Tips for Smooth Travels: Our Annual Trip to Siesta Key

Every year, we go to Siesta Key. We go to the same place, same time of year with each year it gets a little easier and easier because of tips and tricks that I use for each trip. I travel with three kids and when they were younger, we needed to travel with more, but I refused to check “all the things” so I did my research and founds ways to make traveling with children smooth and enjoyable.

First things first, WHERE we go in Siesta Key. We stay at the Sarasota Surf and Raquet Club. We’ve been going there for 8 years and it’s such a perfect spot. We stay in the Y building which is closest to the beach so we can just walk out the door and be on the sand. I like to stay in a room on the second or third floor because it’s not too many flights of stairs, but not on the busy first floor.

Let’s talk about packing and flying. I paid for Pre-check years ago with Southwest. It lasts for years and is worth every penny. You can get through security easier and for the kids and I, we don’t have to take off our shoes or unpack our bags. I feel like I’m doing something illegal because I walk by all the other families in the normal security line and just keep going. I’ve mentioned it to many moms– pay for pre-check! For checking bags, I have a rule: the kids lay out what they WANT to take and then I choose what goes when I pack. My youngest daughter and I share a suitcase usually and then my older two kids share a suitcase. They’re large suitcases so we check them and then we’re done with it.

For carry ons, what my kids want to have on the plane, it must fit in their backpack. If it’s too big or too full, it doesn’t go. My kids are really good about this. My oldest daughter draws and reads. My middle daughter listens to her Yoto on the plane. BEST toy every– no screentime and I find that this toy helps calm her when she’s overstimulated as well. My youngest sleeps when we fly so that’s convenient. Before she falls asleep, I have an activity book that she plays with.

You’re probably thinking, wait you’re flying with kids and not talking about packing their carseats, a high chair, pack n play, etc… that’s because I DON’T! I found the most amazing company called Babyquip. It’s like airBnB for renting baby and kid products. You search by location, then find the products you need and then find a highly rated person to rent from. They will meet you anywhere– so for my experience, my person met me at the airport in the garage and dropped off the carseats, stroller, highchair, and pack n play. Once the trip is over, she met me back at the airport garage, took the items and that’s it! I used this service for a few years. Now we only need carseats so we just get those from the rental car service.

Now that’s talk about the actual trip…

The place that we stay has a keycard entry so that’s a nice touch. The view from the room that we stay in is beautiful. It has two rooms, a living room, dining room with a beach view and a kitchen. The first thing we do once we get checked in and drop off the luggage is go grocery shopping at the local Publix. I make breakfast every morning and pack lunches for every day since we’re on the beach. I pack a collapsable cooler and that’s what I use to pack the waters, sandwiches, fruit, treats and then I pack a dry bag for the chips, plates, napkins, etc. I usually just use the beach bag because it’s big enough.

When planning to go down to the beach, the first day we arrive, I call the umbrella and chair service that is part of the Club we stay at. I book two umbrellas for every day we’ll be at the beach. When we walk down every morning (around 9a), the umbrellas are already set up and then you just tell them how many chairs you need. They are great workers and so helpful so tip well. When booking the umbrellas, it’s nice because it’s the guaranteed spot on the beach with a great view.

Places to Visit In Siesta Key:

• The food is delicious on the main street by where we stay. Siesta Key Oyster Bar has the best crab legs. Olaf’s ice cream is a must! We also like MVP which has sports bar food and my kids love the tacos. Also the virgin strawberry daiquiris! The Daiquiri Deck has delicious blackened mahi mahi bites. I could go on! The food is so good.
• Mote Aquarium
• Siesta Key Jungle Gardens
• Donuts and Dolphins Cruise

There are a lot of other places to visit, but these are our favorites.

Curious about what I pack in my suitcase? I’ll post that blog soon!