How to Plan a Cruise Itinerary That Actually Feels Good

Plan once — enjoy your cruise without second-guessing.

There was a time when I planned cruises in layers.

First the ports.
Then the excursions.
Then, weeks later, the packing.

And somewhere between “Glacier Bay day” and “formal night,” I would realize my shoes didn’t match my plans. Or my plans didn’t match my energy. Or my outfits didn’t match either.

That’s when I started planning differently.

Not more.

Just together.

✨ The Problem With Planning in Pieces

Most people plan cruises like this:

• Pick the itinerary
• Choose excursions
• Later… figure out outfits
• On the ship… second-guess everything

It’s not that anything is wrong.

It just feels slightly disconnected.

You’re in a gorgeous port, but you didn’t pack the shoes that make it comfortable.
You booked a walking tour, but your dress choice says “sit quietly at dinner.”
You overpack because you’re unsure.

And uncertainty steals energy.

🧭 What Changed for Me

When Jamie and I started planning our ports and our outfits at the same time, something shifted.

If we booked a long walking day?
Comfortable, breathable layers.

If we planned a casual dock town?
Easy sandals. Crossbody bag. Sun protection.

If formal night fell after an excursion?
Something that still worked if we were a little tired.

Instead of planning in fragments, we built one cohesive flow.

And the cruise felt lighter.

🌊 A Gentle Cruise Planning Framework

Here’s the rhythm that works for us:

1️⃣ Start With Energy, Not Just Excursions

Before booking anything, ask:
How do we want this port to feel?

Relaxed?
Exploratory?
Photogenic?
Food-focused?

That guides everything.

2️⃣ Map the Port to the Outfit

If the excursion involves:

• Lots of walking → supportive shoes + breathable fabrics
• Boat rides → layers + wind-friendly hair plan
• Markets + photos → hands-free bag
• Formal dinner → consider what you’ll realistically feel like wearing

Now your suitcase has purpose.

3️⃣ Reduce “Backup” Packing

When your itinerary and wardrobe align, you don’t need five “just in case” outfits.

You pack with confidence.

And confidence weighs less. 🧳

💛 Why This Matters More Than It Sounds

Cruise days are full. Even relaxing ones.

The fewer tiny decisions you have to make on board, the more present you are.

You’re not standing in the cabin thinking,
“Did I pack the right thing?”

You’re standing on deck thinking,
“This is exactly what today needed.”

That’s the difference.

🌴 Our April Cruise

For our upcoming cruise (which I’ll be blogging in detail soon), I’m building itinerary pages and style pages side by side.

Not because it’s fancy.

Because it feels calm.

And calm travel is my favorite kind.

💬 I’m Curious

When you travel, do you:

A. Plan activities first, then pack later?
B. Plan outfits first, then fit activities around them?
C. Or do you map them together?

Tell me in the comments. I love seeing how different brains plan.