The Ultimate Babymoon in Islamorada Florida

When looking for the perfect babymoon destination, I knew that we wanted to go somewhere warm and relatively easy to get to. Given the times we are living in, international babymoon locations were completely out of the picture. Although we could have went to the Caribbean, there are so many COVID testing restrictions in place now that it would have only added additional stress to a trip meant to DE-stress and relax.

Babymoon in Islamorada at Cheeca Lodge and Spa

Our top babymoon goals were rest, relax, eat good food, and spend quality time together before we add our newest addition to the family in 3 months. As excited as we are to add baby Tamburo to our future travels, we know that the way we travel is about to look a whole lot different!

After lots of brainstorming destinations from the Carolinas to the West Coast; we landed on the Florida Keys. Check out all the details on our Islamorada babymoon below.

How to Get to Islamorada:

Islamorada is located in the Florida Keys; approximately 30-45 minutes south of Key Largo and ~30 minutes north of Marathon. Lucky for us, coming from Atlanta we only had a quick 1.5 hour flight into Miami. We rented a car at SIXT and took off on the hour and a half journey to Islamorada. (Or maybe you just want to stay in Miami..?! Check out my 48-hour Miami travel guide here).

Immediately after landing we were welcomed with that lovely Florida sunshine. With our sunroof open and windows down, we enjoyed the scenery as we drove on the Overseas Highway past Key Largo, Plantation Key and into Islamorada.

Technically, you could also fly into the Key West airport but from my experience, that is always more expensive and it’s about the same if not a bit longer of a driving distance.

Where to Stay in Islamorada Florida on your babymoon:

If you’ve been following along my blog for a while, you know that I actually really enjoy the travel planning process. One of my favorite parts is the research that goes into finding the perfect accommodations for our trip. I could scour the internet for hours looking at gorgeous resorts, spas, and hotels of all types and never get tired of it.

There is no shortage of awesome accommodations in the Keys. With a little research and an old friends’ recommendation, we landed on Cheeca Lodge and Spa. Although a bit of a splurge, this resort truly has it all right at your fingertips.

Babymoon at the Cheeca Lodge and Spa in Islamorada Florida

With so many details to share about our stay at Cheeca, I have created a second blog post specifically highlighting and reviewing our time at Cheeca Lodge. You can find that here (coming soon)!

To keep it brief, Cheeca is conveniently located close to some of the top restaurants and bars in Islamorada. Better yet, if you don’t want to leave the resort, you don’t have to. There are endless activities to keep yourself busy staying in, while never leaving the property itself. From water sports to tennis and even a 9-course 3-par golf course, there truly is something for everyone.

Our favorite part was the ease of eating at their 3 main delicious restaurants, swimming in one of their 3 pools, 2 hot tubs; relaxing in our resort-view suite and playing a nice competitive game of tennis to kick off the days.

The pier at Cheeca Lodge and Spa and the gorgeous views from the pool

Where to Eat & Drink on your Florida Keys Babymoon:

Nikai Sushi:

Craving foods that are “off-limits” seems to be my new norm and that includes sushi. I have been craving sushi for the past several months so finally we found ourselves at the hotel’s on-site restaurant, Nikai where I was able to treat myself to a big bowl of steamy edamame and a sushi roll. Just tell the waiter that you can’t have raw fish and they will accommodate the roll accordingly. We loved the atmosphere; especially the rooftop terrace where we sat overlooking the ocean and pier out front.

Sushi roll and mocktails at Nikai Sushi Restaurant at Cheeca Lodge and Spa on our babymoon

Mia Cucina:

Another great on-site dining option at Cheeca. Mia Cucina is full of Italian offerings and they start you off with the best ‘tomato cheesy bread’. Think pizza, salads and amazing gelato to finish it off. This turned out to be the most affordable of the 3 on-site restaurants that we visited.

Atlantic’s Edge:

Last but not least, the third main restaurant at Cheeca that we visited. (Technically there is the tiki bar but its food offerings are essentially the same as Atlantic’s Edge and then 25 South which we didn’t get to visit).

Atlantic’s Edge is definitely the ‘fanciest’ menu of the three and the most expensive. We opted to just get breakfast there to save some money and the breakfast did not disappoint. We went big and enjoyed their acai bowl, lattes, the alligator reef lobster blt omelet, AND …their cuban french toast. I would be lying if I said we didn’t eat our way through our babymoon.

Enjoying a delicious mocktail mojito at the pool bar at Cheeca Lodge and Spa in Islamorada
Enjoying a no-jito by the Cheeca poolside

Marker 88:

Marker 88 is a fantastic place to watch the sunset. Times continue to be a little strange given COVID, so of coarse there was social distancing, less tables available, longer waits, etc. However, there was still a lively atmosphere, live music, and gorgeous views while you wait. Everything on the menu looked delicious but I can only speak to the crab cake starter (SO good), the shrimp zoodles (healthy but still tasty) and buffalo chicken sandwich (not your typical item at a seafood restaurant but surprisingly very good!).

