Father – Son/Daughter Getaways

The title says “father” only because I’m writing this post from my perspective and incorporating actual concepts I used with my daughters.  My original objective was to somehow make up for years of job assignments that called for extensive travel.  I actually modified an idea one of my IBM bosses used with his kids for the same reason.

The extra bonding I was able to achieve with my daughters and the stories we both are able to tell forever have immeasurable value.  I’ve shared this idea with friends and co-workers, many of whom have adopted or modified it for their own use.  If you also like the idea, help me spread it to others.

My father-daughter getaways were first and foremost an opportunity to spend one-on-one time together.  I chose to couple this with a vacation trip to somewhere my daughters had never seen before.  But jumping on an airplane is absolutely not required.  The most important thing is the one-on-one time together.  I also incorporated various educational exercises, not in the academic sense, but rather life lessons and other rudimentary skills.

With three daughters, I decided to have three formal, pre-planned father-daughter getaways with each.  There ended up being more than that with various impromptu outings and local ventures, but these were more significant and as soon as I did them for my oldest daughter, the standard was set for the other two.

If you’re not already familiar with our “standards” parenting tool, read my article titled “Establishing Standards (if have multiple kids)“.

Here’s what I did:

After Elementary School

During the summer after elementary school and before middle school, I took my daughters to Washington DC to see our nation’s capital (see related blog post titled “Washington DC with Kid(s)“).  During elementary school, kids learn about our system of government and they learn about significant Presidents.

The site visits during our getaway were mostly the traditional tourist destinations in and around Washington DC (White House, Capital, Washington Monument, Smithsonian Institute, Mount Vernon, etc.).  But I involved each of my girls to select the final list of destinations they were most interested in.  Interestingly, there was about 80% overlap amongst them (the big must-see things) and the 20% differences gave me something unique and special with each of them.

The educational exercises I incorporated into the trip were as follows:

  • Navigating an Airport – During the travel day to Washington DC, I explained every step, starting with tracking where we parked in the parking lot, getting the boarding pass, figuring out if our flight was on time, checking bags, passing through security, finding our gate, etc, etc.  Then, for the travel day back home I gave my daughter our flight information (airline, flight number) and confirmation number and said “get us home”.  I told them before the trip that this was going to happen so they could pay attention and ask questions during the outbound travel day.  And on the return day we arrived at the airport an extra 30 minutes earlier than usual so that time pressure was eliminated.  If they asked me a question, I usually shrugged my shoulders and said “remember how we did it on the way here?”  Once at the home airport I said, “get us to our car”.
  • Navigating the Subway System – Very similar to the airport navigation exercise but in this case related to the Washington DC subway system, which is a great one to learn on because it’s very clean, safe and simple to learn.  For the first 2-3 subway rides, I explained how to read the subway map to determine the best subway line(s) and route, as well as how to find the right platform to stand on for the selected train.  After that, it was their responsibility to do it all.  If we jumped on the wrong train or were going in the wrong direction, I just let it play out for a bit.  Nothing bad is going to happen other than wasting a little bit of time.  That was part of the lesson too.

My daughters loved the empowerment they felt during both exercises.  I think it gave them some personal confidence, and that was definitely part of my objective.

After Middle School

During the summer after middle school and before high school, I let my daughters pick any city in the continental US (see related blog post titled “New York City with Kid(s)”).  Using frequent flier miles and hotel points from my road warrior days, we set off on a 4-day father daughter trip.  It’s potentially no surprise that all three of my daughters selected New York City.  Like with Washington DC, I involved each of them in the planning of the exact activities we would undertake.

The educational exercises I incorporated into the trip were as follows:

  • Itinerary Planning – I suggested several things to see and do, but worked collaboratively with my daughter to build a day-by-day itinerary.  We used a map to determine which desired destinations were close to each other and also got online to learn the best time to see certain things while avoiding big crowds.  In some cases we were able to order tickets online for a specific day/time, which locked in portions of our itinerary.  As you would expect, some things went faster and others went slower than expected, which meant we had to adjust our plans and improvise.  Exactly the purpose of the exercise.
  • Budgeting – I told my daughter exactly how much I was able to spend on the vacation, leaving out any flight and hotel costs.  Then I told them that they could spend it however they wanted.  I helped them understand how much taxi rides, subway rides and Broadway shows typically cost.  And anything we ordered tickets online for had known costs.  I also described the concept of a daily budget for miscellaneous, unforeseen or opportunistic expenditures.  But it was up to my daughter if we rode the subway versus took taxis.  Same for how many shows or really nice restaurants we went to.  We kept a tally of how we were doing versus the budget and each night would decide if adjustments were needed.  As you can imagine, we adjusted almost every night.  Exactly the purpose of the exercise.

Senior Year of High School

This wasn’t a trip to a particular destination and wasn’t purely a one-on-one activity with my daughter.  But I wanted to mention it since it was another special bonding opportunity and something my girls still talk about.  At the start of their senior year, I told them I wanted to take them to a concert of one of their favorite musicians/groups.  I also bought an extra ticket for a guest (which could mean boyfriend).


This idea can work for any parent.  But for those that are also road warrior travelers or have a job that demands 60+ hours per week most of the time, I hope this blog post gives you some ideas for extra parent-child bonding via one-on-one getaways.  Both my daughters and I have lasting memories from them.

If you like the idea, feel free to make changes so that it matches your personality and interests, and creates the best experience for you and your child.  Then spread the word to others you think could benefit.

See my other blog posts on parenting here.

Author: Gordon Daugherty

Gordon Daugherty is a best-selling author, seasoned business executive, entrepreneur, startup advisor and investor. He has made more than 200 investments in early-stage companies and has been involved with raising more than $80 million in growth and venture capital. From his 28-year career in high tech, Gordon has both an IPO and a $200-million acquisition exit under his belt. Now, as co-founder and president of Austin’s Capital Factory and as author of the book “Startup Success”, Gordon spends 100 percent of his time educating, advising, and investing in startups.

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