An Affair to Remember

(original published on August 11, 2014)

I am having a love affair and his name is “Travel.” Traveling is thing I do when I want or need to escape my normal life.

My first adult vacation was a visit to San Francisco in 2003 with one of my closest friends. For that trip, I did a ton of research on things to do, what to eat, and how to get around.

Golden Gate Bridge, San Francisco, CA (c) Winter Shanck, 2011
Golden Gate Bridge, San Francisco, CA
(c) Winter Shanck

This was the beginning of an affair to remember.

Since that inaugural trip, I’ve been to Anchorage, AK; Austin, TX; Baltimore, MD; Charleston, SC; London, England; Newport News, VA; Philadelphia, PA; Portland, OR; Providence, RI; Richmond, VA, San Francisco (3 addition trips); Savannah, GA; and Seattle, WA. Sometimes these trips were for business, but I always manage to include a ton of fun no matter the reason for the journey.

After all of these trips, here’s what I’ve learned:

 Practical Advice

1 – You don’t have to spend a ton of money to go on a great trip.

Take a 4-day weekend trip.  Try to book a trip that leaves Thursday evening and returns the following Monday evening or on Tuesday. Book this last minute vacation through companies such as Travelocity and Expedia. They have pages specifically tailored towards finding a great last minute deal.

2 – Book your vacation at least 6 months out.

  • Use the “vacation packages” option on, etc. All of these sites will allow you to book a flight + hotel or flight + hotel + car with at a discount. In addition to this, you can choose which airline you would prefer to travel and the hotel of your choice. I prefer to use search function.
  • Avoid major holidays.  All hotels and airlines jack up the prices during major holidays.
  • If possible, begin your trip on a Tuesday, Wednesday or Thursday.
  • Finally, if you want to stay 7 days, try searching different weeks in the month to see if any week is cheaper than the others.

3 – The biggest expense, no matter what, will be the hotel.

  • To diminish this cost, try the suggestions under #2.
  • If you’re taking a road trip, look into B&B or use sites like airbnb. B&Bs are usually cheaper than staying in a hotel.

4 – Be prepared.

  • If you’re like me, packing for vacation might not go a smooth as you hope.  After forgetting a toothbrush at least 4 times, forgetting shower shoes, and forgetting socks, I decided to create a “travel checklist” of the general items that I would need to take for every trip, whether it is for business or for pleasure.  You can use the checklist below as a starting point to decrease the angst and anxiety that tends to show up when packing for a trip.

Travel Checklist

  •  Carry a guidebook or create your own, especially if this is your first time visiting a place.  Knowing where to go, what to see and what to eat before hand allows you to have a general idea of what you want to do while you’re on vacation. There is nothing like going on vacation then coming home and realizing that you missed something that you might not get the opportunity to see later.  While I was in Rhode Island, I didn’t realize that it was known for its rum production.  Holy cow!  I love rum. I really wish I knew about this before hand because I don’t have any plans to revisit Rhode Island anytime soon. I have much grander places on my horizon.  Future post will contain guides that I will create for future trips. You can see two examples below of the types of guides I create for the restaurants I wanted to try.
  • Tripadvisor is your best friend.  I use this all the time to check for real reviews and images from real peoples.  I always check to see if the hotel I’m considering has been reviewed and if any images were uploaded. I also use this to check to see what are the most popular things to do before I travel.  I compile all of this information along with additional information into a document that list where I potentially want to stay and what I potentially want to do while I am traveling.

The example below is the restaurant list I created for my vacation in Charleston last year.

charleston food guide

  The example below is a finalize guide after my trip to Seattle in 2012.

seattle food5 – Ship souvenirs home.

I always buy a ton of souvenirs.  So much so that in previous years, I’ve had to perform a Jedi mind trick just packing my bags so that they could be carry-on on my way home.  Last years in Charleston was the first time it dawned on me that I could ship my souvenirs home. It was a pretty genius moment for me. This allowed me to simply repack my two carry-on bags without have to check a new bag (because I always have to buy a bag to accommodate the new purchases). I highly recommend doing this if you are a classic super souvenirs buyer.

Do you have any travel tips?  If so, please post them in the comments below.


– Winter

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