How to Plan a Trip Like a (Type A) Boss


When my husband and I were going to bed after our first day in Puerto Rico, I said “What time should I set the alarm for?” He responded, “You’re kidding right?” I wasn’t and he knew it. Of course, since I’m a thoughtful and compromising wife, we slept in a number of days too. My point is that if you’re type A and like to maximize your time in a destination with lots of activities, this blog post is for you. If you’re more go with the flow, take it with a grain of salt and hopefully you’ll still walk away with a few handy tips.

How to plan a trip

Decide where you’d like to go.

This one is especially personal and you may already know exactly where you want your next adventure to be. If you’re more open, I recommend looking at Kayak Explore; just input the airport you’d like to depart from and your timeframe and it will show you discounted flights all over the world. It’s not uncommon to find flights from U.S. airport hubs to Europe for as cheap as $500 this way. Its downsides? Sometimes those super-cheap flights are at inconvenient times. Also, the more specific your travel dates, the less you’re likely to save. Here’s an example of using Kayak Explore with Atlanta as the home airport:

Using Kayak Explore

Create a Pinterest board for your location of choice and pin the heck out of it.
Start with any and all pins that look interesting and narrow it down later. Many of my pins will be for inspiration and to get me excited about a locale, though some will be informational or logistical. Over time, I’ll go back and read the blog posts associated with particular pins, making note of tips I want to remember. I find myself referring to blogs more than any travel book these days.

Book your flight if you haven’t already.

At times I’ve been guilty of starting to plan a trip that I don’t end up going on, often because I find a better deal to travel somewhere else. So before you get too carried away, make sure you can find a flight that fits with your travel dates and price range. You probably know the usual tips: monitor prices, book on a Tuesday and travel mid-week for better deals, and clear your cookies so “they” can’t tell you’re looking and raise the price on you.

Start making a list of “musts” and “maybes”

It’s hard to gauge in advance how long activities will take. Personally, I prefer to list more activities than I think I’ll have time for. Then if I have a free afternoon because the museum only took me 30 minutes, I’ll have a variety of options at my fingertips.

Cluster items by relative location using Google maps for reference.

I don’t want to spend more time than I need to in the car or on the train. Therefore, I scope out my destinations on Google maps and cluster them accordingly. For example, if I visit the Dublin Zoo, I may as well go to the nearby Deer Park the same day (or vice versa). This process may also help you find something you wouldn’t have otherwise read about. For example, in planning an upcoming trip to Cleveland, I looked at where the Rock n’ Roll History Museum is and saw that there’s a nearby park on the water. How convenient! I’ll make a note of it and will go if I have time and if it sounds good in the moment.

Reserve your hotel, hostel, Airbnb, or other accommodations. 
Hostels and Airbnb are my accommodations of choice at the moment. Though there are of course cons of staying in a hostel, I could go on and on about the pros. For starters, they’re cheap and often centrally located, you have access to a kitchen, they typically have free or cheap breakfast, and you can get in on some great free activities. Free walking tour? Free happy hour? Treasure hunt? Yes please. Check out this post for more tips about staying in a hostel.
As for Airbnb, the only con for me has been having to update the host with my arrival time. At a hotel you can typically just show up, whereas with Airbnb the polite thing to do is communicate when you plan to arrive and let your host know of any travel delays. My best tip? Make sure the reviews of the host mention that communication was good. No one wants to arrive at their destination and then have to wait awhile to get inside.

Take note of when places are open.

Museums may not be open on Sundays or Mondays. Plan accordingly; these may be great days to take a tour or do another all-day activity that will be open.

Consider whether or not some sort of pass (for transportation or attractions) would be cost-effective.

Find out whether or not your destination has some kind of city pass, travel pass, or other discount card, then do the math. Price out what you’re likely to spend anyway compared to the cost of a pass. For example, I recently found that if you’re visiting the Casa Loma and the CN Tower in Toronto, you may as well buy a Toronto City Pass for the same price. Then you’ll also have admission to a few other tourist spots as well. Check out my post about the London Pass here to get ideas for maximizing your pass benefits.
I’ve also saved big with travel or transportation passes. My favorite example is the Swiss Travel Pass. This pass quickly pays for itself in transportation alone and gets you admission to over 500 Swiss museums and other activities.

Book any tours or tickets to events that could be at risk of selling out, or ones in which there is a significant savings (in money or time) if you purchase in advance. 

For an upcoming road trip to Niagara Falls, I’m booking our wine tour ahead of time since there’s one particular day that works best for us to take it. When I saw the musical Wicked with my friend Alicia in London, we made sure to buy tickets in advance so we could get decent but affordable seats. At the Skydeck in Chicago, having bought your ticket online saves you time in line. Alternatively, I like to avoid purchasing too many tickets ahead of time because it’s a hassle and it locks you into your plans.

Make a packing list.

Again, Pinterest is a great resource. Just type in “Pack for ___” and you’ll be set. While you’re at it, find out what’s in my suitcase here.

Exchange currency if needed.

It’s important to do your research about current exchange rates and shop around a bit, though the best rates tend to be at your bank or credit union. Only exchange money at an airport if you’re in a pinch, as these tend to be the worst deals. Of course, it’s also ideal to travel with a card with no foreign transaction fees and save your cash for when you need it.

Print your travel itinerary and all booking information. 

Yes, I do this on an old-fashioned printer, in addition to having these available electronically. You never know when your battery will die, and I will admit that it’s fun to have my tattered and scribbled on itinerary as a souvenir afterwards.

Be flexible and open-minded. Not everything will go as planned and some of the most memorable experiences will be the ones you just stumble upon. 
What’s your #1 trip planning tip? Post it below! Like this post? Help me get the word out by pinning this image:


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