what I can remember. It was raining the day we went, but they have picnic tables outside which would be nice if the weather was good!

Duck Key
Hawks Cay Resort
Resort is rather upscale, however, you don't need to be staying there to visit for the day. We parked, went through the lobby, and right out to the pool. They have several swimming pools, a private beach, lagoons with dolphins, and a lagoon for paddle boarding. Pool-side cocktails and bartenders that will come to you while you relax by the pool - can't beat that! Restaurant with outdoor seating which overlooked the pools.

Key Colony
We went here for Happy Hour. Crowded, but with a fun atmosphere. Seems to be a favorite spot among the locals. DRIVE SLOWLY when you're visiting Key Colony. 
Key Colony Inn Restuarant
Somewhat fancy (but I use that term loosely when referring to anything in the Keys). Seafood, American cuisine, and pasta available. Good food and piano man for entertainment

The Brass Monkey
Our favorite late-night bar. Great music from Freddie Bye. Atmosphere that can be described as smoky, dark, and slightly sketchy. Good for people-watching (expect some crazy drunks!). This is a local hangout. Don't bring your kids.
Sunset Grille
Family-friendly. Outdoor/semi-outdoor seating. Sunday Funday  is a great time to go to get good food and drink specials. There is a pool to enjoy, along with corn hole boards. Live music and other entertainment is common. Fun drinks with cool souvenir mugs. Best place to go to view sunset (if not in Key West). Right next to the Seven-mile bridge on the Marathon side.
The Wooden Spoon
Serving breakfast and lunch only. It's one small room that's crowded with people, mostly locals. A good place to stop for a quick meal, but expect to be treated like a local. Genuine southern hospitality from the servers, as long as you're patient and understanding that they are really busy. Come in, grab a seat, and don't be afraid to share a table with another party (you just have to sit any place you can find)!
Sweet Savannah's 
Ice cream, pastries, cakes, and more! A cute little bakery.
Nice place to stop for a quick lunch. Food and service were both good. I had the crab cake sandwich and Brian got a burger.
Porky's Bayside BBQ
Bar and restaurant with a casual atmosphere. Live music most nights. We tried the "beer butt chicken" which was an entire chicken that was roasted while sitting on a can of Miller Lite. It was really tasty! Mostly pork options, but there was some seafood on the menu.
Turtle Hospital
Tours every hour, but you may want to call ahead to reserve your spot. This place is usually busy. Expect the tour to last about an hour or a little more. Educational presentation about the history of the hospital and the sea turtles, and also a tour to view the sea turtles that are currently in recovery.
The Dolphin Research Center
Fun, interactive, and educational. This is a great spot to swim with dolphins if you're willing to spend a couple hundred bucks. The staff is very friendly and offer a variety of shows and sessions to learn about dolphins and view them close-up! Also see exotic birds and sea lions while you're there.
Helicopter Rides
This is on my to-do list for our next trip! There is a small airport in Marathon that you will see on the Overseas Highway. The advertisement offers helicopter rides starting at about $100.
Crane Point Nature Trails and Museum
Nature trails and historical sites. Expect about a $15 entry fee/person. The trails are about 1-2 miles long, but it is a self-guided tour and each trail is optional. You will really be one with nature - expect to see a lot of bugs! One group we saw had rented kayaks and then stopped their kayak at a dock to get out an explore the area. I think that would be fun, but I'm not sure where they got their kayak rental. Maybe a quick Google search is all I need to do!
Sombrero Beach
This beach has not ever been too crowded when we've been. Great place for swimming in the ocean or snorkeling. The water has always been very calm and swimming pool-like. Last time we were there, dolphins came right to the shore!
Walk, run, bike, fish, or just stop here for the view. This is the longest bridge in the Keys. The old bridge is still partially functioning. Stop by the Sunset Grille after your walk for a refreshing drink.

No Name Key
No Name Pub
"A great place if you can find it!" Umm...good luck finding it! But it really is pretty neat. Lots of dollar bills on the wall! Great pizza, casual atmosphere. Slow service, but nobody seems to mind. 

Big Pine Key
Big Pine Key Flea Market 
Open on Saturdays and Sundays. Fresh produce and a lot of inexpensive crap to buy. Don't wanna miss it! 

Key West
There is a lot to do in Key West! If you're going just for the day, expect to pay about $20 to park. You can literally walk everywhere in Key West. There are so many bars and restaurants to choose from that I didn't bother to list any here. Brian and I just enjoy bar-hopping along Duval Street and visiting the shops that are along the street. See below for a more specific list of the few things we've done while in Key West:

Butterfly Museum
Beautiful exhibit - definitely worth a visit! Thousands of butterflies everywhere.
Mallory Square
This place comes alive at night, usually around sunset. Lots of live entertainment and good people-watching.
Sunset Cruise with Fury
Brian and I did the sunset sail, which we really enjoyed. Two hours of sailing with all-you-can-drink beer and margaritas. Live music and dancing on the boat. So much fun!
We really enjoyed staying the night here. Quiet atmosphere and decent pool. Happy hour with free beer and margaritas. Just steps away from Duval Street.

Leave comments below if you have anything additional to add. I'd love to hear from those of you who visit the Keys more regularly. Brian and I will be on the lookout for more things to do next year!