For the past several years I started booking another trip to Key West in January to break up the monotony of the winter season up here in New Jersey. During our most recent trip this past October, we wound up meeting a very nice couple from Nashville, Brent and Julie who were staying at the Gardens in a room next to near us. Low and behold they were returning the same time, so my husband and I were excited to see them again.
About a week before our arrival, I saw that the weather in Key West was going to be a mix of both cool and mild temperatures making it a bit of challenge of what to pack – let alone how to fit everything in our carry on luggage. I wound up making sure to pack a lighter weight jacket, a hoodie and leggings which worked out perfectly for me.
And for the plane I figured that we would both be dressed warm to begin with so that would be another option if it did get cold while we were there. (As a side note, people may think that 60 degrees is not that cold. However in Key West, if you are near the water and there is a strong wind from the NW, it does indeed get chilly. Plus some places don’t even have heat)
Sunday – January 16 – Arrival Day
A few days earlier, it was forecasted that a snow storm was going to hit the mid-atlantic area on Sunday, the day we were flying out. Luckily the storm slowed down a bit and was not supposed to arrive in our area until later that evening. However we did wake up to extremely cold temperatures. I looked at my phone on the way at the airport and it said 2 degrees. I thought even 60 degrees would feel a lot better then this.
The flight was nice and smooth which not much turbulence until we got further south. The storm that was supposed to hit our area later that night was coming from the south. The pilot actually took the plane away from the storm, changing the usual 2 and 1/2 hour flight to 3 hours.
Unfortunately the forecast for Key West was rain. As we neared the Keys, most of them were covered by clouds. It did get a bit bumpy as we got closer to landing, but all and all it was a pretty smooth flight. Once we landed we walked down the tarmac in the rain. This was the first time we had ever experienced rain arriving in Key West. It usually happens while we leave. I thought it doesn’t matter, I am in my happy place!
We were one of the first people off the plane so we were able to get a taxi right away. The rains started to dissipate during the ride to the Gardens Hotel. (And yes we booked another stay – making it our 26 time staying there. I have looked at other places but nothing else seems to get my attention to book so I continue to book it each and every time. No judging here.)
Soon I could see the yellow walls that surround the Gardens Hotel and that feeling of returning “home” was set. The taxi had to drop us off away from the entrance since part of the street was flooded. I remember the last time we were there for Tropical Storm Elsa, the area right in front of the entrance gets a lot of water collected on the road.
We walked by the bar area and saw a familiar face, Phil the bartender. We were going to have a drink first but there weren’t any open seats at the time. So we said hello and made our way out onto Angela St. The rain had stopped and the road was clear from all of the water.
We made the usual turn onto Duval which always brings a smile to both myself and my husband. You get the feeling that yes we are back again. We joked too about how due to the fact we have been coming back to Key West several times a year now, it feels like one long trip and the time spent back in NJ is just a break.
Since it was a Sunday there wasn’t any entertainment going on that I wanted to see. We walked by Jack Flat’s to see about checking out one of the NFL Playoff games but it was packed. So we kept walking and I suggested that we could head up to the Galleon for a drink since it tends to be quieter then the other places along Duval.
While we were walking, my husband reached out to our friend Charlie (who lives in our home town) and his wife who were in Key West the same time. They were at the aquarium but said that they would meet up with us when they were done.
We made it down Front St. to the Galleon and walked around the boardwalk to the Sunset Tiki Bar. We found two seats at our usual spot and saw Ramsey was bartending. She welcomed us back and poured our favorite go to drinks at the Tiki Bar, sweet tea vodka with water and lemon. While we were catching up we also saw Phil who manages the bar. He too welcomed us back. It was so nice to be back.
Then my husband got a call from our friend Charlie. It was him and his wife’s first time in Key West so trying to tell them where the Tiki Bar was, was a bit of a challenge. So my husband told them he would meet them on Front St. by the A&B Lobster House sign. My husband did find them and walked them back to the Tiki Bar. It was so nice to see them again. And it was quite ironic that we hadn’t seen them in quite some time, but here we are in Key West hanging out together.
