How I Stumbled into Travel Planning

I’m currently in the planning phase of my New York trip and I’ve had a stunning realization.

I’m not just planning the average trip for myself; I’m actually a travel agent – responsible for the travel enjoyment of my entire party of five (and growing)!

Maybe taking responsibility for everyone’s travel enjoyment is an overstatement, but I sorta feel like it’s true.

I’m not even sure how I earned this position.  Although, I must admit that after seeing the Megabus free ticket deal, I updated my Facebook status to alert everyone of my plans to travel to NY and I enthusiastically encouraged others to book tickets too!

As the Fates would have it, they thought my idea was just wonderful, and a group trip was born.

I’ve finally nailed down a location for lodging, after a lot of hard work (most of which was totally unnecessary) and I’m moving on to the next part of my planning – deciding what the heck to do in New York.

Making sense of travel plans – photo by koalazymonkey

Now that the major planning part is out of the way, I want to share a few of the organizing tidbits that I’ve learned:

Plan Early:  I’m a procrastinator by nature.  I just hate schedules and deadlines.

In order to combat this, I started planning this trip early.  Everyone’s transportation was scheduled within a week of deciding on this trip.  Planning for lodging started immediately and I booked a room on Priceline as a backupLuckily, AirBnb was the perfect solution for my group.

Now that I have the basics completed, it’s time to move on to the really hard part – collecting money.

Are you taking AT LEAST 3 overseas trips a year? If not, I'll send you my FREE travel guide. Get more travel in 30 days with these easy steps!

Set Deadlines:  I know I just said that I hate them.  That doesn’t mean that they aren’t useful.

There is a charge for last minute cancellations on the rental apartment, so I must know pretty quickly who can’t put their money where their mouth is.  Those who will back out are forced to do so right away, and not the night before traveling.

Prepare for Cancellations:  People are usually very excited about the idea of a trip, but when it’s time for a head count, you may find that your travel party has shrunk.

My travel party did some growing, shrinking and has seemed to stabilize.

With so many changes, I decided on lodging with a lax occupancy policy.  I also have a few people who have changed their dates to arrive or depart early, and this has thrown me for a loop.  I’m trying to figure out the best way to charge them for their portion of the rental apartment.

In the future, I’ll probably do a set price – no matter how long you decide to stay.  As you can see, I’m learning.

Limit Input:  I wouldn’t suggest that you don’t ask for any feedback, but limiting the amount and context of feedback can be key to making sure that you are able to move forward with any plans.

I initially asked for feedback for each location that I was interested in pursuing.  I also asked for help finding a location.  The problem is that it’s hard making a final decision with opinions from so many different people.

In the end, I picked a place and told people how much they owed.  I trusted my decision, and so did the rest of the group.

Delegate:  I could do it all, but I would pull all my hair out!  Plus, there are so many talented folks in my group.

One of my travel companions is great at finding cool things to do and I’ve employed her as the event coordinator.  Her duty is to find out what people want to do and make a group calendar.

It’s coming along quite nicely.  The first thing on the list is Good Morning America!  That should be exciting.

Provide Timely Information:  Keeping the group updated and providing them with information keeps everyone on the same page.  It also provides an opening for anyone to express concerns or ask questions.  I’ve started sending out weekly emails and I can sense an increase in excitement.

Remember to Enjoy Planning:  While travel planning can be stressful, the rewards are so worth it!  I remind myself that after all the planning is completed and money exchanges hands, that our vacation is going to be tons of fun.  I can hardly wait.

This is the first real “group” that I’ve planned travel for and it has really been a challenge.  The enjoyable part of planning this trip is knowing that some of those tagging along have never been to the Big Apple.

As the travel agent ;-), I’m rewarded with the thought that I’m encouraging travel and helping others experience more of this world.  I don’t expect this to be the last trip that I plan.

  • Anonymous

    i’m so glad i stumbled upon your blog. your post came up while i was researching flats and scams on craigslist (just out of curiosity, trying to find one post that is not a fraud and it’s proving to be quite a task :D)
    now i can’t hardly wait for you to post about your trip to nyc. i am going there in april and need some fun recommendations 🙂 i still have time to decide where to go, what to see, where to eat, but every time i think about planning i get panic attack from all the options 😀
    have fun in nyc 😉
    i’ll be waiting for your post(s)

    • It is a challenge getting through all the scams! Our list of things to do is so long and varied. For example, we have ice skating in Central Park, having a rooftop dinner, walking the Brooklyn Bridge at midnight and going to the Good Morning America taping. We leave this weekend and I’m finally getting excited! Can’t wait to share my adventures!

  • Angela Myers

    LOL. I think I wrote this! I am the “official” travel planner for my family and friends. As a matter of fact, on of my girlfriends called me at 6am yesterday. I thought it was an emergency so I answered and she said, “Hey. What do you think of cruises?”. I hung up! LBVS

    • LOL! She must have been too excited to double check the clock! LOL! I have a “family” trip coming up in March, and what I’m starting to learn is that excitement fades in conjunction with the trip dates and money due dates! 😀

  • Interesting post, I am so glad that I have visited your site. Really useful information!

    • Thanks, Nicole! I’m glad that you found the post useful. Do you have any big travel plans in the works?

  • You and I seem to have something in common…I too am always the group planner. Not really something I enjoy all the time, but at least it usually means we’ll get to do the things I like, and I know we will get there on time:)

    Look forward to hearing about your trip to NYC!

    • Good point! It has been a challenge, but I am really looking forward to this trip. I’m sure that I’ll have lots of fun stories to share! 🙂