How I plan trips today
By Laura, co-founder of Sundays Online
This post is about how I currently plan trips — and what’s inspired us to build a better way to do it.
My starting point
Usually, I begin with a country or city in mind, even if I haven’t locked in dates yet. At this stage, I try not to overthink it — it’s more about exploring possibilities and reducing that “where do I even start?” overwhelm.
Step 1: Everything Goes
Let’s say I’ve decided on Italy but haven’t narrowed down which region or city. I’ve dreamed about visiting for years, but it’s impossible to see it all in one trip — so it’s time to get tactical.
I open Google Maps and start pinning everything: restaurant recommendations from friends, museums, architecture, hotels, random spots from social media… anything that catches my attention. I add little notes about where I heard about each place.
Meanwhile, I research travel times between regions and how easy it is to move around. Soon, I start noticing clusters — areas where I’ve pinned a lot of interesting things. That’s usually a good indicator of where I’ll want to spend more time.
TL;DR: Whether you’re deciding where in a country to visit or where in a city to stay, Google Maps helps you visualize clusters of interest and shows you where your trip naturally wants to go.
Step 2: Get honest
Once I’ve mapped things out, it’s time to get realistic. I like to stay in one place for at least three nights so I can unpack, settle in, and actually enjoy it. Constantly moving can make a trip feel more like a marathon than a vacation.
Choosing accommodations is one of my favourite parts, but I’ve learned not to get swept up by what’s “popular.” Just because an area is highly rated doesn’t mean it’s right for the kind of trip you want.
TL;DR: Stay where it makes sense for you. If you don’t love museums, skip the museum district. It’s your vacation — plan it your way.
Step 3: Narrow it down
Next, I look for non-negotiables. Am I attending a wedding? Do I have concert tickets? Those get added first.
From there, I move to Google Sheets — my favourite tool today for visualizing a trip. I’ve tried plenty of travel apps, but nothing beats being able to see everything in one clean overview.
I’ll also go back to Google Maps and organize my pins into lists like Rome – Eat & Drink or Florence – Sights, complete with emojis for easy scanning on mobile.
This is the phase I spend the most time in. If the trip’s six months away, I’ll casually plan over time — adding notes, chatting with friends, watching travel videos, and letting inspiration strike.
TL;DR: You can’t do it all — but by exploring early and organizing ideas, you’ll build a trip that fits your interests and travel style.
Step 4: Prioritize!
Even once the plan feels “done,” I keep adding ideas. The goal isn’t to schedule everything — it’s to have a pre-vetted list of great options for those unplanned moments. That way, when you find yourself with a free afternoon, you already have a bank of places you’re excited to check out.
TL;DR: Book the high-priority things first — tickets, reservations, or special events — then build the rest around them.
Step 5: Keep an open mind
Even once the plan feels “done,” I keep adding ideas. The goal isn’t to schedule everything — it’s to have a pre-vetted list of great options for those unplanned moments. That way, when you find yourself with a free afternoon, you already have a bank of places you’re excited to check out.
TL;DR: Keep curating your list. The best discoveries often come from being flexible.
Help us build the future of trip planning. Get notified when Sundays Online’s first product, Sunday Planning is available in beta here.
