Derek and I celebrated our first wedding anniversary (a couple of weeks early) in Islamorada last week. Since I’d never been to the area before, I thought I would share a bit of where we stayed, what we did, and where we ate.
Where We Stayed…
As much as we LOVE Key West, we were hoping to stay on a Key with a reputation of being a little more on the quiet side of things. After doing a little research on Trip Advisor we discovered Islamorada was known for great fishing, quiet resorts, and delicious restaurants. Once we picked an area, we narrowed it down to Postcard Inn on Holiday Isle based on reviews and a pretty website (I’m a sucker for a good website).
I was impressed with Postcard Inn’s website, but I’d be lying if I said the property itself impressed me. It was basically an old motel that had recently been renovated to give it a more modern look. Unfortunately the “updated look” was really just a fancy paint job.
Our room was close to $300 a night and it was basically 4 walls with a king sized bed wedged in the middle. We didn’t have a closet or much room to really walk around. The walls were discolored in areas, the shower curtains had mildew on them, and the walls were paper thin.
The beach was nice thanks to the beautiful view of the ocean, but the pool was basic and the swim up bar could have used an update.
I also wasn’t a fan of the exact location. If we wanted to go anywhere off property we had to drive, nothing was within walking distance. We found ourselves hopping in the car to drive to breakfast, lunch, dinner, and if we needed anything else.
However, the resort was quiet and we were big fans of that. There were always chairs available by the pool, the drinks at the bar were always provided with a heavy pour, and the views were fantastic. I’m so happy we stayed in Islamorada (and I would return in a heart beat!), I’m just not sure I would go back to Postcard Inn.
Where We Played…
Unfortunately, the weather the first few days of our trip wasn’t the greatest. We had really nasty clouds every morning, but it usually cleared up in the early evening – just in time for unbeatable views of the famous Florida Keys sunsets.
On our second night we paid $35 a person for a sun set cruise with Islamorada Boat Tours, which were docked at the Postcard Inn marina.
The sunset cruises last an hour and a half and set sail an hour before the sunset. You’re allowed to bring whatever food or drink you would like aboard. Derek and I opted for a bottle of champagne.
I highly recommend taking a sun set cruise if you’re ever in the Florida Keys. The captain took us around Islamorada and gave us some history on the area, as well as taking us by some gorgeous houses. The boat ride was leisurely and so relaxing. We even lucked out with the clouds clearing just in time for a picture perfect sun set over the water.
Beautiful. Absolutely beautiful.
On our third day, Derek and I had a couple’s massage at Island Body & Soul. The location was small, quaint, and gave off the perfect relaxing Island vibe. The owner was very talkative and very friendly. We both loved our massages and highly recommend Island Body & Soul if you’re ever in the area.They do offer massages on the beach, but it was unfortunately too windy for us to take advantage of the day we went.
We originally weren’t planning on making a day trip to Key West. It was still an additional 2.5 hour drive from where we’d be staying and our plan was just to relax and do nothing. The rain and clouds were actually what encouraged us to change our minds and spend the day in the car, versus staying in our hotel room.
In the end, I’m so glad we decided to make the trip. We left early to beat the traffic and the drive was gorgeous. It was a straight shot down and a straight shot back. We had just enough time in Key West to check out our favorite spots, without feeling overloaded by the thousands of tourists spending their holidays on the tiny island.
I would highly recommend dedicating a day for a quick trip to Key West, it’s 100% worth it.
The sun FINALLY came out to play on our last day and we took full advantage by renting paddle boards from the Aquaholic Adventures shop on property. They were $30 an hour, but would only have been an additional $10 for every hour after that.
I’d only been paddle boarding once in Orlando, but Derek had never been. The water was very calm and flat around the hotel – perfect for beginning paddle boarders like use.
We both LOVED it. Derek was skeptical going into it, but in the end was asking if we could go paddle boarding again when we’re in Tampa (hell yeah!). AND that’s after he fell off a couple of times.
Leave it to my husband to test the limits on paddle boards.
Where We Ate…
I can not recommend Marker 88 enough, hands down my favorite place we ate at while in Islamoradra. You can read my original review HERE. I would recommend planning your dinner around sun set. That was our goal, but we missed it by a few minutes. Also, if you’re gluten free they have a dedicated gluten free menu and even offer gluten free dinner rolls.
This was a cute bakery that specializes in crepes, pastries, and espresso drinks. It’s run by a husband and wife team, and their daughter works as a server. If you’re gluten free they offer the option of buckwheat crepes.
I ordered the nutella and strawberry crepe and asked if there was a possibility of getting a scrambled egg on the side (they also offer savory crepes with egg, so there were eggs on the menu). The server was very polite and said she could do a sunny side up egg, but wasn’t sure on the scramble.
The restaurant is set up with an open air kitchen, so we could hear everything being said in the kitchen. We heard her politely ask the chef about the possibility of scrambled eggs and his response of “No scrambled eggs!” said loudly, in a very thick accent that resembled the soup nazi screaming “no soup for you!” on Seinfeld. Both Derek and I started cracking up and the saying “no scrambled eggs for you!” became our new tagline for the trip.
No scrambled eggs for you!
OMG. The sticky buns! Amazing.
We ate breakfast here one day and Derek and I each ordered omelets, which were good but nothing special. According to Yelp, they were famous for their sticky buns, so I ordered a mini sticky bun to-go. First of all, I loved the option of the mini sticky bun. It was the perfect size for one. I ate it later that afternoon and it was still very moist and full of delicious cinnamon nutty flavor. I should have got a whole box of them. Delicious!
Derek and I wanted to keep it easy by eating on property for our last day. Unfortunately the on-property restaurant was packed. We sat down and watched the server ignore us for 10-15 minutes. We eventually left without being served, both in terrible moods.
I turned to Yelp and found Debbie’s Deli down the street, which ended up being a blessing in disguise. The deli wasn’t much to look at from the outside, but never judge a book by its cover (especially when it has a near perfect rating on Yelp).
I instantly loved the shabby chic deli. We were greeted with paper menus and told to help ourselves to the drink case and let them know when we were ready to order.
I ordered the veggie loaf, which was huge and loaded with some much-needed roasted veggies, havarti cheese, and homemade hummus, all on fresh baked bread.
Oh, man, this sandwich was good. I devoured the whole thing and loved every bite.
Derek ordered the cobb salad. I’m not sure this photo does it justice, this bowl was HUGE and filled to the brim with toppings.
In the end we were so happy we weren’t able to be served at the other place, otherwise we would never have discovered Debbie’s. This place earned 5 stars from both us.
Breakfast with a view! This was probably our cheapest breakfast of the trip, so if you’re looking for a great view with lower prices this is your best bet. It was very casual with a traditional breakfast menu. I had the basics: eggs, toast, and grits. The food wasn’t special, but the scenery wasn’t bad.
The cutest cafe with the BEST coffee on the Island. I drove out of my way to get coffee here. This place put Starbucks to shame (which is good since the closest Starbucks was 30 minutes away!).
Again, it was a GREAT trip. If you’re looking for a quiet, low-key getaway, I recommend staying in the upper Florida Keys. Derek and I both loved it and can’t wait to return (hopefully when the sun’s out!).
What’s the last vacation you took? Would you go back?