What I Pack for a Fall Trip to Italy: Travel Essentials for Women Who Love Style & Security

This September, I went to Italy for a mix of love, family, and cozy fall vibes. My cousin was getting married in Siena, a small town in Tuscany that felt like it came out of a movie. And since I was flying all the way there, I thought — why not turn it into a little adventure? So after the wedding in Siena, I spent a few days exploring Venice and hanging out in Madrid too.

It wasn’t a solo trip, but I still wanted to feel put together, comfortable, and most of all, safe. Fall in Italy can be kind of all over the place — chilly in the mornings, warm by lunch, and sometimes rainy. But with a few smart pieces, I felt ready for anything. Here’s everything I brought (plus a couple things I wish I hadn’t packed).

If you’re someone who likes to look good, stay comfy, and feel totally at ease while traveling — this post is for you.

🌍 Where I Went: A Quick Look

Siena, Italy — A beautiful Tuscan town with warm brick streets, wine everywhere, and the sweetest wedding spot.

Venice, Italy — Canals, bridges, tons of walking, and that crisp fall air.

Madrid, Spain — Sunny days, big parks, and laid-back cafés.

🍂 What I Actually Packed (and Used!)

1. A Secure Crossbody Bag That Goes With Everything
   This bag was a lifesaver. I wanted something cute that worked with all my outfits, but still kept my stuff safe while walking around, hopping on trains, and sitting at cafes. Something comfy that was not too big nor too small.

Mine had:

• Zippers that lock (super helpful in busy places)

• Pockets that block RFID scans for my passport and cards

• A strap and lining that can’t be easily cut

• A clip I could hook to a chair at restaurants

It made me stop worrying. I didn’t have to keep checking on it — it stayed close, looked great, and worked with every look.
If you’re still deciding between bags, check out 5 Must-Have Features in a Crossbody Travel Purse for Women. It breaks it all down.

2. Tiny Travel Umbrella
   It rained a couple times in Tuscany, and I was so glad I had this. It was small enough to toss in my crossbody.

3. Light Blazer
   Perfect for layering, kind of dressed things up without trying too hard. I wore it on the plane, to a nice dinner, and even over my dress at the wedding rehearsal.

4. Two Go-To Shoes

• Neutral sneakers (walked a ton in Venice!)

• Cute flats for dinners and the wedding

FYI: Don’t even think about packing heels — cobblestones are no joke.

5. Cozy Warm Scarf
   I brought a soft wrap that worked as a blanket on the plane, a shawl for churches, and a little extra style boost in pics.

6. White Midi Dress
   Worked for the after-wedding brunch, dinner nights, and even just casual days with sneakers. It was a great all-in-one piece.

7. Phone Charger and Miu Miu Sunglasses
   I also packed my phone charger (a must!) and my Miu Miu sunglasses — because even in fall, the Italian sun shows up. 😎

8. Pack of big bandaids- Okay, this might sound random — but trust me. I always bring a big pack of bandaids, especially the big ones, to stick on the back of my heels before I even feel a blister coming. It’s my little trick to stop shoes (even the comfy ones!) from rubbing my feet raw after long days of walking. Especially helpful in Venice where you're on your feet a lot.

Want more tips like this? Don’t miss 5 Tips to Pack Stylishly & Light for Your Next Trip.

🍁 Easy Fall Outfits That Worked Fall in Italy is all about layers. Here’s what I lived in:

• Linen pants + white tee + blazer + sneakers

• Jeans + long sleeve loose top + scarf

• Cropped black pants + blazer + flats

• Normal sleeve + loose cropped jeans + wrap

I stuck with beige, black, white and olive so everything mixed and matched easily.

🙋♀️ Feeling Safe Without Sacrificing Style Even though I wasn’t traveling solo, I still noticed how much more relaxed I felt with the right bag. I wasn’t clutching it or stressing about it being open. I was sipping wine in Siena, bag clipped to the chair, or walking through Venice feeling totally at ease.

It was quiet confidence. And that felt really good.

Want to feel more secure while traveling? You’ll love 3 Travel Safety Tips Every Woman Should Know.

🧳 Final Packing List for Fall in Italy

Clothes:

• 1 light blazer

• 1 wrap scarf

• 1 white midi dress

• 2 long sleeve tops

• 1 light sweater

• 3 bottoms (linen pants + jeans)

• 2 pairs of shoes (sneakers + flats)

• Undergarments + socks

Accessories:

• Earrings + travel perfume

• Sunglasses

• Travel umbrella

Essentials:

• Secure crossbody bag (locking zippers, slash-proof strap, RFID protection)

• Passport

• Phone + charger

• Toiletries + makeup (travel size)

• Pack of big bandaids

👉 Fall in Italy is something special. The colors, the food, the cozy layers... everything just feels slower and sweeter.

So pack smart. Keep it light. And choose pieces that help you feel like you.

Because this trip isn’t just about where you’re going — it’s about how you feel along the way.

Want to see the bag I used the whole trip? Click here to check out the secure crossbody that helped me travel with total peace of mind.

Arielle