How to Plan for an Amazing Trip (My Way)

I recently found a great airfare deal and booked myself a Ticket to Paris. Just me. No one else. This is my first ever solo Trip, and I’m a little nervous but also very excited. Okay, considering that I don’t really speak French, I’ma lot nervous. But in the words of Dr. Sheldon Cooper, “If there were a list of things that make me more comfortable, lists would be on the top of that list.” So I’m making a lot of lists in preparation for my trip.

As I dive into doing this trip 100% my way for 100% me, I thought it might be helpful to show you what my Travel Planning process looks like.  But first, a disclaimer: I am a highly structured, type A, over-planning kind of person, even on vacation. If you prefer to be a little less organized more spontaneous than me, you might want to follow this guide loosely and omit anything that seems like it might be too much effort.

Step 1: Have No Destination or Date in Mind

Yes, you heard it here first. The best plan starts by having no plan. Amazing vacations often present themselves as unanticipated opportunities in the form of cheap airfare. When you choose your destination or dates first, you lose a lot of flexibility in how much you will need to spend. My family and I have flown from Baltimore to both Peru and Iceland for around $200 per person round trip. It can be done. And since we want to travel as much as we can, it only follows that we need to do it as cheaply as we can.  After all, money saved on this trip means more money for the next trip!

Step 2: Start Putting Together a Destination List

One of the first places I look once I’ve booked my tickets is Pinterest, which I have written about before. Pinterest is great because not only is it a place to find destination ideas, it’s also a place to keep destination ideas. As soon as I’ve booked a trip, I create a board for my new destination and start pinning away. At first I pin everything that looks even vaguely interesting. For instance, my trip is to Paris but I’m pretty much pinning everything in France that I find of interest. I’ll be able to go through later and scale down, but if I find 3+ points of interest relatively close together outside of the city, that might make for a good day trip.

Depending on how anal organized I want to be, I might then set up a different board for each day of the trip with the activities for that day. I realize that it sounds over the top, but when you’re in an unfamiliar place, it actually makes sense to plan a day’s activities according to where they are located. Less time in transit between points makes for more time to see the sights.

The only caution I have to offer about using Pinterest as part of your travel planning process is to not allow your board to become oversaturated with images. You only need one pin with helpful information about visiting, for example, the Eiffel Tower. You do not need eight to twelve pins about the Eiffel Tower because they all have stunning images to go with them. The more you look at pictures, the less impressed you will be when you stand before it in person.

Other sites I like to peruse for things to see at a particular destination are Roadside America (US travel only) and Atlas Obscura. Both of these sites offer tips for seeing things that are off the beaten path and not likely to be on every tourist’s must-see list. They also usually have some history attached to them, which you know I love.

Corollary to Step 2: Accept That You Can’t See it All

Unless you are visiting your destination for a very long time, you will have to prioritize what things you want to see and do on your trip. You cannot realistically expect to see every great architectural wonder, museum, monument, cathedral, park, and restaurant in one week’s time.

If you compile a massive list of all the places you want to see, and add to it all the places someone (friends/family/blogger/travel guidebook) recommended that you see, you are going to end up with a very long list. And when you find that you only have time to do about 20% of the things on that list, you will probably be disappointed and/or feel like your trip has been a failure.

I prioritize my destinations into three distinct lists:  Must See (I will not forgive myself if I don’t do this), Should See (important in order for me to consider the trip a success), and If There’s Time (everything else). The Must See List should be reserved only for iconic sights and experiences – things that, if you don’t do them, you won’t feel like you really even went to that location. In the case of Paris, it would be visiting the Eiffel Tower and seeing the Mona Lisa in the Louvre. The Should See list will have a reasonable amount of attractions/activities – between one and four per day. The If There’s Time list, if you’ve kept track of all those recommendations, should be the largest list.

Step 3: Finding Lodging

A lot goes into finding the perfect place to stay. Here are just a few of the things you must consider:

• Expense – How much can you afford for this portion of your trip?
• Area – What sort of neighborhood do you want to stay in? Hip and trendy, or residential and quiet? How safe is the neighborhood you’re considering? Do you want to have a room with a view?
• Type of accommodations – Do you want complete privacy? Do you want to be able to fix some of your own meals? Do you want to stay someplace that provides you with breakfast each day? Will you need local staff to provide you with recommendations on where to go?
• Convenience to public transport – If you aren’t renting a vehicle, you may want to make sure that you are within walking distance of a subway station or bus route

As for when to book, I’ve found that you want to do it far enough in advance that you have plenty of options (particularly if you plan to stay in an Airbnb or private home), but not too far in advance in case your itinerary changes. There is nothing worse than booking a place for an entire week, only to decide later that you want to spend part of the time elsewhere. I’d say three months ahead is probably a good window, but you can go with less advance booking if you’re staying in a hotel.

Step 4: Buying Tickets in Advance

I will admit, this step is riskier than the others. The potential benefits of buying your admission tickets in advance are:

• Little to no time spent waiting in line when you arrive at the attraction.
• Allows you to start paying for your vacation expenses before you go
• No need to worry about an event being sold out; your admission is guaranteed
• Some venues offer a cheaper admission rate when booking online.

The potential drawbacks of buying your tickets in advance are:

• Your plans change and you cannot go on the day for which you purchased admission
• You forget to take your tickets with you when you go (or lose them, or they get stolen, etc.)

Now, as you can see, there are more pros than cons here. Also, in many cases, venues who offer online admission sales either are not date specific or will honor your ticket on a different date if you cannot use it on the date you originally booked. These days, you will most likely have an email or other electronic record of your ticket, which should suffice if the printed version got lost.

Step 5: Keep it Together, Girl!

This is where my type A super-efficient personality makes most people roll their eyes and groan. I color code all of the information I’ve assembled (green for financial, blue for nighttime activities, orange for daytime, hot pink for anything in the Must See category, etc). Then I make a folder or three ring binder with all of the information I will need for my trip.

I keep everything that I need together and sort it by day. Typically, each day’s packet will include:

• a list of activities for the day
• maps and/or directions on how to get from A to B
• printed admission tickets if purchased online
• brochures or other information about what I will be doing (opening and closing times, special significance, etc.)

It might be important to note that I do not carry the entire binder around with me – just that day’s pertinent documents. Apps are great, but I’m old school enough that I like paper. Using paper doesn’t have me at the mercy of finding a wifi connection.

YMMV

I cannot stress enough that this is the process that works for me. Following these steps is what gives me peace of mind so that I can relax and enjoy my trip. If you prefer to be impetuous and plan as you go, that’s great. You do you! The point is to be prepared for your trip, know what you want, and not spend valuable vacation time under stress.  Bon Voyage!

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