Step-by-step advice on choosing destinations, building itineraries, and staying organized without losing your mind.
Trip planning should be exciting—but let’s be real, it can quickly spiral into stress: too many tabs open, too many opinions, too many choices. Whether you’re dreaming up a solo escape, a family getaway, or a bucket-list adventure abroad, having a simple system can turn trip planning from chaos into calm.
In this week’s edition of Ready, Set, Roam!, I’m sharing a step-by-step guide to planning your perfect trip—without losing your mind.
🧭 Step 1: Get Clear on Your Why
Before you dive into Google rabbit holes, start with a simple question:
What do I want this trip to feel like?
- Do you need rest and recharge?
- Are you craving adventure?
- Looking to check off iconic sights or immerse yourself in culture?
Your “why” will guide your where.
🌍 Step 2: Choose a Destination (or Narrow the Options)
Once you know what kind of experience you want, think about:
- Timeframe: How many days do you have?
- Budget: Flights? Driving? Hotel vs. Airbnb?
- Season: What’s the weather like when you’ll go?
- Travel type: Solo, family, group, romantic?
📌 Pro Tip: If you’re indecisive, choose 3 dream locations, then compare flight prices, travel time, and weather to help one naturally rise to the top.
🗓️ Step 3: Map Out the Big Picture
Now that you have your destination, sketch out the bones of your trip:
- How many nights?
- What cities or regions will you visit?
- How are you getting from place to place?
Don’t worry about the small details yet—just create a loose structure. Use tools like Google Maps or Rome2Rio to visualize travel logistics.
🏨 Step 4: Book the Non-Negotiables
This is the “lock it in” stage:
- Flights or primary transportation
- Accommodations (at least your first stop)
- Must-do activities that book fast (like national park passes, tours, or event tickets)
Booking these early gives you peace of mind and a solid foundation to build around.
📋 Step 5: Build a Flexible Itinerary
Start organizing your days, but leave space for spontaneity.
Use a simple Google Doc or spreadsheet to note:
- Morning / Afternoon / Evening blocks
- Key sights or experiences you want to include
- Time estimates between locations
📌 Pro Tip: Only plan 2–3 major activities per day max. Overscheduling kills joy. Balance must-sees with downtime.
📱 Step 6: Save Everything Digitally
Create a folder on your phone or in Google Drive for:
- Confirmation emails
- Booking codes
- PDFs of your itinerary
- Offline maps or guides
Use apps like TripIt, Notion, or Evernote to keep everything in one place.
🧳 Step 7: Prep the Fun Stuff
Now comes the fun pre-trip phase:
- Make a packing list
- Download shows, books, or podcasts
- Create a trip playlist
- Learn key phrases if traveling abroad
- Dream up your travel photo goals
💡 Bonus: Don’t Be Afraid to Delegate
If you’re traveling with others, divide the planning:
- One person books lodging, another handles transportation
- Share a collaborative doc so everyone can contribute
Travel planning doesn’t have to be a one-person show.
