(How To) Take that Vacation!

This past Tuesday (January 31) was National Plan Your Vacation Day.  Did anyone actually sit down and plan a vacation that day?  (Please tell!)  I didn’t, but I didn’t have too.  I’ve been planning my vacations (yes, that’s an s at the end) before the idea of them ever even surfaced.  Since I am a teacher, I have set times when I can actually get away.  There are both pros (lots of time to travel) and cons (it’s always the most expensive time to travel) to that, but it is helpful knowing ahead of time what I have to work with, schedule-wise.  The rest is the fun part, picking the location!

I have been very fortunate, especially in the past few years, to have been able to travel multiple times a year and to some very phenomenal places.  As in most cases, time and money are key, but perhaps even more important than that is priority.  Experiencing the world became a priority for me 6 years ago after my husband died.  His death made two points very clear to me.  One, life is very short.  And two, material possessions don’t compare to adventures and are much heavier and bulkier to carry around.

So as a teacher/single-mom/sole-parent/Brooklynite, I decided that after I put a roof over our heads, food on our table, and clothes on our back… traveling was in the top 3 on my priority list.  And I just made it happen.  So, I thought I’d share some of the things that I did to help make my desire to vacation a reality…

Start Small

I have always had a thing for Europe.  The castles, the landscape, the history, the accents… I love it!! However, 15 years ago, I was married and child-free, but money and time were both very tight. Other than a trip to Scotland right after I graduated college, I never saw myself in Europe again or anywhere else for that matter.  My mistake was that I was so obsessed with going to Europe that I didn’t consider or research other places that would be more reasonable for me to travel too, so I didn’t.  It took me 9 years to realize how many wonderful, exciting, and gorgeous places were literally at my doorstep.  And my very first vacation as that sole-parent was for a long weekend (5 hour drive) to Maine, with my son.  Which leads me too my next tip…


This is the only photo tha I can easily access from this trip, but the Maine folliage in the fall is amazing and looking back at pictures of my son floods my mind with memories and my heart with love.


Maine had never been on the radar for me.  I was reading a National Geographic Travel magazine at a hair salon when I came upon an article on Kennebunkport, Maine.  It was less than a half a page long, but I was captivated.  I wanted to see this quaint town on the ocean.  Not only did I find that it lived up to that article, by experiencing it first-hand for myself, I became more alive.  (I even met a very handsome man and chatted with him for an afternoon, but that’s a whole other story, lol).

Maine hooked me, no pun intended.  I was determined to find the best vacation spots that I could afford (which meant within driving distance) and enjoy with my son (those child-free years were over and I didn’t have anyone to watch him anyways).  So I Googled like it was my job and I talked to people.  I did my research.  And even though it wasn’t Europe, I learned to appreciate the experiences that I could give myself and my son and it meant so much more!

On a Columbus Day weekend we went to Essex and Mystic, CT.  My son loves trains so we spend a Day out with Thomas at the railroad station in Essex.  That followed by a walk through of a life-sized dinosaur infested park at The Dinosaur Place.  We spent the night in a reasonable, safe, and clean hotel, then spent the next day in Mystic.  We ate pizza at Mystic Pizza (Julia Roberts, anyone?) and befriended a beluga at the aquarium.  Good.  Good times.

Travel with Someone

Whether you are by yourself, a single-parent, or have a family… travel with others (and the more you like them the better!)  My first big vacation with my then 2 year old son was a 9 day trip to California.  I had the time, but I didn’t have the money to spend 9 days in California.  What I did have was a brother who travled with us and helped to split the cost of the hotels and the car.  That made a big difference.  A huge difference.  An I can actually pull this off difference.

caAside from the laughs and memories, I also got to see some pretty amazing views in CA.  We started in the LA area and drove up the Pacific Coast to San Fransisco and Napa.  This photo is take from Manhattan Beach.  🙂

A Support System:  Now while that trip with my brother was very helpful in splitting the cost, it was not helpful mentally.  I was with my two year old son 24/7 X 9 minus the 45 minutes my brother spent with him in the pool so I could have a glass of wine in peace. It was a draining vacation in many ways and if you have kids, a vacation can easily feel more like extra work than a vacation.

