Planning Your Vacation Like a Pro

To travel is to live.

Hans Christian Andersen

Traveling is one of my favorite ways to spend my time off and my hard earned money! As I have mentioned before, I am a planner both inside and outside of work, so I thought I would focus this post on how I prepped for my recent vacation abroad.

Here is the process I typically going through when planning a trip.

Choosing a destination. A lot of things come into play when choosing your destination. For me, I consider how much time I want to spend away (including travel time), what kind of trip I want to have (relaxing, active, or a mixture of both), what the weather will be like, and how much money I want to spend.

Google Flights has actually been a really great tool to compare flight prices for different dates and destinations. I also consult family and friends to see if they have any must-visit spots. Cooler weather (think fall layers!) is usually good for walking around and exploring, and avoiding stormy seasons is important for tropical getaways. You need to decide which of these factors is most important to you, narrow down your choices, and make a decision.

Planning what to do. After choosing your destination, you can then start identifying the activities you want to do, sights you want to see, places you want to eat, and so on. You need to pick out a hotel for each spot you visit and plan your travel from one place to the next if you have multiple destinations.

The internet is clearly a great place to find lists of top attractions, hotels, transportation options, restaurants, and nightlife. I find myself digging into multiple websites, reading countless reviews, and making lists of what I may want to do while on my trip. I actually found a cool website called Visit a City that allows you save the activities you want to do into an itinerary. (Sounds like an agenda to me!) It has cool features like pre-populating activities based on the kind of trip you say you want to have, mapping out the time you should spend at each spot, grouping things that are close to each other, and noting opening and closing times. I filled it out for each city I planned to visit and used it as a guide.

And of course, I consult family and friends! They have great information to share based on their experiences, which helps save you time and can help narrow your research on what to do, where to stay, and how to travel from place to place.

Packing. Oh, packing. It can be a stressful process, but it does not have to be. I actually use a packing list (an Excel spreadsheet in Google Drive) that I have been refining for years.

The first and second columns of the list are static – an exhaustive list of items I may want to pack (column A), and the category to which each of these items belongs (e.g., clothes, toiletries, accessories, electronics) (column B). Before I begin packing, I go through this long list of items and identify whether or not I need to take each item on this specific trip (column C). Then as I begin to pack, I sort the list by category and put a checkmark next to each item once it is safe in my suitcase (column D). If I’m traveling with someone, I share the document with them so we can “pack together” for our trip – creating separate columns for them if they care to use them.

Either after each trip, or even while packing for the trip, I add to or delete items from column A based on what I have learned. (Sounds like lessons learned to me!) For example, I recently deleted “DVDs” and “DVD player” from my list – something I actually took with me on a trip to Hawaii a handful of years ago! I’d say I was a little late to delete that one, but better late than never.

Enjoying the vacation. The day has come! Make sure you give yourself enough time to get to the airport, go through security, and have a second to breath and get some snacks or a cocktail before boarding. Then once you arrive, refer to your itinerary and enjoy yourself!

And remember that you likely will not get to everything on your list, and each day may not work out exactly as planned. Build in some free time for exploration and ask your hotel concierge or other travelers you meet for recommendations.

Or if you planned a total relaxation beach vacation, get yourself a Mai Tai, a good book, and a floppy hat – and you’ll be all set!

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