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’s winding canals and then hopped over to Madrid to soak up some late-September sun in the parks and cafés.
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 a mix of weather — chilly in the mornings, warm by lunch, and sometimes rainy. But with a few smart pieces, I felt ready for anything.
In this post, I’ll share exactly what I packed, what I wore, and the safety essentials that gave me peace of mind — plus a few things I wouldn’t bring next time.
Key Takeaways
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Layering is everything for fall travel in Europe. Mornings, afternoons, and evenings can feel like different seasons.
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A secure crossbody bag changes everything — less worry, more enjoyment.
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Stick to neutral, mix-and-match pieces to pack lighter and get more outfit options.
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Comfortable shoes are non-negotiable on cobblestone streets.
Table of Contents
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My Fall Packing Essentials for Italy (and Madrid)
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The Secure Crossbody Bag That Was a Lifesaver
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Tiny Travel Umbrella
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Light Blazer for Every Occasion
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Two Go-To Shoes
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Cozy Scarf That Doubled as a Blanket
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A White Midi Dress for Multiple Events
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Bandaids (Yes, Really)
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1. Where I Went
Siena, Italy — A beautiful Tuscan town with warm brick streets, incredible wine, and a wedding venue that felt straight out of Under the Tuscan Sun.
Venice, Italy — Canals, bridges, crisp air, and lots (and I mean lots) of walking.
Madrid, Spain — Sunny days, leafy parks like Retiro Park, and laid-back cafés where time slows down.
2. The Mindset I Packed First
Before I even touched my suitcase, I thought about how I wanted to feel on this trip:
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Comfortable enough to walk for hours without worrying about blisters.
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Stylish enough to feel confident in photos and dinners out.
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Prepared enough to not waste energy worrying about my belongings.
That last one — safety — was important to me. Even though I wasn’t alone, I knew that busy train stations, packed streets, and popular attractions can make anyone a target for pickpocketing. And I didn’t want to spend my time clutching my bag or looking over my shoulder.
3. My Fall Packing Essentials for Italy (and Madrid)
The Secure Crossbody Bag That Was a Lifesaver
This bag was the MVP of my trip. I wanted something cute, versatile, and secure. Mine had:
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Locking zippers for busy areas
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RFID-blocking pockets for my passport and cards
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Slash-resistant strap and lining
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Chair clip so I could hook it at cafés and restaurants
You can check the Thafael Crossbody Travel Bag here
It went everywhere with me: to the wedding brunch, on the vaporetto in Venice, wandering through Plaza Mayor in Madrid.
If you’re still deciding, check out 5 Must-Have Features in a Crossbody Travel Purse for Women — it breaks down exactly what to look for.
Tiny Travel Umbrella
It rained twice in Tuscany and once in Madrid, and I was so glad I had this. Small enough for my bag, big enough to keep me dry.
Light Blazer for Every Occasion
A neutral, lightweight blazer pulled everything together. I wore it:
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On the plane
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For a nice dinner in Venice
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Over my dress at the wedding rehearsal
It worked for both comfort and polish.
Two Go-To Shoes
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Neutral sneakers — perfect for miles of cobblestone walking in Venice.
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Flats — for dinners, the wedding, and museum days.
Pro tip: skip the heels. Cobblestones and stilettos do not mix.
Cozy Warm Scarf
This soft wrap worked triple duty:
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Blanket on the plane
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Shawl for churches
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Style boost in photos
White Midi Dress
Great for the after-wedding brunch, dinner nights, and even sightseeing with sneakers. I love pieces that can be dressed up or down.
Bandaids (Yes, Really)
I always bring a pack of big bandaids and stick them on my heels before shoes start rubbing. This saved me in Venice where I was walking 15,000+ steps a day.
Related: 5 Tips to Pack Stylishly & Light for Your Next Trip
4. Easy Outfit Formulas That Worked Every Time
Fall in Italy is all about layers and versatility. I stuck to beige, black, white, and olive so everything mixed and matched easily.
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Linen pants + white tee + blazer + sneakers
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Jeans + loose long sleeve top + scarf
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Cropped black pants + blazer + flats
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Midi dress + sneakers + scarf
This approach made packing easier and mornings stress-free.
5. Feeling Safe Without Sacrificing Style
Even though I wasn’t traveling solo, I noticed how much more relaxed I felt with the right bag and a few smart habits.
In Venice, my bag was clipped to my chair as I sipped a spritz in a busy piazza. In Madrid, I wandered El Rastro market without that constant “is my bag open?” anxiety.
It was quiet confidence — looking good, feeling good, and knowing I had what I needed without fuss.
For more tips, see How to Avoid Pickpockets While Traveling.
6. Final Packing List for Fall in Italy
Clothes
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1 light blazer
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1 wrap scarf
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1 white midi dress
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2 long sleeve tops
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1 light sweater
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3 bottoms (linen pants + jeans)
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2 pairs of shoes (sneakers + flats)
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Undergarments + socks
Accessories
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Earrings + perfume
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Sunglasses
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Travel umbrella
Essentials
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Passport
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Phone + charger
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Toiletries + makeup (travel size)
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Pack of big bandaids
FAQ
What’s the weather like in Italy in September?
It varies! Tuscany was cool in the mornings (low 60s°F) and warm by midday (mid-70s°F). Venice was cooler, and Madrid was warmer and sunnier.
Do I need an anti-theft bag if I’m not traveling solo?
Yes. Pickpockets target anyone in busy tourist areas. A bag with security features keeps you more relaxed.
What should I avoid packing for Italy?
High heels, heavy coats, and anything that doesn’t mix and match with multiple outfits.
How do you dress comfortably but still stylishly when traveling?
Stick to versatile basics, layer, and use accessories like scarves to change up your look.
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