The Florida Keys
History
The Florida Keys are made up of a bunch of islands with a 110-mile highway connecting them so we can enjoy it's beauty with ease. In the past, the islands were relatively isolated until the completion of the railroad from Miami to Key West in January 1912. This was headed by Henry Flagler and forever changed the Keys. In 1935, the railroad was demolished by a hurricane and was not rebuilt. Luckily for us travelers the government started to build Route 1 that year, which was completed in 1938.
What To Do
Key West
The southernmost point of the U.S., and the southernmost point of Route 1 is in Key West! We explored this island for one day and enjoyed all it had to offer us. Here is information on parking that we felt was helpful. You can parallel park on the street for free as well but the closer you get to the downtown area the harder it is to find the parallel parking.
Ernest Hemingway House
*CASH ONLY* Currently it's $17 per person to enter the home. There are tours at certain times throughout the day that really bring Ernest Hemingway to life. One of the most interesting things you'll want to see at the home are the polydactyl cats (with 6 toes). It was really fun walking around and seeing which of their paws had the genetic alteration :)
Duvall Street
This is the main street in Key West that you'll want to see. Some of the bars on this strip have historical significance and are really fun! My favorite bar is Flying Monkeys. They have delicious slushy- or milkshake-like drinks. There are also lots of shops you can go into.
The Mid-Upper Keys
Sombrero Beach in Marathon
This free public beach caught our attention with the beautiful sunset, clear water, and relaxing atmosphere. Free parking is right out front. We came here for the sunset and came back the next morning for some beach time. Bring your snorkel gear here! There were lots of fish.
Blue Hole in Big Pine Key
This (free) little wildlife haven surprised us with two alligators just hanging out below the pier. Parking is just off the main road on Big Pine Key and you can walk around the small lake.
Other To-Dos from the locals
We heard that Sunset Pier is huge at sunset (on Key West) as it has many attractions. Ronald Augustine the palm reader is spot-on at the pier. Dry Tortugas National Park will take a full-day of exploring; you can take the ferry to the park from Key West. Bahia Honda State Park (on Big Pine Key) is apparently really nice as long as there hasn't been a big rain recently. The Turtle Hospital (on Marathon) is supposed to be a good attraction. Robbie's (on Islamorada) allows you to feed the tarpons, and Theater of the Seas is a dolphin show to music (on Islamorada).
Accommodations
We were looking for a reasonably-priced stay that we could relax on the water. Rainbow Bend Resort on Grassy Key did the trick. If you are looking for something more upscale, try Tranquility Bay Resort on Marathon Key. The views at Rainbow Bend were spectacular; I even was able to convince my parents to wake up for the sunrise! The staff is very friendly and can help you plan out your time while on the Keys. If you stay here Thursday through Sunday, they have a high-end restaurant right on the water for dinnertime - be sure to make reservations! We missed out on this.
Where To Eat
Mrs. Mac's Kitchen on Key Largo
We needed something to eat on our drive from the Miami airport to our hotel. Mrs. Mac's Kitchen (the original) had a high rating and we wanted to see why. Boy were we impressed! We would come back here in a heartbeat. The fish was the best we have ever had.
Island Fish Company on Marathon Key
This was a fun hangout spot with good food/drinks and a solid atmosphere for what we were looking for on the Keys. They have a sunset view here, too. Apparently you can feed the fish on the pier during the day.