Long Weekend in Key West

Pop some popcorn, y’all! It’s vacay picture time! 🙂

Over MLK weekend, Chris and I took a trip to Key West with our friends, Danielle and Quinn. We’d actually been to the Keys with them before, but it was a family trip and we brought all the kiddos with us. This time, it was an adults only weekend and so we got to have a whole different Keys experience!

(Links to my blog posts about family-friendly travel in the Keys can be found here, here, here, here, and here.)

I flew into Key West on Friday night from a work trip, so I met them at almost 9:00pm. We started our trip out strong with tattoos (read all about that experience and the meaning behind my tattoo here). After tattoos, we hit Duval Street for some celebrating. Duval Street is the main street in Key West with all the bars and restaurants on it. We stayed at the La Concha Hotel and Spa by Crowne Plaza, which was in a perfect location, right on Duval. I don’t know if I would recommend this hotel, though. The room was a little out dated, there were not many amenities on the hotel property, and there were issues with our bill when we checked out. BUT! If you’re looking for a comfortable hotel based on location alone, this is a great option. We were in the middle of everything!

On our first night, we bar hopped a lot. I really liked Mangoes, which is an outdoor bar on Duval. The bartenders were kind of grumpy, but the drinks were good and the atmosphere was great. You could sit out by the street and watch everyone come and go while you listened to the house band. It was lots of fun! And – BONUS! – it’s directly across the street from Paradise Tattoo, if you’d like to commemorate the night!

We also wandered down to the legendary Sloppy Joe’s for some rum runners and new t-shirts. We’d gotten t-shirts here when we were on our other trip, but it had been a few years and Chris and I LOVE their tee’s. So comfy!

We had midnight hot dogs and sausages from a street vendor and then headed back to our hotel after that.

The next morning, we were supposed to meet for breakfast at Glazed Donuts, but SOMEONE in my hotel room (hint: Chris) had a hard time getting going after the late night before, so we missed it, but Danielle and Quinn said it was delicious! Get there early, though. The line was super long. Danielle suggests their Key Lime Pie donut and Quinn suggests their apple fritters. 🙂 .

After breakfast, we met down by Mallory Square to do some walking around and shopping.

At 11:15, we met the ferry for Latitudes Resort and took it over to the island where the resort is located. We had reservations for an early lunch and it was beautiful! We ate outside and ended up having a two hour+ meal! That’s the thing about the Keys. They run on island time, which means service is slow because life moves slow. We all had to remind ourselves that we were on vacation and that it was totally acceptable to just sit still for a long lunch! I think that’s one of the things I love about the Keys. It’s a great place to teach yourself how to relax because the locals do it so easily and naturally!

After lunch, we had a few minutes before the ferry would come back to take us back to Key West, so we decided to stroll around the island a little bit. Latitudes Resort is located on a private island that has both resort cottages and hotels, but also private residences. We spent an hour walking around, looking up homes on Zillow, and picking out our retirement homes. Mine was only $8.3 million, so totally obtainable. If you have some time to spend, I highly recommend the ferry ride and lunch at Latitudes. It’s a fun, relaxing way to spend a late morning or early afternoon.

After lunch, we went back to hotels for naps and resting up for our evening. We met Danielle and Quinn at the Hemingway House around 4:30 that afternoon for a little tourist fun. I love the Hemingway House, but I especially love the cats at the Hemingway House because they don’t give a damn about rules or the historical importance of their home or the fact that tourists are swarming them. They just do their thang.

If you aren’t familiar with the Hemingway House, the cats there are famous for having six toes. They are also famous because there are so many of them! They just roam the property while you’re walking around taking a tour. It’s pretty funny. They even have a cat cemetery! My favorite is the cat named Kim Novak. 🙂

At the Hemingway House, you can opt to take a guided tour through the property or you can float around yourself and read the plaques. We chose to just float around on this trip, but I’ve done the guided tour before and it’s really great, too. I kind of wish we’d brought the kids here when they were with us last time. They would have really liked it, I think.