Unfortunately they were leaving the next day so we wanted to show them a couple of places that they hadn’t visited to yet. So we said goodbye to Ramsey and Phil and knew that we would see them again.
Then I suggested why don’t we sit at the Gazebo. And that’s what we did. While we were waiting for Brent and Julie, I noticed another familiar face. It was Jim the General Manager at the Gardens. I wanted to make sure I said hello and thank him for always accommodating us in our usual room. So I walked over and chatted with him fo r a few before walking back to the Gazebo.
Before we knew it, we saw two faces emerge from the surrounding gardens. It was Brent and Julie! They came in through the back way so we weren’t expecting it. It was so much fun to see them again.
I was getting cold so I didn’t want to go to Kaya Island eats, even though that’s where I originally wanted to go to that night. So we decided to walk down to Blackfin Bistro. My husband was craving a burger and I was just plain old hungry since I hadn’t eaten all day.
We walked down to the Blackfin Bistro. The bar was empty so we grabbed two seats. The bartender read us the specials and the catch of the day (I think it was snapper) served with a light curry sauce which seemed to fit the bill for me. So I ordered the special while my husband ordered the burger. We first shared their escargot appetizer which I remembered from last time. It was so flavorful filled with garlic and butter.
I was surprised how quiet the restaurant was. There were a few people in the back outside section but that was it. Then our bartender brought out our main courses. The fish was delicious and the curry sauce wasn’t too strong. It paired well with the fish. My husband of course loved his burger. I stole a few fries and they were tasty. You can read my review here: https://www.tripadvisor.com/ShowUserReviews-g34345-d1581064-r826052075-Blackfin_Bistro-Key_West_Florida_Keys_Florida.html
While we were finishing up we heard from Charlie and his wife, Elaine. They were on their way to Mangoes. So after we paid our bill we walked down to Mangoes. It was definitely getting chilly. Charlie and Elaine were already sitting at the bar so we sat down next to them. My husband and I each ordered a drink. We only stayed for one since it was a long day. I was feeling the travel day and the drinks that I had throughout the afternoon and evening.
We decided to meet up for breakfast the next morning before they had to leave. So we said good night and walked back to the Gardens. I couldn’t wait to get some sleep. I don’t think it took me any longer than a couple of minutes.
Monday – January 17 – Breakfast Club Too, Hogs Breath, Lola’s
We were meeting our friends Charlie and Elaine for breakfast before they had to head back home. We walked down to Breakfast Club Too where they already grabbed us a nice table outside protected against the wind. They talked about how much they enjoyed Key West for their visit and would love to return. I told them how they now have the Keys Disease. Once you come down to Key West you just want to keep returning.
You can read my review here: https://www.tripadvisor.com/ShowUserReviews-g34345-d13526247-r826050143-The_Breakfast_Club_Too-Key_West_Florida_Keys_Florida.html
They weren’t leaving until later on in the afternoon, so after breakfast we walked down to the Bight. It was pretty cool to see some of the Christmas decorations still displayed around. I noticed though they were starting to take the decorations down.
We eventually said our goodbyes and wished them safe travels if we didn’t meet up with them later at Hogs Breath. So we decided to walk down to the Galleon to the Sunset Tiki Bar for a drink. We saw the owner Phil again and he was setting up for a grroup of sailors that were coming in later that afternoon. Apparently there were these sail boat races going on all week and they would come to the Galleon after they were done for the day. They weren’t scheduled to arrive until 3 or so, so we had the place pretty much to ourselves.
Then we agreed to motivate and walk down to Hogs Breath to see our friend Zack Seemiller play. Since we arrived on a Sunday, we hadn’t seen him since our arrival so I was excited to see him again. We walked in and of course the seats I wanted were taken. They were no seats available and I was a bit frustrated, but knew if we gave it time, eventually someone would leave.
