Have you ever heard of the term Key's Disease? It's a real thing. There's something so quaint, timeless and effortless about these tiny little islands in the southern most point of Florida. Everyone always seems to be cheerful and optimistic, no one is in a rush and a good time is to be had at every turn.
Some of you may know this but the Florida Key's started my existence in Florida. Six years ago I moved to Key West for a job without knowing a single person! Sometimes I can't believe I did something so spontaneous but I'm beyond thankful for my time that I spent there and the incredible people that I met.
Fast forward to now: Every summer Chris plans to dive for lobster with a couple of close friends- this year we decided to make it a family trip and travel down for a few days so that he could lobster and we could vacation- one can never "over" vacation. We arrived to our resort La Siesta in Islamorda on Friday after a long day of traveling. This was our first time staying at the resort and we thoroughly enjoyed our stay. The rooms were extremely spacious and the amenities were plentiful. The offer a pool, breakfast, beach, boat ramp- including dock space, bicycles, paddle boards and kayaks. The resort also offer access to two sister resorts the Amara Cay and Pelican's Cove which I highly recommend visiting.
You can shop Lilly's looks below (actual bow: Splendid Bows, actual sandals: Gap Kids)
You can shop Lilly's looks below (actual bow: Splendid Bows, actual sandals: Gap Kids)

(Actual Bag: Zara, actual romper: Zara)
Our first night there involved more of exploring the resort and catching up with friends over dinner. The next day I planned to take my daughter, Lilly down to Key West for a few fun activities. You wouldn't necessarily think of Key West being super child friendly but there really is so much to do with children while on your vacation. Our first stop was lunch- while I have an enormous list of all my favorite restaurants including but not limited to (Santiago's Bodega, Bagatelle, A&B Lobster, Louis Backyard) We decided to try out a French creperie across from Blue Heaven (my original choice- but closed). Our lunch was delicious and filling and in the perfect location of a little sight-seeing. I elaborated to Lilly about all the six toe kitties at the Hemingway house and she was eager to go visit them all. The Hemingway House is the famous residence of Earnest Hemingway. The house is truly remarkable and the gardens are immaculate. Lilly loved touring the home and was beyond joyed to see all the kitties running around and in the most inconspicuous places.
After our excursion in the heat (it's uncomfortably hot in August) we ventured over to Maria's gelato spot. My friend, Hollie knows Maria quite well and she's known for the best authentic gelato in the keys. Her machinery even came from Italy! I ordered the Key lime (when in the keys) and Lilly had the mango- both were unbelievably Delicious! She's located near Mallory Square and worth every penny!
We couldn't stop with just the gelato... I had promised over and over again to Lilly ...the Key Lime Pie on a stick. I personally had never had one and I was curious to give it as try as I love anything in the form of Key Lime. We visited the cute little shop right off of Mallory Square and were pleasantly surprised with their selection of all things key lime. Lilly had the chocolate key lime pie on the stick while I opted for the strawberry key lime pie on a stick with white chocolate- both were phenomenal! The girls thoroughly enjoyed their visit here!
After getting our sweet tooth fix, we headed over to Mallory Square- the best time to go is before sunset when all the vendors come alive and the views of the sunset going down over sunset key are magical. Unfortunately, we went a little earlier as I had to get back to Islamorada... so the girls had plenty of open space to run around, chase the chickens, view the water and just have some fun.
After a day well spent in Key West, it was time to head back to Islamorada. From Islamorada it's roughly a 2 hour drive to Key West. Once we returned, we enjoyed a nice dinner with our friends at the resort and Lilly's grandparents came to pick her up for the rest of the vacation. Chris was able to go back out lobstering and I could catch up on a little R&R and work.
We couldn't stop with just the gelato... I had promised over and over again to Lilly ...the Key Lime Pie on a stick. I personally had never had one and I was curious to give it as try as I love anything in the form of Key Lime. We visited the cute little shop right off of Mallory Square and were pleasantly surprised with their selection of all things key lime. Lilly had the chocolate key lime pie on the stick while I opted for the strawberry key lime pie on a stick with white chocolate- both were phenomenal! The girls thoroughly enjoyed their visit here!
After getting our sweet tooth fix, we headed over to Mallory Square- the best time to go is before sunset when all the vendors come alive and the views of the sunset going down over sunset key are magical. Unfortunately, we went a little earlier as I had to get back to Islamorada... so the girls had plenty of open space to run around, chase the chickens, view the water and just have some fun.
After a day well spent in Key West, it was time to head back to Islamorada. From Islamorada it's roughly a 2 hour drive to Key West. Once we returned, we enjoyed a nice dinner with our friends at the resort and Lilly's grandparents came to pick her up for the rest of the vacation. Chris was able to go back out lobstering and I could catch up on a little R&R and work.

