Bye, America—Hello, Italy: Here's What I'm Buying for My 14-Day Trip to Rome, Ponza, and Milan

In 10 days, I'll already be in Rome, probably one Campari and four stores into my two-week trip around Italy. We're starting in the capital before traveling to Ponza for a handful of days spent doing absolutely nothing. Once we've hit peak relaxation—my skin as tan as it'll get and my hair still crunchy from the seawater—we'll be off again to Monza for the Italian Grand Prix. Finally, I get one day in Milan to eat, see pretty things, and take advantage of the VAT tax benefits. It's a lot to pack for (especially in a carry-on suitcase), which means I need the next week and a half to plan my outfits. It also means that some pre-trip shopping has to be done. Luckily, one of my favorite things about traveling is buying stuff to wear while I'm away.

I'm sharing my Italian summer vacation wish list (2025 edition) below on the off chance that anyone reading this is also heading on an end-of-summer trip and in need of a jumping-off point. There are walking shoes that double as dinner shoes, shorts that can be dressed up or worn to the beach, and my pick for summer 2025's chicest bikini. Dresses, accessories, eyewear, and more all await.

Reformation

Fern Satin Short

When I go on vacation with a carry-on suitcase, I need my pieces to work for multiple occasions. These can go from the beach to dinner with just a few easy tweaks.

I had these in brown on my last Italy trip and wore them every single day, walking tens of thousands of steps per day. I accidentally got them drenched in one of NYC's crazy storms and had to get rid of them, so this trip is giving me an excuse to get a second pair.

These look so expensive for $13 sunglasses.

Alfie

Open Back Cotton Poplin Top

Just wait until you see the back of this top. It's such a statement piece.

Totore Vintage Studio

Necklace With Gemstone and Tassel

You don't have to spend hundreds of dollars to tick off this beautiful jewelry trend. Etsy has so many options to choose from.

MANGO

Balloon-Style Pants With Elasticated Waist

I ordered these genie pants within seconds of finding them.

Havaianas

Slim Square Flip Flops

The square toe makes these look way more upscale than standard flip-flops. At the same time, they're so comfy, so you can wear them while you're at the beach, heading to lunch, and shopping.

Chan Luu

Caprice Sterling Silver Crystal Toe Ring

A perfect toe ring to further dress up my flip-flop outfits.

This sheer lace dress has Italian vacation written all over it.

Camila

French Twist Stick Hair Fork

For twisting up my sun- and sea-soaked hair.

gucci

GG Terrycloth Bikini

I swear this is the chicest bikini I've ever seen.

j.crew Collection

Wrap Skirt in Silk Organza

This sheer midi skirt does it all. It just needs a tank top and some easy accessories to create a winning outfit.

Elaree

Supple Bucket in White Wood

This beaded bag is going viral on fashion IG right now.

This sarong will be so fun to accessorize with on my trip.

Helsa

Mini Dress With Lace in Tech Poplin

Any dress that requires zero work deserves a certain place in my suitcase. This is one such dress.

ZHOUMEIWENSP

French Large Hair Claw Clip

I'm not the type of person who goes on vacation and does their hair every day, so I cannot travel without a handful of hair clips.

H-O-R-S-E

The Short Short

If you buy one pair of athletic shorts this season, make it these.

tumi

International Carry-On

Okay fine, so I already own this one. I'd buy it again, though.

Tropic of C

Universo Bralette

Trying to channel Kendall Jenner in this bikini that she wore earlier this summer.

Shop the matching Luna Bikini Bottom ($100).

Polo Ralph Lauren

Twill Classic Sport Cap

For when I get a little too much sun.

j.crew

2025 Rollneck Sweater

I always pack at least one item that will keep me warm if it happens to get a little bit chilly on a summer trip. I love this roll-neck sweater because it's cotton, so it's still breathable.

I actually already got these for my trip and have been trying desperately not to wear them before I leave. They're so flattering and elegant.

Bottega Veneta

Marella Thong in Light Butterscotch

I keep coming back to these beautiful thong sandals with an Intrecciato footbed. Bottega's shoes are the most comfortable because of the rubber grips on the bottom.

This cuff feels like a fun alternative to the metal versions I see everywhere online.

Madewell

Oversized Button-Up Shirt in Poplin

I just got this striped Madewell shirt and have already come up with a handful of different ways to wear it.

A classic wardrobe item that I pack on every single trip I go on.

Nordstrom

Polo Sweater Dress

Just a simple T-shirt dress that will work for any occasion.