Islamorada and the Florida Keys with Kids

img_4315.jpgMy parents visit Islamorada (village of islands) in the Florida Keys almost every year in the late winter.  With a baby in tow, 2018 seemed like the perfect year for a relaxing family vacation.  While the other trips with our son were either spontaneous or were tied to weddings (in the case of Nebraska, New Jersey & Kentucky) this was the first “real” vacation we had planned as a family.

Our vacation planning didn’t start off quite how we expected. Almost as soon as we found a rental home, Hurricane Irma hit and devastated a lot of the Keys.  We had flights booked and were determined to go to contribute to the tourism in the Keys during a time when many people were going elsewhere.

How to Get to Islamorada

There aren’t any major airports in the northern part of the keys, so the quickest and most cost effective option is to fly in and out of either Fort Lauderdale or Miami International Airport.  We flew into Fort Lauderdale-Hollywood International Airport since Southwest Airlines flies there and I find it much easier to navigate than the Miami (both the city and airport.)  We rented a car and drove about 2 hours south to get to Islamorada, which is just south of Key Largo.

Where to Stay in Islamorada

I loved Islamorada for a relaxing, family vacation and definitely recommend getting a rental home through AirBnB or HomeAway.  Unfortunately, with the hurricane hitting, the first two rental properties we booked were in pretty bad shape and could not be guaranteed to be fully repaired by our trip.  The third one we found within our price range ended up working out perfectly and had the 5 bedrooms and heated pool that we were looking for.  We loved the outside area with the heated in-ground pool, covered patio and dock along the water and could have spent all day every day outside at the house.

Tip:  This might be obvious to most people, but be sure to ask about stairs (inside and outside) and fencing around the pool when renting a house with small children.  We discovered after arriving that the house was a little unsafe for kids with a steep spiral staircase inside and lack of fence between the back of the pool area and inlet.  This was the first time we ran into this issue- lesson learned! ALSO keep in mind that many rentals in the Florida Keys are monthly, especially during winter months.  With a limited inventory of weekly rentals, I’d recommend booking early to make sure you have the most options within your price range.  If you’re looking for more of a resort setting in Islamorada,  Mooring’s Village is supposed to be a great a higher-end option and Drop Anchor Resort has more reasonably priced accommodations, with both being family-friendly.

What to Do in Islamorada

  • Fishing– If you have slightly older children, deep sea fishing is the biggest draw to Islamorada.  The guys went offshore fishing one day and had a great time with Captain Larry Wren with First Choice Charters at Whale Harbor Marina.  While they didn’t catch the sailfish they initially went out for, they had a great day and caught wahoo, red snapper and king mackerel.
  • Walk with the Manatees- Islamorada is known for the manatees that inhabit its many inlets and waterways.  One of our favorite things to do was to go for walks in the morning and search for the manatees. On the left you can see how close they came up to the dock in back of our house, and we spotted several walking in the neighboring streets.
  • Theater of the Sea– One of the main attractions in Islamorada, Theater of the Sea is primarily made up of a few rotating shows throughout the day.  We saw the dolphin show first and my 3-year old niece, along a few other kiddos, was chosen to feed the dolphins.  The next show we saw was the sea lions which our 10-month old LOVED.  The look of pure joy on his face was priceless- I wish I had more pictures!  There was also a short bottomless boat tour and fish and reptile walk where we learned more about the rescued sea turtles that resided there.   It’s recommended that you set aside about 2-3 hours to see the shows, with more time added if you want to partake in some of the extras including, painting or swimming with sea lions or dolphins.  We didn’t do any of the animal experiences this time but definitely will consider it in the future when the kids are older.
  • Robbie’s Islamorada– One of the main attractions at Robbie’s is feeding the fish, which really is really just trying to throw food at a pit of fish with sharp teeth before one of the nearby pelicans snatches it out of your hand.  (I know, i’m really trying to sell it!) I didn’t get too close since I had my son in the stroller, but my niece and my brother had a blast.  There’s also an open air market with several local vendors for handmade souvenirs and paintings, and we took some time to have a drink outside at the bar and restaurant while they were playing live music.
  • 29136660_10160073931125207_5927166322881331200_oAnne’s Beach– This is a beautiful public beach from what I could see, but unfortunately it had not yet re-opened from the hurricane when we were there.  Luckily, we had access to a private beach through our rental property.
  • Key West– It’s just about a 2-hour drive from Islamorada so totally doable for a day or quick overnight trip.  We were fortunate enough to have the grandparents babysit overnight for a kid-free dinner and night out (which, let’s face it, we could barely stay up past 11pm.)  We stayed at the La Concha Hotel & Spa; a boutique hotel right in the heart of Key West.  The rooms were beautifully decorated and the on-site facilities including the pool and the central location were perfect. I would definitely stay there again.  For dinner that night we were craving sushi and had a yummy dinner at Mangoes Key West and went to a few bars before before ending the night with an amazingly huge and yummy cookie sundae right across from our hotel at Mattheessens Key West.  The grandparents drove the kiddos down the next day and we visited the Key West Butterfly & Nature Conservatory.   The look on my son’s face when seeing butterflies come right up to him for the first time was priceless, and while the conservatory was small it was jam-packed with beautiful plants, birds and butterflies.  We also took the requisite photo op at the Southernmost Point and spent time aimlessly walking around before the hot Key West sun quickly tired the kids out.

