Islamorada Has My Heart

My husband and I have made it a tradition to go back to the spot of our engagement each year on our anniversary. On our first anniversary I was pregnant with Juliet. Our second, we got to bring Juliet while I was pregnant with Anniston. And now, for our third, we got to bring both of our girls, and share one of our favorite places with them.

Our week started a little rough. Every storm tracker you looked at had Hurricane Matthew headed our way. By Wednesday, we had our hurricane shutters on the house, and had our whole family worried about how our 1960’s home, a mile from the beach, would hold up in the storm.

We were still planning on heading to the Keys on Friday morning, hoping to escape the storm and relax on a beach that was not standing in the way of the Category 4 hurricane. But, Thursday morning we received a call from The Moorings, our hotel in Islamorada, and they actually offered us an extra night, no charge, if we wanted to come early. I packed up myself and both girls in under an hour and by noon we were on the road.

It started raining the minute we drove up to our cottage, but we barely noticed, because we knew it was still better than sitting in a house with two kids, and possibly no electricity.

The best thing about staying at The Moorings is that it is a village of 18 cottages and homes directly on their own private beach. For us, this meant Juliet got her own bedroom, we had a full kitchen, two bathrooms, we didn’t have to deal with crowded beaches, and there is no one in a hotel room next to us to complain about a whiny toddler or crying baby. It is the perfect family vacation.


We spent the first day indoors, only leaving our house to grab pizza from our favorite little pizza place down the road. But, the entire rest of the weekend was spent either at the beach or the pool. Juliet had the time of her life chasing the birds on the beach, shoveling sand onto anything and everything, “swimmin” in the pool with her “ducky”, and lounging in the many hammocks, which she swore were swings, along the beach. It was the first time Juliet really enjoyed playing in the sand, and it was hands-down because of her crocs. She has always hated the sand and refused to walk in it, but this time I left her shoes on and she ran laps around the beach. I’ve heard from so many moms that their children won’t play on the beach or walk in the sand, so if you haven’t tried this yet, do it.


I’m not sure if a little bit of sibling jealousy has kicked in recently, or if Juliet is just a true mama’s girls right now, but she basically will not let me put her down. That meant that my husband got in a lot of quality time with Anniston throughout the weekend.

This was probably the biggest factor in making our vacation with two kids, under two, stress-free. I was in charge of Juliet and my husband was in charge of Anniston, for the most part. Kevin hung out on the lounge chairs with our sleepy baby while Juliet and I played, swam, and basically did whatever she wanted to do.  We did manage to squeeze in some pool time with baby A between her naps, and she seemed to love the water as much as her big sister.


We also make it a point, every year, to go to Morada Bay for dinner at least one night while we are staying at The Moorings. It is the restaurant where our parents were waiting to surprise me, after Kevin and I got engaged. The restaurant is on the bay side of the Key, directly on the beach, so it has the most amazing sunsets. Although dinners are a little earlier for us these days, and we knew we wouldn’t actually catch the sunset this time, we still wanted to take the girls to one of favorite spots.


The weekend flew by, and before I knew it I was dropping Kevin off at the airport for another week away for work. But this weekend was our first vacation as just us, a family four. It was relaxing for us while being almost magical for Juliet. Watching her eyes light up when she saw birds that she could chase, listening to her say “bye boat, bye swimmin” each night as we went for our walks on the beach, and just taking in every ounce of a 20-month-old’s excitement to be in a new place, made this a weekend I will remember forever. Plus, with a backdrop like this, I couldn’t help but take a million pictures of my little beach bum. I could not have asked for a better vacation, and I am already looking forward to next year.


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  • Reply Rosa

    Sounds like an amazing vacation! I’ve never been to the Keys but this looks perfect! Also, where is your blue striped top from? Love it!

    October 18, 2016 at 10:11 pm
    • Reply colleen

      Thanks! The keys are absolutely beautiful!! My top is from J Crew and it is still available!!

      October 18, 2016 at 10:24 pm
  • Reply Stephanie (Ortner) Stadler

    Colleen – This post has MY heart! I’ve seen you post your blog but haven’t had a chance to read through anything until today. My husband and I got married at Pierre’s. Our ceremony was right there in front of the leaning palm tree and our reception was upstairs in the restaurant. Islamorada is everything to us, so it makes me so happy to hear that someone else has fallen in love with this little island paradise as well!

    November 3, 2016 at 10:43 am
    • Reply colleen

      LOVE that our little special place is special to you as well! It really is a dream there.

      November 16, 2016 at 10:28 pm

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