Welcome to The Upgrade List.

If you're a client, thank you for being here and for trusting me with your travel. If you're new, welcome to the club.

I know I've been a little MIA, but we're back and better than ever. Every Friday, this newsletter is going to do three things for you:

Now let's get into it.

Before I became the person who designs trips, I was the person with 47 iPhone notes, three group chats, and a voice memo I never listened back to.

Visiting St. Vincent & the Grenadines was actually my birthday trip this year and I will fully admit I did not plan as far in advance as I should have. What I did have was a shared notes app situation that looked a little hectic and a lot of research that needed to make sense fast.

So I put my travel agent hat on, looked at what was actually feasible, and turned the chaos into a week I'd do again tomorrow.

Here's the thing nobody tells you: the research is usually there. It's just not organized. And that's exactly where I come in.

How do I turn my research chaos into an actual itinerary?

You have the tabs. You have the saved posts. You have a note called "SVG maybe??" with 100 restaurants, hotels, and activities that have no logical order. The problem isn't that you haven't done the work. The problem is nobody showed you how to turn it into something you can actually execute.

Here's how I think about it:

Step 1: Sort by type, not by hype. Stop organizing by "things I want to do" and start organizing by category: where to sleep, how to move, what to eat, what to experience. Four buckets. Everything lives somewhere.

Step 2: Reality-check the logistics first. This is where most itineraries fall apart. You can't do everything in one day because one thing is on the mainland and another requires a ferry. SVG taught me this personally. La Soufriere hike is a full day commitment. Bequia requires a ferry from Kingstown. Build around the logistics, not around the wishlist.

Step 3: Anchor your days, not your hours. You don't need a minute-by-minute plan. You need one anchor activity per day that everything else orbits. The rest fills itself in.

That's it. Three steps from 100 saved posts to something that actually makes sense.

If you want me to do this with you in real time, that's exactly what a Trip Design Session is. 60 minutes. Your chaos, my framework. You leave with a plan.

Mandarin Oriental Canouan — St. Vincent & the Grenadines

Canouan is one of those islands in SVG that looks fake. Like someone described "perfect Caribbean island" to AI and this is what came out. Except it's real, it's quiet, and most people skip it because they don't know it exists. We actually stopped by on our boat charter day and I made a mental note to go back properly.

Mandarin Oriental Canouan is the property I'd point you toward and the reason is straightforward: booking through me changes what you get at check-in.

Here's what's included when you book through COTC:

The rate stays the same. The experience doesn't.

And there's a deal running right now worth paying attention to. Book by July 23 and you get your 4th night free plus a nonstop inter-island charter flight from Barbados to Canouan included. That's up to $600 per guest in flight value, on a private 9-seater King Air with leather seats, full AC, and curated refreshments. Flights run Wed & Sat from Barbados, Thu & Sun from Canouan. Travel window is May 2 through July 26, 2026.

This is the kind of offer that makes a trip make financial sense in a way it didn't yesterday.

→ Want me to check availability and perks for your dates? A Perks Check is free.

St. Vincent & the Grenadines — 8 days, the version I'd actually plan for you

This one is personal. I went for my birthday, two couples, 8 days. Here's how I'd structure it for someone starting from scratch.

Days 1–4: St. Vincent mainland

Base yourself at La Vue Boutique Hotel. It's a boutique property with views that make no sense for the price. This is your mainland anchor.

Mandatory: Hike La Soufriere. Clear your day for this. It's a commitment and it's worth every step. You'll want a guide.

Beach hop day. SVG's mainland beaches are underrated and you need at least one slow day to just exist.

Days 5–8: Bequia Take the ferry from Kingstown. The crossing is about an hour and runs on a schedule, so build your day around it, don't assume you can just show up. We stayed at Gingerlilly Villa which I'd go back to without thinking twice.

Non-negotiable add: Charter a boat for a day. We hit four islands — including Canouan (worth it just to see it) and Salt Whistle Bay on Mayreau which looks genuinely photoshopped. Lobster BBQ on the beach was the highlight of the whole trip.

Two things nobody tells you:

Want this designed for your specific dates, travel style, and group size? That's a Trip Design Session.

That's the thing about travel chaos, it's not a sign you're bad at planning. It's a sign you're interested in too many good things. The job is just turning all of it into something you can actually live.

If this issue gave you a direction, share it with someone who's been staring at a notes app full of "maybe" destinations.

And if SVG just made your list, don’t forget to grab my exact birthday itinerary 👇🏽

Talk soon,

Jo

www.carryontravelclub.com