Miami Bound: Heading for a Super Long Vacation? Here's What We're Doing to Make the Most of it

Miami has been a huge part of our family for a few years now.  From the beach, ocean breeze as you sip your coffee, the family time together, and the food, it is a place that has come to be called home.

As of this past May we finally have a Condo to call our own and will be spending the second half of summer there.  Coming back just days before school begins, my husband and I both working, and a desire to explore South Florida means a lot of planning so this all goes without a hitch.  

Here's a basic outline of how  our three week vacation will go.  Can't wait to post after the trip with an update.

1. Work backwards and Evaluate What's Important to you and What's Needed:

We are fortunate where both my husband and myself are not limited by location when it comes to our businesses.  That being said, shipping for Driven Day will need to be outsourced, my husband may have to travel back or have quiet for business calls at times. And we both need designated times to work without balancing supervising kids in the pool or making an important work call in a car with our family on the way back from tubing. 

Be realistic with what each person and your family needs and come up with a plan of what works.  

2. Work Backwards:

Think of what you're coming  home to as well and what needs to be done in advance.  Being away for such a significant amount of time requires a lot of advanced effort.  

Prescription refills for medications.

Uniforms that need to be purchased so you have adequate time to tailor if needed.

Checking who needs new backpacks and lunch boxes.

Cash to tip counselors before we head outta town.

What's happening to your mail while you're gone?

Setting up your work team to be able to work independently while you're away, order fulfillment, auto reply if needed, prep needed for future projects, you name it.

3. Create a Basic Schedule:

Part of the enjoyment of vacation is the lack of schedule, being able to go to sleep later if you feel like it, leisurely time at a park you're relaxing at just because you can.

The flip side is we all crave structure.  Below is the one we created for our family.  Rule number one is that it's okay to not stick to this.  I just have a relief knowing we have a plan if needed.  This provides structure if necessary, a concrete time for our favorite activities so kids aren't asking every hour when are we going for ice cream, and appreciating each day while still knowing the fun that lies ahead:


Nicer more leisurely breakfast, think pancakes, eggs and bagels, no rush to get dressed right away etc.. Some park or outdoor more "holistic" activity.


Regular day of sun and pool.  Easy homemade dinner aka crockpot meals, baking sheet chicken etc...


Easy trip where only one adult is needed.  When I think of boating, long drives to the Florida Keys, or any heavy water activity I know both of us need to be on hand.  Tuesdays will be more the type of trips where my husband can stay back and put in a regular day of work, without me burdened with shlepping 10 bikes out of the car. Or perhaps the juggle struggle, hiking up a crazy waterfall on my own.  The flip side, I may need some quiet work time.  So  having a fun ice cream shop to go to, a cute farmer's market to check out is a perfect win win.


Bike and Beach Day.  We plan on buying bikes that will stay at our condo upon our arrival to Miami, and ordered scooters on Amazon.  We hope to do a lot of fun family bike rides and scootering expeditions.  (Thinking in advance, everyone riding a two wheeler before we fly out next week #almostthere).


Full day trip, where we explore all the fun places South Florida has to offer as a family.  Will post our full itinerary upon return.

Friday:  Shabbos (Shabbath) prep.

A Few Other "rules" we've been working on leading up to the trip to make it enjoyable for all:

1. Streamlining the pool.  Everyone takes their towel and goggles, mom brings a bag of some snacks and grab a pool toy if you can carry it.  This is my favorite backpack

and I'm beyond obsessed with everything about it,

We want swimming to be something easy and fun, not stressful and where I become a bag lady.

2. Encouraging independent play at our condo.  It's unfair and unrealistic to expect to be entertaining the kids non stop from sunrise to sunset.  Being thoughtful about the activities and toys we keep around and their accessibility is just smart.

3. Working on the basics:  Putting something away before we take out something new, focusing on the trip and activity we're doing instead of what's coming up next ( I always do this, its a problem :)), Opening the door for someone who has groceries in their hand, you name it.

Driven Day Resources I'm using for our trip:

Our Packing List Printable


Our Shabbos Pad



Stay tuned for our post Miami round up. It will include our itinerary of all our adventures, what worked and what we will remember for next time, games and crafts to keep kids busy in smaller spaces, and tons of fun ideas for future vacations.  Comment below with what you want to see!