Florida Keys Brewing Company:

Never would have thought that our first stop on our babymoon would be at a brewery but there we found ourselves, hanging out in the colorful and tropical setting of Florida Keys Brewing Co. For the guy, it’s great as there’s a big selection of local beers and for the girl (if you’re also pregnant) there is a food truck (this go around it was a taco truck) on site with good food and a fun atmosphere to match it.

Hungry Tarpon:

Located at Robbies of Islamorada, Hungry Tarpon came highly recommended on almost all of the blogs that I read before our trip. This was the perfect off-site breakfast choice as we were looking for something for budget friendly in a laid-back environment and that’s exactly what Hungry Tarpon was. This place looks like it gets pretty rowdy later in the day as it’s essentially a dive bar (or at least the looks of it).. walls covered in dollar bills and a very casual staff. The food was cheap and came in huge portions. You can’t go wrong with a stack of chocolate chip pancakes and their burrito fria diablo.

Exploring Robbies after Breakfast in Islamorada Florida
Robbies of Islamorada

Midway Cafe and Coffee:

Looking for something on the healthier side? I know I was. Typically on vacations, I am able to find more wellness-focused restaurants and cafes. I have to say, I had a much harder time finding healthy spots around Islamorada but I did come across Midway Cafe and Coffee right down the street. This became my go-to two days in a row for their fresh fruit smoothies, almond milk lattes, and healthy scrambles. As far as what to get, I’d recommend their breakfast pita, skillet your way, and the island greens smoothie.

Midway Cafe is the perfect healthy breakfast or lunch spot to grab a smoothie in Islamorada Florida
Fresh fruit smoothie at Midway Cafe in Islamorada

Lorelei Restaurant and Cabana Bar:

Known for it’s breathtaking sunsets and mouthwatering, famous key lime pie. Lorelei Restaurant and Cabana Bar is a must-stop for an evening sunset and dinner if you have the time. Live music, views over the water, tasty frozen cocktails/mocktails, casual seafood entrees and their famous ‘ frozen’ key lime pie make for the perfect date night out.

Enjoying one slice of Key Lime Pie after another on our babymoon to Islamorada Florida
The famous ‘ frozen’ key lime pie at Lorelei

What to Do around Islamorada:

Take a road trip:

Driving through the Keys can be an activity in itself. The Overseas Highway that stretches from the upper keys of Key Largo all the way down to Key West is unique and comes with gorgeous views. Put the windows down, turn on some good tunes and cruise from Miami to Key Largo, through Islamorada, down to Marathon and beyond. Maybe even make your way all the way down to Key West for some extra fun!

Sunset Sail:

This was one thing on our itinerary that I was REALLY looking forward to but sadly didn’t happen thanks to the high winds. (Although, trying to do a sailing excursion while 6 months pregnant on high-wind rocky waters probably would have been a disaster anyways)

Cheeca Watersports does offer it’s own sunset sail which is who we signed up with. However, I have to say if we could do it over again, I would book elsewhere. Long story short- we were not impressed by the communication of the Cheeca Watersports staff and we got cancelled on twice with very short notice. The other company we looked into booking was Sundance Watersports. By the time we got cancelled on the 2nd night (because not enough people were signed up?!), I tried to call Sundance but they were completely full. Learning lesson – book with Sundance to begin with and you have a better chance of getting out on the water!


There is an abundance of water sports available throughout Islamorada. From stand up paddle boarding, to kayaking, to learning how to wind/kite surf to all-day boating, snorkeling and scuba diving excursions; there is truly something for everyone. I was pretty limited being very pregnant and once again, the high winds made it difficult to go out for an afternoon of kayaking but if we end up back down in Islamorada we will definitely take advantage!

Sport Fishing:

Can’t speak to this but I can’t write an entire blog post about Islamorada and NOT mention sport fishing. Islamorada is the sport fishing capital so if you have a love for fishing, you can’t miss out when you come here.

Bumping at 25 weeks pregnant on our babymoon in Islamorada Florida
Heyyyyyo baby! Baby T at 25.5 weeks getting some much needed Vitamin C
happy as a clam sitting on the end of the pier at Cheeca Lodge and Spa on our babymoon!
Happy as can be – Dad-to-be

Thanks for checking out our babymoon! I hope that this provided a glimpse into where to stay, eat, drink and explore around Islamorada Florida. Feel free to reach out directly with any questions.

If you are looking for other great destinations to visit with your significant other, check out my post here sharing some of my very favorite spots around the world.