How to Plan a Vacation

There's a difference between a good vacation and a great vacation. There's even a difference between a great vacation and a life-changing, awe-inspiring, soul-shifting vacation. Maybe I think too much into it. Maybe I put too much stock in the ability that new and unique places and cultures and landscape have to change perspective, bring clarity, and boost creativity. Or, maybe I've planned and experienced some beautiful trips that have shifted my perspective on travel.

In today's post I want to walk you through my process - my several month long process - of planning a vacation that will be truly memorable. We'll look at:

  • In a *relatively* post-lockdown world, when to start planning a vacation
  • How to choose a destination and type of trip
  • Determining your budget
  • How to travel like a local
  • A Google Maps travel hack that you need to know
  • How to travel stress-free - yes, it's possible
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Hotel Vintage 3

When to Start Planning a Vacation

Pre-COVID, I read a rule that in order to get everything booked with relatively decent prices on airfare and accommodations you needed to plan and book 4 months before an international trip and 2 months before a domestic trip.

Obviously, COVID has changed the way most of us go about things, but especially travel. I started seriously planning our big trip this year - it's a domestic trip - mid-June. We're going mid-September so it was a good 3ish months out.

You know what I found? Everything was booked for September. Ok, not everything but a lot of the places I had researched were filled for the weekend dates. Airfare was a nightmare to find and 2 out of 3 restaurants didn't have reservations available. Lesson learned.

To be fair, we are going to Maine in mid-September during the fall foliage and many of the hotels and inns in the area are boutique with only 10-20 rooms, so that may play into it a bit, but I have a feeling really good domestic trips are not going to be easy to book spur-of-the-moment over the next couple of years.

So, here's my new rule: start researching places to visit 5-6 months before you're planning on vacationing. If you can, solidify your vacation dates 4 months before traveling and book in your accommodations and restaurant reservations 3 months before.

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How to Choose a Destination

Last year, yes, 2020, Lee and I were doing some preliminary planning for a 2-week Ireland trip. When March of this year came around we started looking at our vacation dates for the year - we like to do a big trip in September - and seriously talked about going overseas, Ireland, or England, or Scotland. After a few chats, we came to the conclusion that we didn't feel comfortable yet about traveling overseas with COVID still raging through countries.

We're fully vaccinated, but the likelihood of countries not being fully open, closing before we got there, or going back into lockdown was pretty high. So, for 2021 we opted for a domestic trip that would be much easier to plan.

General Travel Tip #1: Never assume this one time is the only time you're going to visit a certain location. Don't try to fit everything in in one trip.

Choosing a US-based vacation location is much easier than choosing an international destination, but a few things I like to do when deciding:

  1. Pop into Barnes and Noble or your local bookstore and pick up a book - yes, a physical book - on the destination in question. There's something about seeing a place in a book and reading a few lines of text about the location.
  2. Trust your gut - this is a vacation after all. If you're not super excited about a location choose a different one! We were initially planning a California ( LA and Joshua Tree) vacation but pivoted when it just didn't feel exciting at the moment.
  3. Follow a few tourism accounts, hashtags or content creators on Instagram that are local to the place you're deciding on. Sometimes it just takes on photo to spark a desire to visit.
  4. Take into account the weather. Lee and I like the cold. Like we really prefer cold temps to warm, so while September in Greenville is still in the 80s we prefer escaping to a climate that's chilly - one of the reasons a trip to LA just didn't sit right. We wanted fall weather.
Lake lure

How to Determine Your Budget

This is obviously an intensely personal decision, but I believe it comes down to your income and your yearly priorities.

Lee and I as an engaged couple a few years ago found our travel interests were 100% aligned so we determined that throughout marriage that would be something we prioritized.

As we've gotten a little older we're able to increase the travel fund a little more each year.

We've also realized a few things through some 'not so great' travel experiences:

  • where we stay (i.e. our accommodations) are intensely important to us. We'll normally spend 50% of our trip budget on boutique inns and high-quality hotels.
  • we have never done the "typical tourist traps" at any destination. So on a trip to Seattle instead of spending $$$ to visit the Space Needle we boarded a $12 ferry and had one of the most memorable days visiting Bainbridge Island.
  • good food is also very important to us so honestly a good 30% of our budget goes toward eating at amazing restaurants. We typically visit 2-3 extremely nice restaurants in an 8 day trip and sniff out local favorites for other meals.
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Train Travel 16

How to Travel Like a Local

While, "travel like a local" is definitely more associated with international trips I think the same principles apply to domestic trips as well. Even if you're just heading up the road or down the coast of your own country, local travel often means finding beautiful vistas, darling inns, delicious restaurants and local shops that may not always have prominence in Google searches or blogger's travel guides.

My biggest "travel like a local tip" is to give yourself the freedom and permission to explore. While I'm all about researching and planning there is also something to be said about spontaneity. I like to think about it as planning to be spontaneous. It satisfies my type-A planner personality and also the understanding that the best things, places and people often just fall into your lap.

If you're a bit like me in the sense that leaving lunch up to chance just seems too risky, here's a few things you can do to prepare for spontaneity:

  • get a feel on Google Maps the area where you're going or exploring. Even if you do venture off the beaten path, check out the surrounding 15 miles or so.
  • search local restaurants, inns, etc. on Instagram and Pinterest before popping on Google. Often a photo grid of a restaurant will give me a much better feel for the food and atmosphere than a marketing website will.
  • have a backup location in mind. When it comes to food, hanger is a real thing so you can easily come prepared with a couple suggestions or at least the location of a nearby grocery store in case nothing pans out.
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Falls 1

This Google Maps Travel Hacks Will Change the Way You Travel

Three years ago I learned a very important travel lesson: all your research and planning means nothing if you can't remember it. I don't remember who I saw this travel hack from - maybe Gal Meets Glam (Julia and Thomas) but I adopted it very quickly into my own planning and it has been a game changer. I'll walk through it below, but I also posted an IGTV video that has the process in video walkthrough form if you're curious about how it actually works.

  1. Open Up Google Maps
  2. Click on the menu and Your Places > Maps
  3. Create a new Map at the bottom of the left menu
  4. Title the Map as your destination
  5. Add your first point of interest to the map
  6. Customize the icon with colors and icons
  7. Continue to add locations with custom colors and icons
  8. These locations will always stay on the custom maps so you can continue to add to it and reference during your trip

Watch the IGTV Video for a more detailed, visual explanation of the process.

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And while I know this post didn't cover some areas of interest like packing and what to wear, I firmly believe a good, stress-free, wonderful trip doesn't culminate in the perfect outfit or best packed bag – although those are great things to prep – it is rather in the planning and resources that a trip is won and lost.

Let me know if you have any questions, thoughts, or comments on this post!