Vacation Questions to Ask Today

For some people, summer vacation is already planned, reservations are made and tickets are purchased. But there are others, who are still digging out from under the winter snow blankets, and need a little push to get summer vacation plans started. Here are some time tested questions that will help you go from winter blues to summer fun!

Vacation Questions to Ask Today

Vacation Questions to Start Asking Now


Before you can plan your summer vacation, you need to know who you are planning to accompany you. Is this a solo trip? Just your nuclear family unit? Are you planning to share the trip with another family or friend?

crowne plaza family

Our kids are getting old enough now that we need a little more space when we stay in a hotel. That’s why we try to grab a suite instead of just a double room. Recently, when we were staying in Louisville, we checked out the Crowne Plaza. Talk about a great way to enjoy some family time! There was plenty of room to spread out, play games and relax without feeling like we were stacked on top of each other.


What is your purpose for this vacation? Many of our vacations are spent on the road, traveling from one historic destination to the next. We love taking the long road trips that let us see and experience something new around each new bend of the road. We’ve been working on getting to all 50 states before the kids graduate from high school. Right now, I’m at 32 and the kids are 15. Looks like we’ve got quite a few more road trips in our near future!


But last summer, we decided to take a trip with one purpose – relaxation. We rented a condo on the beach and spent the whole week just enjoying the sand and the waves. We took a dolphin cruise on the Southern Star in Destin, FL and went out to eat at some great seafood restaurants, and just focused on the time to relax.

Figure out the purpose for your trip before you start making your definite plans. Ask the other participants and see what they would like to get from the vacation. Knowing the WHAT will help you decide on the direction of your vacation.


There are some families who get season passes to the big theme parks. They have a time share on the beach or in the mountains and know that every year they will be traveling to the same destination. But others like us, love to hit the road and discover new things. We are already hashing out ideas that will take us as far north as Boston and New York City or out to some western states we have not explored.


If you can be a little flexible, you will be able to find a potentially cheaper vacation option. If you are traveling by plane, is there a cheaper day to book a flight? Are you planning to rent a condo? Some have restrictions that only allow you to check in and out on certain days of the week. If you are planning a cruise, look at the off season to see if you can save some money by going at a different time of the month.


How will you pay for this vacation? There is still plenty of time to start saving money so you won’t have to fund your vacation on credit. Do you have a rewards program at work that allows you to earn gift cards? Maybe you can save those redemption points to buy gift cards for your travel. Can you put aside a certain amount of money each week so you will have a summer fund? Resolve to spend none of the change that accumulates in your pockets and purse. Designate those coins for vacation. You might be amazed at how quickly they add up.

Look at your credit cards, bank accounts and utilities. You may find that you have been earing loyalty points or perks that can be cashed out just in time for vacation.

Cleaning house could be a financial boost for your summer plans as well. Do you have old electronics, books, sports gear or collectibles that could be sold on ebay or at a yard sale?

What are your plans for summer vacation? Got any tips for planning that will help us all save some money and get away? I’d love to hear!

Excerpts of this article first appeared in the print edition of the Advocate Messenger, Danville, Kentucky 2/28/16.

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