Are you looking for a getaway that feels like you’ve left the U.S. for somewhere in the tropics but doesn’t require a passport? Look no further than the Florida Keys!

We recently explored two of the hundreds (yes, there are hundreds) that make up the Keys. There are several ways to get there. Many people fly into Miami and drive down all the way to Key West, stopping along the way to check out the sights-I’d love to do this on a future trip. You can also fly directly into the Keys. Key West International sees the bulk of commercial flights. Or, you can fly into one of the small airports scattered on other keys. For this trip, a friend flew us in a private plane, so we chose to fly into Marathon and use it as our base of operations.

We rented a car and spent one night and two days in Key West and then returned to Marathon for three days and two nights. Since this was a short trip and our first to the Keys, we chose to only spend time in those areas, although we did see more of the archipelagos as we drove the hour drive between the two on the Seven Mile Bridge. Even if you fly directly into Key West, I would recommend renting or hiring a car and driving on this bridge. It was a unique experience to be surrounded by gorgeous water on either side for miles.

Each key seems to have its own personality and Key West is definitely the party animal.

Key West

After arriving in Key West, and dodging a few dozen roosters (they are everywhere!), since we only had a short time in the city, we drove straight to the center of the Conch Republic’s downtown area. Something to note: parking is not plentiful and you will pay a premium for parking in the downtown area. If there had been more time on our trip and it had not been so late in the day, we would have definitely parked at our hotel, The Parrot Key Hotel and Villas, and taken their shuttle downtown.

Hemingway House

Key West has long been a haven and inspiring spot for many authors, musicians, presidents, and other celebrities. Jimmy Buffett blew out his flip-flop and stepped on a pop top there. The original Margaritaville is in Key West. We didn’t make it there this time though. We did make it to the home of who I would argue was Key West’s most famous resident: Ernest Hemingway. We headed to his house to see this gorgeous home and the six-toed felines who have become the second-most famous residents of the home. I loved reading Hemingway’s work in high school. Some other members of our group had not shared my affinity for Papa Hemingway, but by the end of the tour, everyone was glad we had taken the time to visit. The home itself is beautiful and the grounds are as well. Hemingway was a fascinating person and really embraced Key West and many anecdotes about his time in Key West were shared with us during our guided tour. The tour is included in admission and I highly recommend you join the group tour. We really got so much more information than we would’ve gotten on our own and she was very engaging.

The Southernmost Point

Yes, this is touristy. Yes, this is crowded. Yes, you could get technical and say it’s truly not the southernmost point of the U.S. But should you do it? Yes! To me there is something cool about going to these types of iconic points and taking a photo there. So, stand in line (get a drink before you get in line if it’s hot out, or if you just want a drink), do your obligatory photos, and check out the neat statue of the conch blowing greeter, Albert Kee, who was the unofficial island greeter to everyone who visited Key West.

Duval Street

Let me give a little disclaimer, in my opinion, Key West is not the best vacation spot for taking your kids. Yes, there are some places I think kids would enjoy (Maritime Museum, Butterfly and Nature Conservatory, Florida Keys Eco-Discovery Center), but I would not take my kids down Duval Street. Duval Street is filled with restaurants, bars, and shops. The shops hang t-shirts outside with all sorts of colorful sayings on them. If you don’t want to have a lot of interesting, possibly awkward, conversations with your kiddos, don’t take them there.

At night, Duval seems to turn into one long night club. It reminded me of Vegas without the gambling and the lights. When a friend asked a bartender if he could take a traveler on the streets here (for those of you who don’t know, in this setting a traveler is an alcoholic drink you can take to go), she said, “You can do whatever you want here. It’s Key West.” That about sums Key West up in one sentence. Like I said, it can be fun for adults, there are restaurants, bars, and nightclubs galore, but don’t take your kids here for ice cream at night.