My husband ordered us a couple of beers and then we saw a few seats available at the Raw Bar. A nice couple moved over so I was able to sit down, but it was difficult because there was a tree right next to the seat. I managed to squeeze in while my husband stood near me. As predicted a few seats did finally open up and I beelined to grab them.
Finally we were able to relax and enjoy the music. Stephanie was bartending as usual and she always takes care of us. While we were listening to Zack I saw a familiar face, it was his mom. She was staying with Zack for a few months so it was nice to see her again. Then Zack’s son came in as well, Kai. So we chatted for a bit.
We wound up staying until Zack’s show was over where I had to get my usual photo with him. He was off that evening but mentioned that we could do breakfast the next morning.
So before we made it back to the Gardens we stopped at a liquor store located right on Duval on the side just past Angela St. to grab a bottle of white wine since Lola’s is a BYOB.
Then we needed to relax for a bit before making our way to the Gardens Bar. Phil was bartending so it was nice to see him again.
We talked for a few before Brent and Julie showed up. It was fun hanging out with them. The dinner reservations were for the 8pm seating. Lola’s has two seatings, 6 and 8pm. I was getting hungry but the glass of white wine helped curb my appetite.
We walked down to Lola’s and notice a lot of people standing around outside. The 6pm seating was still finishing up so we had to wait several minutes. It wasn’t too long before we saw everyone exit the restaurant. Then the owner mentioned that they would start calling the reserved parties one by one to be seated. Luckily we were the first to be seated, which was a good thing because it was starting to get a bit breezy outside.
Our appetizers came out next and again everything was delicious. Brent and Julie had the scallops and my husband had the calamari which was served like a filet or steak. My husband really enjoyed it. I had the roasted artichokes which also didn’t disappoint.
There was a little lull until we had our main course, but we didn’t seem to care because we were having such a good time talking. Finally our dinners were served. The sea bass itself was amazing. I think it was probably the best sea bass I have ever had. And even my husband who is not a big seafood fan loved it. It was definitely worth the wait.
You can read my review here: https://www.tripadvisor.com/ShowUserReviews-g34345-d19247202-r826050901-Lola_s_Bistro-Key_West_Florida_Keys_Florida.html
After dinner we walked back to the Gardens and grabbed a couple of seats at the Gazebo for a night cap. We hung out until about midnight before calling it a night. We mentioned to them that Caffeine Carl and Zack were playing at the Tuna the next afternoon and they wanted to go, so we told them we would meet up with them the next day.
Tuesday – January 18 – The Smokin’ Tuna and Red Shoe Bistro
The day beforer I mentioned to Zack and his mom that we would meet them at Breakfast Club Too for 9am at Hogs Breath. When I first woke up it was a few minutes before 8am. I thought let me just close my eyes for a few more minutes before getting ready. Unfortunately the clock was on my husband’s side of the bed, so when I woke up again I asked him what time it was. It was 8:40am and I knew we wouldn’t be at the Breakfast Club Too in time since we both had to shower. I texted Zack and told him that we were running behind. We agreed to just try it another day.
We walked in and the place was pretty quiet. I was happy that we were able to find a couple of seats at the bar. We always wind up talking to a few locals hanging out there which makes it kind of entertaining. For breakfast I wound up going with the La Te Da scramble (which is basically scrambled eggs served with sour cream and fresh chives).
Eventually we motivated ourselves and made it back onto Duval. We noticed that parts Duval of were closed. There was a lot of maintenance going on, between cutting down trees, working on the roads, etc.
While we were walking down the street we noticed that the Key West Women’s Club building was completely covered. Later we found out it was for treating termites. (And then the next day we walked by the cover was gone.)
We walked down to the Bight again and I kept taking pictures because I couldn’t get over how beautiful the sky looked.
