Pick a Place & Plan the Trip

On a recent trip, we were listening to a guy playing acoustic guitar at a tiny bar. It was chilly, we had done a bunch of hiking, were sipping whiskey, and between sets, we struck up conversation with the people next to us (let me start by saying that I know it seems like it will never happen… but our kids are plenty old enough to find themselves dinner then head back to the hotel and chill while we go to live music… and it is every bit as amazing as I imagined it would be way back when it seemed like it would never happen). Anyway, we started chatting about places we’ve visited and they talked about places they’ve visited and they said that we MUST adventure to Iceland and camp the perimeter. It is amazing! and then Ecuador… and at that moment… My lifemate and I decided our new method of choosing our next destination… we will take the advice of whatever slightly tipsy people we meet on the road… and plan from there!

So, the money has been saved, time-off allotted, and while sometimes picking the destination is relatively straightforward, planned around a reunion, event, conference, or visiting family but often, that isn’t the case. There are so many amazing places to see that it is hard to narrow it down! But don’t freeze-up! or throw in the towel or settle on the same thing as always! There are options!

• Create a bucket list, watch travel channels, retrace movies, do something philanthropic, or take a class
• Go on a tour: religious or literary or art or music or wine or river-boat or National Park or self-guided
• Keep vigilant watch for deals you can’t refuse on trains or airlines or resorts (my favorite way to choose)
• Go to every state, visit every ballpark, climb every mountain, forge every stream, follow every rainbow!
• or strike-up a chat with the couple sipping whiskey! You never know, it might be us!

However a place is picked, next comes the fun part! By far, the easiest option is going to a vacation destination (like a resort): After booking, simply show-up, and sometimes, that is the greatest thing in the whole world!! But, when ready for a little more adventure or something unique, here are some steps. They shouldn’t be tackled all at once, just thought about over time. If time is not available, find a blog or abridged review that gives a solid over-view and work from that.

• Talk to People / Pinterest / Internet Search / Library — The general idea is set, now plan activities, outings, and events. Start with a pretty broad list. Ask friends or family or social media what they loved or would have skipped. Borrow travel library books. Perform internet searches on locations and absolutely add pictures and articles to a Pinterest board for each trip. Look for hikes, museums, attractions, historical sites, artistic venues, etc.
• Figure Limitations – Check the places that are MUSTS and note the specific days open, hours, costs, and special events.
  • It is the worst to plan around an experience only to discover it is closed on Mondays or needs advance purchase or reviews are terrible
  • Stretch the budget and create unique experiences by avoiding tourist traps and instead hang where the locals are hanging
  • If a free talk, tour, or docent is offered, TAKE IT!! The kids / spouse may complain at first, but it is so informative and interesting!
  • Specifically check for local events, art shows, fests, live music, parks, hikes, or free tours that might be available
  • Random fests are seriously the best– and who knows, Tequila Mockingbird at Ska-fest in British Columbia might be life-changing!
• Star a Google Map – Sign into the google account, go to a map, and mark those places as favorites. It puts a little star on the map so that you can see how close or far the activities are from each other. At this point, there is no need to narrow anything down, the goal is just to figure out the landscape and where things are located.
• Broadly Plan Days – This is just an outline, not an exact schedule. Figure basic days based on limitations, events, and proximity of locations. For example, visiting Chicago, it would make sense to do Navy Pier on the same day as Maggie Daley Park and the Bean– and probably best on a fireworks night, but trying to get all the way to the Brookfield Zoo would be a different day. Just look at the stars, group them into constellations and figure out the priorities by order of importance. This step is often tricky because some things are contingent on weather and it is rough to tell just how much time one should allot to various places.
  • Allow for flexibility if possible – especially for weather and crowds and traffic and the unexpected
  • Make a list (ideally on the google spreadsheet) by priority and time allotted with optional extras noted
    Remove areas that totally get cut from the list for price, time, distance, or lack of interest
• Figure Transportation / Lodging – Sometimes, the lodging and transportation are planned ahead with day-trips from home-base, other times it is a genuine road trip. Head-over to the Lodging Blog for more advice on this….

At this point, I don’t want people to think that I’ve got every detail planned before we walk out the door, I REALLY do not. I buy tickets for events that I know we will want to see, generally we have lodging planned (sometimes we don’t, especially when camping). I have broad ideas of what the group would like to do and occasionally places in mind we might want to eat.

While commuting, eating, or waiting, I put on my Julie hat (yes, I just showed my age and made a Love Boat reference) and ask the gang what kinds of things they will be in the mood to do next. More than once, especially on last minute things, I’ve not even started researching until we are waiting to board the plane! or in the car with our road-trip playlist blasting or while the kids are in the pool (and I have my tablet and a travel goblet of wine). This shouldn’t be pressure and it can be pretty cursory or a little more in-depth, but it rarely works to over-plan.

And one more thing: Try to take a variety of trips, go away as a couple, as a family, maybe even on a personal retreat. Going away as a couple now and again (we try to do it once a year) helps stay connected as a couple but it also helps the kids appreciate the experience when they are invited along.

• Lots of times, a real vacation at a resort is what a family needs. NOTHING wrong with that
• Strike up conversation with all sorts of people! It is fascinating and often the best recommendations
• My lawyers tell me I need to make a disclaimer here:
  • Don’t always take the advice of random real people– sometimes they are crazy
• Airline or train ticket discounts are great ways to plan trips. $49 to NOLA?! Okay! NOLA it is!
• Going to a favorite band at a unique venue is awesome and feels a little like being a groupie
• Avoid “4-corners” (places not worth the time, distance, or money) – better to skip than cut short the amazing
• $300 a month aside can garner a pretty solid family trip each year (or use the tax return)
• Bring a GPS – sometimes internet on phones is dicey and asking people isn’t always successful
• Ask locals or park workers for the best viewing spots for sunrise and sunset and local events
• It keeps everyone more engaged to limit electronics to pictures only (except during agreed down-time)
• Avoid packing the agenda too tightly or the family will claim that they are on a forced death march