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How To Vacation On A Weight Loss Journey

Hey Friend,

Joani and I just got back from a short but amazing weekend getaway to Miami Beach.

We shopped, we ate incredible food, and we racked up close to 25,000 steps a day. I even got a workout in at one of my favorite outdoor gyms right on the beach. 💪🏻

As we enjoyed ourselves, I couldn’t help but smile at what trips like this have come to mean…

We’re able to go, indulge, enjoy ourselves, stay active, and never feel like our health is holding us back — or like we’re digging ourselves into a hole.

And here’s the thing most people don’t realize:

Just because Joani and I are “at our goals” doesn’t mean trips like this happen by accident.

There’s a strategy behind them — a rhythm we’ve built to let us enjoy the moment without sacrificing progress or coming home with regret.

So in today’s Tuesday Deep Dive, I want to walk you through my go-to vacation strategy — one that helps me (and our clients) enjoy food, fun, and freedom without guilt… and without needing to “fix it all” when we get back.

Let’s dive in.👇

1. Get Clear On Your Goal For the Vacation

Like any effective strategy, this starts with a clear goal and intention.

In my experience, there are only three types of vacation goals:

1. Lose weight

2. Maintain weight

3. Gain weight (and fix it when you get back)

The goal you choose dictates the approach you take.

If your goal is weight loss, that means tighter food decisions, more restraint, and fewer indulgences.

If your goal is maintenance, you can be a bit more relaxed — but still need structure and intention.

And if your goal is to gain and reset later, then the only strategy you need is for recovering after, which is a topic for another newsletter 😂

Here’s why this goal-setting is so important:

• It shapes your planning and preparation.

• It defines your limits and boundaries.

• It sets your expectations so you don’t end up frustrated or reactive.

The mistake most people make?

Going into a trip with no clear goal or plan — and then feeling guilty, discouraged, or confused about their results.

Decide ahead of time. Clarity here is everything.

2. Stock Up On Essentials Before You Go

I always pack protein bars or pastries and everything I need for my daily hydration cocktail.

Sometimes I’ll even grocery shop when we arrive if we have a kitchen available.

On this most recent Miami trip, we didn’t have a kitchen — we knew all our meals would be at restaurants. 

So we packed about 15 protein bars and protein pastries in our bags. 

We used those on the way there, on the way back, and during the day when we didn’t want a heavy meal or indulgent snack.

Last year, when we did have a kitchen, we bought:

• Eggs

• Keto bread

• Chicken breakfast sausages

• Real Good Brand chicken nuggets

• Other simple staples for easy, healthy meals

The idea is simple: when you’re prepared, you don’t have to rely on willpower.

And when you’re not prepared, things tend to spiral.

So stock up, whether you’re flying, driving, or staying with family. Your future self will thank you.

3. Maximize Activity and Daily Movement

Vacation usually means more restaurant food — and even “healthy” restaurant meals are higher in calories and lower in protein than you’d think.

The best counterpunch to that?
Moving. Walking. Training.

Every trip I take, my goal is to crush my step count and get in a strength workout every day if possible.

This requires planning and commitment — but it makes all the difference.

Before we travel, I ask myself:

• What clothes/shoes do I need to pack to stay active?

• Where can I work out — gym, beach, hotel, bodyweight?

• Are there activities I can plan that are naturally more active?

• Are there travel-heavy or sedentary days where I’ll need to sneak in a quick session?

On our Miami trip, we walked around 25,000 steps a day and I hit the outdoor beach gym for a strength session.

That activity alone helped offset any extra calories we ate.

If I know I’ll be getting lots of steps and workouts, I can be a little more relaxed with food.

If I know activity will be lower, I tighten up my food choices.

Either way: plan for movement, or plan for struggle.

4. Conserve Calories for When It Counts

Weight loss or maintenance goals mean it can’t be a free-for-all all day long.

So I ask myself two key questions:

1. What meals or treats do I really want to indulge in?

2. What meals are just for fuel?

On this trip, my indulgence of choice was dinner.

I knew we’d be super active all day, and that dinner would be our more relaxed, social meal.

So I skipped breakfast or stuck to coffee, had a protein bar or something light for lunch, and saved my bigger meal for the evening.

(P.s. the nachos at Oh Mexico! on Espanola Way in Miami Beach are 🔥)

You might be the opposite. Maybe breakfast is your indulgent meal, and the rest of the day is dialed in.

The point is: choose your indulgence with intention, and plan the rest of the day around it.

And again — this is where your expectations matter.

If you set a goal of weight loss, that means accepting more restraint. Period.

It’s not a punishment. It’s a choice — a smart one.

And your goals are worth it.

5. Remember What Really Matters

So you set your goal.
You came prepared.
You moved your body.
You made smart food choices and indulged with intention.

Now what?

You come home. You step on the scale.
Maybe it’s up. Maybe it’s down. Maybe it’s flat.

It doesn’t matter.

What matters is this: you’re in this for the long haul.

And one trip — even a few imperfect days — won’t make or break your success.

If you’re committed to building a lifestyle that lasts, then this trip was a chance to practice your lifestyle, not escape it.

And when you approach travel this way, something powerful happens:

You become the kind of person who can go anywhere, do anything, and live life fully — without losing yourself in the process.

So whatever happened on your last trip — learn from it. Smile about it.

And keep going.

You’ve got a lifetime ahead of you.

Make it one you're proud of. 💪

— Matt

When you're ready, here's how I can help:

If you're looking to lose weight sustainably while building a flexible lifestyle that you enjoy, I can help.   Apply for coaching here in the Healthy & Whole Mentorship Program.  

Disclaimer: This email is provided for educational and informational purposes only and does not constitute providing medical advice or professional services. The information provided should not be used for diagnosing or treating a health problem or disease, and those seeking personal medical advice should consult with a licensed physician.