An 8 Step Guide to Planning Your Vacation Like a Pro (2019)

“Click Me to Pin Me! Sharing is Caring!”

When you hear the word “traveling” what do you think of? Relaxing while sipping margs on the beach? Snorkeling in the deep sea? Flying through the clouds? I bet I can guess what you don’t think of!

The tedious process of planning.

Yikes! It’s not the most fun part, but it’s something we have to do. Planning for travel can be extremely overwhelming sometimes. So, why not make it easier by breaking it into simple action steps? This post covers the most important steps you’ll need to take before you head out on your getaway! You’ll be roaming the streets and flexin’ for the ‘gram before you know it.

1. Choose a Destination

This part seems like the easiest, but that isn’t always the case. There are soooo many factors to account for. I like to start with my own personal bucket list of travel locations. However, there are many places out there to find travel inspiration and unique destinations:

  • Do a Pinterest search for best travel destinations in 2019
  • Search Instagram travel accounts and hashtags, such as #travelblogger or one of my favorite accounts, TravelNoire
  • Search YouTube for travel vlogs

Other things to take into account are flight costs. Do a quick Google search to anticipate how much flights/ bus tickets/ train tickets cost to get to your destination. Is it within your budget? I remember when I THOUGHT I wanted to go to Hawaii for spring break last year. Once I saw those flights, the idea was laughable! Miami here I come.

Planning to go abroad? Stop right there! Make sure your passport will be at least 6 months from the expiration date in relation to when you’re going abroad. It’s also recommended to have at least 2 blank pages.

Once you’ve figured out which city (or cities) you’d like to visit, set some dates!

2. Set Your Dates

When are you heading out? When are you coming back? Do you have any personal commitments that restrict certain times of the month?

The time you vacation can make or break your experience. For example, planning to go to Florida between June and November could be risky times for a hurricane. Do some research about your destination before you end up in a sticky situation!

Ideally, it’s best to book your trips at least 4-5 months out. If you’re a procrastinator like me, then you might have to make some adjustments when it comes to cost and location of accommodations. Now that you’ve got those dates and the destination, it’s time to get to business.

3. Book Your Flights

This is probably the most important part of the entire process. Say it again? Okay.

This is probably the most important part of the entire process.

Last minute flights tend to skyrocket, and the booking of airfare is definitely a tricky thing to tackle. So let’s break down some things you should know before you move forward.

  • Research your flights in Incognito or Private mode. Have you heard of cookies? No, not the round tasty ones. These are small files stored on your devices that record your browsing activity. When airlines see you’re constantly checking for flights, they’ll hike the price up. This gives you the perception that they’re high in demand, and need to be purchased quicker.
  • The best day to purchase flights is Tuesday at approx. 3pm EST.
  • Websites such as Expedia, Priceline, and Kiwi can help you find the cheapest options. Just be sure to check the fine print!

Now that I’ve dropped some knowledge, you can go onward to booking that flight! Once you’ve committed to buying your flights, you basically have to go now. That’s why I like to do this first! It feels like I’m making the commitment.

I usually forgo buying airline ticket insurance, but make sure to explore the option if you anticipate a potential hiccup for a trip you’re booking in advance.

4. Research Points of Interest

You’d likely think to book the hotel right after the flight, but I like to start looking at points of interest first. If you know where you’ll be visiting, you can book your stay near places you’ll visit (or by the public transit stations!).

There’s a vast amount of information coming at you from all directions, so I say to always to start with Pinterest and Instagram. Pinterest bloggers are always documenting their experiences, complete with all the photos and details! These travelers will help you find both the touristy things to see, but also some places frequented by the locals.

Instagram is a little-known, yet perfect way to find to go. A simple search, such as #LAFun or #VisitDC will reveal some gems! Also, many cities have tourism pages that highlight fun areas to visit. I’m visiting Los Angeles next month, and the Life Hacks LA page has already blessed with a cool museum I’d like to visit!

