Labor Day Weekend in Key West

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As a semi spur of the moment decision, Matt and I headed off to Key West, FL this Labor Day weekend. I really cannot stress enough how much I love and appreciate having so many vacation destinations merely a hop, skip and jump away. We drove down Friday night and avoided much of the holiday traffic, only taking us 4 hours from West Palm. Unfortunately, we hit major slow downs and heavy rain on our voyage home Monday afternoon/evening. Regardless, this was by far one of our best trips yet (I feel like I say that about every trip. 😉 )


Lodging:
Through Hotels.com, we booked An Island Oasis Bed and Breakfast . We decided on this hotel mainly because of cost and location. We ended up paying around $470 after tax for 3 nights. Not great, but not a horrible deal either considering it was last minute and a holiday weekend. The location of this hotel was just a block or so from the Southern Most Point on Key West. Getting to the southern end of Duval Street was an easy walk from the hotel, although our legs became pretty tired after walking from one end to the other several times (Duval Street is actually a little under 1 mile from north to south but can take up to an hour to walk because of crowds.) Aside from the close proximity to Duval, several cute eateries, scooter rentals and of course the ocean were all nearby. The hotel itself was charming as are most bed and breakfasts. Since it is located towards the southern end of Duval, it was much quieter than other hotels closer to the hustle and bustle of the main strip. We stayed in the very basic economy room with a Queen Bed. The room decor was pleasant with a tropical theme of reds and greens. We were located on the first floor right next to the front door so did have some outside noise but nothing to complain about. Despite the tiny size of the room, I was really impressed with how stocked the room was with just about everything a traveler might need. On the wall was a tiny TV which we didn't even get around to watching on this trip. On the dresser, the hotel provided a coffee maker with various flavors of cream, a bottle opener, a mini fridge, microwave, paper towels and a whole slew of other misc items that I wouldn't even think of being in a basic hotel room. The bathroom was also clean and included an actual shampoo and shower gel dispenser in the shower in lieu of mini bottles. A hair dryer was also included in the cabinet. My only complaint about the bathroom would be the water pressure wasn't as strong as I would have liked, which seems rare anymore in most hotels anyway.

In regards to service, An Island Oasis was very accommodating to late arrivals like ourselves. The office is only open until 4 PM, so we were left an envelope with our room key and a welcome kit which made checking in very easy. The hotel did offer a daily continental breakfast from 9-10 but we slept late every day so I cannot speak to the quality of that feature. Sleeping late also made room service a bit of a problem and we didn't have our room cleaned once during our stay. It was almost like you get one shot early in the morning and that's it. Several times around noon I left the door hanger requesting the room be cleaned on the outside of the door but nothing ever transpired from my action.

Dining:
Cracker Barrel in Florida City
True to tradition, we decided to stop at Cracker Barrel to catch dinner on our way to Key West Friday night. I ordered the Chicken Orchard Salad and Matt ordered his tried and true Chicken and Dumplings with pink lemonade. His meal was good, mine was just so-so. We also made the mistake of ordering the peach cobbler which was absolutely terrible and mushy. We took one bite and left the rest. Yuck!

Cowboy Bills in Key West
Judging from the home page alone, this is not exactly the classiest place in Key West. Luckily, Friday night was pretty slow and no scantily clad ladies (or men) were riding the mechanical bull. We had a pretty low key and fun time here to welcome in our long weekend. The bar itself is pretty big and split into 3 or so areas. As we walked in from Duval, several couples were salsa dancing to a live band. Midway through the bar is another area where there are several pool tables ($1 each game). Outside is a more country themed bar with live music and the mechanical bull. Overall, this seems like a great place to grab a beer and play a few games of pool although I can definitely see it getting pretty crazy during season.

Red Fish Blue Fish in Key West
Red Fish Blue Fish has become a favorite stop of ours since we discovered their key lime pie. We went here Saturday afternoon for lunch. We started off our lunch with the delicious calamari as shown in the picture. Matt ordered the Chicken Carbonara which he was not crazy about. I ordered the best Ahi Tuna dish I have ever had and a Rasberry Margarita. The Key Lime Pie was delicious as ever and we learned that it is made with all key lime juice, no sugar like other places make theirs. I should also note that the service was really great here and the staff very helpful in giving recommendations on tours and such.

