Islamorada, Florida  What a TRIP!

Our recent visit to Islamorada in the Florida Keys was such a huge success. We were all very sad to leave, Islamorada provided us with 5 days of some of the best R&R we’ve had in a long time.

We choose to stay at Cheeca Lodge because they are just the very best accommodations when visiting Islamorada. For a family, there is really something for everyone. The hotel grounds are lush with tropical foliage and we love the walking paths that are lit in the evenings with tiki lanterns, it’s so pretty.


Upon our arrival with Cheeca Lodge, we were greeted by the front desk staff and a glass of champagne and fresh fruit water for the kiddos. The ambiance sets the tone for the terrific visit ahead.

cheeca-roomWe lucked out and got the 700 building which is a short walk down the tropical path to both the adult pool and the family pool located Ocean front. The rooms at Cheeca are larger than your average double queen room at other hotels. The bathroom offers both a sunken tub and separate shower, which is great when you are traveling with the kids. Our son loved the bubble baths after a long day in the sun and sand. The balcony is screened in and has a small bistro table with chairs so that you can enjoy your morning or evening on the patio watching the tropical birds and even iguanas running around. The screen helps with the bugs – it is the South and the bugs can be fierce but the screen is perfect. We brought a deck of cards and enjoyed playing gin-rummy outside after dinner.

fishing-jackThe kids all found their own little slice of heaven at the hotel. Our youngest loves Camp Cheeca, while our son hits the pier for some fishing. The hotel provides fishing poles and you can purchase your bait right there on property, so it’s convenient for Mom and Dad. We practically had to drag our son off the pier for lunch and dinner. It’s perfect for the kids because it’s safe and there are a ton of other kids from all over the world fishing. Our son met many other boys from as far away as the UK and others from Alabama.

Camp Cheeca is great for kids aged 5 and up, they spend the day playing in the sun and water and offer arts and crafts such as coconut painting. My daughter loved camp so much she didn’t want to leave when it was time for us to pick her up. There are endless activities for the kids if they decide to not do Camp, from paddle boarding, kayaking, fishing, bike riding, swimming and tennis. All complimentary and included in your daily resort fee.

With several restaurant options on property from Sushi to Italian you don’t have to go far to enjoy a nice meal with the family. The resort also offers kids night out so that parents can enjoy a romantic dinner over looking the ocean.

cheeca-sushiWe dined our first night at Nikai Sushi, it’s on the roof top of the hotel and has a breath taking view of the ocean, the warm breeze and delicious food made the first night a perfect way to kick off the vacation.

For those of you who know us, breakfast is one of our favorite meals of the day. Our kids are breakfast connoisseurs — and it was unanimous that Cheeca has a really great breakfast buffet. view-from-breakfastThe tables overlook the beachfront and if you’ve not seen a Islamorada morning on the water, you must put it on your bucket list. The ocean is calm and glassy and the sun shining on the water is such an amazing way to start your day. I also love that breakfast is available until 11:30am so if you aren’t an early riser, you don’t have to rush to breakfast!







I found myself a nice little shady spot around the family pool that I could relax and catch up on my favorite magazines. The staff at the pool were so friendly and accommodating, they made sure you had everything you needed from ice cold water to fresh towels. They have a great little menu poolside that includes a kids section, they take your order and deliver it to your chairs poolside. Our favorite was the fish tacos and goat cheese salad. Yum!

DAY 2: Adventuring around Islamorada

We had planned a boat rental for the day so that we could do a little snorkeling and the boys could do a little off shore fishing. Thanks to the help of the folks at Keys Boat Rental located at Smuggler’s Cove we had a perfect little 19ft Angler for the day. With the help of the bait shop at Smuggler’s, we were setup for fishing and a great map of the best snorkeling off Islamorada. We picked Hen and Chicken Reef because it was directly out of the channel and slightly to the North. We tied up on the buoy and the kids jumped into the beautiful blue waters. Immediately they were greeted by a school of parrot fish wearing bright yellow lipstick, our youngest was thrilled that they were all around her.

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Our next stop on our boat adventure was to the Islamorada Sand Bar, where you can anchor and wander around the sand bar looking for star fish, small fish and of course take in the sights and sounds of other boaters parked next to you. We happened to come in next to a group celebrating a wedding from North Carolina and joined in on a game of Sand Bar Baseball… It was a riot!

To keep everyone in our boat happy (the fisher boy) we headed out of the sand bar after a few hours of relaxing and went straight out about 1/4 mile to a 15-18ft depth to drop our fishing poles. We had frozen shrimp for our bait, per the suggestion of the Smuggler’s bait shop owner. There were plenty of bites but unfortunately we didn’t catch anything. I like to think that we fed the fish on our way back into the marina 😉

It’s all good though, everyone on the day trip had a great time and did something they each enjoyed.

Upon returning the boat to the Smuggler’s Cove marina, we were met at the dock by a gentleman who helped us tie up and as part of the rental you are responsible for the gas on return. The whole day on the boat cost us a whopping $15!!! Yep, that’s right. An entire adventure on the water in our own boat …. total cost: $250 for the full day 8am-5pm and the gas: $15 = $260!

