Siesta Key, Florida with a One Year Old! — Caffeine until Cocktails

Overview of Siesta Key

We have been going to Siesta Key seriously for almost ten plus years. It has become a second home. Literally my parents and my in laws both have second homes there. We are aware that traveling with a baby can be a lot of work but, we strive to make sure we do it because we want to have all of the experiences and memories with our little man. Siesta Key Beach has been rated #1 beach for the last several years. It is a beautiful area. During high season or spring break time it is a bit WILD with crazy traffic and hard to get into restaurants. I have not been during this time in quite some time. This year, we went December 27th-January 3rd and I think this is a perfect time to go with kids. It is not too hot but, still beautiful.

We normally fly out of St. Louis but due to the cost around Christmas and New Years for flights, we flew out of Nashville to save about a $1,000. We drove down the night before and stayed at a hotel very close to the airport. I stress A LOT about car seats and traveling and how to store them and which one to bring. Elliott, of course, on this trip was transitioning to a convertible car seat. This is the one we just moved into. So we actually just brought the infant seat carrier so it was not so big and bulky and we would not have to move the car seat once we parked our car at the airport. We did bring our Bobs stroller with us and I will always bring to Florida because it is easy to navigate on the beach. If you read my post about traveling to Florida with a 5 month old, it gives a lot of good products we used for two weeks in Florida with little E. Another great option for baby supplies/needs while you are on vacation in Siesta Key, is to rent the baby equipment. This company will deliver the items you rent and pick them up. There are lots of options for travel and how to get on the island. I have done it several different ways but we typically always have a mini van and drive from the airport in Tampa. Other options are to fly into Sarasota or Punta Gorda. Sarasota is probably the easiest and closest especially if you can get a flight into there. The uber ride would only be about 20 minutes or so. If you are not traveling with children, I do think this would be easiest. There are loads of free options on the island to get to the village and walking is always easy to do as well.

We have stayed several places on Siesta Key but this place at Crescent Royale, has been a favorite of ours. It is a two bedroom two bath. The master has a walk in closet that fits a pack and play perfectly to allow the baby to sleep. It has a pull out couch if you more kids than will fit in the second bedroom. Also it has a pool and is located directly across the street from the beach. It is about 3/4 mile walk to the village but the trolley and “Johnny free ride” picks up right out front as well. This condo does have an elevator. Another thing we do is have our groceries scheduled for delivery using instacart. We have them delivered about an hour or two after we arrive. One thing we do is bring life jackets/water wings for little ones and just check them in the carseat bag because you don’t get charged for that.

Restaurants

Disclaimer: If you are here in March/April expect to wait at least an hour for dinner or more. The island is crazy busy with spring breakers. It is sometimes easier to catch an early early dinner or cook at home!

Siesta Key Oyster Bar is super family friendly but I suggest going early for dinner or make it a Lunch meal. They do accept reservations via yelp. I highly suggest the grouper bites, bucket of fun, ice cold draft bud lights and the tuna poke! Love their food. They usually have live music too. If able to go without kids this place is always a good time.
The Cottage is a nicer restaurant that you can usually always get into but they do not accept reservations. We went there for dinner around 6-6:30 in December and were able to get in no problem. The tuna tacos, lobster bisque and Cottage salad are my go to menu items and TO DIE FOR!
We love to go Sun Garden Cafe for breakfast. Check it out around 8-9 am before the breakfast rush arrives and sit on the patio. I always go for an omelet or the breakfast burrito! They do have high chairs and Elliott liked to sit outside on the patio.
Gilligan’s is another fun atmosphere that is a bar/restaurant/turns nightclub at 11 pm. The food is good and it is loud which I always think is fun for kids.
The Hub is a tex mex/baja grill. It is family friendly and loud which are all things I look for in a restaurant to take my son too.

I could go on and on about amazing restaurants on Siesta Key and neighboring keys! I highly suggest checking out Boatyard, Casey Key Fish House and Turtles which I find are all family friendly and on the water. Search on yelp and also always look for reservations with a big group or I always suggest an early dinner time with kiddos!