Where to Eat 

We made a lot of family meals at home but here are a few favorites for laid back family dining:

  • Lazy Dayz– One of the most popular restaurants in Islamorada and a great choice for our first night out.  They have a ton of fresh seafood options, a number of indoor/ outdoor seating options and live music right on the beach.IMG_4314
  • Lorelei Restaurant & Cabana Bar– We went here for breakfast with the kiddos when the guys were out fishing one morning.  We were looking for a casual waterfront spot and it was exactly what we wanted.  The restaurant is probably known more for being a drinking establishment than a breakfast place, but our food was decent and the kids loved all the birds and fish by the water.
  • Midway Cafe– We stopped here in need of a quick caffeine fix one day and of course we had to try the key lime pie.  Midway is known for serving the original key lime pie (the “real” kind with merengue on top) and it has a great selection of breakfast, baked goods and specialty coffee drinks.  The decor is bright and cute, service was great and all the food I saw coming out looked yummy. Shoutout to the owner who made all 6 of our lattes with a hand espresso press!
  • Morada Bay Beach Cafe– This is an outdoor cafe right on the beach for a little more of an upscale lunch spot (but still kid friendly during the day.) I had the Beach Cafe Salad with ahi tuna that was super fresh and the Ketel Beachside to drink.  This place is also known for their monthly adults only full moon party right on the beach, and it’s a filming spot for the TV show Bloodlines.
  • Islamorada Fishing Company–  I like this place more for the ambiance (waterfront, live music) than the food but we took advantage of their fresh fish preparation option.  Since Islamorada is known as a fishing town, many of the restaurants let you bring the fish you catch to have them prepare it and serve family style with sides of your choice.  Its a nice option if you like the atmosphere of going out to dinner but want the satisfaction of eating the freshest fish you just caught. It’s also connected to the Bass Pro Shop, which was an attraction in itself.

29066672_10160074167970207_3778540011717132288_oBetween the warm weather in the late winter and the relaxing, laid back vibe and being so close to the water everywhere you go, Islamorada was the perfect family vacation.  I can see why my parents kept going back, and we would definitely think about going again in the future.


*Our trip took place in March 2018, several months after hurricane Irma hit, and I was saddened to see that so many towns, attractions and homes were still in shambles.  One of the many benefits of tourism is that it boosts the economy, especially in a time of need, but if you can’t visit the Keys anytime soon, consider donating to one of the charities listed here


Will’s Trip Stats:  Islamorada & Key West, Florida // March 2018 // 10 Months Old

Children’s Book Inspiration: Deep Deep Sea by Frann Preston-Gannon

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