Planning to Travel: Five steps to always take

No matter when or where you are planning to travel there are five things you need to do to make your trip successful. 

One of the passions that the Elegant Baker and I share is our love of travel.  We take several “mini” trips a year. For us those are long weekend road trips up four or five days away to some new part of the country.  We also plan at least one ‘major’ trip a year. This is a three to four week long trip, usually to a foreign destination. Last year, we spent nearly a month in Italy. It is safe to say that we have planned and taken many dozens of trips together.  

I share this so that you understand that we have a lot of experience planning for our travel.  We’ve learned a few things along the way — some of it we’ve learned the hard way.  

Pick the place and time

I know.  It sounds almost too simple to note.  But one of the most critical steps to planning a trip is selecting the basics of the trip.  Where are you going? When are you going? And how long do you plan to be there? This will serve as the fundamental framework of your trip and your plan.  From this you can begin planning to travel in earnest. You can book lodging, and start investigating activities to plan.  

Of course for smaller or focused trips this part can be easier. We need to be in Maine for a weekend in August for Steve’s wedding.  We might ask “Do we want to add a day at either end for ourselves”? But likely the dates are firm and the itinerary centers around the wedding.  

Larger trips, however, can be a different story.  When we were planning our trip to Italy, we started broadly with “Let’s go to Italy in September”  Easy enough. But then we were looking at specific destinations. Rome, Venice, and Florence were our original thoughts.  After some research, we ruled out Venice. We then needed to decide if we wanted a third destination at all and if so where.   We soon settled on Puglia, the stiletto heel of the Italian boot. With the third destination set, we needed to determine exact dates.  This leads to the next two steps, which often happen with a lot of back and forth between them. Specifically, building an itinerary, and planning activities. 

planning to travel Martina Franca Puglia Italy
Martina Franca, Puglia, Italy
Build an Itinerary 

Building an itinerary begins putting the specifics into a trip.  Where will we be on what day? And what will we be doing? For our Italian trip, we planned at least five days in each destination.  We decided we wanted to start with the most northern city and travel south. We finished on the Adriatic coast in Puglia. This allowed us to take advantage of the weather during our trip.  Once we made the big decisions, we started filling specific details. We added which city we would sleep in each night. We added when we would need transportation between cities. This is the first stage of building an itinerary. Planning to travel can be complicated and can take many passes to complete.  With each pass, you will add more detail as you identify more specifics.

There are many ways to record your itinerary.  Old fashion pen and paper. With a Word/Google doc or Excel/Sheets worksheet.  Also, there are several apps that purport to do it for you. In my own experience they are all lacking something.   I’ve tried many of the options, and none are perfect. What I have settled on is a Google sheet which is shareable, and stores in the cloud.  I can have access on my laptop while planning the trip, and on my iPad and iPhone when on the road. As long as I can get an internet connection, I can reach my itinerary. I can add more tabs with location specific information if I need to.    My method has its drawbacks, but it works for me. I’ve attached a view of my itinerary from our Italian trip below. 

planning to travel itinerary
Plan Activities

Hand in hand with building an itinerary is planning your activities.  What do you want to do when on vacation? Sit on a beach? Visit a museum? Research family history? Shop?  I find it helpful to build these activities into my itinerary when planning to travel. You don’t want to ‘over plan’ activities, but you do need to have a sense of what you want to do and when.  The Elegant Baker and I have found that planning two large blocks a day works for us. A morning and and afternoon block generally suit our needs. We try to have only one activity per block. This allows us to relax and enjoy whatever we’ve chosen.  We can do that without cramming our schedule too many activities and too much detail. It also allows us to move at a more leisurely pace between activities. This way we get take in the vibe and feel of wherever we are at.  

I find that is also important to plan activities because as you do so you may find a few things.  For example, you may find a particular museum is closed on Tuesdays, so you wouldn’t want to plan it for a Tuesday.  Or you may find that you want to attend a concert or a show where you need to buy tickets in advance. Laying these things out in detail has real advantages.  It allows you to be sure that you know what you need to do before you leave for your trip. Which leads me to my next tip

Book early. 

As you know, we are planners and spend significant time organizing our large trips.  But for trips large or small, it is important to book as far ahead in advance as you can.  

Planning to travel can have its financial advantages too.  Often you will find airfares lower than booking close to your trip.  You also can be assured of getting a seat on the flight you want by having plenty of time ahead to buy.  

The same is true with lodging like hotels and especially AirBnBs.  You have the most selection of the best inventory if you buy well in advance.  On our trip to Italy, we booked our AirBnBs seven months in advance. And we STILL lost 3 different ‘first choice” apartments to others booking early as well.  

Some things you NEED to buy tickets early for.  For example, to visit the Alhambra in Granada Spain, you need to purchase a ticket in advance.  You can only buy tickets for a timed entry. We find to get the most out of a site like the Alhambra, it is best to enter early and spend as much time as possible visiting. 

planning to travel alhambra spain
The Alhambra, Granada Spain

Tickets go on sale up to a year ahead, but you can still find tickets available 2 months out from your planned trip. Any closer than two months out, and you are unlikely to find tickets at all.  If you wait until two months ahead, tickets will only be available for only the least desirable times. To ensure that you get a ticket for the date and time you want, you need to buy at least 7 – 8 months ahead of your scheduled visit.  I know it seems a long time in advance. But tickets are limited and extremely desirable. You get the best chance of meeting YOUR needs but planning early.  

Travel Insurance. 

Knock on wood, we have never actually had to make a claim against our travel insurance.  But I know that it is possible that someday we are likely to. Because we plan so far ahead, we can’t always be sure what may happen that could cause us to have to cancel the trip.  We also can’t always anticipate delays or other issues that could cost us money. Finally, and most important, trip insurance can cover the costs of medical emergencies abroad. In our experience a comprehensive, cancel for any reason policy will run about 5% of the total cost of the trip.  Perhaps a bit steep, but we find it worth it for the peace of mind.  

You can find travel insurance at a good comparison site like or direct through a specific provider site like Allianz. I have had good luck with both, although I tend to prefer buying from Allianz direct.

There are many other things that go into planning to travel, and I will cover more later.  But I find these five element are the most important to making the trip successful. I hope that you find useful insight here and give it a try next time you plan a trip. 

Trulli House, Puglia Italy
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