How to Decide on Where to Travel to Next

At a time when the rest of the world has stopped travel access and you can barely cross state borders domestically, how do you plan something to look forward to? I always looked forward to traveling – but choosing was the hardest part. Here’s how I look at where I want to go next and make decisions.


Being a total history nerd married to a history teacher comes with its perks – a shared desire to travel and see the world. We had big plans to go to Spain this year and take advantage of the travel high we had from our Italy trip, but as you know….2020. So instead we made a few adjustments and tried to make the best of local day trips or finding places that were off the beaten path where we felt safe to visit and still get some travel in.

We are more optimistic in 2021 so here’s to hoping we get a little flexibility back in our lives. I know that everyone approaches planning travel differently – so wanted to share how we plan:


1 //  Pick a few places and create a mini bucket list for the coming year. It’s like goal setting. Now that it’s on paper or out in the universe, it is more likely to happen than when it was only an idea. We will most likely consider more local or accessible places this year that don’t require flights (but we can squeeze a few in – just in case). 🙂



2 // Ask people about their experiences and stories if they have been there before. It’s even better if there are family or friends that live in those locations that can share a genuine perspective on things to do and see,  outside of the tourist places that can be found from a Google search. If their stories get us excited, we leave the location on the bucket list. If it feels more ‘bleh‘ or just not interesting for this coming year, we parking lot  it. What I mean by that is we set it aside for further consideration later.



3 //  Decide on the ‘must see’ list. If you are going to a specific city or town  such as New York City or San Francisco, decide on your ‘must see’ attractions. If you are visiting a country, decide on your ‘must see’ cities and towns.  What we do is we make a list separately from one another so that there is no negotiation up front. What the mister would like to see may be different from what I would like to see. This keeps it fair and unbiased. We took this approach in planning Italy last year.

Then we share that list out loud, talk about it and plot it on a map. (I printed out a clip art map like the ones we used to color in elementary school.) After we plot points on a map, we look to see if there are areas of concentrated points. For Italy, there were very clear clusters of areas that we wanted to visit. That is how we found our priorities for the trip. Negotiation done.




4 //  Now that the ‘where’ is decided – look at pricing. Some of the items on the list will look really expensive right out of the gate but don’t be discouraged just yet. Write down what it could cost for lodging, transportation, food, activities, fees, events, museums, tours, etc. Get to a total dollar number (regardless of the sticker shock) so that you can see what your all in price would be.

From there, you can start to get creative with points, sales, deals and rewards. We like to travel as cost effectively as possible so that we get the most bang for our buck. There are always package deals when you book through certain airlines, credit card points you can apply or other ways to help cut the cost. Use what’s available to get that number to the lowest point possible. In this phase of the process, we start to drop items off the list that may not jive well with the budget such as a tour or an event. If you can gain something more worthwhile for that sacrifice – do it.  

For example, we got a great deal on for our stay in Florence. We were faced with whether we keep the savings and leave for Tuscany or use it to stay one more day in the city. We chose to extend for another night in Florence and we are glad that we did. It was one of the best parts of our entire trip.



5 // Once the map and budget is set – make decisions and start your booking process. We typically start with booking flights since that tends to be the largest expense and you don’t want a great trip booked with no way to get there!

That helps us to lock in the date and rates that we are comfortable with and then we build from there! I recommend focusing on transportation overall first so that portion is done. I find that we are more willing to flex on the places to stay.  Remember that you may not know the local language when you get there, so take care of anything that may require additional assistance here in the US, including currency needs.

Either way – start booking. We have found that if we wait too long to start the process, the idea of travel goes back to just being an idea. Don’t let that happen!



6 // Locked in. Start the packing list!! All those visions of the trip become more real by the day and plan to pack accordingly. Be aware of whether there is a lot of walking for flats and sneakers or whether or not you can carry your luggage long distances. That would definitely change your mind on what to bring. In Italy – we stayed for 2.5 week so we actually took care of laundry while in Italy, cooked in the apartments we stayed in a few nights, and had a fantastic time. I am thankful that the mister was willing to power through the cobblestone streets with my luggage. Love you!

Have the most amazing trip and continue to enjoy the world! It is worth every penny spent. ❤ 



Traveling is a blast and we love to do it together. What are some of the places that are on your list this coming year if we are able to get some flexibility back for it?

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Author: Jackie

A marketing professional and lover of all things fashion and style, blogging on nights and weekends.

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