My wife and I visited Key West this past week (Monday 6/3 - Friday 6/7). I wanted to write this report because when planning on our trip I found it very helpful to read the reports of others. I had been to Key West once before (ten years ago) but my wife had never been.
The first wrench in our plans happened when after booking a trip that we planned on being a party trip we found out my wife is pregnant. We still had a great time, and she was a great sport as we went from bar to bar. Leading up to our trip the weather report was awful and unfortunately the weather was not great while down there. We only saw the sun/blue sky for half the day on Thursday. To be honest it did not stop us from having a great time. About the only thing that it kept us from doing was seeing one of those Key West sunsets. It didn't rain a ton, it was mostly just overcast. Anyways just wanted to get that part out of the way.
We flew out of Boston direct to Miami and landed at about 9:30. We made the plan to drive from Miami and fly out of Key West on the way home, which worked out great because the drive down was a lot of fun, but not sure if I would have wanted to do it on the way home too. We picked up our rental car from Budget and left the Miami airport at about 10:15. I always thought the Boston airport was a complete cluster but this Miami airport really takes the cake. Right after getting off the plane there was zero signs directing us to the rental cars, it was quite a process finding them, and then once we did find it, getting to the highway was a process. We rented the car only for the day, checked into the hotel and I then dropped it off at the airport and took a cab back.
The ride down was great, we took our time and enjoyed the sights. We stopped on Marathon Key and went to lunch at Sparky's Landing in Key Colony Beach. This place was a great restaurant to stop at. About 2 hours from Miami and about 1 hour to Key West, it really broke up the trip nicely. The stuffed mushrooms were the best I have ever had. My wife had the cheeseburger and I had the fried oyster po' boy and they were both excellent. After a nice lunch we were back on our way. We finally hit Key West at about 2:00 PM. We stopped at Kmart on our way in to pick up some supplies and then we were on our way to our hotel.
We finally arrived at the Simonton Court Historic Inn and Cottages. I will be writing a review on this hotel as well, but to summarize, this place was outstanding and we couldn't have asked for anything more. So close to all the action but still quiet on the grounds. Clean rooms/grounds, lush tropical grounds, great pool area, and great staff. This place is highly recommended. We checked in and the front desk receptionist showed us around the grounds. We stayed in the Mimosa room which is in the Mansion building on the third floor (no elevator). It has beautiful vaulted ceilings, a large bathroom with a large shower, and a nice small deck that overlooks the pool.
After a swim in the pool we left our room for the night. We had the intentions of eating at Sunset Pier and watching a sunset, but since it was cloudy we decided to wander around and just see where the night took us. We made our way to Duval Street and the first bar we saw was Fat Tuesday, so we went in to get a drink. The bartender there was very nice, and we sat and talked with him for a bit. One thing I saw on the door (and saw in every bar there) was that it is illegal to carry drinks on the street, when I was there ten years ago I never remembered that being an issue. The bartender said it was just something that the bars had to put up and that we wouldn't get hassled with a drink on the street, and that turned out to be the case as I had no issues the rest of the trip.
We left Fat Tuesdays and made our way further down Duval Street, we ended up at the great Captain Tony's Saloon. I am sure most Key West travelers are familiar with this famous dive, and we actually went here every day we were there. I love a nice dive like this place. On the way in I made sure to toss a quarter in the fishes mouth and got it in on my first try. We stayed there for a few then made our way over to the Rum Barrel. We had a few appetizers for dinner and continued on our way. Our final stopping place was the Green Parrot. I had never been there before but had heard good things about it before and we were not disappointed. They were actually doing charity bingo so we stayed there and played for a while. That ended at about 9:00 and we had been up since 3:00 AM so we decided to call it a night and headed back to the hotel.
