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How To Get Ready For A Vacation

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It’s been a while since our family has been on a big trip. At the beginning of the year, we were thinking about taking the RV to Yellowstone. Both my spouse and I had never been and our son would love seeing the animals. Personally, I have a goal in life to see a bear, just one time in the wild as a ode to my late grandma “B.” But I digress. We continued to debate what we’d do this summer/fall and after going to Mexico, it was clear. We needed to go somewhere sunny and with a beach! Destin, FL it is!

Credit Wikipedia for this enticing picture of Destin.

My folks had been before and said it was great. Relaxing and beautiful sandy beaches. Since they live within driving distance from Destin, we figured we’d ask them to come along for the vacation. I mean, who doesn’t love built in babysitters when on vacation? With that now decided, I thought it would be nice to share with you all, how we go about prepping for the trip. I.e. in terms of logistics, activities, etc. So below I’ll go through my process, to hopefully pass along some helpful tips.

Vacation Prep

Accommodations and Flights

Since properties can book up fast, we tend to start by figuring out our accommodations. For that, I typically start with and as always, they had many options for a family of four adults, one toddler and one 12-year old dachshund. My criteria for this trip was pretty simple:

  • Close to the beach
  • WiFi/Internet
  • Parking
  • Washing machine (optional dryer, though in the US, it’s super common to get both)
  • Two bedroom/two bath (or more)

When we travel with Charlie, we always try to find a place with at least one bedroom. We don’t mind that he sleeps in our room when we’re away. We just need a quiet space for him to nap and go to bed away from the rest of the house.

TIP Start researching properties at least 3-4 months ahead for popular destinations. When I started looking a month or so ago, the supplier was about 60% sold out already and our trip is in late summer. If you think you’re going to a really popular place, I.e. during spring break in South Padre Island, you should book it at least 5 -6 months out or more.

Consideration for Destin rental property

Next, we book our flights about 2-3 months out from our trip to Destin. If we’re going international, I should caveat that we do this at least fourth months before our trip. I’ll reiterate from another post (The Grass Just May Be Greener in Finland), that if you choose to have your little one sit on your lap, you’ll need a paper ticket and that requires at few weeks for the airline to mail it to you via the post office. Since we have flyer miles through Alaska Air and therefore Delta, we always use one of these airlines to book our tickets. If i don’t have miles, then I typically book flights via Expedia. For this trip, and since he’s two, our son will have his own seat.

Lastly, we typically get a rental car. However, for this trip, my folks are driving from their home to meet us in Destin, so a rental is not necessary. But if you do need a rental, you should be booking that around the time you book your flights. TIP a lot of companies provider their employees with company discounts. Check with your employer to see if that’s the case for you. Why not try and save a little cash?!


Now the fun part begins. For this trip I plan on keeping the schedule fairly open. The last several trips have been extremely packed and we’d like to actually relax and regroup. The company I work for starts picking up after the summer and the team I’m on has plans to launch a new regional policy and I’m responsible for a lot of the milestones. Getting some good R&R will be key to wrap up the summer.

We will be gone for just over a week and having a couple of bigger activities on the list is a great way to break up the trip. When I start to research my destination, I typically start by going to TripAdvisor. But that’s not a one and done stop. It’s good to see what the local tourism bureau recommends as well as maybe getting a travel guidebook. For this trip, I honed in on these activities:

Dolphin cruise activity (via TripShock). Looking forward to this!

Typically for me and in a destination like Destin, I will bring a couple pairs of shorts and 2-3 tops and intermix them. I’ll have a washing machine, so if something gets dirty, it’s easy to throw in a load of wash. Of course I’ll have a swimsuit, and 2-3 pairs of shoes, but for a nice night out I’ll typically pack a long maxi dress for warm weather. You can always dress it up with some fun statement pieces or get something locally! But packing for Charlie, has come down to a science. Depending on location, I swap in different items, i.e. swimsuit for jacket, etc. Here’s a list of what I will pack for Charlie:

  • Swimsuits (x2): I like the iPlay Swim Trunks (or girls iPlay swimsuit set) because they come with a built in diaper.
  • Swim Zip Rash Guard: the zipper makes it so easy to get on and off without a fight. I’ve used the over the head ones and when wet, it’s like trying to get your kiddo out of a Chinese thumb trap
  • Day/sleep diapers: enough for 6-8 changes a day and enough sleep diapers for one diaper a night, plus 3 extra. For this trip I’m not as worried about having enough. But when I travel internationally, I make sure to have enough. Diapers abroad can be expensive.
  • iPlay reversable bucket sun protection hat
  • Sunscreen – i.e. Babyganics
  • Enough clothing to cover 1/2 of the trip
  • Jammies to cover 1/2 the trip
  • Aden + Anais Babas (his security blankets). I have six total and I will bring them ALL
  • Crocs Unisex Crocband II PS Sandal
  • Sneakers and 3-5 pairs of socks
  • Baby monitor by Infant Optics – so easy to use and doesn’t take up much space in the suitcase
  • 2-3 of his books
  • A small suitcase full of his favorite toys. We take this on the plane with us and also add some of his favorite snacks to have on hand during the flight.
  • Shampoo/body wash; I like Mustela’s 2-in-1 Hair and Body Wash
  • Favorite stuffed toy
  • Sheets for crib

Thankfully my folks are driving down, so I’ve asked them to bring the following that we keep at their house:

Next Stop, Destin!

With the reservations done, I am starting to feel the excitement and looking forward to a relaxing vacation. I do think we’ll end up going out to dinner in Destin a few times so we don’t have to always cook, so in the couple of weeks I’ll set up some reservations.

Destin Surf Hut. We are looking forward to some yummy gulf seafood!!

Overall my macro to-do list is:

  1. Book our hotel/vacation rental
  2. Book flights
  3. If applicable, book rental car
  4. Finalize activities
  5. Pack



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