It was nearing the time that we were supposed to meet Brent and Julie at the Tuna. So we left the Tiki Bar and walked down to Duval to the Tuna. The place wasn’t too crowded so we sat at the bar leaving two extra seats available. Then we noticed the stools they have at the Tuna now are very awkward. They have a back on them but they are all metal and kind of flimsy. Then I noticed instead of the tables in front of the stage, they have high top tables and chairs, which makes sense because now you can see the band if people wind up dancing in front (like last time during Fantasy Fest I couldn’t see a thing).
Then Zack’s friends Natalie and Ron showed up so it was nice to see them again.
After the show we took a few pictures before heading back to the Gardens. Zack was playing at Ramshead later that evening but I had a feeling it would be too cold to have dinner since everything is outside. We returned to the Gardens to relax for a bit before sitting at the bar for a few.
While we were sitting at the bar we were trying to figure out where to eat. Phil, the bartender mentioned the Flaming Buoy so I gave them a call. Unfortunately it went to voicemail so then my husband thought of the Red Shoe Bistro since it was close by. I originally wanted to go back to Kaya Island Eats, but it was getting chilly and I needed to go someplace indoors otherwise I would not enjoy myself.
My husband called the Red Shoe and they said they were full but if we sat at the bar they could accommodate us. I was so happy that we found a place to eat. We headed down to Petronia St. to the Red Shoe Bistro. When we walked in the place was packed. The previous handful of times we have dined there, I usually choose the first reservation they have which is 6pm, but it was later in the evening, probably closer to 8pm. The owner sat us at the bar and told us the specials. For our appetizers I had the shrimp toast and my husband had the sea scallops and deviled eggs. It did sound strange, but I tried one and the combination actually worked.
The last time we dined at the Red Shoe my husband really enjoyed the beef stroganoff so that’s what he wound up ordering again. The catch of the day was black grouper so I had to order that.
Dinner was served nice and promptly. Again I was quite hungry since we hadn’t eaten since breakfast. Both our meals were excellent. One of the owners came by and I had to thank him for accommodating us last minute.
You can read my review here: https://www.tripadvisor.com/ShowUserReviews-g34345-d21141783-r826052828-Red_Shoe_Island_Bistro-Key_West_Florida_Keys_Florida.html
While we were finishing up a couple of people walk in and started calling my husband’s name. I was like who in the world is that? It turned out it was the parents of one of my husband’s high school friends. I thought what are the odds? Only in Key West! They were staying at the Orchid Key Inn and getting ready to sit down for dinner. We were getting ready to leave so we said goodbye and made the short walk back to the Gardens and called it a night.
Wednesday – January 19 – White Tarpon, The Tree Bar and The Smokin’ Tuna
Since we had a later dinner both of us weren’t too hungry. So after grabbing coffee at Cuban Coffee Queen we wound up walking around back up towards the Bight.
Then I remembered I noticed the other day that the White Tarpon now serves breakfast so I suggested why don’t we give it a try. Before walking in, we both took a quick peak at the menu and it looked like they had everything that we would want to order.
We walked in and sat at the bar. All the windows and doors were open so it was a little breezy. It was a nice view however to see the water while waiting for breakfast. For breakfast I had the smoked salmon and bagel while my husband had a couple of eggs over medium. The food was good and satisfying. I would definitely go back.
You can read my review here: https://www.tripadvisor.com/ShowUserReviews-g34345-d1632255-r826052431-White_Tarpon_Bar_Restaurant-Key_West_Florida_Keys_Florida.html
When we were done, we wound up walking around as usual. The sky was once again so beautiful. The temperature seemed to be finally warming up where I could actually take off my jacket.
We eventually wound up stopping at the Tree Bar to see our friend Tracey working.
We planned on going back out to the Tuna later that night to see Caffeine Carl and Just George so we wanted to make sure we were pacing ourselves.
