Travel Planning 101: Creating the Trip of a Lifetime without Spending a Fortune or Losing Your Mind

Scrolling through social media, it seems like everyone is going on fabulous vacations. Do you ever wonder whether they all have personal assistants or have inherited a small fortune? It can seem unbelievable that someone can plan and execute a chic and thoughtful trip within a reasonable budget while working full time.

But fear not, over the last 10 years, I've tried every format and method of vacation planning and have honed the most efficient, effective steps for creating the trip of a lifetime without spending a small fortune or losing your mind watching YouTube videos of a guy on a motorized wheel cruising down a nondescript street in rural France (you've been there too right?).

Crafting a great trip is both an art and a science--I've created a few worksheets as your canvas and to guide you through the process. Feel free to download, edit and enjoy!

Worksheet # 1: Brainstorming

Whether you’re dead set on a specific location or the world is your oyster, spending a few minutes looking at the big picture will make the time you spend actually planning and booking your trip much more efficient, focused and rewarding.

This worksheet is divided into four parts and asks you to:

  • Zoom out and set the high-level parameters and goals of your trip (travelers, dates, budget, potential locations, and much more)

  • Spend 10-15 minutes systematically analyzing each potential trip

  • Dive deep into your top two destination contenders for your trip

  • Decide on a destination with confidence

Worksheet # 2: Itinerary Filler

I used to call this document my "brain dump note" because it started with a note on my iPhone where I would list every possible idea I had for a trip--every site, activity, restaurant, bar, bakery, shop, etc. I heard about. This doc provides a more structured approach to gathering ideas for your trip. See a cool restaurant on Instagram? Add it here. Your cool cousin tells you about her favorite vintage shop? Space for that too. You see something on a Going Places guide that speaks to you? Add it in here as well (bonus: each Going Places guide includes a link to a super detailed itinerary filler). The more you include on this, the easier planning your trip will be.

Worksheet # 3: Travel Overview Grid

This worksheet was the biggest game changer for trip planning. It breaks the day down into bite-size time blocks where you can slot in your picks from worksheet # 2. While it is focused on the details of each day, the grid structure also allows you to compare across days. Have a week in Rome and want to squeeze in two day trips? Probably best not to schedule those back to back? Looking to see a specific performance or visit a museum on a particular day? Add in any activities or experiences with a set date/time and easily plan around them.

Worksheet # 4: Detailed Itinerary (Extra Credit)

This worksheet is for complex trips where extra detail is needed (or for those super detail-oriented trip planners). It prompts you to consider how to get to/from locations, set more specific times for starting/ending events, etc. It certainly isn't necessary for every trip and may be even too detailed to use while you're away, but I found it extremely helpful when planning our 10 day trip to Paris and Champagne because it ensured I was leaving enough time between activities to enjoy, make stops along the way and never feel rushed.

These worksheets add both structure and flexibility to your travel plans as they ensure you make time for all the experiences you'd like to enjoy while providing you with extra ideas so that you can change plans or fill in gaps with ease.


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