There’s a reason my entire business is built around removing the stress of planning, because I know firsthand how overwhelming it can be.
When it comes to my own vacations, I don’t wing it. I found a spreadsheet that compares options side-by-side and makes making confident decisions easier (continue reading on to get access to this). Over the years, especially as a travel planner and now as a mom I’ve become increasingly selective and realized that great travel planning really is an art.
So I'm going to walk you through exactly how I planned our recent trip over March Break with my family. And how...after A LOT of eliminations I chose Windjammer Landing Resort and Residences (in St. Lucia).
My Planning Method (The Spreadsheet System)
Before I book anything, I plan my personal trips the same way we build Guess Where Trips…with a slightly obsessive level of research and attention to detail.
Here’s what I typically compare (before booking vacations).
- Country / Destination → I filtered for places I hadn’t been before, but that still felt safe and easy to get to. St. Lucia kept rising to the top.
- Resort Style → Family vs adults-only, plus overall vibe (family resort vs romantic vs boutique). I was specifically looking for something family-friendly.
- Room Type Options → This was a major factor. I filtered for resorts with 2-bedroom suites, villas, or plunge pool rooms, something that actually works for a family.
- Amenities / Activities → I looked at the full list: beach, kids club, watersports, yoga, tennis, babysitting, etc. I wanted enough to do without needing to over-plan every day.
- Food + Beach Rating → I track this as a combined “quality” signal. Windjammer Landings consistently showed up as good food + great beach, which is a rare combo.
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Price + Value Ratio → I compare USD vs CAD and calculate a rough value score. Windjammer Landings wasn’t the cheapest, but it had a strong value-to-experience ratio for what you get.
Destination Decision: Why St. Lucia
St. Lucia kept rising to the top. It checked every box:
- Easy to get to
- Warm, reliable weather
- Safe and comfortable
- Enough to do, but still relaxing
- Direct-ish flights
- Incredible scenery (mountains + beach)
- Not overly commercialized like some Caribbean destinations
- Felt like a real escape, not just a beach vacation
Resort Selection: Why We Chose Windjammer
After comparing multiple resorts, Windjammer Landing Resort and Residences stood out in a very specific way:
Villa + Resort Hybrid:
This was the hardest thing to find. It’s incredibly rare to get villa-style accommodations at a full-service resort with tons of amenities (plus an all-inclusive add-on) for a good price.
- The space and privacy of a villa
- Most spaces have a private pool
- The amenities of a full resort
*this was our own personal pool at our villa!
Beach Quality:
- Set in a protected cove
- Calm, swimmable water
- Never felt overcrowded
It felt intimate...not like a packed resort beach.
*they had water nets, hammocks, trampoline and docks kids (and adults) could swim up to!
Kid-Friendly:
A good kid-friendly resort is hard to find. It had:
- Enough for kids to stay entertained
- But still felt calm and elevated
- Had so many special touches like a kids window at the ice cream shop, and mini beach chairs.
But what's nice is you're not surrounded by constant noise or overstimulation.
*our kids loved these mini beach chairs that were available throughout the property
Food Quality:
This was a big one for me! I needed:
- Multiple restaurants (like 4+)
- Consistently good meals
- Easy options for kids without sacrificing quality
*this was from the steak restaurant on-site
Activities & Things to Do
- Water sports
- Pools
- Excursions
- On-site variety
Enough to fill your days, but not so much that it feels overwhelming.
*the catamaran tours were included in the all-inclusive package
Views & Layout
The entire resort is built into a hillside with:
- White villas cascading down toward the ocean
- Unreal views from almost everywhere
- A layout that feels unique and memorable
*this was the sunset view from our room!
Honest Considerations:
No resort is perfect, and this is where the spreadsheet really helps you be honest.
Hillside Layout
- It’s steep
- You rely on shuttles to get around
For most people, it’s part of the charm...but it’s worth noting.
Motion Sensitivity (for Kids)
Because of the winding roads and shuttle rides If your kids get car sick easily, this could be a factor. Not a dealbreaker, but something to be aware of!
Want My Spreadsheet?
If you’re planning a trip and feeling overwhelmed, this will change everything.
Download the vacation comparison spreadsheet I use HERE.
* You'll need to click "make a copy" after opening the link to access information and use the spreadsheet for yourself.
Or if you trust the process, and want to book Windjammer Landing Resort and Residences use this link here (and code GWT) for a discount.
Disclaimer: After choosing Windjammer, I reached out with a few final questions—and they ended up offering a couple of extra perks in exchange for an honest review of our experience.