I have gone away twice with a support system aka a family vacation.  One was with my sister and her family and the other my sister-in-law and her family.  I rarely saw my son, so to say.  Both times, he spent more time playing with his cousins then needing me for something.  I had some time to myself and it was wonderful.  Because there were multiple adults, we also switched up who was watching the kids and were actually able to create a night-life for ourselves.  One night it was ladies/ guys  night out, another was couple’s night out.

So if the stress of a “vacation” with kids is holding you back, ask around.  Maybe someone you know would like to team up.

Travel Alone

No one else up for a big trip?  No one else shares your desire to see a particular tree in a particular botanic garden across the state (true story, lol)?  No problem.  Go alone!  I have traveled alone twice and I absoulely loved it!  That in and of itself is an experience (and a whole other post) and one that I look forward to doing again.  My first trip alone was to Las Vegas, yes you read that right.  Why Las Vegas alone?  Well… it was February and I wanted to go somewhere warm and it was by far the cheapest vacation I could find.  So I took a deep breath and just did it.  It was amazing!  The strip, the food, the galleries, the Grand Canyon… I had an absolute blast.  And BTW… with phones and technology, are we ever really alone?  I was constantly texting and Facebooking and keeping in touch.  It definitely helped to take away any lonliness that I felt.  However, I wasn’t completely alone.  When you travel you get to meet people… fascinating, interesting people.

vegas           One word:  magnificant!  Speaking of meeting people… I spent the day touring the Grand                     with a woman that I met on the tour.  We had alot in common and we spent the whole day                 together.  It was a fun and interesting day!

Be Smart with Your Money

First, you need to start with some money to begin with.  For me, I was already stretched thin and living paycheck to paycheck.  My money was used for the basic necessities.  I couldn’t cut back by making my own coffee instead of going to Starbucks or DD every day.  I couldn’t cut back from that weekly mani-pedi.  I couldn’t cut back on any extras because I wasn’t splurging, I couldn’t.  What I could do was keep my head my bank account above water enough so that when I got my tax returns, I had an automatic savings plan that I dedicated to travel.  It wasn’t easy, but once I got the itch to travel it became much easier to give up some things manage my money differently in order to make it happen.  It’s different for everyone.  What can you manage (because I know how hard it is to give up something you enjoy entirely, and you shouldn’t) differently to open up some extra cash flow?

Timing is everything.  Flights are expensive and if you are going someplace across an ocean or you are pressed for time, you kind of don’t have an alternative.  I am an Expedia fan, but there are lots of other sites that compares prices for you.  Being flexible on dates and times can also make a huge difference.  If you are not a teacher and if you do not have any kids, take advantage and look a great deal, they do exist.  You can also read this article for more tips.  Even the time and day you book can save you lots of money, I book on Tuesdays all the time!

Pick what you want to splurge on… hotel, food, excursions?  Maybe you can do it all, but if you can’t, it is still worth making the trip!!!  I have stayed in rental homes many times before.  Many times they are larger than a typical hotel room and cheaper.   I’ve been lucky that they have all been very nice and clean, and they all have come with a kitchen.  That can be extremly helpful in saving some money by not eating out for breakfast, lunch, and dinner every single day.  I know, who wants to make dinner on vacation?  But making some toast and eggs and having some OJ in the fridge (maybe even that bottle of champagne, mimosa?) can make for an effortless breakfast and can save so much, especially if you are travleing with your family and kids.


This was my view every morning during my vacation to Puerto Rico.  Our two bed, two bath               rental apartment with a large terrace was literally on the ocean.  The tradeoff was that we                 were a bit “out of the way.”  But we had a car anyway and the extra 10 minute drive was no               sacrifice for what we saved, the space we had, and the view we had in return.   

Make your money work for you!  I have a couple of travel rewards credit cards.  I am still searching for the best one for me and you should definitely do some research of your own.  You can start here.   In April, my husband, son and I are going to Palm Springs, CA.  We used our Jet Blue points and all three of us flew for free!

Make the Time

We are all busy people.  I have yet to take a vacation with my husband where he doesn’t get a call from work.  But atleast he is willing and able to leave the actual job site and he will only think about work for the duration of those calls.  We all need to decompress and to step away from our jobs for a bit.  It gets to be to stressful.  We all need that recharge.  Sometimes you just have to bite the bullet and let it go.


So who is ready to do some vacation planning now?  I’d love to hear of your travel plans.