Our first full day in Key West. We decided to walk up to the Cuban Coffee Queen for breakfast and we were not disappointed. The breakfast sandwich on the Cuban bread was delicious. They also use ice cubes made of coffee in their iced coffees so it does not get watered down (wish Dunkin Donuts would do this). After that we went back to the hotel for a bit before heading out to the Key West Aquarium. We walked through there, it was fairly small but we went when they were doing the feedings which was interesting. After that we walked around the Mallory Square area and ended up at Sunset Pier for lunch. I had an order of Conch Fritters and my wife had a mozzarella/tomato salad. With a pregnant wife we went back to the hotel for a quick afternoon nap. She took a nap and I went for a swim in the pool, we actually did this every day we were there. We headed back out and went to the Conch Republic for a few drinks, seemed like a nice place but we did not eat there. We took a few pictures over at Shrimpboat Sound and then headed back to Duval for dinner. We ate at Carolines Cafe on Duval St. The food here was very good, we had bruschetta for an appetizer and I had a Cuban mix sandwich and my wife ordered a chicken sandwich. Great food at pretty good prices. From there we went to the Lazy Gecko and Captain Tony's once again.
We got up and went to Pepe's for breakfast, another great meal! Very good food, and nice people working there. After breakfast we headed over to the Cuban Coffee Queen for some coffee. We headed back to the hotel for a bit because my wife wasn't feeling great, and it actually worked out well because a storm rolled through. Once the storm settled down and my wife felt better we headed out. We first went to the Shipwreck Museum. It looks like they do guided tours but we opted to do it our selves. It was actually really interesting in there and we enjoyed it. After that my we walked down Duval St and went to the Ripley's museum, yes I know its a tourist trap, but we have been to them in other cities and my wife really enjoys them. After that we went back to the hotel for the afternoon nap/swim routine. We decided to do our one "upscale" dinner and went to Santiago's Bodega, which was absolutely fantastic, really top notch tapas. We ordered the mozzarella burrata, mini quesadilla's, potato croquettes, the beef short ribs, and the beef tenderloin with bleu cheese butter. All of these tasted great but if you go the mozzarella, short ribs, and tenderloin are absolute must orders. I had a few glasses of the red sangria which was also great. After dinner we walked up to Duval St and started the night with a few cocktails at the bar at Fogarty's. The bartender was very nice and was from Massachusetts as well. After here we went back to....you guessed it, Captain Tony's!. We went here and watched the Bruins game. If you recall, on Monday on our first visit there I tossed the quarter into the fish's mouth. I was told on Wed. while there that for it to be done right it has to be done after a few beers and tossed over your shoulder backwards while coming out of the bar. So upon our departure I attempted it again, I missed the first try but was right on with the second try.
Our last full day in Key West. And for the first time all trip we had sun and blue sky. We were up early and went to Harpoon Harry's for breakfast. After eating a great meal we stopped by the Cuban Coffee Queen one last time. We then did the walk on the dock that goes around the Conch Republic, A&B, the Commodore etc. We went back to the room for a minute then headed back out. We trekked all the way down to the Southernmost point. It was a great walk, but it was very hot and humid, maybe the clouds were a blessing in disguise with a pregnant wife walking so much. After we went there we stopped by the Southernmost Beach Cafe for a drink and to have a seat for a bit. We then walked back to our hotel going up Duval St, stopping in many of the shops along the way. We then stopped into Lobo's Mixed Grill for lunch. I would say that this was the second best meal that we ate after Santiago's. I had a Rib Eye Steak wrap that was awesome. We walked back to the hotel and got ready for our last evening. We started the night at about 4 PM at the Lazy Gecko, we were there for a bit when it happened, the sky just completely opened up. It was like we were in the middle of the hurricane. At this point we just bounced around between Sloppy Joes, Irish Kevin's, and the Lazy Gecko. We then made our way over to Captain Tony's for one last visit and put up a business card underneath the Rhode Island license plate (I am a native of Little Rhody). At this point the power was out on that side of the street but that didn't stop us! We then made our way back over to Fogartys where we had some cheeseburgers for dinner and they were very good. Back to the hotel after a few beers there.
Rough day of travel, our flight out of Key West was delayed by two hours, which caused us to miss our connecting flight in Miami. Due to bad weather in Boston our 3:15 flight didn't take off in Miami until 5:30. We made it back to Boston in the middle of a monsoon pretty drained.
All in all it was a spectacular trip. We loved Key West and will always remember the place fondly. Every hotel/bar/restaurant/attraction employee we met could not have been nicer and more accommodating. We honestly did not have a bad experience at any of the places we went in this trip report and we would highly recommend all of these places. Feel free to post any questions!Edited: 7:01 pm, June 09, 2013