Rum Bar at the Speakeasy Inn in Key West
This cute little place we found by default as we were walking up and down Duval one afternoon. It's a Bed & Breakfast, but the doors are open and welcoming to a quaint little bar right there in the lobby. I can't stress enough how much I loved the atmosphere here. It was definitely a breath of fresh air from the normal big/loud Key West bars. I ordered the Painkiller drink and Matt ordered Rum Punch, both were excellent and we will definitely come back here on future trips.

Margaritaville in Key West
I'm a bit disappointed in us for visiting Margaritaville as it's just about as tourist trappy as they come. Needless to say, we wanted to grab some quick drinks before our Ghost Tour and Margaritaville was the first place we laid eyes on. I ordered the Rasberry Colada which tasted a lot like Pepto Bismal. Matt ordered the Bahama Mama which was good. We also tried the Jamaica Mistaica wings which were alright but nothing fabulous.

Two Friends Karaoke Bar in Key West
Two Friends was another repeat visit for us based on a positive experience last trip. I can't speak on the quality of the food here, but the drinks are solid and the live music is surprisingly good as well. It almost seems like this is a place where lots of locals go a few times a week. Every time we've been here, the karaoke has been surprisingly good. This go around I ordered a Mimosa and Matt ordered Pink Lemonade with vodka which came to $16.00.

Mallory Square Food Vendors
It's tough to tell which vendors will be constants and which are just passing through on Mallory Square. But, I do want to note that the one night we caught the sunset, we tried the Conch Fritters and Lemonade which were both really good. The sauce that went with the fritters was excellent so I hope this vendor continues to be here.

Old Town Mexican Cafe
Matt and I both love Mexican food and noticed this place during one of our strolls up or down Duval Street. The problem was that we didn't note the name at first glance or where exactly it was located. As a result, finding this place again was quite the challenge for us but we were on a mission! After several google searches for Mexican Food in Key West and failed attempts up and down Duval, we found it again! The second problem was that we were already pretty stuffed before coming here. This was a problem because the food really was excellent and we ended up leaving so much behind. 😞 The chips and salsa were delicious and paralleled Chi Chi's salsa which speaks worlds in Matt's world. Matt ordered the Steak Quesadillas and I had the Avocado Salad. We will definitely return here next visit...on an empty stomach of course. 😊

Better Than Sex in Key West
For anyone going to Key West, this is by far my top recommendation on places to try. We really wanted to eat here last visit, but due to a time conflict, we were unable to. This go around, we made it! I should note that the hours are kind of off so it's important that you know the schedule: Wednesday-Sunday 6PM=1AM. The owners also tend to take vacations and will close for short periods of time. Basically, this is a very romantically themed dessert place. It's relatively small and intimate inside with minimal lighting (they provide mini flashlights to read the menu) and a live pianist. During our visit, the place was pretty full so we opted to order to go. The menu is so funny to read as each dessert or drink has a highly "romantic" name and description. We decided on the "Peanut Butter Perversion." OH.MY.GOSH. So good!!!!! I dread to think of how many calories I consumed with that massive piece of chocolate/peanut butter goodness, but it was well worth it. I have heard that Better Than Sex also has the best Key Lime Pie so next time I may have to try that out.

Kohr Brothers Sofe Serve in Key West
If you like soft serve, this fits the bill. I had a mix of pumpkin/vanilla with rainbow sprinkles on top. For whatever reason, this place only accepts cash which was kind of a pain.

Banana Cafe in Key West
Matt and I went here for breakfast on Sunday morning per a TripAdvisor recommendation. The atmosphere is charming and true to the reviews, the food pretty good. I ordered the Egg White Veggie Omelet which I really liked. Matt wasn't as crazy about his Cheddar and Bacon Omelet or the Orange Juice. Since this place is known for it's crepes, we ordered the Pineapple Crepes for dessert. For future reference, we will probably stick with ordering crepes here from now on as they are their specialty and incredibly tasty.