The following day was full of fun with the girls...we did a couple of photo shoots for the blog, met a few friends at the bar over ice cold pina coladas and made plans for dinner at Pierre's. If you visit the Keys and have time to stop for dinner, a drink or even just to view the property- I highly suggest it. I've been a fan of Pierre's for almost 6 years now- way before it's popularity to bloodline. The food is incredible and the property is breathtakingly beautiful. The grounds are full of beautiful flowers, chickens, roosters- the house offers so much character and alone is the show stopper. We also decided on doing a few photo shoots here, which is why you probably noticed I was there...day after day. A fun fact: during a full moon- they participate in what's called a "Full Moon Party" I've personally never attended but I've heard it's worth checking out. Across from Pierre's is a resort called the Moorings- while we didn't stay there- I've been for a visit or two. The property offers a beautiful- tranquil stay. The resort offers cottages full of amenities and breathtaking views- the property is lined with beautiful tall palms and has been home so several major productions. Also beside Pierre's is a more casual dinning area on the beach called Morada Bay- the two properties practically connect but I hear the food and drinks are delicious! One must is that you arrive to Pierre's before sunset- have a drink at the bar downstairs and venture off onto the back porch. You'll catch the sunset in one of the most beautiful places- it's practically an attraction to Pierre's.
Our next day was our last full day and the vacation mourning had already set in with the thought of going back to reality. After breakfast at Robbie's (which if you've never been - you must go...and feed the tarpon) we decided to take the boat out to the sandbar to relax. This is something we'd do every weekend in Key West so it brought back all the nostalgia from Snipes. We packed a cooler and off we went- the weather was beautiful and the water was crystal blue- it couldn't have been a more perfect day. If you don't have a boat- don't worry... there is a boat service that will take you to the sandbar. After spending a few hours out in the water- we decided to head back in to get ready for dinner. We decided on a quaint place right on the water called "Lazy Days" most people coming to Islamorada LOVE Lazy Days- the atmosphere is fun and laid back. I recommend sitting outside on the bottom floor vs upstairs inside- the atmosphere is very different. We were surrounded by tiki torches, live music and a beautiful night. Our food was delicious- especially if you love seafood! One item you can't skip out on is the key lime pie martini... I know several other places outside the keys will make them but there's no comparison to a REAL Key Lime Pie Martini from the keys...


A couple of other restaurants in Islamorada worth checking out:
The Green Turtle- featured on the food network, Lorelei's, Mac's kitchen for key lime pie, Chef Michael's, Florida Key's Brewing, Sea Grapes Wine Bar and Bistro.
Things to do in Islamorada:
Theater of the Sea, Alligator Reef Light House, Snorkeling, Indian Key State Historic Park, Charter fishing
Driving to Key West:
Make a stop at : Square grouper in Cudjoe Key- phenomenal restaurant- order the tuna wasabi egg rolls. Baby's Coffee: Best coffee shop in my opinion- order the Cafe con leche. Hogfish on Stock Island- order the hogfish- it's a must!
I love your post and pictures!
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