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Exploring Islamorada

by Meghann on January 2, 2014

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…

Postcard Inn at Holiday Isle


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…

Sunset Cruise

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.

Island Body & Sol Spa

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.

Key West

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.

Paddle Boarding with Aquaholics

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…

Marker 88

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.

Bitton Bistro Cafe

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!

Bob’s Bunz

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!

Debbiy-Doo’s Deli

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.

Lorelei Restaurant & Cabana Bar


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.

Midway Cafe and Coffee Bar


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?

1 Michelle @ A Healthy Mrs January 2, 2014 at 9:52 pm

Sounds like an amazing trip!
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2 The Many Thoughts of a Reader January 2, 2014 at 9:56 pm

That looks like a perfect couples vacation! Maybe some day when I can take one of those without the child we can visit there! The Keys are in our plans eventually but that looks like a great trip! We are ended to Panama City for spring break this year. Any recommendations on cool places that aren’t ridiculous touristy? (I know this is such a cliché spring break trip but it’s a friends uncle’s house so it’s dirt cheap to stay on the water!)

3 Sabrina January 2, 2014 at 10:02 pm

Now that I my kind of vacation! I haven’t been to the Keys in nearly 15 years. This year my boyfriend and I made a goal to go somewhere besides Tampa and Orlando when we want to get away. It’s between the Keys or St Augustine.
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4 Ali January 2, 2014 at 10:17 pm

OMG, the paddle-boarding looks like so much fun! I’m going to have to try that sometime. My husband and I just got back from 11 days in New Zealand, and we would definitely definitely definitely go back. We’re already planning our return trip! So much to do and see. There’s never enough time on vacations. 🙂
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5 Julianna @ Julianna Bananna January 2, 2014 at 10:31 pm

haha i’m cracking up at the soup nazi reference! that’s one of my favorite seinfeld episodes, cracks me up every time.

sounds like a great trip! 🙂
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6 Sara @ LovingOnTheRun January 2, 2014 at 11:19 pm

Wow this looks so peaceful! I could really use a beach vacation – maybe next year!? My husband doesn’t get vacation time this year so we aren’t going to be able to go many places. Glad you all had such a great time!
Sara @ LovingOnTheRun recently posted..Progression Back to Running

7 Mrs. Swan January 2, 2014 at 11:37 pm

Ahh man! I wish I realized you were going there. Mangrove Mike’s is an amazing place to eat and I would have totally recommended it to you.
Mrs. Swan recently posted..Life is good.

8 Becky @ RunFunDone January 3, 2014 at 12:08 am

Oh my. I love the Keys.

I’m sorry that you were disappointed in your hotel. We got married in the Keys, and the resort manager for the resort that we eventually chose (which was great) was like, “When you look at other hotels, look for mold…” He was right. You can get ocean anywhere in the Keys, but ocean with nice rooms that are not full of mold and mildew is harder to find!

I’ve been to Bob’s Bunz. In Hollywood, we loved going to Islamorada Fish Company, because they give you this super delish sugar bread with your meal…but in Islamorada they don’t have any sugar bread at their Islamorada Fish Company location! So disappointing!
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9 Mary January 3, 2014 at 2:49 am

Such a shame about the hotel but good food and sunsets like that definitely make a trip! Glad you still really enjoyed it.
I love your black and white maxi dress.
Our last vacation was to New York for new year last year and we both loved exploring the city that never sleeps. We’d like to go back one day but there are so many other places I would love to visit first.
Our next trip is to Italy for our honeymoon in August and I’m really looking forward to it!
Mary recently posted..It’s all about the veg!

10 Jelena@ThoseLittleThings January 3, 2014 at 5:25 am

We went to Croatia last September and stayed in Green Lagoon resort, close to Porec and Rovinj. It was only 4 days, and we loved it so much that we are planning to go back this year again

11 Laura@SneakersandSpatulas January 3, 2014 at 8:23 am

What a bummer about the hotel, hate when that happens! And at almost $300/night…ouch! Looking at your pictures, it makes me even more excited to go on vacation to Mexico in March! I’m ready for some warm temeratures.
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12 Melissa (fitnessnyc) January 3, 2014 at 9:21 am

You look gorgeous in that black and white dress! And you’re smokin on the paddleboard. I am drooling all over looking at the veggie sandwich!!!
Melissa (fitnessnyc) recently posted..Fit Foot Forward

13 Lesley Moore January 3, 2014 at 9:22 am

My family went to Key West for the first time in Sept. 2012 and we fell in love with it. I really appreciate your detailed post because we have plans to go back in the near future!
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14 Runner Girl Eats January 3, 2014 at 9:46 am

I love islamorada. We stayed at something cove? and loved it! Big rooms with a full kitchen and gorgeous views. The Hilton is also really nice. Marker 88 and Lorelei’s are both fantastic…now I’m def craving fresh seafood and the beach!!