We were there for about an hour, so by the time we left it was 5:30 and we were ready for some food and drinks (which was really the main objective of our trip). We went around the corner to Rams Head Southernmost, one of my new favorites! We had appetizers and drinks here for an hour or so while we listened to the house band. We ordered the nachos. Do yourself a favor and order the nachos. My stomach is growling just remembering them. It was such a cute spot! We noted that they had a DIY bloody mary bar, so we made plans to come back here again.

We didn’t have actual dinner plans and the sunset while we were sitting at Rams Head, so we decided to just meander down to Mallory Square to see if any of the festivities were still going on, but it was pretty dead. If you’ve never been to Key West before, there is a huge celebration every night at sunset at Mallory Square. Lots of vendors, lots of music, lots of food, lots of fun – and all while you watch the most beautiful sunsets ever.

Quinn took us over to this tiny little restaurant on Mallory Square, though, that I would never have known about! On the far end of the square, tucked back behind a resort and hidden by a nondescript wall, is a little restaurant called Sunset Pier, which is the more casual restaurant on the Ocean Key Resort Property (they have a more formal restaurant upstairs called Hot Tin Roof, which we heard was amazing.) We sat outside on their boardwalk at a little table on the water and watched all the booze cruise boats heading out for their cruises. It was so fun to cheer and yell at the boats as they went by because they were all lit up with lights and there were bands playing and everyone was… well… drunk… It was such an unexpected, cute, fun place to have dinner! I ordered the grilled shrimp salad and I kind of wished I’d ordered something with even more shrimp because the six little ones I got were not enough – they were so delicious!

From Sunset Pier, we headed over to Hog’s Breath Saloon. I hadn’t been to Hog’s Breath in at least ten years, but, like most things in the Keys, it hadn’t changed at all. We sat at the bar for a while and I made everyone play the drinking game “Never Have I Ever.” They hated it. I loved it. 🙂 .

From here, the night gets a little hazy for me. We continued to bar hop all the way down Duval Street. I especially liked The Bull and Whistle Bar. The first floor is the Bull, which is a little louder and rowdier. We parked ourselves in the Whistle, which is on the second floor. The guys played a few rounds of darts and Danielle and I sat on the balcony yelling at people as they walked by (did I mention I had enjoyed a few adult beverages by this point in the evening?). I also may or may not have dropped a lime from my drink down into a bridal party that was out for a bachelorette weekend and accidentally hit a bridesmaid and then that bridal party may or may not have come up into the bar looking for whoever threw a lime at them…

I plead the fifth.

On the third floor of The Bull and Whistle is a bar called the Garden of Eden, which is clothing optional. YIKES! We did not venture into that realm, but we really loved sitting next to the stairs leading up there and watching all the people who didn’t know it was clothing optional walk up and then immediately run back down. Good times.

But the best part of the evening was that Jimmy Buffet popped into Margaritaville unannounced and did an impromptu concert! We weren’t in the restaurant when that happened, but we piled outside with the crowds to get a listen (we couldn’t hear anything, really…). The security guard told us that he was in town recording. Apparently, he has a private recording studio in Mallory Square and when he comes to town to record, he almost always stops in and does a casual, unannounced concert for guests. SO COOL!

It was getting late at this point and we were all ready to sit for a bit, so we accidentally found Willie T’s. If you’re ever in Key West and you don’t go to Willie T’s, you need to seriously reconsider the direction your life is taking. It was my favorite bar, by far. We sat at an outside patio table and watched all the drunk 20-somethings hit on each other in the more bar-like area. We also listened to this AMAZING guy play the guitar and do all these mix ups and remixes and blends and all that musical stuff that I don’t know the name of. But he was awesome and played all our favorite music. We put a dollar up on the wall and even came back the next night to sit at the same table and check on our dollar.

Also, I remembered that I had a tattoo. Here’s my tattoo at Willie T’s.

Also, Quinn got a cigar and I held it like a weirdo.

At this point it was WELL past midnight, so Quinn and Danielle headed off to their hotel and Chris and I headed to ours. But before we did, Chris and I stopped at a little pizza place that’s right inside Rick’s Bar. Rick’s is a little too young for me, I think. Also, maybe a little too skanky and possibly a little too STD-ish. BUT! The pizza was delicious and Chris and I sat at the tiniest table in the world in the alleyway leading to Rick’s and people watched for another hour. It was a great ending to a really fun day.

