The Happiness in Planning a Vacation

---

The idea of this trip started when I read Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel by Rolf Potts. While we aren't exactly planning a "long-term" or "world" trip, there were enough interesting points in this book that sparked my interest. Most likely, this is because whenever we travel as a family, we tend to enjoy just spending time doing what we would normally be doing on a weekend at home, but transplanted into another city with new surroundings, people, and stimuli. We enjoy visiting the local parks and malls, taking the subway to new areas, dining at local hot spots, and sometimes even people watching while our kids play on a playground--all activities you'd probably find us doing on any given Saturday. At some level, this is a simplification of Potts' concept of long-term travel.

Another key point, which we sometimes stumble into, is that travel should be spontaneous, and that you will have the best experiences getting lost, asking for directions from a local, and finding your way back. Having our subway break down in the Bronx and trying to fight 20 non-English speaking locals for a bus back into Manhattan could be put into this category, and we still laugh about this today (we also had a 1 year old and it was 20 degrees--the story gets even better).

With these concepts in mind, I pitched to Jessica the idea that we should just take off for a month and just go somewhere with no destination in mind. At first, I think she was a little hesitant but then I explained more about the concept and that the vacation should revolve around what we and our kids are up for.

Eventually, some opportunities, plans, guidelines, and then boundaries and restrictions started falling into place, and we ended up with a 3 week window between obligations at home in which to travel. In addition, by being flexible, I was able to secure some cheap one-way tickets on Southwest to Baltimore. We have always talked about visiting the Northeast again with a focus on the historic areas in Washington DC, Philadelphia, and Boston, so we decided to spend our time city hopping. Whenever we are tired or reach the end of our window, we will fly home using some saved one-way rewards which can be booked at the last minute.

Over the next couple of months, I was able to take advantage of additional deals on hotels in various key cities and even a $9 JetBlue flight to Boston from Newark, which saves us an Amtrak or bus trip. Now, you may say that I have violated the second concept of spontaneity in travel. Maybe this is true for a 'pure' Vagabonder, but realize that we also have 3 young children and a budget, so it is to our advantage to at least have a framework of a schedule in place. However, we do still intend to plan each day as it comes in order to not push ourselves or our kids too much and to stay flexible so that we can take advantage of other last minute opportunities. Yes, I have marked certain days on my Google calendar for the various cities that we plan on visiting, but I still have no hotels or activities booked for a good 2 weeks of our trip. Instead, I have been studying locations, finding example rates, and tracking key hotel deals so that when the day comes, we can use whichever deal and hotel that fits our budget, location, and time constraint at the time.

As we travel through the next 3 weeks, I'll provide more details on the deals and plans that got us to where we are. For now, I am enjoying the happiness that comes with planning a vacation.

-Jason

---