Before we went to the Tuna we had some time to sit at the Gardens Bar and talk to Phil for a little bit. He always has some story to tell. We were having a nice time and then Brent and Julie showed up. They were joining us that evening because they wanted to see the band at the Tuna as well.
I suggested that we should walk on over a little earlier so we can grab a table and order something to eat. On our way there I texted Carl to see if he could get us a table, but he was on his way as well to the Tuna, but said to check with his wife Erin about getting a table.
It was getting late and we all agreed it was time to go back to the Gardens. We would have stayed until the end of the show but it was for the best. We made sure to get a few pictures before leaving. We thanked Erin and Carl for helping us with the table situation.
We made it back to the Gardens and had a night cap at the Gazebo before we all retired for the evening.
Thursday – January 20 – Power Outage, The Tuna Again, Willie T’s, Kaya Island Eats
Since we had a late dinner the night before at the Tuna we weren’t exactly very hungry. We decided to walk down Simonton towards La De Ta. While we were walking I noticed the clouds were getting dark again. We turned down a side street and walked to Duval. Once we hit Duval the skies opened up. Luckily we found a canopy on the corner where we were able to ride out the rain for a few minutes.
While we were standing at the corner we thought that we should try Moondog for breakfast. Once the rain stopped again, we walked down to Moondog Cafe. Apparently everyone else had the same idea. We were going to walk inside but it was packed. No one was sitting outside obviously because of the weather.
We found out that a transformer blew and the entire island didn’t have any power. We made the best of it ordering a couple of breakfast beverages and talked to a nice couple from Minnesota. Eventually the power did finally return, probably about an hour later.
It was getting later and we told Brent and Julie we would go with them to the Tuna to see their friend Erica Sunshine Lee who was playing the 1pm set. We still hadn’t had anything to eat but decided that we would grab something at the Tuna.
We walked back out onto Duval and to the Tuna. when we walked in, there were only a handful of people there so we were able to grab a table. Then Brent realized he forgot his glasses so my husband went back with him to the Gardens. When they came back, my husband told me how Brent told him about this short cut that cuts off so much time.
Usually when we go to Cuban Coffee Queen, we walk down Simonton and make a left onto Southard St. However if you walk down Josephine Parker Way behind the Firehouse and make a left down this little lane called Mo’s Way, Cuban Coffee Queen is right there. I know it isn’t very far to begin with, but after all these times staying at the Gardens we never knew, but now we do.
We ordered a couple of appetizers while Erica Sunshine Lee was setting up. She came on over to say hello to Brent and Julie. She was very friendly and charming. Once her show started we just sat back and enjoyed hearing her sing.
One of the appetizers we ordered were the garlic parmesan fries. Wow is all I have to say. They are delicious don’t get me wrong, but if you have any intent of talking to anyone the rest of the day you may want to cover your mouth. The amount of garlic they put on those fries!
It was getting later in the afternoon and I wanted to catch Zack at Willie T’s. So we told Brent and Julie we would meet up with them later at some point at the Gardens.
We walked down Duval towards Willie T’s. When we walked in I saw an empty table to sit at. While I was clearing off the empty bottles, we saw two familiar faces Janice and Matt. So we wound up sitting with them for a bit while listening to Zack play. Kai was also playing with him so that was a nice treat.
Then my husband got a text message from another friend of ours Wayne. Wayne and his wife Karen were going to go to the Tuna to catch Cliff Cody but knew we were at Willie T’s so they wanted to stop by and say hello. It was nice to see them again as well. That is another reason why I enjoy coming back to Key West, seeing all our friends that we have made along the way.
After Zack’s show I asked about perhaps trying breakfast again the following morning. I suggested our usual place we go to before we leave, Sarabeth’s. We had a super early flight on Saturday so I knew that we wouldn’t be able to have breakfast that morning.
We made tentative plans (again) to meet up at 9am for breakfast. We said our goodbyes and made it back once again to the Gardens to regroup for a bit.