Things To Do

Rent a boat. We always rent a boat from CB’s outfitter/boat rental. We love renting from them and it so much fun. We usually boat down to Casey Key/Venice area and eat lunch and then park on a small island. They provide life jackets for kids but we took my little man one when he was 5 months old and at a year. We packed a life jacket for him both times. This is the life jacket we used for under thirty pounds but once he is over thirty pounds we will use this one.
Mote Aquarium is an awesome trip with kiddos! If visiting in Winter Months or summer time it will take approx 30-40 minutes from Siesta Key but during high season March/April it could take up to 90 minutes to get there. There are plenty of fun restaurants near the aquarium and you can always check out St. Armand’s Circle.
St. Armand’s Circle has tons of restaurants and shopping AND ice cream at Kilwin’s is a must for the kids of course!
Venice Beach—The beach where you can hunt for Shark Teeth. There is also a restaurant on the beach near the Venice Beach Pier called Sharky’s. It is super fun and kid friendly.
Ringling Circus Museum is also located nearby in Sarasota. Another family friendly activity to do on a rain day or if you are visiting during the cooler months.
Siesta Beach—It is the most beautiful white sand you will literally EVER see in your life. For my little man I packed water shoes this year because he was now walking. For little people I think water shoes are always so helpful so they don’t step on anything. We love this brand and he can also where out on the town as well.
*Sunday night is the drum circle on the beach around sunset. Just google the sunset time for the day you are there and it will give you a better idea of what time to plan for.
Something that we did this time was having family photos done. We used Black Pineapple Photography and it was the best decision I have ever made. Liz the owner is literally soooo talented and amazing at what she does! She friendly and knows exactly what to do to get the perfect shot on the beach! You can see some of the pictures we took with her above. The dress I wore is linked here. Elliott’s outfit can be found here.

Another thing I like to tell people visiting is that Siesta Key is about 2 hours south of Orlando which obviously is Disney, Sea World and Universal and about 1 hour south of Busch Gardens in Tampa! Tampa is an easy day trip and would be super fun to do with kiddos!

Tips for Kids

Pack water shoes. There can be shells down by water and I found it helpful for Elliott to wear these type of shoes.
Swimshirt and Swimhat! The sun is crazy even when it is overcast! When Elliott was smaller we loved these one piece swim outfits. When it comes to swim diapers I prefer the washable/reusable ones like the ones here.
The past two times I have flown with Elliott I wear him through the airport. I love the ErgoBaby 360. We have used for the past year and it has been so helpful for travel! We then use the stroller to stack all of our stuff on.
Another thing I like to tell parents is that when traveling especially with little ones who needs snacks pack plenty or buy in the airport.We wiped our tray table down and laid out snacks for E to go to town. You will see a picture below of our snack set up.
If you have questions about flying with breast milk like we did feel free to check out my breastfeeding essentials blog post. This trip did I learn something new and if you have thawed our breast milk in bottles and it is less than 4 ounces they do not have to do a thing to it. I always encourage parents with breast milk to read the TSA rules and ask questions. This is your milk don’t let them bully you! Also this is our cooler we bring on the plane with breast milk in it. We used the big cooler to haul our frozen milk for the trip and then I used this small cooler for milk for the travel day. They sell bigger ones but I like the size of this because I can easily access the milk I need in our diaper bag at my feet.
We always wear jammies when we travel and a sleep diaper just in case we can’t get up to change the diaper or something happens. YOU NEVER KNOW!
We also always pack a small blanket to cover Elliott’s face in hopes we can get him to fall asleep.

ALRIGHT! I think I have provided y’all with enough information to get you started! If you have any questions about Siesta Key please feel free to let me know! I kind of feel like a “blogger expert” in regards to taking kiddos to Siesta Key! We have been traveling there with my cousins and niece and nephews for years prior to me having a baby! Last piece of advice when traveling with kids expect the worst prepare for the best! Happy Vacation Planning!

-Jessica