Key West Adventures

Life is all about balance; some adventures can be the pursuit of good food and live music. This will be a little different from my normal adventure blog post.  Stacey and I decided to take an overnight trip to Key West and enjoy some good food,  live music, and drinks.  She has been a few times and loved it; this would be my first time. 

We took the Key West Express leaving from Fort Myers to Key West. https://www.keywestexpress.net/. The ferry starts boarding at 7 a.m. from Fort Myers and returns daily, boarding at 5 p.m. I suggest getting to the dock earlier on the return. We showed up at 4:50, and there was a pretty long line; this made it hard to find a good seat. There are really no bad seats, just seats by the windows that have better views. The ferry ride is stable and not too rough for a ship ride. This is a 3-story ship with concessions and a bar on the main deck. They offer breakfast and lunch items. On the trip out, we got a couple of breakfast sandwiches and Bloody Mary's.

Short Video of the Key West Express outside decks

Bathrooms are easily accessible and clean; located on the main deck and 2nd deck. At the stern of each deck is a small open-air seating area. On a nice day, this can be a pretty cool experience. The top deck is all open-air and has a great view. The ferry takes about a 3.5-hour ride. They do have multiple TVs with movies and sports playing on them. We were able to get a window table for the trip to Key West. We took a tablet to watch a movie and ate our breakfast. 

Once the ship was docked, we walked around the boardwalk area. We found the Sunset Tiki Bar Pier to eat an appetizer and get a drink and they even had live music. Stacey got a rumrunner, and I chose the Crazy Lady Honey Wheat. This is right on the pier, as the name suggests, what a great view of the Gulf. I could easily sit here all day just watching wildlife and boats. But there was still much to explore of this cool city. 

We walked around Old Town Key West, in search of some more good live music. Willie T’s was the only other place we could find playing live music this early on a Sunday. They had a one-man band playing 90’s music. We got conch fritters, Stacey got the frozen rum runner, and I got another Crazy Lady.  We've got a theme going I guess.

Willie T's

We had a few drinks, listened to music, and then continued to walk around Old Town. We ventured down Front Street, looking through all the shops. There are so many cool little shops in this Old Town area. Shopping isn't really our thing, but seeing the cool little shops is neat. 

Off to find our accommodations for the night. We stayed at this cool little Bed and Breakfast called the Caribbean House https://www.caribbeanhousekw.com/ Small room with a bathroom. Exactly what is needed for a one-night stay. The Caribbean House has an outside entry to each room. This is nice not to bother other guests. They have a nice breakfast area, and our room had a small seating area outside the room. Overall, a great clean place to stay. 

https://www.caribbeanhousekw.com/ 

After getting into our room, we went to check out the winter celebration carnival. It was a cool, very Christmasy festive carnival, not something you really associate with Key West. We checked it out for a few minutes, then headed for dinner. I wanted something with outdoor seating. One would think that every restaurant in Key West would have outdoor seating. We searched around and ended up at Island Dogs Bar https://islanddogsbar.com/ This was a cool little place on Front Street. You could sit and people-watch all night if you wanted. Stacey got a rum runner, and I got a Crazy Lady beer. I’m starting to really love this beer. We weren't super hungry and ordered a small Island Style pizza (shrimp, pineapple, and pepperoni) to share. It was a thin crust, so it was gone in minutes. We looked around for some live music and didn't see much, forgetting it was Sunday night. We opted for walking around, looking at different houses with Christmas lights. We saw the Hemmingway house and a few other larger homes with Christmas lights, they were well done without going all crazy with lights. As we made our way back to the B&B for the night, we stumbled upon Willie T’s again, and still a band playing.  We hung out for quite a while and wandered back to the Caribbean House. 

Day two, the nice thing about staying at the Caribbean House is that there is a great place to eat across the street at Blue Heaven. Blue Heaven https://www.facebook.com/blueheavenkw/

 is a busy place, but it does have a full bar/coffee shop across the street while you wait.  Stacey got an amazing spicy Bloody Mary, and I got coffee with Baileys, or should I say Baileys and coffee with the amount of Baileys that was in it.  Our number was called, and we passed through the gates into the past. Apparently, this place back in the 1930s held gambling, cockfights, and even Friday night boxing matches refereed by Ernest Hemingway in this backyard. Very cool place, it has a bar with a wooden water tower above it, seating is patio furniture, and roosters are running around everywhere. I'm guessing descendants from the cockfighting days. They have live music all day with an Island Style band playing on the morning we were there. The food was amazing. We both got the Rooster special with banana bread. We sat finishing our drinks and listening to music. Really didn't want to leave. But we had other plans.

Off to the Southernmost Point Buoy. This is definitely a tourist trap but still a cool thing to see. Of course, it was busy there, but we were able to get our picture taken by the buoy.  This also has a live webcam and we took the opportunity to have a friend take a screenshot while we were there LOL. 

After checking out the buoy, we tried to get to a point on the map that would have offered a beautiful view of the ocean. No luck, as it was part of the military base there. Here is where alternative plans come into play again. Plan B was to walk Old Town streets again, checking out the things we missed the first day. We stopped in at The Two Friends Patio Restaurant https://twofriends.com/  to have lunch or drinks and an appetizer. Conch fritters again, LOL. Finished and back to walking the streets, looking at shops. Now, later in the afternoon, we needed to eat an early dinner so we could catch the 5pm ferry. It was such a nice day we wanted something by the water, Boat House Bar & Grill https://www.facebook.com/boathousekeywest  We had about an hour and a half to kill before our ferry departure and ended up back at Willie T’s with another good band playing. Stacey got a piece of Key Lime Pie. We both got drinks to pass the time waiting to board our ship.  There is a ton to do in Key West but given it was my first time and we'd only be there for a day, the goal was to explore.

Overall, the food and drinks anywhere we went was good.  Our favorites were Blue Heaven, Willie T's and Boat House.  Since we were there on Sunday/Monday, and it was cold during our stay (in the 60s) it wasn't as lively as Stacey had remembered from past trips.  Usually the Irish bar is overflowing with people, the line to get into the drag bar is wrapped around the corner, and you can hear music competing for air space every where you went.

Next time we go, we'll have to make the drive down stopping in Key Largo, Islamorada for snorkeling, The turtle sanctuary, Marathon Key and once in Key West rent scooters to check out more of the island as well as the shipwreck museum, maybe even see a Drag show.