The Vacation Conundrum

My family loves to take a good vacation.  Whose doesn’t?  But as the family travel planner, I always take the vacation planning process as a personal challenge.  How do I make each trip memorable?  What kind of new things to see/do/taste/learn can I plan?

The first threshold question is always, where should we go?  Typically it depends on time of year and how much time we have to travel.  Obviously, the longer the trip, the more adventurous we can be. 

I also try to factor in time-zone changes.  If we only have 4-5 days to be away, is it worth battling our internal clock adjustment?  That’s not to say we haven’t done a 4 day trip to London, or a 7 day trip to Maine.  Given the amount of traveling we do as a family, my kids have become adept at adjusting quickly and stealing naps in trains, planes, buses and cabs as needed. 

With rare exception, we don’t go to the same place twice.  It’s a big world out there and we only have so much time to travel.  Plus, my wife has visited all 50 states and many countries so when provided an opportunity to take our kids to a new state or place, we usually take it (even if it means driving 2 hours from Jackson Hole to have dinner in Idaho).  The few exceptions to our no repeats rule are Disney World (we’ve gone every 3 years since my son turned 3), Okemo (for New Years Eve/Day skiing in Vermont at least 4 times) and Telluride (for the Telluride Film Festival for 17 out of the last 18 years).

The next question I grapple with is what kind of trip should this be?  Are we flying solo, planning each activity on our own?  Are we enlisting the help of a travel agent to custom plan a tour just for our family?  Are we joining a tour with multiple families?  We’ve done all of the above and many variations in between.  We generally prefer to do our own thing, not being tied to anyone else’s schedule.  We can do what we want, when we want.  But when we are strangers in a strange land, don’t speak the language, etc., those situations sometimes warrant taking a tour or hiring a guide.

Where we stay is often dictated by location, but we also look for unusual experiences. For every resort we’ve visited, we have also stayed in less common accommodations like a treehouse hotel in California, tented camps in the Serengeti and octagonal bungalows on a cliff in Costa Rica.

As for activities, I always try to mix active and passive things to keep vacation interesting, get some exercise, and maybe interact with our new location in ways that might give us a better sense of the place.  Some of my favorites include a taking a cooking class in Florence, whale watching in Alaska, hot air ballooning and big game watching in Tanzania, snorkeling in the Galapagos, canoeing among the alligators in Florida, sunset yoga on Waikiki beach, hiking in the Grand Canyon and among the sequoias in Yosemite, going to gladiator school in Rome and experiencing a fjord rib-boat safari in Norway.

Where will our next adventure be?  Good question. I can’t wait to decide.

- Frosty