Planning + Productivity

How to Plan Your Best Vacation Yet

If you’ve ever experienced planning anxiety over a vacation, this guide will help you break down the process so you can enjoy stress-free travel.
This post may contain affiliate links. Read my full disclosure policy here.
 
I've never enjoyed planning trips but I LOVE to travel. Which is why I'm so glad I found this guide to stress-free travel. From picking the place, booking lodging, and deciding what to do, I now know it's possible to enjoy even the planning process behind travel! #stressfreetravel #travelplanning #vacationplanning

I bet you didn’t know this about me—I’m a 24/7 travel planner.

Of course, that’s because we travel full-time in the RV! So I have a lot of experience over the past year (going on two!) as an RVer.

But even before we started living the RV lifestyle, Joseph and I made weekend and week-long getaways a priority. We’ve always had a hankering for adventure … but not so much spontaneity.

It just so happens that ironing out the details of a trip ahead of time fuels the research-lover and planner in me just as much as the experience! Especially if I can do it on the cheap.

So whether you can relate OR planning all the details isn’t your favorite thing in the world (you’d just rather pin pretty vacation spots and go already!) I’d like to help you focus on the three most important elements of any memorable trip so you can enjoy stress-free travel!

  • Where to go and when
  • The best places to book lodging
  • How to plan a custom-to-you itinerary that you’ll LOVE

That way, you can spend less time planning and more time anticipating all the fun you’ll have once you get there.

Although for me, the two often go hand in hand. 😉

woman overlooking a peaceful lake scene

The Most Important Thing to Know First

The Internet abounds with sample itineraries and lists of the best places to visit. Offline, well-meaning friends share all the spots they enjoyed about your upcoming destination (sometimes without asking if you want to hear about them!).

And visitor centers will load you up with more pamphlets of areas to see than you can possibly fit in one week.

I don’t know about you, but all those options send me into overthinking oblivion as I stress about all the things I might miss!

But our goal today is stress-free travel! And the best way to filter the places you will enjoy is to know your vacation style ahead of time.

woman hiking

What do I mean by vacation style?

Well, when you dream about your best vacation EVER, what does it look like?

  • Are you out exploring new places every day or would you rather lounge by the hotel pool or beach and read for hours?
  • Do you prefer museums or the outdoors or popping in and out of small town boutique shops?
  • Do you want to hit up all the touristy spots or experience hidden gems located off the beaten bath?

Maybe you like a healthy balance of all those things. Knowing your preferences ahead of time will make planning your trip so much easier.

This is also helpful to define expectations if you’re thinking about vacationing with other people and their style is completely different than yours!

Want a fun way to save up for your vacation? Don’t miss these ultra-creative savings tracker ideas!

Step 1: Choose Your Stress-Free Travel Destination

This one is a no-brainer if you already have a travel bucket list carefully written down in Evernote or a few must-see spots lingering in the back of your mind.

If you don’t have any ideas yet, now is the time to start collecting them!

bullet journal travel bucket list layout

Stumped? Think of your friends who post gorgeous vacation photos on social media. Write down the places they’ve visited that you’re dying to go, too! Don’t forget to search popular travel blogs and Instagram accounts.

My favorites are:

One of the reasons why I chose the RV life is because there are so many places I want to see in my lifetime and it made more sense (cost-wise too!) to visit them this way rather than hop from one Airbnb to another.

parked RV

But don’t forget to take into account your budget as well.

A smaller budget might mean more road trips. A larger one might include plane tickets and international travel. That’s not to say you can’t travel via plane on the cheap, but how you will travel will often determine where you go.

If you’re curious about whether it’s cheaper to fly or drive, this post breaks down all the costs you need to consider.

Step 2: Decide When to Go

Choosing a time to go on your vacation involves more than just picking a week on your calendar and submitting a vacation request.

If you have kids in school, then you’ll need to think about their schedule, of course, and summer/holiday breaks will probably be the more convenient times to pack up and explore as a family.

But don’t forget to consider peak season and temperatures.

I’ll give you just two examples of why this matters for stress-free travel:

  • Florida is PACKED from December to March, so you’ll need to make reservations early if you plan to visit during that time.
  • Death Valley National Park in Nevada jumps into the 100’s during June to August, so it might be better to explore this area before May.