Key West Restaurants and Bars

Sloppy Joe’s

We had to go here after we heard so much about it on the Hemingway House tour. This place is constantly crowded. We got here right away when it first opened for lunch on Sunday and had no problem getting a table right away. They have live music every day, even during the day. We enjoyed the band, loved homage to Hemingway decor, and enjoyed the excellent service. However, our food was just so-so. To be honest, I’ve had a better sloppy joe in the school lunchroom or from a can of Manwich. Granted, I’m not a sloppy joe connoisseur, but everyone at our table who ordered one felt the same way. We also had conch fritters. These are something you just have to try while in the Conch Republic. These were the first I’ve ever had. They reminded me of hush puppies and I’m pretty picky about my hush puppies, so these were not my favorite. My verdict for Sloppy Joe’s is it’s a great place to hang out and listen to music, but if I’m ever there again, I’ll save my appetite for another place.

Prime Steakhouse

We ate here for dinner. We put a lot of research into where to eat that night. Just kidding. My friend opened her Open Table app and found the top-rated restaurant for the time we wanted to eat, and this is what came up. I usually have low expectations when we book a place like that. Walking up, I wasn’t even sure we were at the right place. We had to go upstairs at what looked like an office building and then go around a corner. We even thought of going back. I’m glad we didn’t. This place was great! They had indoor and outdoor seating. We chose to sit outside. The weather and service were perfect and the food was delicious! We all had steak (because that’s what you order at a steakhouse)and I am usually disappointed when I order steak at a restaurant because my husband can grill a mean steak, so it’s a lot to live up to. This one did not disappoint!

Captain Tony’s Saloon

This is the first and original Sloppy Joe’s. It has some neat, old brickwork and other eclectic touches like bras hanging from the ceiling. It also claims to be the oldest bar in Florida, but there’s another bar in St. Augustine, Florida, that also claims to be the oldest. I’m not sure who’s telling the truth. One truth we did fine is it’s hard to get a drink at Captain Tony’s. At least on the day we were there. There was only one bartender and customer service was not his strong suit.

There was so much more to see in Key West, but that was all the time we’d allotted there on this trip, so we stuck to our plan and headed to Marathon.

Marathon Key

Marathon is a sharp contrast to Key West. The vibe in Marathon is much more laid back and boating and fishing are the draw here. You could probably take the kids anywhere on this island.

We enjoyed hanging out at the man-made lagoon and the pool at our hotel, Tranquility Bay Beachfront Hotel and Resort, going out to eat, relaxing and spent a day on the water in a boat we rented.

You can rent boats at many places in the keys, but we found Marathon rental rates to be cheaper than the ones in Key West. You can choose to charter boats with a captain or take group tours, but since one of our friends was familiar with Marathon and we had a couple of experienced boat operators, we chose to let him be our captain so we could go at our own pace. We had a wonderful day exploring coral reefs, eating on the water, and just riding and exploring. I highly recommend exploring Marathon by water if you can. I had never snorkeled in deep water before and I loved the experience!

Marathon Restaurants:

Lighthouse Grill

We shared a variety of dishes here and enjoyed them all. Their tuna appetizer was my favorite. Except for the four, yes four, desserts we ordered for the table. The chocolate cake and mascarpone cheese cake were my favorites.

The Butterfly Bar and Grill

This restaurant is on the property of Tranquility Beach Resort. We shared appetizers here. The cheeseboard was the standout for me.

Marathon Grille and Ale House

I think this is the closest thing Marathon has to nightlife. It is in a strip mall, but don’t underestimate it. This sports bar delivered good food at good prices and a lot of fun!

Castaway Waterfront Restaurant and Bar

Dock your boat and come inside this Old Florida hangout that serves seafood, sushi, and a ton of beer! Their sushi and beer menus (I think I heard them say they had over sixty beers on tap) were huge! And the sushi was delicious. They also serve a crazy hot dog that has sashimi tuna and caviar on top! I wasn’t sure if I would like it, but I tried a friend’s and it was so good! We had a great time here and also spotted a manatee who came up to visit.

I am so blessed to have been able to enjoy Key West and Marathon and hope we can escape there again soon!

North America

“I’ve gone to look for America”- Simon and Garfunkel

The Florida Keys