The 6 Things I Do When Planning a Vacation

planning a vacation

One of my favorite things about traveling is planning a vacation before we leave. As you may have noticed, I am not the type of person that can “just wing it” for most occasions. I, at the very least, like to see if there is anything I want to make sure not to miss while we are traveling, but more often than not, I do some extensive research before we leave. It can get messy when I am reading countless articles, pinning like crazy and doodling things in 5 different notebooks. This is where my planning process comes in handy.

There are 2 places I keep my travel plans, Trello and Evernote. They both have specific purposes in my planning process, and I will be sharing about Trello for travel more in-depth in another post. For now I am going to give an outline of what I like to do before I travel in order to prepare, and make sure we don’t have regrets of missed opportunities while we are visiting somewhere.

planning a vacation

Search on Instagram

I have posted about my love for hashtags over and over again, and here I am mentioning it again. Hashtags are a great way to find out about where you are traveling to. For example, if you are going to Brooklyn and want an insiders view of things that are happening, search #brooklynnewyork on Instagram and you will see a wide variety of photos. You can also do this by the geotagged location. You can look up a specific place, or a city and look through the photos to see if anything sticks out to you. There will often be photos of hotel views, or amenities like the hotel pool, and it’s nice to see this from an actual person. Who knows what type of fancy camera or photoshop the hotel used for their photos. If you want to know more about travel hashtags, check out this post.

Search on Pinterest

This is the same type of thing as searching on Instagram, except you get a much wider set of options to check out. Using the New York example again, you are able to search for a location and all of the results on Pinterest will guide you in the right direction. If you are looking for free things to do, places to stay or great places to eat, you will likely find all of these recommendations from other bloggers or residents. Keep in mind, this will work better for larger destinations, there aren’t many options for smaller towns.

Ask for recommendations

My favorite way to plan for a trip is to ask others that have already been there! This is a great blogging resource that we often overlook. There are so many people out there that have already experienced wherever you are going, ask on social media on in a blog post for recommendations based on location. Ashley has been a huge help with this for various locations, and I’m so thankful for Simi and Megan while I was planning our New Orleans trip.

Check out Google maps

It’s always nice to get an idea of where you will be staying and where you will be going. Thankfully Google maps is a lifesaver when it comes to this, and street view is a huge benefit. I love the option to make a custom map and pin places we know we want to go, this helps when we are looking for something close to us and also allows us to get aquatinted faster. It’s also convent when deciding the location you want to stay in.

Look into Transportation options

This is often a deciding factor in where we will be staying. I like to find out the options for public transportation, car rentals and ride-share services like Uber or Lyft. When we were planning New Orleans, I looked up the cost of an Uber from the airport to our Airbnb and it was MUCH cheaper to just rent a car rather than getting an Uber to take us everywhere. We ended up still using Uber at night, but having out own car was great and saved us money in the end. We also knew that we had the option of the bus 3 blocks from our house, and the street car was less than a mile away.

Search events or festivals happening while you are there

Most cities will have a calendar of events, it’s nice to know what is happening while you are in a new location for many reasons. There are oftentimes street closures you should be aware of, larger crowds, higher prices for food, hotels, and transpiration could be a problem as well. The benefits could be great as well, maybe there is a festival you want to attend or a unique exhibit at a museum.

What do you do while you are planning a vacation?

24 Thoughts on “The 6 Things I Do When Planning a Vacation

  1. I’m definitely big into the research and planing before a trip. I hate trying to figure out details while I’m on vacation. I much prefer to do all the bare work ahead of time so I can just relax and enjoy during the trip. And big ditto to all the resources you listed. The only thing I’d add is sometimes I’ll buy the Lonely Planet guidebook, mainly if I’m doing a longer trip to another country. I love the details and how it’s organized by area. And it’s a great resource for finding things to do on the fly.

    • YES!! I feel exactly the same way. When I am actually away on vacation I love being able to simply check the details I already have figured out. I love a good guidebook, but I typically only buy them for european trips as well, I need to look into them more!

  2. These are GREAT tips! I am definitely pinning this! You are the travel master! I love that checking Instagram was your first tip. I completely agree- I always check Instagram first to get that local perspective!

  3. I always check out google maps when booking a hotel! It’s saved me from staying in really bad areas multiple times =)

  4. Love the “Look on Instagram” tip. I think I did this without really realizing what I was doing when I was planning my trip to Europe last year. And now I fully plan to do it for planning my trip to Washington DC/New York this summer! 🙂

    • It helps so much! I love being able to see the area I am going before I get there, and actually from another humans perspective. DC and NY will be so fun- I am right in the middle of them!

  5. Megan on March 14, 2016 at 2:33 pm said:

    I’m about to say something shocking…. I don’t go to Instagram first. I actually don’t think I ever looked on instagram until recently when planning our trips later in 2016 and I’m pretty sure it was only after you mentioned it while chatting! My favorite social media channel and I never thought to use it for travel planning. Insane. But I totally get it and have started planning for….ICELAND! And yes, Pinterest is still my favorite resource for trip planning!

    • I love using Instagram as a top source because it helps to see things from another humans perspective, rather than just the google car or what guide books and bloggers will show you. Iceland is going to be AMAZING, I can not wait for you to go!

  6. We just got back from a trip and I loved doing all the research beforehand. I was constantly checking Instagram, Pinterest, and Google for recommendations, tips, and any insight.

  7. I am all about not having to rent a car when I travel, so transportation is key!! I never really thought to look on IG before, but I definitely need to!!

    • I specifically like looking on Instagram because of the “real life” factor, it’s nice to see what other people are doing wherever you are going. I agree- if we don’t NEED a car, I would rather not have one.

  8. Great tips for planning. I’ve in the early phases of planning next summer’s road trip to the East Coast of Canada, and I will definitely be using these tips.

  9. I don’t think that I could survive without Pinterest when planning all of vacations and weekend trips! It’s such a great resource for just about everything in one place. I love finding out what other bloggers have done in the places we’re going to visit! It’s like getting travel advice from a great friend who’s already been to where you’re going!

  10. Such great ideas! Every time I tell myself I am going to look up the transportation, that happens about half the time, what a timer saver it is already knowing the local transportation!

    • Thank you! I am really getting good at transportation because I accidentally booked a hotel in the very wrong part of Canada before, thankfully I caught it when I was looking at public transit options.

  11. Very cool, I typically make Pinterest boards around a trip or vacation then write out a list on my phone notepad too. Instagram is awesome for that now, I see pictures of places people have been and keep a list of those cool places I want to visit too!

    • Thank you!! I typically do the same with Pinterest and then organize it on Trello (which is a post for next week!) Instagram has been amazing when I am planning trips!

  12. I need you to plan my next vacation haha the extent of my planning is find a hotel and then wing it lol

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