Anniversary Trip to Key West

On September 30th, my husband and I celebrated our one year wedding anniversary. Earlier in the year, we had actually booked a trip to Jamaica to celebrate our anniversary, but we unfortunately ended up having to cancel it due to our move to Florida and my husband starting his new job (can’t really take a vacation when you just started three weeks ago!) We still wanted to do something special to celebrate though, so we decided on a weekend in Key West.

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From where we live, Key West is about a six hour drive or a 3.5 hour boat ride on the Key West Express. We thought the boat ride would be a cool experience, so we hopped on board and got ready to set sail! The boat departs every morning from Fort Myers, and returns every evening. We were going for the weekend, so we booked our tickets to depart on Saturday morning, and return Sunday evening. Round trip tickets for both of us were $280 ($140 a piece,) and we got a small discount for booking at least eight days in advance. There was also a $26 parking fee to leave our car while we were gone, which we paid online when we booked our tickets. The entire booking process was very simple and we received an e-mail with our boarding passes and all of the information we would need. If you’re ever in Florida and looking for a quick way to get to Key West, I definitely recommend the Key West Express!

boat

Once we arrived, we decided to go ahead and take our bags to our hotel so that we didn’t have to carry them around. We stayed at the Truman Hotel, which is an adorable little boutique hotel located right in the heart of Old Town Key West. It was located just off of Duval Street (which is the main street where all the bars and shops are,) so we were very close to all the action, but not right in the middle of it, which is exactly what we wanted. We had a great experience with this hotel and I would definitely recommend it. The office staff was very nice and helpful, the room was nice, modern, and clean, and the pool was perfect for an afternoon cool down.

pool

After dropping off our bags, we headed straight to Margaritaville for lunch.  We spent the next few hours walking up and down Duval street, just taking everything in. We’re not big drinkers, so we didn’t really stop at all the bars along the way, but we did check out several of the shops. We knew we wanted to go to the Sunset Celebration at Mallory Square before dinner that evening, so after walking around for a while, we went back to our hotel for a quick swim (it was HOT, and we really needed to cool down) and to get ready for the evening.

whistle bar

marg ville sloppy joe's

Sunset Celebration is something they do every evening, and it was amazing. Mallory Square was packed with street performers, vendors, and of course, people. If you want  get good photos of the sunset, I recommend getting there early to get a spot right up front because otherwise people WILL sit in front of you and block your photo-taking view. The sunset that night was absolutely gorgeous, and the whole thing was just a really cool experience.

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After sunset, we went to Duffy’s Steak & Lobster House for dinner. We honestly just chose it because it was right across the street from our hotel, and we were exhausted, so we wanted it to be easy to get back afterward. But, it was actually really good, so we lucked out! After dinner we just went back to our room for the night. We had been up since about 5:00 a.m., had been out in the heat all day, and had walked about seven miles, so we were ready to crash!

mile 0

The next morning we got up nice and early and headed straight to the Southernmost Point. We had tried to go the afternoon before, but the sun was not optimal for photos, and there was a long line, so we decided to wait. I definitely suggest going early in the morning, because there were only a couple other people there and we could take our time getting photos.

sm point

After the Southernmost Point, we headed to breakfast at the Banana Cafe. This was probably my favorite place that we ate the entire trip! The food and the coffee were both delicious, and the atmosphere was really fun and laid back. We had originally wanted to go to Blue Heaven because we heard they have an amazing brunch, but we found out once we got there that were closed for the week. The Banana Cafe was great, but we will definitely be giving Blue Heaven a try next time we’re in Key West!

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Our next stop of the day was The Ernest Hemingway Home & Museum. This was my favorite thing that we did on this trip, and is a must-see in Key West! They offer a guided tour, which I highly suggest if you want to find out more about the history of Hemingway and his home. After the tour, we were able to walk around on our own and you are allowed to take as many pictures as you want! Fun fact: at the time of our visit, there were something like 56 cats on the property, all of which are descendants of the original cats that Hemingway had while he lived there!

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After the Hemingway House we basically just spent the rest of the day walking around the area near Mallory Square since we hadn’t gotten to see much of that area the day before. We checked out the shops, took a stroll through the Maritime Museumstared in amazement at a huge cruise ship that had just pulled in, and spent some time taking photos of the scenery. We chose to walk everywhere on this trip, but I don’t suggest this. We walked somewhere around 15 miles in two days and our feet were so sore and covered in blisters by the time we left. There are tons of places to rent bikes, scooters, and golf carts, and we will definitely be doing this next time. Because we walked so much though, but the end of the second day we were definitely ready to go home. While we waited for the boat to start boarding, we had a couple of drinks at Dante’s which is an outdoor restaurant and pool bar. The pool party thing is not really our style, but if you’re into that, I would definitely suggest checking this place out!

 ship

The water was extremely rough on the boat ride home, and I (along with most everyone else on the boat) got sick. If you’re someone who gets motion sick easily, this is definitely something you should take into consideration before taking the Key West Express. The crew was very helpful, and did everything they could to make the ride as smooth as possible, but hey, you can’t control the ocean! 

water

Overall this was a great trip and it was the perfect little anniversary weekend getaway! We had a lot of fun, learned a few things that we should do differently next time, and we will definitely be going back!