How to Decide Where Your Next Vacation Should Be

iStock_000015429731SmallWhen my fiancé and I were trying to figure out where to honeymoon, we were on completely different pages. I wanted to do Greece or Italy, but he was more interested in an all-inclusive resort where we could just relax, swim, and lay out in the sun. We were at odds until a couple of glasses of wine and the internet one night presented us with a solution.

I have had this issue with a friend, before, too. We knew where we wanted to take our first trip, but after that, we just knew we wanted to go somewhere else the following year. After much humming and hawing, we agreed upon a destination, but it wasn’t easy.

A complete first world problem, often deciding where your next vacation will be is a difficult decision. I have perfected the art of this decision, and thought I’d share the process I go through:

Where is the Cheapest Flight?

Budget does rule over many of my vacation and trip planning decisions, including where I go. One of my favourite ways to pick my next destination is to look at what the cheapest flight option is from my departure airport.

Some of the cheapest flight options are to destinations that you may not have considered, but every city and town has something to offer.

To do this, you can use flight databases such as Skyscanner. In the “to” field, you can input “Anywhere” and it will list all of the destinations by price.

Check Out Some Travel Blogs

There are many popular destinations that are worthwhile, such as New York and Cancun. However, there are also a whole bunch of amazing places in the world off the beaten path.

One way I found out about cool things that are surprisingly close to where I live is by turning my attention toward travel blogs. There are so many interesting little cities, towns, and sights to see.

Reading travel blogs will give you a little bit of inspiration, and if nothing else, also provide you with a few ideas of fun things to do when you reach whatever destination you choose.

Keep an Open Mind

One time, my fiancé and I wanted to go on a short vacation to get out of town on a long weekend. We had our hearts set on a little coastal town in Oregon, but all of the hotels (not that there are many) in that town were booked when we wanted to go.

We stayed at the closest town adjacent to the first one we were looking at, with the intention of driving to the other town every day for the beaches and hiking.

When we arrived in the town in which we were staying, we were struck by how lively it was, and how fun! There was a surprising amount of stuff to do, so we ended up staying there for almost our entire vacation. We did visit our originally planned destination town once, but found that there wasn’t much to do there and were grateful that we got sidetracked like that.

Keeping an open mind will help you take the path less travelled and enjoy places that you may not have planned to visit. It will also allow you to really embrace and appreciate what makes that destination unique. I always surprise myself as to how often I don’t want to do something that I end up loving when I actually do it. It can be difficult to get past the initial hesitation but it has high payoff.


These are just a few ways I decide where I should take my next vacation. How about you?


How to Decide Where Your Next Vacation Should Be — 6 Comments

  1. I can relate to the honeymoon problem you faced. Though I’m not married yet but ‘m living with my boyfriend for the last 5 years and every year we fight a lot when the time comes to decide on the destination of our travel. Yes, I know how difficult it is to converge. Last time we visited Hawaii. Though I was hesitant at first but after reaching there it swept me away my feet. That was the best trip we had in the last five years.

  2. There are only three qualities I look at in a vacation destination: Warm, blue/green water, beach. Oh, I forgot the fourth: pina coladas. 🙂

    • Hahaha! I am not a beach person but I can see what is so enticing about tropic places.

  3. Well I’m in a strange situation because I won a trip to Hawaii so that will be our next vacation. I think cost of flights are so important. For example, we would love to go to Hawaii way more often (and not have to win a trip to justify going) but the flights are pretty expensive from Minnesota. Additionally the cost of hotels there are much higher than, say, Florida. We don’t take many vacations so we tend to only really go places that are warm with a beach, preferably some place we haven’t been before.

    • Oh, I’m so glad you ended up winning, DC! Congrats! That’s so exciting for you.

Leave a Reply

Your email address will not be published. Required fields are marked *

I appreciate your readership and really enjoy hearing your thoughts on different topics. Thank you for contributing to the discussion.