Flamingo Crossing Ice Cream in Key West
Unfortunately for my waistline, I am an ice cream junkie and would eat it daily if I could. We noticed this place during one of our trips up or down Duval and decided to go in. I would highly recommend the ice cream here! The service was excellent and the owner (?) very friendly. I ordered a cup of the pumpkin/coffee ice cream with sprinkles and it was fabulous.

Kimberly's Sweets & Treats in Key West
Every day we passed Kimberly's on our way to and from our hotel. It's a cute little place that offers desserts, smoothies and breakfast. Matt and I decided to swing by on Monday morning to grab some dessert. I feel like it was an off day for this place as several of the appliances to make coffees and such were down and the solo employee seemed a bit stressed. If we were staying around the area again, I'd probably be open to trying a smoothie or ice cream from here next time but will stick to Banana Cafe for breakfast food.

Bentley's Raw Bar in Islamorada
Sometimes, the best places are found by accident...or in this case, insane holiday traffic and growling stomachs. On our way home on Monday, traffic was a mess around the Upper Keys. After crawling on the Overseas Highway for awhile, we decided to find the next restaurant off the main road to stop and grab a bite. Bentley's just so happened to be that place. The calamari here is the best we've ever had. Most of the pieces were the little circles vs. the mini squids which is very important to us. It was served with excellent dipping sauce and fresh chopped tomatoes. Matt ordered the French Onion Soup and Chicken Tenders whereas I ordered Ahi Tuna. I should note that this place isn't exactly the best bet for a budget dinner as each entree' tends to be right around $20.00. We will most likely stop here again to break up our trip.

Activities:
Barefoot Billys Jet Skiing Excursion
This will hands down be one of my all time best memories! After some debate, Matt and I decided to book the Jet Skiing Excursion which went all around Key West and lasted for several hours. I believe our total for the two of us on one jet ski came to $120.00 or so. We were debating between snorkeling at the Grand Tortugas and another tour that including kayaking. The tour offically started at 2 PM but Barefoot Billys encourages customers to arrive the the Reach Resort early to kick back on the beach and enjoy a few drinks which is precisely what we did. This experience in itself was so relaxing. The Reach Resort offers it's own little private beach and pier that extends out into the water. Matt and I arrived around noon and were given comfortable beach chairs on the beach (note: be sure to have some cash on hand as the Reach employees by the beach do work for tips, as do the tour guides). We ordered Mojitos which were expensive but very good and soaked in the beautiful scenery, spending much time on the shaded pier. I can't stress enough how much I loved this place. If we had a wedding reception "do-over", it would be here! The jet ski tour itself was an absolute ball. Matt and I both took turns driving the jet ski which was very easy to operate. Bascially, the tour has a leader and maybe 10 or so other couples/singles or skis. Most of the time, everyone goes in a single file line behind the guide with occasional stops to describe certain landmarks from the water. Midway through, the tour offers "play time" where everyone can just ski all over the place/swim/sun. I haven't laughed so much in a long time and will never forget our experience doing this.

Conch Train Tours
Through one of the kiosks by Mallory Square, Matt and I booked the Conch Train Tour, Hemingway House Tour and Walking Ghost Tour. Our total came to $110 for the two of us. This was my second time on the Conch Train Tour (I went once before a few years ago with my parents) and it's definitely something that everyone should do at least once. Our tour guide was incredibly informative and it was nice and relaxing to kick back and learn about the fun history of Key West. The Walking Ghost Tour was also a pretty fun experience. It's something that we probably won't do again, but it was worth the time to do once. The doll stories are the scariest! The good thing about these tours is that the tickets don't expire. By Monday afternoon, Matt and I were too exhausted to do the Hemingway Tour so we can use those tickets during our next trip to Key West.

Overall, this trip to Key West has to be one of the most fun vacations we've had. I can't wait to go back soon!

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