5. Book Your Accommodations

Besides actually going on the trip, this is my favorite part about planning! The best bang-for-your-buck is by far, Airbnb. Depending on where (and when!) you go, there are so many unique stays for much less than standard hotel costs. I like to use their lists feature to compile a list of places that I’d potentially stay. If you’re traveling with friends, you can share the list to them via iMessage or by copying the link! Just be sure to read the reviews thoroughly, and message the host prior to booking with questions you may have.

Other places to find reasonable accommodations?

  • Expedia and Priceline have deals that allow you to book flights and hotels together for a discount
  • Google Searches
  • Groupon

Hopefully you’ve found the hotel or BnB of your dreams! Now it’s time to get into the nitty gritty.

6. Make a Loose Itinerary

I use the word “loose” because I’m not the type to plan every single detail out. I like to go where the wind takes me for the most part, but it’s nice to have a general idea of where you’re going. For example, I’m going on a quick getaway to Atlantic City this weekend. My itinerary looks like this:

– Brunch
– Beach
– Dinner/ Casino

– Atlantic City Aquarium
– Ocean City Waterpark
– Bar/Club

This is a good place to start, because it’s only a 2-day trip and I can easily Google search for the best casinos and bars in Atlantic City.

For something a little more extensive, such as traveling abroad, I would construct the same loose itinerary with specific places and times. I found some really great food places on Instagram, but these are just sitting in my notes in my phone if they’re needed. If we come across a restaurant that looks good, we’ll go there instead.

Certain trips call for more planning than others, but it’s good to at least write something down rather than nothing. Now that we know which activities are anticipated, and when, we can start researching transportation within the destination.

7. Research Additional Transportation

Is there a free shuttle from your airport to the hotel? Are you ubering everywhere, or taking a rental car? Is there a subway or metro station? Does your AirBnb come with bicycles? I’ve seen this before!

These are all things you should research prior to your departure.

For example, for the Something in the Water Music Festival this year, we found a shuttle that was $5 for the entire weekend. Could you imagine how much money we would’ve spent on Uber rides had we not planned that out?

So how do you figure out transportation?

  • If it’s an AirBnb, ask the host! If it’s a hotel, feel free to call them.
  • Hertz and Enterprise are reliable places to rent cars, and they typically offer military discounts as well.
  • Turo is like the AirBnb of renting vehicles. I’ve seen Corvettes, Mustangs, Mercedes Benz, etc. all on the Turo platform. I definitely recommend, just read the reviews!

8. Some Extra Things to Think About

There’s always extra things to think about before you leave! Here are a few to get your gears turning:

  • Submit a travel notice to your bank, otherwise your cards may be declined in your new place until you contact them!
  • Research vaccinations and other requirements you’ll need for entering a new country
  • Let your family and friends know where you’ll be, for safety!
  • Purchase your travel essentials. You can find my favorites here.
  • Any other responsibilities you may need to take care of, such as notifying your job as early as possible.

Whew! Breathe, you’ll get it done! Are you ready for the adventure of a lifetime?


  • Marissa Strang

    Marissa Strang is a full-time lifestyle and travel blogger based out of the Washington, D.C. Metropolitan area. Travel is her number one passion, and she is on a mission to empower others to make travel a reality for their own lives as well. She’s a strong believer that everyone can experience the joy of exploring the world, no matter the way they look or their socioeconomic status. Marissa creates one-of-a-kind city guides, destination inspiration, and budget-friendly travel hacks for aspiring travelers, especially young travelers and minorities. By creating travel content through her blog, The Marissa Daily, she strives to help others make lifelong memories - one destination at a time. Her journey as a blogger for the past 3 years has led her to visit amazing places and build an engaged travel community that she cares for deeply. One of the principles Marissa lives by, and encourages others to abide by, is that when you look like your passport photo, it’s time to book a trip. Let's go places.

One thought on “An 8 Step Guide to Planning Your Vacation Like a Pro (2019)

Leave a Reply