15 Morgan January 3, 2014 at 10:23 am

I love Lorelei’s! Favorite place to enjoy a meal!

16 Chelsea @ Designs on Dinner January 3, 2014 at 10:29 am

Looks like an amazing trip! The high for Monday is -16 here, and a trip to the beach sounds magical.
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17 Chelsea @ Designs on Dinner January 3, 2014 at 10:29 am

Looks like an amazing trip! The high for Monday is -16 here, and a trip to the beach sounds magical.
Chelsea @ Designs on Dinner recently posted..New Beginnings

18 Scott January 3, 2014 at 10:42 am

I proposed to my wife on Islamorada in 2012. We stayed at a little hotel made up of a dozen little cottages called the Islander, which she’s been going to almost every year since childhood, and has its own beach, which is where I proposed. Lorelei is right across the street and has the best rum runners in the keys! My future father-in-law got so drunk on them that he bought us all Lorelei T-shirts!
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19 Amanda Elizabeth January 3, 2014 at 11:37 am

What an awesome list! I agree sunset cruises are a must they are so beautiful! Looks like a fabulous trip!
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20 Allison January 3, 2014 at 11:57 am

Looks like y’all had a great trip! So jealous!

21 Elizabeth @ Positive Change January 3, 2014 at 1:34 pm

I love sunset cruises! Looks like a beautiful location! Your vacation has inspired me to look at vacation for the summer! 🙂 Last vacation was Disney and we are going back on Friday! 🙂
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22 Belinda January 3, 2014 at 2:13 pm

My hubby and I just went to Maui, and it was beautiful. Expensive, but beautiful. I recently started a travel blog of sorts, still working out the details, but here it is –

23 Bethany January 3, 2014 at 2:34 pm

I have stayed at the Postcard Inn in St. Pete and it was the same – obviously an old motel that they refurbished but not 100%. The bathroom was tiny and not updated at all. But, still reasonably priced for a beach front location and they had a lovely courtyard and funky / retro lobby. Cool concept but I wish they had followed through a bit better.

24 Kelly January 3, 2014 at 2:58 pm

Love this post! Thank you for mentioning places that offered GF options to eat!!

25 CATHY January 3, 2014 at 4:18 pm

Next Time check out and see if they have anything at Kawamme. they are townhouses and the development has a 2 private pools and a private beach. It’s lovely and much better then a hote. 🙂

26 Sarahf January 3, 2014 at 5:56 pm

The hotel sounds so disappointing, I’m glad the rest of the trip made up for it. I haven’t been on a real vacation in a while. I go back to London most years to see my parents, which I love, but I really want to visit Thailand or Vietnam!
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27 AndreaClaire January 3, 2014 at 6:09 pm

Shame about the hotel, but you’ll know for next time! Other than that, it sounds like a great trip. If I’m ever heading Florida way, expect an email asking for suggestions. 🙂

My last trip was to Switzerland. I lived there for a while so I was back to see my friends. I’d do it again in a heartbeat 🙂
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28 Rebecca@Running.Food.Baby. January 3, 2014 at 8:14 pm

Although the location and food looks amazing – $300 for a hotel room – yikes!!! Disappointed I would be!
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29 Annalisa January 3, 2014 at 9:23 pm

I always find the Keys sort of “hokey” but if you look past the tie-dye and dated decor, it’s gorgeous. We did a last minute trip there a few summers ago (flew to Miami, rented a car, drove to Marathon (cheap hotel called the Sandpiper was a great stop), and then spent 3 days in KW. We did a priceline deal for the Hyatt (waterfront) for maybe $80/night off season. We spent the next 3 days snorkeling and scuba. Seriously, KW has the most AMAZING ocean to play in. We’ve traveled all over the world and KW still has the most incredible snorkeling/scuba opportunities. It’s all the water coming together makes such unique ocean beds. We did the Dry Tortugas but that was kind of a bust. it’s a whole day and fairly spend but it was certainly something to cross off a list. I think if we didn’t do it we would’ve wondered what the hype was about.

Best restaurant, hands down, El Siboney for Cuban food. It’s sort of hole in the wall in the middle of the island but it was fantastic.

All this reminiscing makes me want to take another trip! I always thought we’d never go back but after going other places, KW wins for snorkeling.

30 Susan January 4, 2014 at 8:56 am

Sounds like a great trip! My husband and I frequent the keys, as we live near WPB. Lorelei’s is where you go for lunch not breakfast- we always stop and get blackened Mahi 🙂

31 Katie @ A Full Plate January 4, 2014 at 4:32 pm

Love this recap! I think I was in the keys the same time as you all! Some friends and I went the weekend after Christmas. I’ve been to Key West 4 times but it’s definitely not a couples kind of place. Glad to know that if me and my boyfriend ever want to getaway that Islamorada is the place to go!
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