Tag Archives: amazing travel

When is “someday”? Practical tips for making your dream trip a reality

13 Mar

So I’ve written quite a bit about some amazing travel adventures I’ve turned into reality.  But this blog is more than a travelogue.  It is about sharing my (hopefully somewhat helpful) tips on how to help you create your own “someday” memories.

See? Yup, I was outlining this post before writing it.

So I spent some time putting pen to paper, literally, on the mental steps I’ve gone through over the years.  So without further ado…

It starts with “Where do you want to travel?”

For starters, this is all about you.  Also, obstacles don’t live here.  I’ll get to that later in my post.

  • Do some unconstrained thinking:  What travel destinations reoccur in your dreams?  Is there a place you talked about as a child?  It might be the appeal of the mountains or a secluded beach, an iceberg or a leopard, the Eiffel Tower or the Taj Mahal.  All of the above?  Even better.  Maybe it is someplace you’ve seen in a movie?  I will (somewhat sheepishly) admit that I learned about Angkor Wat when the destination was used in 2001’s Lara Croft: Tomb Raider movie.  I was working in Asia at the time, and I rationalized that Cambodia was closer now than it would be when I returned to the United States.  So I went.  For the record, those movie folks had it right.  Totally awesome.

    Angkor Wat in Cambodia. Personal photo from 2002.

  • Make a list without numbers: I advocate writing the list down, although my personal list is mental.  Not having an exact priority is key because fluidity helps when turning destinations into real trips.  If a friend is ready to go to your #2 destination, you don’t want to say “no” because you haven’t been to #1 yet.
  • Answer key questions: What do you like to do on vacation?  What truly makes you happy when you are traveling?  For me, I have fair skin that burns easily, and I like to be active, so sitting on a beach for a week isn’t ideal for me.  I still have plenty of tropical destinations on my list, but I’ll need activities.  If there is a mismatch with some of the places on your list from above, ask yourself if you just want to “see” them or if you truly want to “experience” all of what that destination has to offer.  Focus on destinations that you truly want to experience.  I’m fascinated by Mt. Everest and getting to base camp was the experience I wanted to have, not climbing it.  This is very individual, but be honest with yourself and own it.  No apologies needed to anyone.

Next ask yourself “With whom do you want to travel?”

This is still about you.  And we are still overlooking obstacles.

  • Brainstorm on “Who”: There are so many options.  Spouse or a significant other.  Friends (list them by name).  Family (sibling, parent, cousin).  By yourself.  By yourself (on a group trip).
  • Consider compatibility: While very personal, I typically look at three dimensions:
    • Desire: does this person have a passion like I do to travel the world?
    • Philosophy/Style: will this person want or be able to experience the destination in the same way as I do?  Activity level, attitude towards money, and appetite for adventure are all things you need consider in terms of how they match with you personally.
    • Commitment: Will this person, can this person, commit to trip?  A bigger trip requires a bigger personal and financial commitment (ie. one year out)
  • Reality Check: Will I have fun with this person?  Consider that one person might be great for a long weekend and another for a two week trip off the grid.

Overcoming obstacles: I can’t go on my dream trip because…

I could write a whole post (and still may) on this topic alone.  Hopefully the strategies above have put key building blocks in place.  Still: time, money, safety, fear, guilt…they can all get in the way of your dream trip.

Here is how I did it for Antarctica:

  • Money: I knew I was going to make this dream happen, and I had Polar Buddy identified and secured as my companion.  So I had 12 months to skip a long weekend here or there and put the money towards the trip.  I had a birthday and holiday gifts for which I could request any gear I might need.  And I took smaller trips in the following years.
  • Time: I told my employer when I booked the trip, and I did it between Christmas and New Year’s, a slower time.  Tell your boss you will help put a coverage plan together for your absence.
  • Guilt: I did this trip over Christmas.  I wouldn’t be seeing my family.  Guilt, yes.  However, they were amazingly supportive.  Making a dream trip come true is inspiration for others to do the same.

Enough thinking already… how does this all come together?

  • Start talking: Begin chatting with any of your potential travel companions.  You can be vague at first, “You know, I really want to go to Iceland.  Where do you want to go?” or “Did you see that amazing picture of X hotel on Pinterest.  Wouldn’t that be a fun long weekend getaway?”  See what they say or what ideas they have of their own.

    Ah, Paris. Long weekend in Paris? Mais oui.

  • Think of it as developing a “someday” vacation pipeline: Your spouse may be ready for a long weekend getaway while your childhood friend might be willing to go on safari next year.  Or vice versa.  While planning my trip to Antarctica with Polar Buddy, I was talking with a new friend who turned out to be a big traveler.  It also turns out we both wanted to go to Turkey.  That became my dream trip for the following year.

A few more tips to help you organize your dream trip

I consulted my friend and Professional Organizer Julie of Simplify Me to get some of her best suggestions.  In her own words, here are Julie’s tips:

  • Keep a To-Do list: The list should include all the things, big and small, that need to be done (or purchased) from the time you decide to make your trip happen until the moment you are sitting in that airplane (or train, or car, or llama express) seat.  Writing down all the steps that you need to take will not only make your trip a reality, but will also help you to make sure you don’t forget anything and are not doing a mad scramble right before you are set to leave.
  • Ask for help: If you can’t travel much because of obligations, like pets or family members that need your attention, line up help for these things well in advance. Often friends don’t mind coming by to get your mail, water your plants or make sure your pipes don’t explode in a big freeze.  Book services to take care of pets and family members that may need it.  There are pet care services that can even stay at your home (to take care of fido and snowball, not your mother!).  Also, make sure you have several backups for all the important things, in case something falls through while you’re away.
  • Pack before you pack: Do a dry run of packing a week or so before you really pack for good.  This will assure you’re not forgetting anything, and you will also be able to see how things fit (and if they don’t) into your luggage of choice. This is especially helpful if you are planning a backpacking trip. Most of all, don’t forget to pack a good attitude (I think it’s under your bed) because things sometimes happen a bit differently than planned, but if you’re on a mission to have a great time, you won’t let those bumps ruin your dream trip!

So what is your dream trip?  What are your best tips to make them reality?

Header Photo: Cabo San Lucas, Mexico sunset.  All photos ©W2S Hilary

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