Since it was finally a milder evening, I suggested that we go to Kaya Island Eats for dinner. We made the short walk across Duval to Kaya. It was pretty crowded but once again we found a couple of open seats at the bar. I enjoy sitting at the bar at Kaya because it reminds so much of this place in St. John called the Longboard. (As reference https://www.thelongboardstjohn.com/location/the-longboard-st-john/)
I love the vibe too of Kaya. It definitely has that St. John feel to me. For appetizers I ordered the Tuna Poke Nachos and my husband had the Jamaican jerked wings. It was a great start to our meal.
The last time we were at Kaya I had the mahi mahi tacos, but this time I wanted to try something different. The Rasta Pasta caught my eye on the menu so I went ahead and ordered that with portobello mushrooms and my husband ordered the sliders.
You can read my review here: https://www.tripadvisor.com/ShowUserReviews-g34345-d23162562-r826051642-Kaya_island_Eats-Key_West_Florida_Keys_Florida.html
After dinner we were both pretty tired so we just wound up going back to the Gardens. I made sure, however to set my alarm on my phone so I would not oversleep and miss breakfast again with Zack.
Friday – January 21 – Last Full Day (which always arrives way too fast)
My alarm on my phone worked and it woke me up right on time at 8am. I have never used the alarm on my new iPhone before so I also wanted to test it since we were leaving super early the next day for our 7am flight. It was nice to know that besides using the clock alarm in the room I could set my phone.
You can read my review here: https://www.tripadvisor.com/ShowUserReviews-g34345-d922505-r826053249-Sarabeth_s_Key_West-Key_West_Florida_Keys_Florida.html
Everyone else enjoyed what they ordered. It was a nice time just catching up before we had to leave the next day.
After breakfast I made sure to get my usual photos. We said our goodbyes and told them we would be back in several months and hope to see them again.
On the way back to the Gardens we saw someone on a bicycle heading our way. I turned to my husband and said wait that looks like Gabriel Wright (who plays at Captain Tony’s)? And sure enough it was. We didn’t talk to long but asked him when he was playing again since we had not have seen at Captain Tony’s. Unfortunately he wasn’t playing until the next day and we were leaving. So we told we would catch him the next time we were in town.
I wanted to see if our laundry had been returned. (My husband dropped off our laundry the day before for a mid-week wash.) So I walked in to the office at the Gardens and I was happy to see our laundry was back. I also made sure to reserve a taxi for the next morning at 5:45am. Yikes I thought but it would be good to be home so early in the day.
We went back to the room and packed up most of our things so we didn’t have to try and do everything the next morning (with one eye open). Once everything was good to go, including checking in for our flight, we headed back out.
It was finally a warm day. We walked down to the Galleon and to the Sunset Tiki Bar to see Ramsey (the bartender) one last time. The sailors from the races were scheduled again to arrive after the final race which wound up being earlier than the previous days.
This time one of the main courses there was a filet mignon option, so my husband ordered that. I decided to try the pompano as my main course. We were served the first course like last time and then for our appetizers I wound up going with scallops this time.
There was a bit of a wait in between the appetizers and our main courses, but again the food was delicious. It was a perfect way to spend our last night in Key West.
We finished up our dinner and walked back to the Gardens. We wound up staying a bit later then I wanted to, just talking and having a great time.
It was finally time to say goodnight and goodbye (which I hate goodbyes). We thanked them for a wonderful time and would see them again at some point in Key West.
Saturday – January 22 – Leaving Key West
It looked like a beautiful morning but then the pilot told us it was 16 degrees. Once we landed we walked off the plane and it was like a shock to the system. It is amazing after just a week some place warm, you forget how cold, cold actually is.
As always Key West continues to be my happy place filled with both beauty and great people. And a place where we have made lasting friendships with both locals and visitors alike.
Thank you so much for taking time to read my blog.
Until next time…..