Plus more popular times will also mean more crowds and require earlier-in-the-day arrivals.

At Glacier National Park, we pulled into the Logan Pass parking lot at 7:30am and were too late. We had to walk a mile to the start of our hiking trail from another location down the road. (And then the actual hike was 12 miles!)

couple smiling in front of a scenic view

It was worth it though. 🙂

Step 3: Book Your Accommodations

Gone are the days where our only options were hotels! When we’re not RVing, Joseph and I LOVE to stay in Airbnbs.

Airbnb has come a long way from staying in a stranger’s random guest room (which we have never done and never want to do, thank you very much).

On Airbnb, you can filter your search so you have the whole place to yourself. And you often get even better lodging than you would at a hotel for the same (or cheaper) price tag.

Recently we stayed in a lovely condo in NC for $70/night—ONE BLOCK from the beach. All the hotels in the area were over $100 for cookie cutter rooms.

woman barefoot on the beach

Other lodging options include:

  • Hotels. Obviously! But try to stay in the same company line so you can earn rewards faster OR book through Hotels.com. This site even rewards frequent users with free nights so you can enjoy more stress-free travel!
  • Campgrounds. Whether you own an RV or rent one, you’ll find plenty of free and paid campgrounds listed on Campendium.com along with user photos and reviews.
  • VRBO. I’ve never personally booked a Vacation Rental By Owner spot but have friends who regularly find amazing deals through this site!
  • Bed & Breakfasts. Introverts beware—you usually eat breakfast around a dining table with other folks. But you usually stay in some really cute rooms.
  • Hostels. If you’re traveling internationally and don’t mind sharing a room with others on the cheap, you might want to comb through HostelBookers.com.

Step 4: Draw Up Your Itinerary

This planning step is my absolute favorite part—deciding what to do on your trip!

You probably have an idea in mind depending on your destination, but if not, here are my favorite hacks to load up your list:

  • Search “things to do in [LOCATION]” on Google or Pinterest.
  • Visit the area’s tourist website (town, national park, etc.)
  • Check out Instagram hashtags for the locale you’re visiting. For example, #CharlestonSC or #WilmingtonBeach! You never know what you might find that’s not on any of the must-not-miss lists.

Keeping your vacation style in mind, jot down all the ideas that interest you and your family as options.

Charleston sightseeing bucket list

Many itineraries feature a day-by-day, hour-by-hour schedule, which I personally think is way too rigid. You’re on vacation (stress-free travel, remember?)! You don’t want one extra long traffic jam to have the ability to derail your entire day.

For the sake of your budget (and sanity!) plan ONE epic excursion, then fill in the rest of your days with smaller sights (based on what you’re feeling that day … or the weather) as well as time for margin and rest.

If I’m feeling super creative, I’ll list our itinerary in my bullet journal, but I’ve been having SO much fun playing in my new favorite app, Notion, that I created my own Travel Planner inside!

travel planner in Notion

Notion allows me to link text to more information and screenshot directions. Not every national park is GPS-friendly! I also like to include where we are staying and any confirmation numbers so they are easy to grab.

Plus, I can access Notion on any device. Think of it as Evernote, but way better!

STEP 5: Have the time of your life!

There’s nothing quite like exploring a brand new corner of the world (or anticipating the arrival of an upcoming trip!).

And if you’ve ever experienced planning anxiety over the actual logistics of getting there, I hope this guide helps you break down the process in a fun and step-by-step way so you can enjoy stress-free travel.

Related: The Top 5 Best Souvenirs For Minimalists

Now you just need to decide what to pack.


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How to plan a vacation...the stress-free way! From picking the place, booking lodging, and deciding what to do, use this vacation planning checklist to create a customized itinerary your whole family will love.

Let’s chat in the comments!

If you could visit any destination in the world, where would you like to go?

Disclosure: Some of the links in the post above are affiliate links. This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. Read my full disclosure policy here.

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2 Comments

  1. Perfect timing on planning vacations! I am looking for a vacation place this summer that’s not too far away from us (we live in Florida). I saw your BuJo page on Charleston, SC. I’ll have to look into it. Did you enjoy your trip there?

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