I love when a great plan comes together…

We were pretty wiped out from the full day in the hot sun so we decided to grab a pizza on the way back into the hotel. There is a little restaurant just on the other side of the road from Cheeca called “Tower of Pizza” they offer a great little menu from pizza to Italian dishes. We ordered pizza and their chicken parmesan and it was a huge amount of food that was very tasty. They will deliver to Cheeca too, but picking up is just across the street. You can actually walk out the front gate of the hotel and it’s just to your South. They offer dine-in tables too if you want to eat in.

Day 3: Pool side fun and birthday dinner celebration

We set this day to be a “nothing” day. Meaning, we had zero plans except for dinner at 6pm. Our youngest pleaded to do the half day PM camp and our son of course wanted to be loaded up with bait and left to fish at the pier, ALL DAY LONG. I found a spot poolside and our oldest joined me with a book. Knowing the kids were having a great time, it was really nice that I could truly relax and enjoy some time in the sun. I actually closed my eyes for a little poolside nap for about 20 minutes. When was the last time you napped ocean front ? Exactly. 

Around 3pm we pried our son off the pier and the 4 of us grabbed some bikes from the guest adventure house and rode to the ice cream shop just outside the resort. Our youngest isn’t the best at riding just yet so we wanted to do this while she was enjoying camp. The main street can get a little busy outside the resort, but there are sidewalks some of the way. The bikes were great, they had little baskets on the front for all our wallets and waters. The little ice cream shop was cute and offered a great selection. My husband rode a little further while we were enjoying our ice creams to his favorite little cigar shop just North of the resort called “Cigars in the Keys”, the family owned shop has a great selection of cigars and the pricing is very reasonable. We sent a few hotel guests to the shop once they smelled the cigar my husband enjoyed on the beach later that afternoon. Check them out!

We headed to our dinner reservations at Lazy Days which is about 3 miles South of the hotel. The restaurant is an open air space that offers an upstairs dining experience both inside and out overlooking the ocean and they recently opened the beachfront dining which has tables directly on the beach. We reserved a few weeks in advance because they do get busy and there is always a wait for the outside tables. The menu is typical Keys entrees; seafood, steak and lots of conch! They offer a daily chef special that has at least a dozen entrees to choose from. My husband and I started with their recommendation of Oysters Rockefeller and they were really good. Lots of sauce and cheese! We both chose entrees from the chef specials, I had the blackened rib-eye and he had the snapper sautéed in a key lime butter. Large portions and delicious flavor on both our meals. The kids ordered from the kids menu which offered a great selection such as steak, chicken, fish and burgers. They both had the steak and it came with fries. Our oldest had the Filet and she said it was really good too.

We passed on desert because we were so full, there was just no space left — I had spotted a Starbucks that was newly opened the previous day on our way back from the boat rental and we thought a little after dinner coffee was the perfect way to end the day. The Starbucks is located in the Post Card Inn parking lot.

DAY 4: More relaxing and Camp Cheeca

We pretty much did absolutely nothing on this last day of our trip. Camp, fishing, relaxing poolside, eating and sunbathing.

After another perfect breakfast buffet on the water, I hit the chairs to enjoy my magazines and the kids were off to their pier fishing and camp activities. The weather was perfect, although hotter and more humid than the previous days, the pool was the fix for that.

Around 3pm we decided to head out on the kayaks and take in the view of the resort and neighboring properties. I’m not sure if you watch Bloodline the netflix TV series, but it’s filmed next door to the Cheeca Lodge at a place called the Moorings. It’s a great show filmed in Islamorada and if you watch it, you can easily point out many spots featured in the show. From the kayak you can paddle along the beach and see the resort and the main house where the tv series takes place. Just off the beach is an old tree that broke off during a lightning storm and settled in the water. It’s now home to many little creatures and fish that you can see in the foot of water. We saw several Rock Lobster and the tiniest little tropical fish. Bring your snorkel mask if you’ve got one, you can have a lot of fun out there.

When we returned to our room that afternoon, we were greeted by a delightful tray filled with fresh fruits, cheese and a bottle of champagne and sparkling waters. The card attached was thanking us for our stay and was signed from Bob, the new general manager of the hotel. It’s this type of first class guest service that makes Cheeca Lodge the best accommodations in Islamorada. During our week stay, the room was always clean, fresh towels upon our return from the beach and even a turn down service with shell shaped chocolates on our pillows. Fresh bottled water for us in our room each day, complimentary. It really is the little things that make your stay that much more enjoyable.

Our last night we dined at one of our favorite spots, the Lorelei restaurant. It’s waterfront dining is situated on the Florida Bay “Back Country” and offers the most amazing sunset dinners. The food at lorelei’s is excellent. Our favorites is their conch chowder, fish tacos and their chef prepared daily fish entree. michaeltrixxEach night there is live music, some of the best in The Keys. A few nights a week they offer a magic show by a gentleman named Michael Trixx — he is a former rock band bassist and his magic show is outstanding. It happens just after sunset and the lighting and specials effects with his show are not to be missed. My kids look forward to the show every time we visit.

The cons of this trip… having to leave!



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