6 Things You'll Regret Not Packing (From a Woman Who's Planned Dozens of Group Trips)

Whether you’re jetting off on a weekend escape or leading your dream group getaway through Morocco or Greece, packing can make or break your experience. Over the years, I’ve led countless women’s trips around the globe—and trust me, there are a few things you really don’t want to forget.

These are the five items I see travelers regret leaving behind time and time again (and yes, I’ve made the same mistakes too).

1. A Lightweight, Stylish Scarf

Sounds simple, right? But this one piece can be your best friend. It’s a cover-up at religious sites, a shawl for chilly evenings, a makeshift beach blanket, or even a pop of color in your photos. I always recommend bringing a lightweight, breathable scarf that folds up tiny but packs a punch in versatility.

Pro Tip: Go for a neutral tone or a vibrant print that matches your capsule wardrobe. Bonus if it doubles as a sarong!

2. A Compact Power Bank

I can’t tell you how many women I’ve seen scramble for outlets at airports, on buses, or during long tours. Between snapping photos, using Google Maps, and staying in touch with the group chat, your phone battery will take a hit.

Pack a power bank that’s small enough to toss in your day bag but powerful enough to charge your phone at least once. It's peace of mind in your pocket.

Travel organizer note: I carry extras on group trips—because there's always one person who forgets. Don’t let it be you!

3. Good Quality Walking Sandals

It’s tempting to go for fashion over function, but hear me out: your feet deserve better. Comfortable, supportive, stylish walking sandals are a must—especially for cobblestone streets, market days, or spontaneous hikes.

You’ll thank yourself later when your feet are still happy after a full day of exploring.

4. A Packable Day Bag

You don’t always want to carry your main purse or backpack while exploring. A foldable, lightweight day bag gives you the flexibility to travel light or bring back that unexpected market haul without overstuffing your luggage.

Bonus use: It doubles as your “personal item” on the plane or even a beach bag.

5. A Mini First-Aid Kit (Curated by You)

I know, I know—this sounds a little mom-ish. But hear me out. You don’t need a full-blown pharmacy, just a small zip pouch with essentials you know you’ll need: your favorite pain reliever, motion sickness tablets, blister pads, allergy meds, and a few Band-Aids.

On group trips, I’m the unofficial first-aid fairy. But when you're traveling solo or independently exploring, having your own stash is empowering.

Insider tip: Add a few electrolyte packets—they’re magic after long flights, beach days, or that third glass of wine.

6. Rain Jacket / Wind Jacket

Trust me on this one: this is my #1 non-negotiable.I never leave home without my rain jacket/wind jacket. It’s lightweight, easy to pack, and serves a double purpose: it keeps me warm when temperatures drop unexpectedly and also protects me from surprise downpours. I highly recommend getting a foldable one that’s small and packable—it tucks right into your backpack or day bag without taking up much space. When that unexpected storm rolls in or you find yourself shivering in a gusty breeze, you’ll be so glad you brought it.

Packing smart isn’t about having more stuff—it’s about having the right stuff. These five things won’t take up much space, but they’ll make a huge difference in your travel comfort and confidence.

And if you’re ever unsure what to pack? Ask your travel organizer. We’ve seen it all—and probably packed it, too.

Ready to travel with us? Join one of our upcoming women’s adventures! Whether you’re craving fresh mountain air and cozy cabins in Montana, or dreaming of island-hopping, history, and sunset dinners in Greece—we’ve got a trip with your name on it.

Check out our upcoming women’s trips here and come travel with a group of fun, inspiring women who love to explore just like you.

With Love,

Lea