On Sunday, we started our morning bright and early with breakfast at Blue Heaven, arguably one of the best places to have breakfast because in addition to serving toast with your eggs, you can also get banana bread. BRILLIANT! And while the atmosphere at Blue Heaven is simply magical with all these little twists and turns and tables hidden in all the corners, my favorite part is that after we finished breakfast, our waitress asked if we wanted to see the dessert menu because OF COURSE YOU CAN HAVE DESSERT AFTER BREAKFAST IN KEY WEST! So, we ordered the key lime pie. Naturally.

After eating grits and key lime pie for breakfast, putting on bathing suits and going to the beach seemed like the right things to do. We headed to Danielle and Quinn’s resort, which was on the water, for what we planned as a beach and pool day. Unfortunately, the weather had other ideas. It was FREEZING out there! So we did what any good Floridian does when it’s too cold at the beach…

We drank until we weren’t cold anymore.

Then, we moseyed on over to the resort next door to the Four Winds Beach Resort for a light lunch, and by light, I mean that I ordered NINE GIANT CONCH FRITTERS and it was the best decision of my life.

The Four Winds resort had this really great courtyard with lawn games right off the beach, so after lunch, we walked out there to check it out. We ended up spending hours out here and had a really great time! Chris and I played giant chess (I asked him if he wanted to play wizard’s chess where every time we took a piece, we had to fight each other to the death, but he said no). We also napped in these huge lounge beds and we played a mean game of bocce ball.

By now, it was about 3 in the afternoon and it started to sprinkle a little bit, so we headed back over to Danielle and Quinn’s resort where we got the great (and totally sober) idea that the pool would be warmer than the cold air, so we all jumped in for an hour. Except, Danielle and I couldn’t get our tattoos in the pool (germs and all that), so we sat on the side of the pool like this until our arms lost all blood and feeling in them.

At 4:00, Chris and I went back to our own hotel and got ready for our one really nice dinner out. We ate dinner that night at Louie’s Backyard and it was – hands down – one of the best meals I’ve had in the Keys. I had the special, which was mahi mahi over potatoes and sweet corn with this cream of something drizzled all over it like seafood gravy and I realize this description is not sounding as good as it was in real life, but I’m a blogger, not a food critic, so this is what you get. But, trust me. It was delicious. Almost as good were the steamed mussels and the conch-something or other appetizers that we had. They were DIVINE.

Aside from the food, Louie’s Backyard won all the awards from me for the atmosphere and location. It is right on the water and we were there at sunset, which was beautiful!

And the restaurant itself is this little house that is just the most romantic place ever. (Nevermind that I also made them play Never Have I Ever here, too…)

After dinner, we headed back down to (where else but…) Duval Street. We bar hopped a little bit and revisisted some of our favorite places. I also auditioned with the manager (who happened to be working the bar that night) to be part of the band at Margaritaville band. But apparently he can’t recognize talent when it sings in his face, so I didn’t get the job.

We ended the night a little early because we were all pretty tired from a weekend of debauchery fun, but not before parking ourselves back at Willie T’s for another night of singing from our tables and drinking rum. I mean, how else do you end a night in Key West?

The next day was Monday and we were all heading home. But before we left, we met for lunch again at Rams Head Southernmost. I had the blackened grouper sandwich and it was perfection. I didn’t even eat the bun, you guys. THAT’S how good the fish was. I also didn’t take any pictures. THAT’S how good the company was.

We had the perfect weekend in the Keys. It was much needed time away from all responsibilities for Chris and me. One of my passions for this year is having fun with Chris. We hang out a lot and we always have a good time together, but really, intentionally having FUN together hasn’t happened in a while because life gets in the way sometimes. So it was good for both our hearts to take a weekend and devote it entirely to each other and to just having a good time.

I am back home now, rested and relaxed and feeling like I can take a deep breath for the first time in a few weeks. All signs of a really great vacation.