Our whole family loves the Florida Keys, I hope to retire there one day with a boat. We have travel down at least once a year. Usually we drive and that way we can take all of our gear, fishing stuff, skim boards, etc. We have also taken the Autotrain down from Washington D.C. and you can read a review of that here. In the past, we have helped many of our friends with their vacation planning to the Keys and so I decided to finally go on and post my list of favorite places. I would also like to say that I am not affiliated in any way with the places I am recommending.
These are as you drive down from Miami -
Sunshine Market on Tavernier Key - This Cuban gem is on the left as you are driving down to Key West in a yellow building. The coffee is wonderful and the to-go foods are great.
Home Away Islamorada/Tavernier Vacation House - We loved renting this house, it was beautifully decorated, had an amazing kitchen, we could park our boat right out front and the owner is a delight. We have rented several times through both Home Away and VRBO and we have had a great experience each time.

Islamorada Fish Company Restaurant at the huge Bass Pro Shop on Islamorada - The food is very good and it is a beautiful location to take photos at sunset. It is also fun when they feed the tarpon, grouper, and HUGE lemon sharks that come right up in the middle of the dockside restaurant to eat. The Bass Pro Shop is also amazing and they give great fishing advice.

Robbies of Islamorada- It is great spot to hire a fishing charter, go out on their night time party boat, and their largest attraction is allowing people to feed GIANT tarpon from their dock. There are also cute little open-air shops.

Indigo Reef and Coral Lagoon on Marathon- We love staying here too. You can park your boat right out in front of your townhouse, they are beautifully decorated, have wonderful linens and great kitchens. If you sign up for their emails you can get significantly discounted rates.
Bahia Honda State Park - This my daughter’s favorite place on earth! The beach is beautiful and one of the only real beaches in the Keys. It is perfect for skim boarding. The fishing from the jetty under the Seven-Mile Bridge is also fabulous!

Big Pine Key Deer Watching - You can almost always find some of the endangered tiny Key Deer on back roads at dusk.

On Key West -
Mangia Mangia - A restaurant with great Italian food that has been there since we honeymooned in 1993. It seems to be a little more of a local place and away from the craziness of Duval Street.
Fort Zachary Taylor State Park Beach - This another gem of a beach in the Keys. It is very clean and you can snorkel right from the beach.

Mel Fisher Treasure Museum - Who doesn’t love treasure? The Mel Fisher story is wonderful and well worth going to see first hand.

Truman Annex - The homes in the Truman Annex are the epitome of the Florida Keys to me. It is one of the most charming neighborhoods in the U.S.

Parrot Key Resort - These are great townhouse style vacation rentals that also have wonderful linens, great kitchens and are beautifully decorated.
The Mermaid & the Alligator B&B - This B&B is another great example of Key West architecture. We even stayed here on our honeymoon in 1993.
