Tips on Trip Planning

Tips on Trip Planning

“How do you plan your trips?”

My initial response consist of a shoulder struggle and “I search Google” but I realized quickly that doesn’t help anyone answer the question. It can be overwhelming navigating through the plethora of information when learning about a new destination and attempting to plan your perfect trip.

First, always start with goals- what do you want out of this trip? This will help define your entire planning process. If you need to see all the churches Rome, experience the madness of Times Square, see every sculpture in Florence, or simply want to sit outside a cafe in Paris- knowing this before planning will save you so much time- especially if you do not want to do any of those things. Everyone vacations differently. We typically plan our trips without much focus on relaxation, but I know full well that is not everyone’s vacation style.

The first phase of trip planning for me consists of information collecting to find out everything there is do to and the variety of things to eat. What do people go here for? What is this place known for? What are the “must do’s”? What do locals do on the weekends? Where is the best (and safest) place to stay? The next phase is to find out what friends and locals have done. I always weigh these recommendations more because I can get a better gauge from a person if certain things will interest us and fit our trip goals.

Get a Google Docs ready to help organize all the information you are going to find- start with a template like the one I use for every trip. I distinguish categories, such as food, bar, activity, and sightseeing. Once I have my complete list I can begin comparing categories to make decisions on things to prioritize. Knowing when places are open and closed will help dictate when you may be able to visit.

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I know this may sound cliche, but when we identity a trip destination one of the first things I go to is New York Times 36 Hours articles. It gives a basic overview of the range of things to do, including “must do” attractions, the cuisine you can expect, and best areas to stay. While it is not necessarily to use the itinerary (we rarely do), having a quick summary of the location in a 36 hour time period is a great place to start.

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Another reference we not only take trip planning from but also inspiration for new adventures is TV specials that focus on travel- not the tourist highlight reels- but ones that deep dive into culture. Two that have been particularly helpful (and we can vouch for several episodes as we tested some of the dining places out ourselves) is No Reservations and Parts Unknown.

After studying maps and learning the best areas for our home base, I rummage through Airbnb listings not only for a place to stay, but for recommendations that can be found on host’s pages and “The neighborhood” section at the bottom listings. We always solicit advice from our Airbnb host because we feel nothing is more valuable than a local’s favorites- “If you had company visiting for the first time- where would you take them?” “Where is your go to coffee or bar?” “What are your top 3 restaurants?” Asking more pointed questions will give you direct answers. Bare in mind that not everyone has the same tastes- this is part of information collecting so you can make the best decision for your trip.

If we know anyone that has been to this new destination I make sure to prioritize obtaining their trip details including places they liked and disliked. It is just as important to know what to avoid! Sometimes we are surprised at the network of people we were unaware of that traveled to places on our travel wish list- even friends of friends. It has been our experience that people enjoy talking and sharing their travel experiences- take advantage of that.

One of our favorite memories from our trips (especially to Italy including Florence and Asti) is attending local festivals. There is no better way to immerse yourself in culture (and food!) than these events. Quick Internet searches can identify these but fair warning that many local festivals will be in the native language- be patient with Google Translate! A bit of homework here can have great payouts.


As I gather all the events, restaurants, bars, and sightseeing options we are interested in, it is time to vet the list to start narrowing things down for our trip. I use personal recommendations as well as reviews found Google, Trip Adviser, and Yelp. One thing I will stress is that I look at the reviews in the native language with more weight than those of a tourist language. This gives a more realistic view of that locals think of these places- can help in avoiding tourist traps. Simply change the review filter to the language of your choice, as seen in the right below.

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It is time to optimize the various pin options in Google Maps to categorize places to visit. This enables us to download our personalized map and access it offline which is key for us since we rarely invest in cell phone service unless it is for an extended trip.

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Final stages of planning including making a basic table to organize you trip. Often times our table turns out much differently when we are there and that is perfectly fine. It’s more of a guide of top choices and to help visualize where our ticketed events and reservations are in the trip. Don’t forget to leave some blank spaces too as it allows you to be flexible, move things around, and most importantly, explore!


Make sure you research the best way to get around in your trip as well. If we are in a place with good public transportation, I always download the map onto my phone for easy and offline reference. You are an easy pick pocket target when it is obvious you are unsure of what to do and where to go. Before leaving your place, examine your route and proceed with confidence!

I hope some of these tips help you in your trip planning! Don’t forget to take advantage my itineraries found in the Reskrib section of each trip. What are some of your trip planning tips?

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