Vacation So You Don’t Need a Vacation from Your Vacation

Have you ever got home from your vacation, plopped yourself on the couch and thought—I NEED A VACATION!

Nice View from My Office
Nice View from My Temporary Office

Vacation, vacation, vacation: such a delightful 8 letter word—in theory. As I sit here and type this poolside the implications of that word seem like such a distant memory. In reality the implications include: accommodations; airline tickets; school vacations; work schedules and coordinating all of those so they match up! Often there is one coordinator of this venture we call vacation and if that is you reading this then I have reached my target audience. For it is with you I can have this candid conversation and keep it real. I consider myself a “sandwich” coordinator. The coordination for my most recent trip included these attendees: myself; my husband; my 8 year old son; my 22 year old daughter; her boyfriend and my Mom-in-Law. I felt “sandwiched” and pulled in many different directions, as a coordinator most often does, but add this well rounded group and added stress was imminent. Nonetheless, I am now typing this article from the comfy confines of my home office (boo) and with hindsight as my driver I will share with you my tips which made this trip an outstanding success and some of the pitfalls that seeing now I could have clearly overcome and will for sure on the next trip (which I am currently planning).  😀


Before I proceed, the unspoken, proverbial rule is: Set a Budget. Download my free budget Financial Spreadsheet and start from there. I know, believe me I know, budgets and fun are not synonymous but I assure you neither is fun and debt.


  1. Schedules-Perhaps one of the most important if not the most important part of planning a vacation is scheduling. For this trip I had to coordinate 3 adults working schedules, one school vacation schedule and the very busy schedule of a very active retiree.
  • When scheduling the call to action has to be to pick the schedule with the most impact, for me that was my 8 year olds’ school vacation schedule. Which for us had the least flexibility.
  • Keep in mind, if you don’t already know, the travel periods of March and April increase rates upwards of 50%. If you do not have flexibility in your scheduling, adjust your budget proportionately right from the start.
  1. Accommodations-Once you have a date the next exciting step is to decide, where are you going to stay? There are many factors to consider in this oh so important step, for any size party. For example, this past trip was a party of 6 (refer to “sandwich” attendees) that I was coordinating for. The previous year it was a party of 3 ladies to a foreign country. Even with half the size party in the previous year, accommodating us all came with its share of unique challenges.
  • When thinking of where you want to stay my recommendation is one bathroom for every two/three max vacationers. To further dilute this, consider who is going to be occupying those bathrooms. For two parents and a child, one bathroom should be sufficient. For 3 ladies, two bathrooms was a must! Summary: adjust according to party size AND the party themselves.
  • Hotel—Timeshare—Suite, OH MY! Depending on where you are traveling to, there are many options for lodging. Keeping in mind the bathroom accommodations, where you lay your head down is a very close second. In my experience with destination locations such as Disney or some all-inclusive resorts, rooms are very small. This “forces” you to have to purchase additional rooms based on party size or upgrade to suites. Both of those options can add lots of dollars to your vacation budget bottom line. My recommendation is to check out the local timeshares. A lot of them rent rooms in 2-3 night+ stays and at a steep discounted rate to fill rooms when the timeshares aren’t being used by the owners. I recently did this in conjunction with the timeshare I own because we traveled on “off” days (more on this in a sec) and had to purchase additional nights. For 6 travelers, we had 3 bedrooms and 2 baths, a full kitchen with dining, living room and laundry room. Togetherness has its merits but sometimes equally so, does solitude.

    Now that's Solitude!
    Now that’s Solitude!
  1. Traveling-Planes, Trains, or automobiles—that is the question. As I mentioned in number 1, peak traveling times command big premiums. I had booked our accommodations and then went to book airfares. Screeching halt! I went on every conceivable site known to my traveling hands and in a nutshell it was around $1,000 per person, round trip. Uh, NO!!! This was for flying Saturday to Saturday, Sunday to Sunday and Monday to Monday and a few combinations of those days. At first panic set in and then.
  • I started checking dates just outside my target traveling dates, not dates before but right after. Checking before still put me into the peak traveling times for my trip, which fell in the March-Mid April peak. I didn’t have to go too far because you know the saying: what a difference a day makes and the difference one day meant for us was a savings of $650 a ticket. We traveled Tuesday to Tuesday. This meant my son had to miss two additional days of school and the adults had to take 1-2 additional days off from work but for a savings of $3,900 and not possibly going at all, it was well worth it!
  • If you are staying in an off-site resort and are traveling with parties of two or more couples, rent two vehicles. I don’t believe I need to elaborate on that topic any further.
  1. Attractions & Dining-I grouped these two categories together because they can be big ticket items and very well could go in conjunction with number 1 when planning your vacation.
  • What is your vacation goal-relaxing on the beach, by the pool, soaking in the sun’s rays? Is it zip-lining in the jungle or visiting as many amusement parks and attractions as you can? Our recent trip to Disney was my Mom-in-Laws first time to Disney. We wanted to show her everything and see it again “for the first time” through her eyes. In theory this is all well and good, but we have an eight-year-old who could care less about parks and could easily spend 8-10 glorious hours in the pool. Add to that my grown daughter and her boyfriend with an agenda of their own as well. My recommendation get somewhat on the same page BEFORE you purchase tickets to parks or excursions. We purchased tickets with the option (for a fee) to hop between parks in the same day. Doing this allowed us all to visit the parks we enjoy but saved us money on purchasing an additional day which net a savings of approximately $500.

    The Most Magical Place on Earth!
    The Most Magical Place on Earth!
  • I am going to dive right in with my first recommendation—Get on somewhat of a same eating schedule, at least for the week. I am a grazer in the morning, my husband likes to eat a little more substantial, my son can eat all day long. So by the time we got to the parks of course one of us was hungry (I will let you guess which one) which added to our food budget and could have been avoided if we loaded up before we ventured out. But hey, it is vacation. Which leads to which type of dining is best. I have done all-inclusive, dining plans and ala carte dining. Budget wise, all-inclusive and dining plans can offer some savings and flexibility but depending on where you are vacationing, offer ok food. My caveat is I don’t find this at Disney, all of their food is exceptional but I observed this past trip and in speaking with other diners, the choices can be limiting. Our timeshare comes equipped with a full kitchen so for us a trip to the local grocery store is always first on our agenda when we arrive. My recommendation here is to not let your eyes be bigger than your stomach. Shop wisely. Unless you plan on cooking and eating everything you bought, this could end up being a budget drainer. Take into consideration eating out, snacking and cocktailing poolside, vacation is no time for deprivation, however, you work hard for your money and vacation shouldn’t be a time to waste it either.
    50's Prime Time Cafe Sampler
    50’s Prime Time Cafe Sampler

    My Favorite Disney Treat of them All!
    My Favorite Disney Treat of them All!

Hopefully you can walk or “fly away” with some useful tips when you go to plan your next vacation. Though Woman Market Ready is always focused on being financially savvy, we are often reminded with sayings such as this—you can always make more money, but you can’t make more time—to enjoy time with family and friends in exotic destinations or right in our own backyards.

Happy Travels! 

Cheers!
Cheers!
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Kimberly

Author; Blogger; Self-Proclaimed “Woman” of all trades and Self-Proclaimed “Master” of some! AFAA Certified Group Aerobics Instructor since 1998; MA Licensed Real Estate Agent since 1995; former Certified Financial Counselor and Passionate Advocator of Financial Education for Women. Tech Geek; Home Cook & Most Importantly, Mother of 3, my #1 Reason for Living!!!